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$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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