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$465,000
3 Beds ⋅ 2 Baths
129 Forbes Lane is ready for you to check out! Set on nearly half an acre in an established Windham neighborhood, this classic and alluring Cape offers 3 second level bedrooms, and a 1st floor bonus room which was designed as a primary bedroom! 2 full bathrooms that have been recently renovated and updated, and approximately 1,888 square feet of living space. A full bathroom on both the first and second levels provides added convenience and flexibility. Inside, hardwood flooring and a gas fireplace add warmth and character, while the traditional floor plan offers plenty of room to make the home your own. Additional features include a vaulted ceiling sun room with a wood burning stove, attached 3-car garage with overhead storage, partially finished basement space with a laundry room offers great potential, unfinished attic storage, a generous rear deck, large patio, and a storage shed. Enjoy a generous yard and a convenient location near Windham's shops, restaurants, schools, and outdoor recreation, with Little Sebago Lake approximately 10 minutes away. This property presents a wonderful opportunity to create a home tailored to your style and needs.

129 Forbes Ln, Windham

Listing courtesy of Elevate Maine Realty.

$489,000
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.

$599,000
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.

$570,000
3 Beds ⋅ 3 Baths
OPEN HOUSE SATURDAY FROM 12 TO 1:30 . What a wonderful location tucked away and yet close to everything like: Schools shopping, recreation, the lakes and mountains. Easy commute to Portland and like new. Rarely seen on the market right now, large rooms, attention to details with upgrades AND a stand alone condo with a two car garage and full basement and low monthly fee of $70.00 for common area maintenance and insurance. 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

36 Belvedere Dr, Windham

Listing courtesy of Keller Williams Realty.

$469,999
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.

$849,900
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.

$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
$450,000
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.

$289,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained and inviting three-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 Sunday, September 26th from 12 pm - 1:30 pm!

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

$523,999
4 Beds ⋅ 2 Baths
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.

$624,900
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.

$459,900
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.

$565,000
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.

$625,000
4 Beds ⋅ 3 Baths
*Back on the market - no fault of seller or property* This is your opportunity to enjoy and reap the rewards of this 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, w/work space/pottery 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.

$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.

$699,000
3 Beds ⋅ 3 Baths
We call it 'The Tree House'--a ranch built bigger and bolder. Set on nearly 10 private acres, this beautifully renovated home is wide, solid, and built to impress: hardwood floors, solid wood doors, statement glass hardware, a true primary suite, and a kitchen with a gas range made for real cooking. This multi-level layout offers a finished lower level, which adds a bonus room and kitchenette, guest suite, in-law space, studio, or office--the choice is yours. Out front, a pollinator garden brings monarch butterflies all summer long. A heated barn rounds things out with its own oil tank, a pro-grade Kellogg air compressor, pull-down loft storage, and a serious workspace. Minutes from Windham Center, area lakes, and an easy Portland commute--with potential for two additional buildable lots behind the home (subject to municipal approval). A transformation, inside and out.

21 Land Of Nod Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$4,200,000
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.

$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
$499,900
2 Beds ⋅ 2 Baths
4.67 ACRES ON COLLEY WRIGHT BROOK — YEAR-ROUND WATER, YOUR OWN PRIVATE WATERFALLS, AND A POTENTIAL BUILDABLE LOT. The entire property conveys: all 4.67 acres, over 300 feet of owned water frontage, and a true Maine homestead just 30 minutes to Portland. Potential second building lot — buyer to confirm with the Town of Windham. Some properties you tour. This one you fall for. Set on 4.67 private acres along year-round Colley Wright Brook — with over 300 feet of owned water frontage and your very own waterfalls — this is the rare retreat where the land itself tells the story. Gather at one of two brookside fire pits, wander the gardens, or simply listen to the water from a porch tucked among mature trees. The 1969 log home is full of soul, built from logs harvested right up the road at Staples Farm. Inside, a cathedral-ceilinged living room is anchored by a grand wood-burning fireplace, while a heated three-season sunroom with radiant floors brings the woods-and-water views indoors all year. Enjoy easy one-floor living with two bedrooms and two full baths, plus a finished office/bonus room on the lower level for work, hobbies, or guests. For the self-sufficient at heart, this is a dream: an outdoor wood boiler can heat the entire home — with soft or hard wood you harvest right from your own land — backed by baseboard hot-water heat, a basement wood stove, and the sunroom's radiant floors. Heat your way, all year long. And the grounds are a love letter to the seasons: established perennial and raised-bed gardens, lilacs and dahlias, tulips and lilies, plus a true edible landscape — apple trees, elderberries, serviceberries, rhubarb, blueberries, strawberry patches, and a full herb garden of chives, oregano, sage, and thyme. Private, peaceful, incredibly scenic — yet only about 30 minutes to Portland. Come stand by the brook and listen. You'll understand.

22 Montgomery Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$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 history. Apartment features a small kitchen, washer and dryer, and private entrance separate. 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. This Maine Cedar Log Home delivers exceptional space, comfort, and privacy. 1031 Exchange friendly. Broker offering free 1-year home warranty.

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 history. Apartment features a small kitchen, washer and dryer, and private entrance separate. 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. This Maine Cedar Log Home delivers exceptional space, comfort, and privacy. 1031 Exchange friendly. Broker offering FREE 1-year home warranty.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$799,000
4 Beds ⋅ 3 Baths
Enjoy the perfect balance of a quiet lifestyle, access to Maine recreational living, local grocery stores, with an effortless commute. Located on a peaceful street just 15 mins to downtown Portland and minutes to Westbrook and quick access to the turnpike. 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, versatile home is ideal.

24 Leonards Way, Windham

Listing courtesy of Portside Real Estate Group.

$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.

$325,000
1 Beds ⋅ 1 Baths
Brand New Price! First time home buyers, down sizers, Investors, builders, developers! Excellent 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 lot. 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 an efficient newe heating system and spacious downstairs laundry--this home is perfect for immediate rental income while you plan your expansion or development of the property. Capitalize on the large open backyard, paved driveway with a 1+ car garage, and two powered storage sheds. Explore the possibilities under the town's RM land use ordinance. Very convenient to Greater Portland, the Sebago Lakes Region, North Windham and Auburn. Perfect lower price point for buyers just starting out! Better than a tiny condo!

549 Roosevelt Trl, Windham

Listing courtesy of Pine Tree Realty of Maine.

$1,175,000
6 Beds ⋅ 5 Baths
~ OPEN HOUSE SUNDAY ~ 8/23/26! 10:30-12pm ~ 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 seen.

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$1,175,000
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 seen.

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$479,000
3 Beds ⋅ 3 Baths
Come see why so many have chosen Dolley Farm Condominiums for their new home! The Harvest 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, while a rear patio extends your living space outdoors. 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. With completed units available, you can settle in and enjoy now! Pet friendly and short walk to Sebago to Sea trail and Shaw Park!

6 Dolley Farm Rd Unit 3, Windham

Listing courtesy of The Flaherty Group.

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