$375,000

2 Beds ⋅ 2 Baths

Beautifully updated and well-maintained home in a desirable Windham location! This move-in-ready property offers a thoughtfully improved interior with modern updates throughout, reflecting pride of ownership at every turn. The home features a bright, welcoming layout with comfortable living spaces ideal for both everyday living and entertaining. Recent updates enhance both style and functionality, while ongoing maintenance provides peace of mind for the next owner. Enjoy the meticulously landscaped grounds that create a welcoming outdoor setting and enhance the home's curb appeal. The lower level offers excellent potential and is ready for your personal touch, providing an opportunity to expand the home's finished living space with updated areas for a recreation room, home office, gym, guest space, or additional living area. Set in a quiet neighborhood yet conveniently located near shopping, schools, lakes, and commuter routes, this home offers the perfect blend of comfort, convenience, and value. A wonderful opportunity to own a turnkey Windham home with room to grow--don't miss it! Offer Deadline by 5 p.m. today, August 5th!

60 Forbes Ln, Windham

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$399,000

3 Beds ⋅ 1 Baths

Welcome to 38 Lantern Lane, a three bedroom Cape in a quiet Windham neighborhood near Highland Lake. The kitchen was fully updated in 2022. Granite counters, a deep stainless farmhouse sink, subway tile backsplash, and new stainless appliances. The butcher block island adds counter space and can be moved. The kitchen and dining area are connected to each other and flow through to the living room, where there is a propane fireplace. Hardwood floors run throughout. The home has been well maintained. The roofing has been replaced, the interior is freshly painted, and there is a generator with hookup for the winter storms. The lot is sunny with woods along the back, and the garden beds are framed and fenced. The covered farmer's porch runs across the front of the house and is a quiet place to sit and take in the nature that surrounds the property. There are walking trails and a playground near the East Windham Fire Station, biking trails nearby, and I-95 at exit 53 is about ten minutes away. Loons, owls, and deer are just some of the sights and sounds of nature that surround the property. Showings start August 7.

38 Lantern Ln, Windham

Listing courtesy of EXP Realty.

$525,000

3 Beds ⋅ 2 Baths

Full of classic New England charm, this 3-bedroom home offers generous living space and a flexible floor plan on a .46 acre corner lot. The updated kitchen features a large center island, new appliances, ample cabinet space, and an inviting layout for everyday living. Original hardwood floors, fireplaces, built-ins, exposed beams, and other period details add warmth and character throughout. Recent improvements include all new windows, updated electrical, freshly paved driveway and new leach field, providing peace of mind while preserving the home's historic appeal. Multiple living and dining areas provide room to gather, work, or relax, and the attached two-car garage adds everyday convenience. Located close to shopping, restaurants, and outdoor recreation, this home offers the space, character, and flexibility to suit a variety of lifestyles.

1 Marigold Ln, Windham

Listing courtesy of RE/MAX By The Bay.

$650,000

3 Beds ⋅ 2 Baths

NEW CONSTRUCTION TO BE BUILT: Experience the best of lakeside living with this stunning new construction opportunity. This thoughtfully designed 3-bedroom, 2-bath home offers modern finishes, open-concept living, and the rare chance to personalize the home to fit your lifestyle. Nestled in a peaceful, scenic setting, the property includes two deeded access points to the lake, making it easy to enjoy swimming, kayaking, fishing, or simply taking in the tranquil waterfront surroundings. Surrounded by nature and nearby trails, this location offers the perfect balance of outdoor recreation and everyday comfort. The home can be customized, with additional options available such as a garage, daylight basement, expanded living space, and other upgrades to create your ideal home. Enjoy the serenity of lake life while remaining just 20 minutes from Portland, offering convenient access to shopping, dining, entertainment, and major commuting routes. Whether you're looking for a year-round residence or a peaceful retreat, this modern new construction home is a unique opportunity to build the lifestyle you've been dreaming of.

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

$949,000

6 Beds ⋅ 4 Baths

Just a short ~0.3-mile walk or less than a one-minute drive to Windemere's private sandy beach on Sebago Lake, this exceptional custom Colonial offers the perfect blend of luxury, craftsmanship, and the Maine lake lifestyle. Welcome to Windemere, one of Sebago Lake's most sought-after private lakefront communities. Offering 3,555 square feet of beautifully finished living space, this custom-built home features a thoughtfully designed floor plan with six bedrooms and three and a half bathrooms, including spacious primary suites on both the first and second floors, making it ideal for multi-generational living or hosting guests. Hardwood floors, quartz countertops, a gas fireplace, a dedicated home office, and both formal and informal living spaces provide comfort and flexibility for everyday living and entertaining. Above the attached two-car garage, a finished bonus space complete with a kitchenette offers endless possibilities as an in-law suite, guest quarters, recreation room, home office, or private retreat. Outside, relax on the expansive patio overlooking the beautifully landscaped backyard while enjoying seasonal views of Sebago Lake. A new roof installed in 2024 provides added peace of mind. Windemere residents enjoy exclusive access to outstanding amenities, including a private boat launch, boat slips (subject to availability), tennis and pickleball courts, canoe and kayak storage, and beautifully maintained common areas with breathtaking mountain and sunset views. The community's private sandy beach offers the perfect place to swim, relax, or spend the day enjoying everything Sebago Lake has to offer. Just minutes from downtown Windham, this home offers the rare opportunity to enjoy spacious luxury living in one of Southern Maine's premier lake communities. Note that the septic system is designed for four bedrooms.

35 Woldbrook Dr, Windham

Listing courtesy of Portside Real Estate Group.

$575,000

3 Beds ⋅ 3 Baths

Move-in ready and thoughtfully designed, this exceptional Colonial in sought-after Belvedere Estates offers the perfect blend of style, comfort, and efficiency. From the moment you enter, you'll appreciate the bright, open floor plan, quality craftsmanship, and beautiful hardwood flooring that flows throughout both levels of the home. At the heart of the home is an inviting kitchen featuring granite countertops, a spacious center island, stainless steel appliances, and abundant cabinetry--creating the ideal space for everyday living, meal preparation, and entertaining. The kitchen opens into the welcoming living area highlighted by a custom feature wall with a contemporary fireplace, creating stylish space. Exit through the sliding glass doors to a generous deck overlooking a level backyard, offering plenty of room for summer barbecues, morning coffee, or evenings with family and friends. The second level is designed for comfort, featuring an expansive primary suite complete with 2 walk-in closets and a beautifully finished ensuite bath with granite-topped vanity and tile flooring. Two additional generously sized bedrooms, all with hardwood floors, share a full bath. Also located on the second-floor is the laundry room adding to everyday convenience. The full daylight basement presents outstanding possibilities for future finishing, whether you envision a recreation room, fitness area, home office, or additional living space, while still leaving ample room for storage. An attached two-car garage provides additional space for vehicles, tools, and outdoor equipment. Built with efficiency in mind, this home offers the comfort of natural gas heating. This property is ready for you to make it your home!

36 Belvedere Dr, Windham

Listing courtesy of Keller Williams Realty.

$489,500

3 Beds ⋅ 1 Baths

Welcome to 47 Running Brook Road, a beautifully renovated three-bedroom ranch offering move-in-ready comfort, an oversized wooded lot, and deeded access to approximately 1,500 feet of shared Collins Pond shoreline and park area. Inside, the main level has been thoughtfully transformed with an open and inviting layout, refinished hardwood floors, fresh paint, new doors and trim, and updated lighting throughout. The completely remodeled kitchen features new cabinetry, granite countertops, a farmhouse sink, tile backsplash, stainless appliances, and modern black hardware. The renovated full bath includes a tiled shower, double vanity, new fixtures, and updated plumbing. All three bedrooms are generously sized, and the spacious living room offers plenty of room to relax around the woodstove. The finished lower-level recreation room provides additional flexible living space, while the unfinished portion of the basement offers excellent storage and utility space. Major improvements completed since 2025 include Anderson windows, new exterior doors, a new oil boiler, a new heat pump water heater, a new chimney liner and cap, updated outlets and switches, new flooring, refreshed landscaping, fencing, and extensive tree clearing. Outside, enjoy a private backyard setting with multiple deck areas, a gazebo, storage shed, and a gorgeous, wooded section of the lot. Deeded rights provide access to the shared Collins Pond park area, where residents can enjoy kayaking, paddleboarding, fishing, swimming, and the lake lifestyle without the cost and maintenance of direct waterfront ownership. With extensive renovations, updated systems, flexible living space, and deeded pond access, this home offers a rare combination of comfort, recreation, and peace of mind.

47 Running Brook Rd, Windham

Listing courtesy of Keller Williams Realty.

$949,900

3 Beds ⋅ 3 Baths

Nestled on an extraordinary 16-acre estate in the heart of Windham, this one-of-a-kind farmhouse masterfully blends timeless New England charm with exceptional modern amenities. Surrounded by breathtaking stone walls, spectacular perennial gardens, and stunning custom hardscaping, the property offers an unparalleled setting of beauty, privacy, and tranquility. At the heart of the home is a dream chef's kitchen, thoughtfully designed for both everyday living and entertaining. Featuring gleaming granite countertops, stainless steel appliances, and a coveted Wolf gas range, this impressive space is as functional as it is beautiful. The home offers three spacious bedrooms and two-and-a-half baths, with inviting living spaces that embrace the surrounding landscape. Relax year-round in the passive solar sunroom, unwind on the spacious screened porch, or entertain on the deck before soaking in the hot tub beneath the stars. Additional highlights include a three-car garage, a garden shed, and an expansive third-floor attic with incredible potential to create additional finished living space, whether you envision a home office, studio, guest suite, or recreation room. Every inch of this remarkable property reflects thoughtful craftsmanship and pride of ownership. From the magnificent gardens to the picturesque stonework and peaceful acreage, this is a rare opportunity to own a truly exceptional country estate--offering the perfect balance of elegance, comfort, and natural beauty, just minutes from all that Windham has to offer. This home has even been pre-inspected for the buyer's convenience. Seller Concessions Available. For a video walk-thru go to YouTube and enter the property address.

605 River Rd, Windham

Listing courtesy of Keller Williams Realty.

$499,000

3 Beds ⋅ 2 Baths

Move right in! Set on a peaceful, wooded lot, 8 Environmental Way offers the perfect balance of privacy and convenience, just 30 minutes from downtown Portland. Thoughtful updates, including a new roof and whole-house generator, provide peace of mind, while deer, birdsong, and surrounding nature create your own private retreat just minutes from shopping, restaurants, schools, and Sebago Lake recreation. Inside, the three-level layout is both functional and inviting. The open kitchen, dining, and family room flow seamlessly together, highlighted by a cozy propane stove and views of the natural landscape. Upstairs are three bedrooms, including a spacious primary suite with two closets and a private bath, plus a second full bathroom. The finished lower level offers flexible space for a media room, home office, gym, or playroom. Storage is abundant with a double-door pantry, generous closets throughout, and a large two-car garage. For added confidence, a pre-listing home inspection has been completed, and a past water test report will be available to interested buyers.

8 Environmental Way, Windham

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com

$599,000

3 Beds ⋅ 3 Baths

This beautiful 3-bedroom, 2.5-bath home will have you celebrating your good luck! Life in this serenely situated Windham neighborhood strikes a perfect balance of comfort, convenience & idyllic charm. Inside, a seamless layout, hardwood floors, lofty ceilings, and mood-boosting natural light await. The kitchen's granite countertops, stainless steel appliances, gas stove, island with storage + seating, and large pantry will inspire every home chef. Open access to the dining area makes for easy chatting while cooking. Beautiful windows and a gas fireplace preside over the living room. A half bath with laundry rounds out the main floor. You'll love retreating to the primary suite upstairs, where peaceful nature views and a private bath create the perfect place to unwind. Two additional second-floor bedrooms and a full bath mean there's room for everyone. Opportunity abounds for entertainment, work, or play in the finished basement. Nature lovers & wildlife watchers will adore this tranquil, tree-lined spot, be it from the front porch, back deck, or around a campfire in the backyard. Evening strolls & bike rides are a breeze in the welcoming, walkable neighborhood. The attached 2-car garage adds everyday ease. North Windham's endless amenities mean you need not leave the bounds of town for a thing. Sebago Lake's public beach is a mere 5-minute drive away. This home will have you singing the praises of a life well-lived - a must-see! Showings begin Friday 7/31 OPEN HOUSE Sunday Aug 2nd 11-1

77 Harvest Hill Rd, Windham

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com

$1,179,900

4 Beds ⋅ 3 Baths

Luxury meets timeless craftsmanship in this exceptional new construction home, privately nestled on 1.84 wooded acres. Offering 4 bedrooms and 2.5 baths, every space has been thoughtfully designed with elevated finishes, abundant natural light, and a seamless blend of elegance and comfort. The heart of the home is a stunning gourmet kitchen featuring custom cabinetry, premium finishes, an expansive walk-in pantry, and an inviting layout perfect for everyday living or entertaining. The spacious living area is anchored by a beautiful gas fireplace, while oversized windows frame the natural surroundings and flood the home with light. Throughout the home, you'll find gorgeous white oak radiant-heated floors, custom tile, and meticulous craftsmanship at every turn. An extended garage provides generous room for vehicles, storage, or a workshop. Outside, the welcoming farmer's porch and stone walkway create timeless curb appeal, while the wooded setting offers exceptional privacy and a peaceful retreat. Combining sophisticated design, modern efficiency with heat pumps, and high-end custom finishes throughout, this is a rare opportunity to own a truly stunning home where quality is evident in every detail.

108 Highland Cliff Rd, Windham

Listing courtesy of Landmark Realty.

$474,000

3 Beds ⋅ 3 Baths

New model completed and available for sale! Come see why so may have chosen Dolley Farm Condominiums for their new home! Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With completed units available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from. Common area pavilion and playground, and a short distance to Shaw Park and the Sebago to Sea trail. Pet friendly!

2 Dolley Farm Rd Unit 1, Windham

Listing courtesy of The Flaherty Group.

$509,000

2 Beds ⋅ 1 Baths

Don't miss this opportunity to own a year-round, two-bedroom cottage on beautiful Sebago Lake! Located in a five-member association, this property includes its own deep-water boat slip, making it ideal for boating enthusiasts. The renovation has already begun, as shown in the photos, giving the next owner a head start on creating their perfect lakeside retreat. The seller has decided to move on before completing the project, creating an excellent opportunity to add your own style and finishing touches. Enjoy the level common waterfront area featuring picnic tables, a fire pit, and plenty of space to relax and gather with family and friends. With a reduced list price, this cottage offers outstanding value and endless potential. Bring your vision and make this Sebago Lake getaway your own!

14 Family Cir Unit 2, Windham

Listing courtesy of Real Estate 2000 ME/NH.

$299,000

2 Beds ⋅ 2 Baths

Welcome to this beautifully maintained and inviting two-bedroom condo, ideally located in the heart of Windham. Enjoy the convenience of being just minutes from shopping, restaurants, and everyday amenities while tucked away in a peaceful setting. The first floor features an open-concept layout with a spacious living room, kitchen, and dining area--perfect for both everyday living and entertaining. Just off the dining area, step onto the newer deck, an ideal spot to enjoy your morning coffee, dine outdoors, or unwind after a long day. Upstairs, you'll find two generously sized bedrooms with cathedral ceilings that create a bright and airy feel, along with a full bathroom. The finished walk-out basement offers valuable additional living space that can easily serve as a third bedroom, home office, fitness room, or family room, with direct access to the private backyard. Conveniently located near Sebago Lake and just a short drive to Portland, this move-in-ready condo offers the perfect blend of comfort, functionality, and location. Don't miss your opportunity to make this wonderful property your new home! Open house Saturday, August 8th 12-1:30!

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

$529,000

4 Beds ⋅ 2 Baths

Welcome to this beautifully updated home in one of Windham's most desirable neighborhoods, where timeless charm, quality craftsmanship, and an exceptional location come together. From the moment you arrive, you'll appreciate the meticulously maintained landscaping featuring mature trees and stunning perennial gardens that provide vibrant blooms throughout the growing season, creating incredible curb appeal and a picturesque setting you'll enjoy year after year. Inside, pride of ownership shines throughout. Refinished hardwood floors, new flooring in the upstairs bedrooms, and new basement flooring create a fresh, cohesive feel, while the bright kitchen features a new window and new appliances. New electrical outlets, fixtures, and recessed lighting installed by Simply Electric LLC add a stylish, modern touch. Additional improvements include a beautiful new front porch, board and batten detailing on the garage, select new cedar shakes, and a professionally cleaned and inspected chimney, reflecting the exceptional care this home has received. The private backyard is equally impressive, surrounded by mature landscaping and colorful flower gardens that bloom throughout the seasons, creating the perfect setting to relax, entertain, or simply enjoy Maine's natural beauty. Perfectly situated just minutes from downtown Windham, you'll enjoy convenient access to shopping, local restaurants, entertainment, and everyday amenities. Portland is only 15 minutes away, while Sebago Lake's public boat launch is approximately 10 minutes from your doorstep, making it easy to enjoy boating, fishing, swimming, and all that Southern Maine has to give. Thoughtfully updated and truly move-in ready, this exceptional property offers the perfect blend of elegance, comfort, and convenience in one of Windham's most sought-after communities.

12 Arcadia Dr, Windham

Listing courtesy of Real Broker.

$539,999

4 Beds ⋅ 2 Baths

SELLER CONCESSIONS ARE AVAILABLE WITH ACCEPTABLE TERMS, PRESENTING AN EXCELLENT OPPORTUNITY TO REDUCE UPFRONT EXPENSES AND ENHANCE THE OVERALL VALUE OF THIS EXCEPTIONAL HOME. REACH OUT FOR ADDITIONAL DETAILS. Welcome to this beautifully maintained, move-in ready home in a highly desirable Windham location. Set back from the road with a spacious driveway, oversized two-car garage, and private backyard, this property combines comfort, privacy, and convenience. The recently renovated kitchen flows seamlessly into the updated living room, creating a bright and inviting space for everyday living and entertaining. Fresh paint throughout enhances the clean, modern feel, while the brand-new laundry room adds both style and functionality. With 3-4 bedrooms and two full bathrooms, the flexible floor plan provides a variety of possibilities, including guest accommodations, a home office, hobby space, or additional living areas. Natural gas and public water add to the convenience of ownership. Outside, enjoy the privacy of the backyard along with a generous driveway providing ample parking for multiple vehicles or recreational equipment. Located just minutes from Sebago Lake, local beaches, boating, hiking trails, shopping, dining, and everything the Windham area and the Lakes Region have to enjoy, this home features thoughtful updates, a functional layout, and an exceptional location. Don't miss the opportunity to make this beautifully updated property your next home.

214 Tandberg Trl, Windham

Listing courtesy of Maine Real Estate Co.

$649,000

3 Beds ⋅ 3 Baths

Built in 2019 and thoughtfully designed for today's lifestyle, this move-in ready Colonial offers the perfect balance of modern comfort, privacy, and convenience. Situated on a private 1.17-acre lot in the desirable Riverside Ridge neighborhood, this home provides a peaceful setting while remaining just minutes from shopping, restaurants, schools, the Maine Turnpike, and a short drive to the recreational opportunities of Sebago Lake. Designed with both everyday living and entertaining in mind, the open-concept main level features an eat-in kitchen with granite countertops, a center island, pantry, and seamless flow into the dining and living areas. In addition to the reported living area, the home features a fully finished and heated bonus room above the attached two-car garage, offering exceptional flexibility as a home office, media room, game room, fitness area, playroom, or guest retreat. Upstairs, the spacious primary suite offers a private bath and walk-in closet, while two additional bedrooms and second-floor laundry add comfort and convenience. Enjoy your morning coffee on the inviting front porch or unwind on the private rear deck overlooking the spacious backyard. Additional highlights include an attached two-car garage with direct entry, generator hookup, on-demand hot water, and an unfinished walk-out basement offering abundant storage or outstanding potential for future finished living space. Whether you're looking for newer construction, modern finishes, flexible living space, low-maintenance ownership, or a convenient location close to both everyday amenities and Maine's lakes region, 3 Lieutenants Drive offers an exceptional opportunity to enjoy the very best of Windham living.

3 Lieutenants Dr, Windham

Listing courtesy of Meservier & Associates.

$475,000

3 Beds ⋅ 1 Baths

Enjoy the best of both worlds with this charming 3-bedroom ranch featuring a 1-car garage, nestled in a peaceful rural setting in Windham while remaining just minutes from shopping, restaurants, and local businesses. The open-concept layout offers a spacious feel, highlighted by hardwood floors and a large front-to-back living room that's perfect for relaxing or entertaining. The primary bedroom provides a comfortable retreat, while city water and a spacious deck add to the home's convenience and appeal. Outside, you'll find two driveways, offering plenty of parking and flexibility. The property also presents future potential, with the town indicating it may be eligible for conversion to a duplex. Buyers are encouraged to perform their own due diligence to verify all zoning and conversion possibilities. Whether you're looking for a comfortable single-family home or an investment opportunity with expansion potential, this property is worth a look!

439 Falmouth Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$499,900

4 Beds ⋅ 2 Baths

Your Maine waterfront opportunity is knocking. This 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage was just pulled from Auction and has been reduced. Boasting a Single Family home with attached apartment and over 3,000 square feet of previous finished space the possibilities are endless. Images in this listing have been virtually staged.

14 Emerson Dr, Windham

Listing courtesy of Excellence Realty.

$599,000

3 Beds ⋅ 2 Baths

Welcome to this beautifully private and tucked-away retreat, gracefully situated on 1.29 acres of peaceful countryside. Offering 3 spacious bedrooms, 1.5 bathrooms, and a 1-car garage, this charming home provides the perfect blend of comfort, privacy, and convenience. Surrounded by the beauty of a serene rural setting, you can enjoy the tranquility of nature while remaining just moments from public beaches, boat launches, shopping centers, and local restaurants, all while being only 25 minutes from Portland. Outside, you'll find a lovely area ready for your dream garden, along with an existing chicken coop awaiting its next flock, creating the perfect opportunity to embrace a simple and rewarding homestead lifestyle. Whether you're spending a day on the water, enjoying nearby amenities, gathering fresh eggs in the morning, or simply relaxing in your own private oasis, this exceptional property offers the lifestyle you've been searching for.

7 Hall Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$2,100,000

2 Beds ⋅ 6 Baths

Set on a beautifully maintained peninsula in Outlet Cove, 68 Outlet Cove Road presents an exceptional Little Sebago Lake setting with expansive waterfront, a private sandy beach, dock, and sweeping sunset views. The level lawn extends naturally to the shoreline, creating an inviting setting for swimming, boating, entertaining, or quiet mornings by the water. Every element reflects years of thoughtful care. Mature plantings, manicured gardens, stone retaining walls, and extensive hardscaping frame the home and lake views. A spacious paver patio and screened porch provide comfortable outdoor gathering spaces, while the sandy beach and dock make it easy to enjoy the lake throughout the day. Multiple outbuildings and garage spaces provide exceptional storage for boats, recreational equipment, tools, and seasonal belongings, while creating an ideal setting for entertaining. Inside, a sun-filled living room with a fireplace and wall of glass captures dramatic water views and flows into the dining area, kitchen, and lakeside deck. The primary suite includes a generous bath, laundry, and beautiful lake views. The walkout lower level features a second living room with a fireplace, an office, and a full bath, providing flexibility for guests or extended stays. Above the attached garage is an additional bedroom and loft area. A separate detached garage includes a heated room above, ideal for a studio, workshop, gym, home office, or additional storage. Recent improvements include a newer high-efficiency oil boiler, whole-home standby generator, drilled well, buried propane, and a septic system designed for four bedrooms. A pre-listing inspection and professionally measured floor plan are available for review. From the manicured grounds and carefully maintained outbuildings to the sandy shoreline and beautifully cared-for interior, this is a rare opportunity to enjoy Little Sebago Lake at its finest.

68 Outlet Cove Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$699,000

3 Beds ⋅ 3 Baths

NEWLY PRICED!! Nature beckons you in the popular Lakes Region! Nestled on 2 acres, this meticulously maintained home offers approximately 2,875 square feet of light-filled living space. A beautiful stone fireplace with woodstove insert takes center stage on the main level featuring hardwood floors, a den/home office and eat-in kitchen area with granite peninsula, stainless steel appliances and maple cabinets! There's easy access to the well built, heavy duty deck overlooking a wooded, private fenced-in yard. Down the hall is a cozy laundry room, full bath and 2 spacious bedrooms. The primary suite tucked in the rear corner, features a tile shower and walk-in closet providing a comfortable and serene environment. The possibilities are endless in the lower-level family room with storage closet, full bath and mudroom. Walk-out access to the custom cedar hot tub provides a luxurious and relaxing experience! The whole-house generator ensures uninterrupted power, and heat pumps on each level provide added comfort throughout each season. A magnificent wildflower garden adds natural beauty and charm to the surroundings of this move-in ready home, minutes from area amenities and bustling North Windham! A home warranty provides peace of mind for this special oasis, just 35 minutes to the Portland Jetport. What are you waiting for?

20 Cross Ridge Dr, Windham

Listing courtesy of Coldwell Banker Realty. 207-773-1990

$499,900

3 Beds ⋅ 2 Baths

Do NOT miss this well maintained colonial style home in Windham on nearly 2-acres! From your recently paved driveway, step inside and find a kitchen that's open to the dining area, and living room around the corner. Kitchen features newer flooring, counters, sink, and stainless steel appliances! Dining area has a sliding door that leads to a rear deck (freshly painted) that over looks your private back yard. First floor also offers wood flooring in the living room, bonus room that could be used as an office, and first floor laundry. Upstairs find another full bathroom and 3-large bedrooms, including a primary with a massive walk-in closet. Basement has great storage and if you need more, there's a shed! Property abuts East Windham Conservation Area land that secures your privacy. Enjoy exploring trails right from your back yard! Only 25-minutes to Portland and minutes to lakes

11 Bruschi Rd, Windham

Listing courtesy of Coldwell Banker Realty. 207-282-5988

$625,000

4 Beds ⋅ 3 Baths

Charming, antique 3 bedroom 1.5 bath New England Farmhouse with an additional 1 level, 1 bedroom, 1 bath In-Law apartment attached. Huge barn, pottery/artist studio, beautifully landscaped, pastoral 3.3 acre lot with gardens, flowers, blueberries, veggies and mature trees offered for the first time in 31 years. This classic home with modern accommodations has integrity and flexibility, it's just waiting for your design. Thoughtful and practical updates and upgrades made throughout the ownership. Lovingly maintained and enjoyed. Enchanting spaces inside and out. The farmhouse boasts a large, eat-in kitchen with a pantry and laundry room adjacent. Beautiful antique cast iron stove. Formal dining room and a 1st floor bedroom with a sizable dressing room/closet. Large, newer French doors lead to a sweet side deck overlooking green trees and fields. New roof on the main home 2024 as well as a heat pump for heating and cooling in 2023. The expansive mudroom separates the In-Law apartment from the farmhouse. In-Law apartment with its own deck was added in 1995. Perfect for personal, family use or for additional income. New roof on the apartment 2023, heat pump in apartment installed 2025. The barn and the back woodstock was used as the owner's pottery studio and wood fired kiln. A stunning piece of structural history, with tons of storage and space for your passions or practical uses. This truly special property offers a solid, warm and practical home on positively cinematic farm land. Tucked away from the hustle and bustle but only minutes away from walking trails and Windham Center for shopping, services, entertainment and dining. Less than 15 minutes to the Maine Turnpike, less than 30 minutes to Portland. Make this historic gem your own bucolic, rural paradise.

305 Windham Center Rd, Windham

Listing courtesy of Portside Real Estate Group.

$419,900

3 Beds ⋅ 2 Baths

Move right into this well-maintained home, perfectly situated on a semi-private lot surrounded by mature greenery. Enjoy deeded right-of-way access to Pettingill Pond for swimming, kayaking, or simply relaxing by the water, all while being just one mile from Windham's shopping, dining, and everyday conveniences. Inside, the daylight basement with a cozy pellet stove offers flexible living space, while the deck just off the kitchen is perfect for grilling, entertaining, or enjoying your morning coffee. A second full bathroom adds extra convenience, making this move-in-ready home an ideal blend of comfort, privacy, and location.

33 Spear Ave, Windham

Listing courtesy of Coastal Pine Real Estate, LLC.

$435,000

3 Beds ⋅ 2 Baths

Welcome to 14 Pope Road in Windham--a place that just feels like home the moment you pull in. Set on 1.7 acres, there's plenty of room to spread out, with a bright, sunny backyard that's perfect for summer nights, backyard games, or letting pets roam free in the fully fenced yard. The barn and shed give you all the extra space you need for storage, hobbies, or projects you've been meaning to start. Farm land zoning allows you to have a horse or goats. Bring your ideas to make it yours! Upstairs, you'll find 3 bedrooms and 1 bathroom with a layout that's easy to live in and make your own. Downstairs is an half bath with laundry and an open kitchen and living room with a door directly to the backyard. A charming covered porch off two of the bedrooms is the perfect spot to curl up with a book. A two car attached garage opens directly into a hallway to stow away shoes and coats. Sellers installed a new well and a new furnace in 2025. You'll love the location--close to Portland for an easy commute, but tucked into a great area of Windham. Property is being sold AS IS. Sellers are motivated to move on to their next chapter!

14 Pope Rd, Windham

Listing courtesy of Maine Real Estate Experts.

$649,000

2 Beds ⋅ 3 Baths

Timeless charm meets lakeside living at this beautifully restored 1920 bungalow just steps from Big Sebago Lake. Rich in character and thoughtfully updated, this 2-bedroom, 2.5-bath home offers nearly 2,000 square feet of inviting living space with original details blended seamlessly with modern comfort. The warm and welcoming interior features a classic wood-burning fireplace, two comfortable living areas, a charming period-style kitchen, and two bedrooms with additional living space that's perfect for family and guests. Step outside to the spacious, west-facing deck where you'll enjoy breathtaking sunsets over Big Sebago Lake. Spend your days taking advantage of deeded access to the lake through the shared right of way directly across the road, offering an ideal setting for swimming, boating, and making lasting summer memories. Tucked away on a quiet dead-end private road, this well-landscaped property also features a new roof installed in 2025, adding peace of mind for years to come. Conveniently located near shopping, golf, and all the amenities of the Lakes Region, this exceptional home is equally suited as a year-round residence or a quintessential Maine getaway.

25 Lake Ave, Windham

Listing courtesy of Keller Williams Realty.

$399,000

2 Beds ⋅ 2 Baths

Just in time to still soak up the most beautiful time here in Maine! Welcome to 47 Anglers, located on peaceful Pettingill pond. Water views, recent renovations, fresh paint throughout, original charm and outdoor recreation, all without the waterfront price tag! This 2 bedroom, 1.5 bath home is located on a private half-acre lot overlooking the pond. Just steps from your front door is your shared water access to put in your kayak, canoe or paddle board. When you aren't on the water you can still savor those views from your three season sun porch. Inside you'll enjoy your renovated kitchen, with stainless steel appliances, large living area, hardwood floors throughout creating warmth along with a cozy fireplace. First floor laundry is located in your half bath, and a full bath and two bedrooms are upstairs. A coveted mudroom, needed for every season here in Maine, whether you are kicking off your flip flops or winter boots. Outside, a one car garage and a large backyard perfect for games and entertaining. Conveniently located just minutes from North Windham shopping, dining and amenities, and centrally located just 30 minutes to Portland or Pleasant Mountain. Whether you are looking for yourself or for an investment property, this home, this location and this price point cannot be beat!

47 Anglers Rd, Windham

Listing courtesy of Portside Real Estate Group.

$599,000

3 Beds ⋅ 2 Baths

Beautiful lot at end of private road. Big back and front yards. Open concept ranch with wooden accent walls, beautiful hardwood floors throughout. Granite countertops.

14 Scout Ln, Windham

Listing courtesy of OwnerEntry.com.

$579,000

3 Beds ⋅ 2 Baths

New Price on this Beautiful Farm Zoned 2.4-acre lot in Windham, Maine, this charming Cape-style home, built in 2006, features 1,547 square feet of comfortable living space with 3 bedrooms and 2 full bathrooms. The property combines country charm with modern conveniences in a peaceful setting surrounded by nature. Enter through the attached garage into a welcoming mudroom finished with warm knotty pine, creating a functional and inviting transition into the home. An oil-fired forced hot water boiler provides efficient, dependable heat throughout the seasons. The outdoor space is thoughtfully designed for gardening, recreation, and relaxation. Beautiful landscaping includes established blueberry, raspberry, and blackberry bushes, a large vegetable garden, and colorful sunflower plantings. A private nature trail leads to Baker Brook, creating a serene backdrop for enjoying the outdoors. Spend summer days by the above-ground swimming pool, unwind in the hot tub, or gather around the fire pit on cool Maine evenings. A chicken coop and an additional outbuilding provide excellent space for hobby farming, storage, or workshop use. Conveniently located near Windham's shopping, dining, schools, lakes, and recreational amenities, this well-maintained property combines the privacy of country living with easy access to everyday conveniences. Sellers are Motivated

7 Mancini Rd, Windham

Listing courtesy of Landing Real Estate.

$719,000

3 Beds ⋅ 3 Baths

Welcome to ''The Tree House'', where every window frames a view of nature. Set on nearly 10 private acres, this beautifully renovated oversized ranch has been thoughtfully updated throughout with exceptional attention to detail. Designed for easy single-level living, the home features hardwood floors, solid wood doors, high-end glass door knobs, 35-inch hallways and doorways, a spacious primary suite with a private bath, first floor laundry, and a beautifully appointed kitchen with a gas range. The finished lower level includes a bonus room with a kitchenette, offering excellent flexibility for guests, extended family, or additional living space. The heated barn features its own oil tank, a professional-grade Kellogg air compressor, loft storage with a pull-down ladder, and ample workspace. Additional highlights include abundant electrical outlets, an exterior hot and cold water spigot, and the pride of ownership that comes with only one previous owner. Located just minutes from Windham Center, lakes, and an easy commute to Portland, this property offers the perfect blend of privacy and convenience. The nearly 10-acre parcel also offers potential for two buildable lots behind the existing home (subject to municipal approvals), with access possible via a new road or an extension of the existing driveway. A remarkable transformation inside and out, this is a place you will not want to miss.

21 Land Of Nod Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$554,900

4 Beds ⋅ 2 Baths

Beautifully maintained split foyer, just 10 years old, featuring open concept living, dining, kitchen space. Kitchen offers stainless appliances, gas range, and opens to large private elevated rear deck. Three bedrooms and a full bath are also on the upper level. Lower level has primary suite with private bath and two large closets. Direct-entry two-car garage is off mudroom. Excellent neighborhood of similar aged homes.

2 Twoey Dr, Windham

Listing courtesy of Town & Shore Real Estate.

$4,450,000

7 Beds ⋅ 5 Baths

This is a rare opportunity to experience luxury lakefront living in this extraordinary, furnished waterfront residence on pristine Sebago Lake. Take in spectacular Mt. Washington views, breathtaking sunsets, abundant natural light and 113 feet of private shoreline.This area of Sebago's Jordan Bay is closest to the airport, the arts, world class restaurants and the ocean. Also just five minutes from local coffee shops, supermarkets, shopping and local restaurants. Multiple premier ski destinations are within an easy drive making this a true four season gem. Share what you will come to love about the Lakes Region with friends and family. Two attached guest suites/apartments seamlessly expand the home's living space for larger gatherings. Each has its own entrance and parking.The main level features a great room, an expansive kitchen, large island with seating for 6, a private office or formal dining room, and a luxurious primary suite complete with a walk-in closet and laundry. The spa-inspired ensuite bath includes a spacious steam shower with dual shower heads and jetted soaking tub. The fully finished walk-out lower level expands the home's possibilities with a dedicated media/theater room, an additional family room with kitchenette, bedroom and full bath--ideal for guests or extended family. Upstairs, you'll find another comfortable living area, two large bedrooms, a full bath, and an expansive deck where you can relax while enjoying panoramic views.Situated on 2.1 acres, the property features mature landscaping with fruit trees, an expansive lawn, playground, outdoor speakers, and a spacious patio with a fire pit--perfect for entertaining family and friends. Exceptional waterfront amenities include a permanent lakeside deck with seating, storage, and direct swimming access. The deep-water dock features a generous 12 x 20 ft seating area, Jet Ski lift, storage for lake toys, and a boat mooring with room for additional moorings.

15 Sleepy Hollow Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$724,900

3 Beds ⋅ 3 Baths

A striking expression of contemporary design, this exceptional residence commands attention with its bold architectural presence and unmistakable curb appeal. Designed for effortless entertaining and everyday luxury, the expansive open-concept interior seamlessly unites the kitchen, dining area, and living room into one breathtaking gathering space. Whether hosting an intimate dinner party or a lively celebration, the home's thoughtful flow invites connection at every turn. A spacious walk-in pantry adds both elegance and practicality. Three generously sized bedrooms provide comfort, privacy, and versatility, creating space for family, guests, or a dedicated home office. Extending the living experience outdoors, the sleek contemporary deck provides the perfect setting for quiet mornings, sunset cocktails, or dining under the open sky. Beyond its striking design, this home is crafted with modern efficiency in mind. High-performance heat pumps paired with an on-demand wall-mounted boiler provide exceptional year-round comfort while enhancing energy efficiency. A spacious two-car garage offers abundant room for vehicles, recreational equipment, and storage. What truly sets this property apart is its extraordinary connection to the outdoors. With direct access to the Mountain Division Trail System, adventure begins at your doorstep. Explore miles of scenic multi-use trails ideal for hiking, cycling, trail running, snowmobiling, cross-country skiing, and year-round recreation, all while returning home to the comfort of refined modern living. This is more than a home--it is a destination. A place where bold architecture meets effortless elegance, where contemporary comfort embraces the natural landscape, and where every day offers the opportunity to live beautifully, entertain graciously, and explore endlessly.

9 Gunpowder Mill Rd, Windham

Listing courtesy of Maine Real Estate Experts. 207-632-6025

$520,000

3 Beds ⋅ 2 Baths

Welcome to this adorable Colonial offering 3 bedrooms, 1.5 baths and a bright, open concept with 9' high ceilings. Recent updates include all new windows and doors, flooring on 1st level and 2nd floor hallway and a Vermont Casting woodstove for an additional source of heat. Enjoy the seasonal views of the Western Mountains and amazing sunsets from your front windows or sitting outside in your Adirondack chairs sipping your morning coffee. You will understand why its named, ''Harvest'' Hill Rd on this natural piece of property with the likes of strawberries, blackberries, blueberries, witch hazel and mint! Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is 5 minutes to both Little Sebago Lake and Big Sebago Lake boat launches and a quick walk or bike ride to the private beachfront of Tassel Top on Sebago Lake. The shops and grocery stores are 7 minutes away as well as minutes from Chipman's Farm Stand and Good Life Market! You are nestled away, yet 20 minutes from the Maine Turnpike, 30 minutes to downtown Portland (South) and 45 min - 1 hr (North) from Pleasant Mountain and Sunday River Ski Resort. Don't miss out on this little piece of heaven and check it out with a private tour today! Seller is willing to give concessions to Buyer at closing.

104 Harvest Hill Rd, Windham

Listing courtesy of www.HomeZu.com. 877-249-5478

$314,900

1 Beds ⋅ 1 Baths

**Builder Incentives Available**.Stop paying rent! Own for $2200 per month*! The Highland offers a peaceful retreat designed for simple, modern living. With 766 square feet of thoughtfully designed space, this one-bedroom, one-bathroom residence blends comfort, style, and convenience in a layout that feels both open and inviting. Inside, contemporary finishes meet everyday functionality with granite countertops, stainless steel appliances, and an in-unit washer and dryer. Large windows allow natural light to pour throughout the home, creating a bright and welcoming atmosphere perfect for relaxing or entertaining. Shared amenities include, a gym, co-working space, community room, dog wash, storage lockers and more! Builder incentives available! *Estimated Principal, Interest, Est taxes & PMI; 5 year fixed, 30 year term, 3% down, 6.830% APR, subject to approval.

10 Stillwater Dr Unit 1128, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

$349,900

2 Beds ⋅ 2 Baths

*BUILDER INCENTIVES AVAILABLE* Own for $2400 per month*! This third floor unit features 9' ceilings and offers 991 square feet of bright, open-concept living. This thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private en-suite bath, creating a peaceful retreat to unwind and recharge. Inside, you'll find timeless shaker-style cabinetry, granite countertops, stainless steel appliances, and an in-unit washer and dryer -- all curated to make daily living feel seamless. Large windows fill the home with natural light, creating an airy atmosphere that feels both welcoming and refined. Inspired by the expansive beauty of Sebago Lake -- Windham's most iconic natural landmark -- The Sebago unit is the largest home available at Windham Village, designed for those who appreciate space, comfort, and effortless living. Shared amenities include, a gym, co-working space, community room, dog wash, storage lockers and more! *Estimated Principal, Interest, Est taxes & PMI; 5 year fixed, 30 year term, 3% down, 6.827% APR, subject to approval.

10 Stillwater Dr Unit 3133, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

$349,900

2 Beds ⋅ 2 Baths

**Builder Incentives Available**.Stop paying rent! Own for $2400 per month*! Offering 991 square feet of bright, open-concept living, this thoughtfully designed two-bedroom, two-bathroom residence blends modern style with everyday functionality. The spacious primary suite features a private en-suite bath, creating a peaceful retreat to unwind and recharge. Inside, you'll find timeless shaker-style cabinetry, granite countertops, stainless steel appliances, and an in-unit washer and dryer -- all curated to make daily living feel seamless. Large windows fill the home with natural light, creating an airy atmosphere that feels both welcoming and refined. Inspired by the expansive beauty of Sebago Lake -- Windham's most iconic natural landmark -- The Sebago style unit is the largest unit available at Windham Village, designed for those who appreciate space, comfort, and effortless living. Shared amenities include, a gym, co-working space, community room, dog wash, storage lockers and more! *Estimated Principal, Interest, Est taxes & PMI; 5 year fixed, 30 year term, 3% down, 6.827% APR, subject to approval.

10 Stillwater Dr Unit 1126, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

$629,000

3 Beds ⋅ 3 Baths

'AMAZING HOUSE, LOT, LOCATION & VALUE' This is the property you've been searching for with the perfect combination of everything you are looking for!! This beautifully cared for newer home has bright spacious rooms with an awesome plan that is both comfortable and versatile. Nestled on one of the prettiest lots in a very desirable small neighborhood with a dead end and gorgeous sun-drenched setting, this home features a 3 bedroom, 2.5 bath open concept design, nice bright kitchen with island and stainless steel appliances, very large pantry, maple floors, slider to deck and great yard areas, front to back living room with gas fireplace, master bedroom with double sinks & tiled shower, huge finished room over the garage adding tremendous versatility to adapt to your specific needs, efficient gas heat, 3 heat pumps for heat & cooling, full farmers porch, and a superior lot & location that is most convenient to everything!!! DON'T DELAY & SEE IT AS SOON AS POSSIBLE!!

13 Maysens Way, Windham

Listing courtesy of Maine Realty 2000.

$575,000

2 Baths

Welcome to this beautifully renovated, turn-key duplex, perfectly situated in one of Windham's most desirable locations. Completely transformed from top to bottom, this exceptional property offers the rare opportunity to own what feels like a brand-new building, while enjoying the flexibility and income potential of a duplex. Each thoughtfully designed unit features 2 spacious bedrooms and 1 full bathroom, with bright, inviting living spaces that are truly move-in ready. Every detail has been carefully updated, including new finishes throughout, fresh interior paint, newer siding, a newer roof, and countless additional improvements that provide lasting quality and peace of mind. To further enhance the property's value, the seller is installing a brand-new septic system prior to closing, allowing the next owner to enjoy years of worry-free ownership. Ideally located just minutes from local schools, shopping, restaurants, and everyday conveniences, with an easy commute to Portland, this property perfectly balances comfort, convenience, and accessibility. Whether you're looking to owner-occupy one unit while generating rental income from the other, or maximize your investment by leasing both units, this versatile property offers endless possibilities. With both units currently vacant, you have the unique advantage of moving in immediately or selecting your own tenants from day one. Properties offering this level of renovation and care are exceptionally rare. Simply unpack, settle in, and enjoy knowing that virtually everything has already been done for you. This is a truly turnkey investment and an outstanding opportunity for both homeowners and investors alike.

243 Windham Center Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$839,000

4 Baths

4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built in 2003, the main house offers nearly 2800sqft, 4+ bedrooms, 2.5 baths, a spacious loft with pool table, and a fully finished basement. High-quality Andersen windows fill the home with natural light, while warm wood finishes and generous living spaces create an inviting, comfortable atmosphere. Savor the heart of the home with custom birch cabinetry, Corian counters, a roomy island, and ample storage for all of your culinary needs. Keep your toes warm all winter long with the luxury of radiant heat floors beneath every step. Enjoy peaceful surroundings, abundant wildlife, and endless opportunities to relax. Nestled on 4.26 acres of impeccably maintained and manicured, park-like grounds, this property invites you to enjoy the serene beauty and a picturesque setting right at your doorstep. A preliminary inspection indicates that the lot may possibly be subdivided, allowing the potential of building an additional rental property or a guest house for family and friends. Unwind on the 8'x24' farmer's porch or entertain guests on the 10'x20' rear deck. The oversized 24'x32' heated two car garage provides ample storage for vehicles, tools, and recreational equipment. Above the garage is a legal efficiency apartment with 1 bedroom, 1 bath, offers excellent rental income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. Additional property updates include a 26KW whole house automatic generator installed in 2022 powering the home, garage, and apartment; heat pumps installed in 2020: a full exterior re-stain completed in 2022; a new house roof installed in 2023: and the driveway resealed in 2026. Most furnishings are negotiable, and most appliances are less than 10 years old. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$839,000

4 Beds ⋅ 3 Baths

4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built in 2003, the main house offers nearly 2800sqft, 4+ bedrooms, 2.5 baths, a spacious loft with pool table, and a fully finished basement. High-quality Andersen windows fill the home with natural light, while warm wood finishes and generous living spaces create an inviting, comfortable atmosphere. Savor the heart of the home with custom birch cabinetry, Corian counters, a roomy island, and ample storage for all of your culinary needs. Keep your toes warm all winter long with the luxury of radiant heat floors beneath every step. Enjoy peaceful surroundings, abundant wildlife, and endless opportunities to relax. Nestled on 4.26 acres of impeccably maintained and manicured, park-like grounds, this property invites you to enjoy the serene beauty and a picturesque setting right at your doorstep. A preliminary inspection indicates that the lot may possibly be subdivided, allowing the potential of building an additional rental property or a guest house for family and friends. Unwind on the 8'x24' farmer's porch or entertain guests on the 10'x20' rear deck. The oversized 24'x32' heated two car garage provides ample storage for vehicles, tools, and recreational equipment. Above the garage is a legal efficiency apartment with 1 bedroom, 1 bath, offers excellent rental income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. Additional property updates include a 26KW whole house automatic generator installed in 2022 powering the home, garage, and apartment; heat pumps installed in 2020: a full exterior re-stain completed in 2022; a new house roof installed in 2023: and the driveway resealed in 2026. Most furnishings are negotiable, and most appliances are less than 10 years old. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$549,000

3 Beds ⋅ 3 Baths

Well maintained and thoughtfully designed, this Colonial offers a functional layout, quality finishes, and room to grow. The main floor features an open living area with a spacious kitchen offering a large island, granite countertops, and stainless steel appliances. The living room is anchored by a gas fireplace and the adjacent dining room opens directly to the elevated back deck, making it easy to enjoy the backyard or entertain guests. Upstairs are three comfortable bedrooms, including a primary suite with a tiled shower and generous closet space, along with the convenience of second-floor laundry. The walkout basement has impressive 10-foot ceilings and offers excellent potential for additional living space, a home gym, or even a golf simulator. Outside, you'll find a sunny lot, a fenced backyard, and a covered front porch that adds to the home's everyday appeal.

11 Belvedere Dr, Windham

Listing courtesy of Keller Williams Realty.

$775,000

4 Beds ⋅ 3 Baths

Stunning Colonial set at the end of a quiet cul-de-sac, nestled along a tranquil pond and perfectly positioned for privacy. Situated on a lot larger than most in the neighborhood, this property offers exceptional outdoor space. Inside, the home features an open layout with beautiful hardwood flooring. The kitchen with center island flows into the dining area and family room with fireplace, creating an ideal space for living and entertaining. A separate living room and entry/mudroom add to the thoughtful design. The attached garage, with direct entry to the home, features pine walls and offers flexible use as either a traditional garage or an entertainment space. Upstairs, you'll find four bedrooms, including an impressive primary suite with a sitting area, generous closet space, and a primary bath, along with the convenience of a second-floor laundry room. The outdoor space truly sets this home apart. The beautifully landscaped yard is private and well maintained, featuring a large outdoor fireplace, a hot tub, and tree lighting that creates a warm, relaxing atmosphere. The rear deck is the perfect spot to unwind or host, while the front awning with built-in speakers adds a unique touch. Additional highlights include a Nest security system, a wireless fence system, a 30x30 detached garage with heat and attic storage, a whole-house generator, and numerous updates throughout. Meticulously cared for, this home offers exceptional indoor and outdoor living--just minutes from town, sandy beaches, marinas, and all that Sebago Lake has to offer.

58 Thrush Ter, Windham

Listing courtesy of A Team Realty.

$549,900

3 Beds ⋅ 2 Baths

Welcome to this charming 3-bedroom, 2-bath Cape offering a bright, open-concept layout designed for comfortable living and effortless entertaining. Features include a convenient first-floor bedroom, hardwood floors, a daylight basement with expansion potential, an office/bonus/bedroom and a stunning oversized new deck--perfect for hosting family and friends or simply relaxing outdoors. Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is just minutes from Tassel Top Park and its private beach access on beautiful Sebago Lake and a short drive to the shops of North Windham. Enjoy the perfect balance of neighborhood living and convenience, with the city of Portland, the Maine Turnpike, and the beauty of the lakes region all within a 20-minute drive. Don't miss this exceptional opportunity to own a home in one of Windham's most sought-after locations. Schedule your private showing today before it's gone!

115 Harvest Hill Rd, Windham

Listing courtesy of Landmark Realty.

$442,000

3 Beds ⋅ 1 Baths

Tucked on a quiet 1.9-acre lot, this 3-bedroom, 1-bath split-entry home has room to spread out. The main level features an open kitchen that flows into the living room, with hardwood flooring, along with two bedrooms and a full bath. Downstairs, you'll find a third bedroom and a finished bonus room that can easily serve as a home office, gym, playroom, or guest space. A partial wrap-around deck provides a private spot to relax and take in the surroundings, while the lot offers plenty of room to enjoy the outdoors. Despite its peaceful setting, the home is just a short drive to North Windham for shopping and everyday errands, with Portland also within easy reach.

106 Highland Cliff Rd, Windham

Listing courtesy of A Team Realty.

$649,900

2 Beds ⋅ 3 Baths

This is the largest single Townhouse unit in the complex and features lake views from every room, 33' width facing the lake and the full-length deck comes with an awning. Property comes with an existing mooring.

1112 Roosevelt Trl Unit 15, Windham

Listing courtesy of Allied Real Estate.

$875,000

4 Beds ⋅ 3 Baths

Enjoy the perfect balance of a quiet lifestyle near the water and local grocery stores, with an effortless commute. Located on a peaceful street just 15 mins to downtown Portland and minutes to Westbrook, this custom home is just 5 mins to Gambo trails & kayak launch. The open main level features a propane fireplace, chef's kitchen with quartz counters and gas range, and a dining area opening to a grilling deck. A custom brick-floored drop station adds high-end utility. A flexible 1st-floor room is perfect for a home office, while the massive finished bonus room above the garage features a sleek wet bar built for entertaining. Retreat to the luxury primary suite featuring a walk-in closet & spa bath with dual separate vanities. Complete with premium finishes, a full-house automatic generator, and a low-maintenance yard, this turn-key home is ideal for professionals. Stunning custom-built 4BR layout with a 3BR septic design.

24 Leonards Way, Windham

Listing courtesy of Portside Real Estate Group.

$459,900

3 Beds ⋅ 3 Baths

Move in ready, three years young, 3 bed 2.5 bath home with beautiful kitchen, large deck with nice yard in an incredible convenient location. This home is spotless and freshly painted. Just six units total in the entire association so you get all the upside of condo living without that big association feel.

14 Voyager Ln Unit 14, Windham

Listing courtesy of Maine Values Real Estate.

$790,000

4 Beds ⋅ 3 Baths

Welcome to 25 Leonards Way! Set on a beautifully maintained 0.84-acre lot in one of Windham's sought-after established neighborhoods, this exceptional property offers the perfect blend of elevated finishes, everyday comfort, & an unbeatable location. Built in 2021, this beautifully kept 4-bedroom, 2.5-bath home offers nearly 2,400 square feet of thoughtfully designed living space with high-end finishes & quality craftsmanship throughout. Step inside to discover hardwood flooring, abundant storage, and inviting spaces designed for both entertaining and everyday living. At the heart of the home is an entertainer's dream kitchen featuring beautiful stone countertops, a stylish tile backsplash, ample prep space, & seamless flow into a generously sized dining area perfect for hosting dinner parties or casual evenings with family and friends. The warm & inviting living room is anchored by a gas fireplace, creating the perfect atmosphere year-round. Upstairs, the home continues to impress with a convenient second-floor laundry room and a beautifully updated primary suite featuring a brand-new custom glass & tile shower designed to create a spa-like retreat & walk-in closet. Recent updates include a brand-new heat pump system providing efficient comfort and air conditioning for summer months. Outside, enjoy a spacious back deck, a brand-new patio, & refreshed landscaping with garden beds, fresh mulch, mature trees, & a beautifully maintained yard creating a private outdoor retreat. The oversized finished two-car garage features a custom wood interior finish and exceptional storage capacity. A full daylight walkout basement is already framed, offering easy potential for future finished living space. Greatest luxury of all is the location, 15 min to Portland 7perfectly positioned between Maine's coastline, ski mountains, & Lakes Region. New school being built in Windham as well. Sophisticated & perfectly located this is truly a must see! 3 bed septic design in disclosure.

25 Leonards Way, Windham

Listing courtesy of Portside Real Estate Group.

$339,900

1 Beds ⋅ 1 Baths

New Price! Investor, builder, developers, home buyers! Exceptional opportunity on highly popular Roosevelt Trail with flexible Residential (RM) zoning, offering potential for limited business use, a home occupation, or multi-unit development. This neat, clean, and sun-drenched property sits on a spacious 0.56-acre lot with 137 feet of prime road frontage. An asset for immediate expansion or development is the existing two-bedroom septic system already on site. The property features a turnkey, updated 1-bedroom home with a modernized heating system and convenient downstairs laundry--perfect for immediate rental income while you plan your build. Capitalize on the large open backyard, a 1+ car garage, and two powered storage sheds. Explore the possibilities under the town's RM land use ordinance. Owner-occupants looking for a business-ready property, savvy investors, and builders--take notice!

549 Roosevelt Trl, Windham

Listing courtesy of Pine Tree Realty of Maine.

$1,199,000

6 Beds ⋅ 5 Baths

Luxury, Serenity, and Versatility Near Highland Lake Immerse yourself in a masterfully executed, 'down-to-the-studs' remodel (completed 2023) marrying organic warmth with modern sophistication. Infused with rich wood tones, textured accent walls, and a curated, boho-chic palette, this striking 6BR/5BA estate feels less like a house and more like a private sanctuary. Designed for seamless entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites--one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations offer ultimate convenience. Flexible Guest Wing / Income Suite: Accessed via an indoor breezeway or a private outdoor entrance, the space above the 3-car garage features 2 bedrooms, 2 bathrooms, and a full second kitchen. This brilliant layout is perfect for multi-generational living, or entirely closed off as a premium rental income suite. Outdoor Oasis & Lifestyle: Sited on a generous, tranquil lot, the property echoes the privacy of the wooded road leading to it. Step onto multiple 'treehouse' decks to take in the canopy, or explore the greenhouse shed and cedar spa awaiting your creative touches. Additional interior flex rooms easily accommodate a fitness studio, remote offices, a theater, or a playroom. Best of all, this private retreat includes deeded right-of-way access down the road to beautiful Highland Lake for swimming, kayaking, and summer recreation. Photos are beautiful, but the texture, scale, and soul of this remarkable home must be exper

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$574,900

3 Beds ⋅ 2 Baths

Perched along the shore of Highland Lake, this exceptional four season waterfront home offers the perfect combination of comfort, recreation, and convenience. Whether you envision quiet weekends by the lake, hosting family and friends all summer long, or generating seasonal rental income, this property delivers an unmatched lakefront lifestyle in one of Southern Maine's most desirable and accessible locations. Shopping, restaurants, golf, skiing, and year round outdoor adventure throughout Greater Portland and the Sebago Lakes Region are all within reach. With 50 feet of water frontage and a newly installed dock system, this property is designed for making the most of Maine summers! The large level lot creates the perfect outdoor living experience, complete with a spacious lawn for games and gatherings, a lakeside fire pit, an outdoor shower, and an expansive deck positioned for morning coffee, outdoor dining, and endless water views. This light filled home features 3 bedrooms, 1.5 baths, and office/bonus room. Additional finished lower level space offers room for guests, recreation, or entertaining space. Numerous recent improvements include a new roof, updated windows and window treatments, water filtration system, and a professionally installed TC Hafford basement system. An over sized two car garage adds more versatility with room for boats, kayaks, snowmobiles, or the ultimate game room setup complete with ping pong or pool table potential, enhancing the home's appeal as a sought after Airbnb or short-term rental opportunity. Don't miss your opportunity to enjoy this amazing year round home, and enjoy the beauty every season in Maine has to offer.

80 Vista Dr, Windham

Listing courtesy of Portside Real Estate Group.

$1,199,000

5 Baths

Luxury, Serenity, and Versatility Near Highland Lake Immerse yourself in a masterfully executed, 'down-to-the-studs' remodel (completed 2023) marrying organic warmth with modern sophistication. Infused with rich wood tones, textured accent walls, and a curated, boho-chic palette, this striking 6BR/5BA estate feels less like a house and more like a private sanctuary. Designed for seamless entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites--one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations offer ultimate convenience. Flexible Guest Wing / Income Suite: Accessed via an indoor breezeway or a private outdoor entrance, the space above the 3-car garage features 2 bedrooms, 2 bathrooms, and a full second kitchen. This brilliant layout is perfect for multi-generational living, or entirely closed off as a premium rental income suite. Outdoor Oasis & Lifestyle: Sited on a generous, tranquil lot, the property echoes the privacy of the wooded road leading to it. Step onto multiple 'treehouse' decks to take in the canopy, or explore the greenhouse shed and cedar spa awaiting your creative touches. Additional interior flex rooms easily accommodate a fitness studio, remote offices, a theater, or a playroom. Best of all, this private retreat includes deeded right-of-way access down the road to beautiful Highland Lake for swimming, kayaking, and summer recreation. Photos are beautiful, but the texture, scale, and soul of this remarkable home must be exper

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$594,900

2 Baths

41 Lotts Dr, Windham, ME - Owner-Occupy Opportunity with Income Potential Live in one unit and let the other help pay your mortgage. This well-maintained 2-unit property offers a spacious 3-bedroom unit that will be delivered vacant at closing, paired with a 2-bedroom apartment currently leased to great tenants at $2,200/month. The 3-bedroom unit features single-level living with an open kitchen, dining, and living area, along with a convenient mud room and brand new in-unit washer and dryer included. Updated finishes throughout, including granite countertops and stainless steel appliances, create a clean, modern feel. Market rent for the 3-bedroom unit is estimated at $2,750/month. The second unit offers a well-designed layout with consistent rental appeal and in-place income, and also includes its own new in-unit washer and dryer. Tenants pay utilities, helping keep expenses low, and off-street parking adds convenience. Ideally located right off the rotary with easy access to I-95, Gorham, Westbrook, Gray, and Cumberland. Just 20-25 minutes to downtown Portland, ~20 minutes to the Jetport, and under 2 hours to Boston. Close to North Windham amenities and Sebago Lake, with easy access to I-95. Financing-friendly, including MSHA, FHA, and conventional loans. A great opportunity for owner-occupants or investors seeking strong rental potential in a high-demand location.

41 Lotts Dr, Windham

Listing courtesy of Dream Home Realty LLC.

$535,000

3 Beds ⋅ 3 Baths

This brand new Maple Colonial home offers a blend of thoughtfully designed living spaces set in a peaceful neighborhood just minutes from local amenities. Enjoy the sunny exposure and spacious open floor plan. The kitchen features quartz countertops, a center island, and new appliances. The first floor also offers a full bathroom, a functional mudroom entry, and a great back deck. Upstairs includes three bedrooms, and a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

5 Shepherd Ln Unit 11, Windham

Listing courtesy of RE/MAX By The Bay.

$479,000

3 Beds ⋅ 3 Baths

New model completed and available for sale! Come see why so may have chosen Dolley Farm Condominiums for their new home! Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With completed units available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from. Common area pavilion and playground, and a short distance to Shaw Park and the Sebago to Sea trail. Pet friendly!

6 Dolley Farm Rd Unit 3, Windham

Listing courtesy of The Flaherty Group.

$535,000

3 Beds ⋅ 3 Baths

This brand new Maple Colonial home offers a blend of thoughtfully designed living spaces set in a peaceful neighborhood just minutes from local amenities. Enjoy the sunny exposure and spacious open floor plan. The kitchen features quartz countertops, a center island, and new appliances. The first floor also offers a den or office, a functional mudroom entry, and a great back deck. Upstairs features three bedrooms, including a primary suite, plus laundry closet and second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

5 Shepherd Ln Unit 11, Windham

Listing courtesy of RE/MAX By The Bay.

$469,000

3 Beds ⋅ 2 Baths

This brand new home offers a blend of thoughtfully designed living spaces set in a peaceful neighborhood just minutes from local amenities. Enjoy the sunny exposure and spacious open floor plan. The kitchen features quartz countertops, a center island, and new appliances. The first floor also offers a full bathroom, a functional mudroom entry, and a great back deck. Upstairs includes three bedrooms, and a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

8 Shepherd Ln Unit 4, Windham

Listing courtesy of RE/MAX By The Bay.

$699,000

2 Beds ⋅ 3 Baths

Welcome to The Cove at Highland Lake! The first of its kind Gated 55+ Lakefront Community nestled on the pristine shores of Highland Lake. Framing is complete at 25 Daybreak Lane! Truly our most decades long and spaciously flexible option, the WINDHAM homes provide both first and second floor primary suite options. Multi-generational, Companion, and Guest-Friendly, owners of these units can opt for stacked or side-by-side laundry on one or both floors of living. This inner unit features two full baths, a functionality first open concept kitchen, a front porch and back deck for sipping in the scenic surrounds, 18ft cathedral ceilings, and not one but two bonus spaces, fit for an office, spare bed, hobbying, or entertaining! This unit also has the option to finish its full-daylight walkout basement for an additional 500 SF of living area. Community Amenities to Include: tennis & pickleball courts, two-level clubhouse with fitness center, full kitchen and function space, plus private access to the over 50 acre parcel with over 6000 feet of nature trails, more than 500 feet of manicured lake front to carry in kayaks, canoes and paddleboards, plus a community maintained dock. Located just 10 miles from downtown Portland, residents will enjoy unbeatable proximity to top rated health care and hospitals, as well as Maine's finest dining and entertainment options. Boating, skiing, golf, shopping, dining, sports & activity clubs... The way 55+ life should be, and you can have it all in The Cove at Highland Lake! Reserve now & for a limited time you may customize your home's finishes!

25 Daybreak Ln Unit 8, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. crystal.chandonnet@verani.com

$494,900

3 Beds ⋅ 2 Baths

Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$679,000

3 Beds ⋅ 3 Baths

This lovely new Windham property offers the perfect blend of privacy, comfort, and convenience. Inside you'll find an open concept layout with 9 foot ceilings creating a bright and airy atmosphere, with true hardwood oak flooring extending throughout the entire first floor and stairwell for added warmth and character. The home offers 3 bedrooms and 3 bathrooms, including a spacious primary suite, plus an oversized bonus room upstairs with the potential to easily function as a true 4th bedroom. Whether used for guests, a home office, playroom, media space, or additional sleeping quarters, the flexibility of this room adds incredible value and versatility to the home. Light fills each room as the home is set on a generous yard with plenty of space to enjoy from the inside out. Find the peacefulness of Maine living while still being incredibly connected, just minutes to the center of Windham for shopping, dining, and daily essentials, with Freeport and Portland only a short drive away for expanded amenities, restaurants, and the coast. For those who love the outdoors, you're surrounded by some of Maine's best nearby hikes and lakes. This is a move that will feel as good as it looks

9 Dusty Rhoades Ln, Windham

Listing courtesy of Salt Real Estate Co.

$1,485,000

4 Beds ⋅ 3 Baths

Enjoy 700' of gated private Sebago Lake frontage with this exceptional estate located at the end of a quiet cul-de-sac. Refined design, extensive recent renovations, and exclusive access to the crystal-clear waters of Maine's premier Sebago Lake -- widely regarded as one of New England's top freshwater destinations for boating, recreation, and year-round beauty. Offering 4,602 square feet of finished living space, this estate features 4 bedrooms including a primary bedroom suite and walk-in closet, 2.5 baths, a 5-bay garage, set on over 2 acres providing privacy in every direction. The first-floor renovation creates an open-concept layout designed for effortless entertaining and everyday living. A stunning custom kitchen appointed with premium fixtures, Calacatta Brazil true white quartzite paired with contrasting black quartzite countertops, and waterfall-edge detailing that creates a sleek modern look. New flooring, recessed lighting, and an integrated sound system elevate the entire main living area. Additional recent improvements include a new 7,000+ sq ft roof, remodeled and updated baths, 15-zone irrigation system, new hot water heater, and a freshly resealed driveway. Multiple outdoor living spaces include a raised stone porch seating area, a large porch with a wooden trellis which is directly accessed from the first floor of the home, and a charming foot bridge overlooking a cascading stone fountain. A perfect way to let the world fade away as you relax in your own private backyard oasis after a day on the lake. Windemere Estates residents enjoy private Sebago Lake frontage with three beach areas, tennis courts, beach volleyball, gazebo, private boat launch, and a residents-only dock (boat slips available by tenure). Additionally, this estate is among a select few in the community to include its own mooring. Privacy, modern sophistication, and Maine lake living all come together at this must-see property. Shown by appointment only

20 Freeman Ct, Windham

Listing courtesy of Holt Realty.

$1,060,000

2 Beds ⋅ 1 Baths

This large, cherished property has been lovingly preserved by the same family for decades, dating back to its early use by the Girl Scouts for camping and swimming. Encompassing just over 28 acres, the land offers exceptional privacy and includes a rare island in the river where children once camped. One of the property's most distinctive features is the river flowing from Sebago Lake, known for its sandy gravel bottom--ideal for wading, swimming, boating, and exploration. Fish often swim right up to visitors. Locals describe approximately seven miles of wild river corridor stretching in one direction to Dundee Dam and in the other beneath the historic covered bridge through North Gorham Pond to Gambo Falls, with additional access to the Pleasant River. The property is heavily wooded with towering century-old pine trees, filling the air with a pleasant pine scent in summer. There also appears to be potential for substantial gravel deposits. The existing 780± square foot cottage was built in the early 2000s by Woodcrafters of Maine and features a living room with wood stove, kitchen, bedroom, and bath on the first floor, plus a large second-floor space suitable for a bedroom, loft, or office. The home has a dug well and a two-bedroom septic system. Additional structures include a tool garage and a music studio. With approximately 844 feet of road frontage and about 743 feet of river frontage per town records, including the island, the property offers rare flexibility for a private estate, compound, campground, or potential subdivision, subject to approvals. Conveniently located just upstream from the historic covered bridge, with quick access to North Windham shopping, Portland, nearby towns, healthcare, and the interstate.

594 River Road Rd, Windham

Listing courtesy of Plowman Realty Group.

$494,900

3 Beds ⋅ 2 Baths

Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$484,000

3 Beds ⋅ 3 Baths

Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from currently under construction.

26 Dolley Farm Rd Unit 12, Windham

Listing courtesy of The Flaherty Group.

$409,900

3 Beds ⋅ 2 Baths

Well maintained classic Cape on a large lot. 1st floor consists of a nice kitchen area, large living room. 1 bedroom on 1st floor and a full bath for convenience. Second floor has 2 full sized bedrooms and a full bath. Hardwood floors. Great location. Seller willing to buy down the mortgage rate on this home. One Year American Home Shield Warranty included from Seller.

39 Pipeline Rd, Windham

Listing courtesy of Cameron Prestige LLC.

$559,000

4 Baths

Rare Investment Opportunity Near Sebago Lake - Multi-Unit Property with Huge Potential. Opportunity awaits. This unique property offers incredible potential for investors, contractors, or buyers looking to create value. Located just a short walk to association access on beautiful Sebago Lake, the property features multiple units and flexible living space with the possibility for rental income or multi-generational use. While the property does REQUIRE updates and improvements, the location and potential make it a rare opportunity in the Windham/Sebago Lake area. Enjoy the benefits of lake access while being conveniently located near local amenities, restaurants, and year-round recreation. Whether you're looking for an investment project, seasonal retreat, or property with income potential, this is a chance to bring your vision to life in one of Southern Maine's most desirable lake regions.

96 Mineral Spring Rd, Windham

Listing courtesy of Krainin Real Estate.

$680,000

3 Beds ⋅ 3 Baths

Welcome to 315 River Road in Windham, a well-maintained gambrel-style home offering space, flexibility, and privacy on 4.7 acres. This 3-bedroom, 3-bath home features a true primary suite along with recently updated bathrooms and hardwood flooring. Heat pumps provide efficient heating and cooling, and a whole-house generator offers added peace of mind year-round. The layout offers functional and flexible living space with over 3,000 square feet, including a partially finished basement ideal for a home office, gym, or additional living area. An attached 2-car garage adds convenience and storage. The exterior is equally impressive with a beautifully landscaped and well-maintained yard, open space, and a private setting that still feels accessible. Conveniently located just minutes to North Windham with an easy commute to Westbrook and Portland, this property offers the balance of privacy and proximity that today's buyers are looking for.

315 River Rd, Windham

Listing courtesy of Maine Real Estate Experts. 207415-2918

$549,000

2 Beds ⋅ 2 Baths

Some properties sell a house. This one sells a lifestyle. Set on the shores of Sebago Lake with your own boat mooring, sandy beach access, and sweeping views of the water and mountains beyond, this condominium offers four seasons of the good life -- boating and swimming in summer, ice fishing and snowshoeing in winter, and quiet lakefront mornings year-round. Inside, hardwood floors and lake views set the tone in the living room, while the kitchen impresses with bright white beadboard cabinets, granite countertops, and full-sized appliances. Two comfortable bedrooms offer flexible living with a primary suite and a spacious second bedroom with plenty of room for bunks, perfect for guests or a full crew of weekend visitors. Community amenities include tennis, basketball, and pickleball courts and a shared dock, all managed by a rock-solid association that covers nearly everything and hasn't assessed in over ten years. Portland, Windham, and Point Sebago Golf Resort are all minutes away, but once you're here, you won't want to leave.

1112 Roosevelt Trl Unit 16, Windham

Listing courtesy of RE/MAX By The Bay.

$785,000

4 Beds ⋅ 3 Baths

Welcome to your opportunity to build a stunning modern farmhouse in the heart of Windham. This thoughtfully designed new construction package blends timeless charm with clean, modern finishes, offering both style and functionality across 2,600 square feet of beautifully crafted living space. This farmhouse style home features 4 spacious bedrooms, 2.5 bathrooms, and a2 car garage, designed with today's lifestyle in mind. From the moment you step inside, you'll appreciate the open-concept layout, highlighted by quality craftsmanship and carefully selected finishes throughout. The complete build package includes everything needed to bring your home to life, from foundation to final finishes. Enjoy peace of mind with a full construction scope including framing, roofing, siding, windows, doors, electrical, plumbing, and a high-efficiency wall-hung combi boiler heating system. Inside, you'll find durable and stylish LVP flooring, beautifully tiled bathrooms, granite countertops, hardwood cabinetry, and a full appliance package including stove, hood, refrigerator, dishwasher, washer, and dryer. Attention to detail continues with 6' baseboards and clean-lined trim, recessed lighting in the kitchen, pendant lighting over the island and dining area, and standard fixtures throughout. Outdoor features include a garage, decks, excavation around the home, tree cutting, well and septic installation, and a finished yard with loam and seed--creating a solid foundation for your future outdoor vision.

014-17-J01 Mimi Ln, Windham

Listing courtesy of The Maine Real Estate Experience.

$829,500

3 Beds ⋅ 3 Baths

This stunning home is bathed in natural light and beautifully appointed. It was purchased 1 year ago as an unfinished new build 3 bed/1 bath home, that is now transformed into a light, bright 3 bedroom 3 bath (plumbed for a 4th bath in the unfinished high ceilinged daylight basement) with a new sunny primary suite, library, laundry and mudroom. Enter the front door to a 2 story foyer and living room which flows into a large open kitchen with cabinets galore. A dining room, powder room with laundry, and mudroom leading to the heated garage complete the main floor. Up the bright open stairway to a spacious loft for study or exercise which leads to a 3 room primary suite with sun filled full bath tucked away from the bedrooms 2&3 that share another full bath. An expansive, fully fenced, 0.7 acre yard surrounded by 34 acres of preserve on 2 sides and fronting onto a cul de sac of just 20 homes. Conveniently located 8 miles from Portland, 5 miles from Gorham center in the charming So Windham village along the Presumpscot River with all of it's recreational opportunities. This home offers much of the best of Southern Maine, with heat pump for year round comfort and a high efficiency FHW natural gas system. Come discover your new home.

32 Pennywhistle Dr, Windham

Listing courtesy of Keller Williams Realty.

$399,900

1 Beds ⋅ 1 Baths

Nestled along the peaceful shores of Pettingill Pond, 12 Shore Road in Windham, Maine has the perfect blend of classic lakeside charm and modern comfort. This inviting property boasts stunning water views, direct access to the pond, and a serene setting ideal for both year-round living and seasonal escapes. Inside, you'll find a bright and welcoming layout with large windows that fill the home with natural light and showcase the surrounding beauty. The open-concept living and dining areas create an easy flow for entertaining, while the kitchen provides ample space for preparing meals after a day on the water. Need more space, you will be pleased to find that this property also has a bunkhouse, perfect for overnight guests. Step outside to enjoy your private slice of Maine's natural beauty--whether it's morning coffee overlooking the water, afternoons spent boating or swimming, or evenings around the firepit under the stars. The property offers convenient pond access, making it easy to embrace the full waterfront lifestyle. Located just a short drive from local shops, restaurants, and all of Windhams amenities. This home combines tranquility with accessibility. Whether you're looking for a permanent residence, a vacation getaway, or an investment opportunity, 12 Shore Road is a rare chance to own a piece of Maine's sought-after waterfront living.

12 Shore Rd, Windham

Listing courtesy of Rockstar Real Estate.

$1,595,000

3 Beds ⋅ 3 Baths

New construction on Little Sebago Lake is a once-in-a-decade event. And this is that event. A sun drenched contemporary three-story residence modeled after a Maine Home + Design award winning home and sited on a private dead-end road shared by just six year-round properties. This home faces DUE WEST, so that every room on the waterside catches the full arc of sunset through the floor-to-ceiling glass. The colors were selected to blend in the surrounding woods and is custom shingled in cedar. Rare public water from the Portland Water District from May-October plus a drilled well for winter months. The 38-foot-deep garage serves for convenient storage and is 10 feet tall. There is opportunity to finish part ! Plumbing is in the garage with a mechanical room, plus parking for 3 cars. An EV charging was added. Inside, new hardwood floors run throughout. The kitchen anchors the open-concept main level with a ten-foot quartz island with double waterfall features. Subzero fridge and Viking induction range plus a double pantry. Central HVAC and a propane fireplace keep the home comfortable year-round. Two decks extend the living space toward the water -- one for morning, one for the long western light. The primary suite has a private door leading to the 3rd floor deck, where you may relax and soak in the views and sounds of the lake. At the water's edge, an original boathouse and a second storage screened structure remain from the property's earlier life, and both can make wonderful bunk or playhouses, fishing shacks or storage for all the recreational needs. For a individual who values waterfront access and flexibility, these buildings represent options that would NOT be permitted today. Water is 8 ft. deep at the dock! Little Sebago is one of southern Maine's finest lakes with over 6 miles of water to explore and enjoy. 30 minutes to the Portland Jetport/Amtrak station, 2 hours to Logan Airport. less than 1 hour to local ski mountains create end

20 Ladyslipper Dr, Windham

Listing courtesy of Judy George Realty.

$494,900

3 Beds ⋅ 2 Baths

Welcome to 9 Shepherd Lane, a newly completed home offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

9 Shepherd Ln Unit 13, Windham

Listing courtesy of RE/MAX By The Bay.

$494,900

3 Beds ⋅ 2 Baths

Welcome to 9 Shepherd Lane, a newly completed home offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

9 Shepherd Ln Unit 13, Windham

Listing courtesy of RE/MAX By The Bay.

$559,000

6 Beds ⋅ 4 Baths

Rare Investment Opportunity Near Sebago Lake - Multi-Unit Property with Huge Potential or make it your home with an inlaw. Opportunity awaits. This unique property offers incredible potential for investors, contractors, or buyers looking to create value. Located just a short walk to association access on beautiful Sebago Lake, the property features multiple units and flexible living space with the possibility for rental income or multi-generational use. While the property does REQUIRE updates and improvements, the location and potential make it a rare opportunity in the Windham/Sebago Lake area. Enjoy the benefits of lake access while being conveniently located near local amenities, restaurants, and year-round recreation. Whether you're looking for an investment project, seasonal retreat, or property with income potential, this is a chance to bring your vision to life in one of Southern Maine's most desirable lake regions.

96 Mineral Spring Rd, Windham

Listing courtesy of Krainin Real Estate.

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