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15 Sleepy Hollow Rd, Windham
$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.

274 Pope Rd, Windham
$2,200,000
5 Beds ⋅ 5 Baths
This beautifully renovated Federal-style home, known as the historic Peter White House, seamlessly blends 1809 heritage with modern luxury. Redesigned by renowned architect John Calvin Stevens in the early 20th century, this landmark estate sits on 11+ pastoral acres in prestigious Windham Hill offering endless possibilities. The recent renovation honors the home's storied past while delivering a sophisticated modern interior. The show stopping kitchen features top-of-the-line Subzero, Fisher Paykel & Wolf appliances with white leathered Brazilian countertops. Maple and pine floors, abundant natural light, and a crisp white palette create an airy, palatial farmhouse ambiance throughout. This complete lifestyle property offers a 5 bedroom, 2 full bath plus 2 powder room home with living and family rooms, library/office, loft, dining room, mudroom, screened porch and partially finished basement, plus a newly renovated studio apartment with full bath and kitchenette in the carriage house that's perfect for guests or income generation. The expansive grounds include open fields, small animal barn, fruit trees, old sugar shack turned wood storage, charming playhouse, and private sauna fitted with a cold-plunge clawfoot tub overlooking a magnificent field that was formerly an airstrip. There's even a spacious garage to house at least 4 vehicles or your small farm equipment. Surrounded by towering pines and maples, this private sanctuary provides rural tranquility while remaining convenient to Portland and in-town amenities and schools. Experience Maine's magic in every season with spring blossoms, summer serenity, brilliant autumn foliage, and winter wonderland snowscapes. Perfect for those seeking the complete New England estate experience. whether a multi-generational family, entrepreneur, or anyone drawn to distinctive historic properties with exceptional land and modern sophistication.

274 Pope Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

16 Cook Rd, Windham
$1,756,000
Every once in a while, a truly special property comes along, one that carries a story of its own and offers an extraordinary opportunity for its next chapter. For the very first time, this remarkable 60.8-acre property is being offered to the market, presenting a rare chance to own a substantial piece of land rich in history, character, and possibility. With approximately 763.9 feet of road frontage, this expansive property offers a wonderful sense of space and an abundance of opportunities for those with the vision to see its full potential. The 2,632-square-foot residence features four bedrooms, two full bathrooms, and one half bath, providing a foundation for whatever the future may hold. Steeped in the traditions of rural living, this property has a long history as a working homestead, where a variety of animals were raised and the land played an important role in everyday life. That heritage remains part of what makes this offering so distinctive. Whether you envision returning the property to its homesteading roots, creating your own private country retreat, or exploring the many possibilities that come with such generous acreage, there is room here for imagination and opportunity. Perhaps one of its most appealing qualities is the balance of country living and convenience. Enjoy the space and privacy of a rural setting while remaining close to town, with shopping, restaurants, and everyday amenities nearby. Even more appealing, Portland is approximately 15 minutes away, offering convenient access to everything the city has to offer. Properties of this size, history, and potential are becoming increasingly difficult to find. Never before offered to the market, this is more than an opportunity to purchase a home and acreage. It is an invitation to become part of a property's continuing story, to appreciate its past, embrace its possibilities, and create something uniquely your own.

16 Cook Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

16 Cook Rd, Windham
$1,756,000
4 Beds ⋅ 3 Baths
Every once in a while, a truly special property comes along, one that carries a story of its own and offers an extraordinary opportunity for its next chapter. For the very first time, this remarkable 60.8-acre property is being offered to the market, presenting a rare chance to own a substantial piece of land rich in history, character, and possibility. With approximately 763.9 feet of road frontage, this expansive property offers a wonderful sense of space and an abundance of opportunities for those with the vision to see its full potential. The 2,632-square-foot residence features four bedrooms, two full bathrooms, and one half bath, providing a foundation for whatever the future may hold. Steeped in the traditions of rural living, this property has a long history as a working homestead, where a variety of animals were raised and the land played an important role in everyday life. That heritage remains part of what makes this offering so distinctive. Whether you envision returning the property to its homesteading roots, creating your own private country retreat, or exploring the many possibilities that come with such generous acreage, there is room here for imagination and opportunity. Perhaps one of its most appealing qualities is the balance of country living and convenience. Enjoy the space and privacy of a rural setting while remaining close to town, with shopping, restaurants, and everyday amenities nearby. Even more appealing, Portland is approximately 15 minutes away, offering convenient access to everything the city has to offer. Properties of this size, history, and potential are becoming increasingly difficult to find. Never before offered to the market, this is more than an opportunity to purchase a home and acreage. It is an invitation to become part of a property's continuing story, to appreciate its past, embrace its possibilities, and create something uniquely your own. Please tour this property with a licensed agent.

16 Cook Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

90 Basin Rd, Windham
$1,395,000
3 Beds ⋅ 2 Baths
Stunning Year-Round Sebago Lake View Home with Dual Beach Access & Mooring. 3BR/2BA, 2,514 SF on a rare double lot (~0.6-0.7 acres) bordered by woods on a quiet, year-round plowed dead-end street. Located in a secluded community along Sebago Basin in Windham, this move-in ready home features beautiful year-round lake views and an expansive screened porch perfect for watching the sunset. Designed for entertaining, the comfortable layout includes a spacious kitchen with abundant cabinetry, a premium Wolf gas range, and a seamless flow into the adjoining dining and living areas. The flexible 3-bedroom, 2-bath floor plan features a primary suite with a custom walk-in closet, a radiant heat zone, and a new furnace. The two oversized upstairs bedrooms are incredibly versatile, each easily accommodating two queen beds plus a private sitting area. Premium amenities support hobbies and wellness right at home, including a private gym, a sauna, a full workshop, and underground pet fencing. Parking is a breeze with a detached 2-car garage, a 1-car under-house garage (3 total bays), and a double-width driveway that holds up to 10 vehicles. Enjoy an exceptional lake lifestyle with deeded rights to two sandy Basin Road beaches and a private deeded mooring on Sebago Basin. A golf cart is included to make shore runs easy, complete with a dedicated golf cart path and parking by the fire pit. Direct neighborhood access to the Rails-to-Trails (ATS Trail) and fishing near the local dam offers endless four-season outdoor recreation. The private yard serves as a natural sanctuary, frequently attracting local deer, turkeys, and songbirds. Located just minutes from North Windham shops, restaurants, and Lakes Region amenities. Experience the ultimate Maine lake lifestyle!

90 Basin Rd, Windham

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

20 Freeman Ct, Windham
$1,375,000
4 Beds ⋅ 3 Baths
Sebago Lake Lifestyle with 700' of gated private beach frontage and an exceptional estate located at the end of a quiet cul-de-sac. Refined design, extensive recent renovations, new roof, 5 bay garage & exclusive access to Maine's premier Sebago Lake - 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 of over 1,000 sq ft gross living area, 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.

58 Lower Beach Rd, Windham
$1,199,000
3 Beds ⋅ 5 Baths
The lake house, elevated. Discover a striking new construction opportunity just one lot back from Highland Lake in Windham with rights of way to the lake. Shared water access to Highland Lake, The exact location, extent, and amount of shared water frontage are currently being confirmed by the attorney. This thoughtfully designed and town-approved 3,036-square-foot residence offers 3 bedrooms, 4.5 baths, a dedicated office, three levels of living and a secluded 800+ square-foot rooftop deck designed to bring a fresh perspective to Maine lake life. Contemporary architecture meets warm, natural design with clean lines, expansive windows and thoughtfully planned spaces for everyday living and entertaining. Inside, the proposed home features bright, open living areas, a sophisticated kitchen and a warm neutral palette complemented by natural wood tones and dramatic black-framed windows. Architectural renderings showcase the vision for a home that feels modern and refined without sacrificing comfort. The showstopper awaits on the third floor. Designed as an entertainer's dream, this level extends the living experience outdoors with an expansive rooftop retreat. Conceptual renderings envision covered and open-air spaces for dining, lounging and entertaining, creating an incredible destination for hosting friends, relaxing after a day on the lake or simply enjoying Maine's changing seasons. Located in the Highland Lake community, the property offers the opportunity to enjoy lake-area recreation while remaining convenient to Windham's shopping, dining and amenities and within easy reach of Greater Portland. With construction yet to begin, buyers may have the opportunity to participate in certain selections and finishes, subject to builder specifications, allowances and construction timelines. 3,036 SF. 3 bedrooms. 4.5 baths. Home office. An extraordinary third-floor entertaining space. One incredible opportunity to create your new home near Highland Lake.

58 Lower Beach Rd, Windham

Listing courtesy of Keller Williams Realty.

10 Flintlock Dr, Windham
$1,150,000
3 Beds ⋅ 3 Baths
Welcome to this gorgeous new home that is almost completed, located in the desirable and sought after Cross Ridge Community. The large lot offers a quiet setting surrounded by natural beauty. As soon as you enter the home you will be impressed by the thoughtful design and elevated quality. There is a space conveniently located to the right of the foyer that can be a den, work-at-home office or a space you design for your needs. The living room is anchored by a gas fireplace with built in shelves on both sides. The unique space in the living room will provide ease of entertaining your family and friends. From the living room you seamlessly enter into the dining area and beautiful gourmet kitchen with an open concept design. The kitchen has a gas stove with a pot filler, large island to entertain while you cook and quartz counters that go up the wall for backsplash. There is a lovely walk-in pantry with matching cabinets and counters to provide extra storage or prep space. The white oak hardwood floors throughout the home provide a feeling of luxury. The second floor has a space at the top of the staircase ready for you to design. The primary suite is a true retreat, featuring a walk-in closet, spa inspired shower and a double vanity. There are also two great size bedrooms and a full bath for family and guests. The laundry room with cabinets and shelving is conveniently located on the second floor. There is a large bonus room over the garage ready for you to create your special space. The daylight basement presents future opportunity to enhance your lifestyle whether for recreation, wellness or extended living space. The three car garage offers space for all your vehicles or create a workshop. Your possibilities with this beautiful home are endless. Central Air and a generator provide comfort and reliability for your home. This is an opportunity to own a truly stunning home where quality is evident in every detail. Some pictures are Ai generated.

10 Flintlock Dr, Windham

Listing courtesy of Maine Real Estate Experts. debcassidy123@gmail.com

Lot #10 Goose Pond, Windham
$998,900
Discover a rare opportunity to own 35.97± acres of private, wooded land ideally positioned near the Windham, Falmouth, and Cumberland lines. Tucked into one of Southern Maine's most desirable and rapidly growing areas, this unique parcel offers exceptional privacy, natural beauty, and proximity to Portland, I-95, and surrounding higher-end communities. The land features mature woods, natural stream corridors, existing trails, and a peaceful setting surrounded by conservation land and outdoor recreation opportunities. A 10-acre town-owned parcel located within the surrounding boundaries creates a unique natural buffer and enhances the sense of privacy and seclusion. This property may appeal to buyers seeking a private estate setting, recreational retreat, long-term land investment, or future strategic opportunity. Survey recently completed reflecting 35.97± acres. Access is currently under review and buyers are encouraged to perform their own due diligence regarding access rights, insurability, intended use, development potential, and municipal approvals. Shown by appointment only.

Lot #10 Goose Pond, Windham

Listing courtesy of Keller Williams Realty.

15 Alpine Dr, Windham
$929,999
3 Beds ⋅ 3 Baths
Welcome to 15 Alpine Drive, Windham--where modern living, incredible amenities, and exceptional garage space come together in one impressive property. Thoughtfully designed for everyday comfort and entertaining, this home is filled with the upgrades and little details you've been looking for.The kitchen features quartz countertops, glass tile backsplash, custom soft-close hickory cabinetry, Kohler cast-iron farmhouse sink, and hand-blown glass island lighting. Enjoy on-demand hot water, Daikin heat pump cooling, dimmable LED lighting, whole-house fire sprinklers, and extensive smart-home technology. Ethernet is wired throughout, along with integrated Sonos audio in multiple rooms, garage, deck, and pavilion.Outside is your own private retreat! The approximately 150'x100' fenced backyard features a 16'x37' heated inground pool with Roman end and LED lighting, 6-person Vita Spa hot tub, and 28' custom pavilion with power and lighting. Hunter WiFi-controlled multi-zone irrigation and rear gate access toward neighborhood ATV/snowmobile trails add even more convenience.Car enthusiasts, hobbyists, and anyone needing serious space will love the HEATED 32'x40' garage with 12' ceilings, three 10' doors, 9,000-lb Rotary automotive lift, sink, extensive overhead lighting, generator wiring, Ethernet, and multiple 120V/240V receptacles.Pool, pavilion, hot tub, smart-home features, privacy, trails, and an incredible heated garage--all the little things you've been looking for are already here. Why build when your dream home is right here? Windhams private community crossridge is waiting!

15 Alpine Dr, Windham

Listing courtesy of Elevate Maine Realty.

14 Rocklinn Dr, Windham
$875,000
3 Beds ⋅ 3 Baths
Welcome to 14 Rocklinn Drive, a custom-built Colonial in one of Windham's most desirable neighborhoods. Built in 2003 and set on 1.7 acres, this well-maintained home offers just over 3,000 square feet of finished living space, three bedrooms, and 2.5 bathrooms. The bright, open main level features beautiful wide pine-board flooring, large windows, and a freshly painted kitchen with high ceilings, dining space, and a generous pantry. The living room's gas fireplace and large windows create a welcoming place to relax and enjoy opportunities for birdwatching. The first-floor primary suite includes an updated ensuite bath, walk-in closet, and nearby laundry room. A spacious bonus room off the kitchen features new hickory flooring and custom cabinetry. Currently used as an art studio, it could also serve as a home office, gym, hobby room, or recreation space. Upstairs, two generously sized bedrooms, a quiet reading nook, and an updated full bath with new granite countertops and fixtures provide comfortable additional living space. The unfinished basement offers ample storage and a workshop area with custom cabinetry. Outside, enjoy summer gatherings on the large back deck or meals with friends on the screened porch overlooking the yard. A private quarter-mile walking path invites you to explore the peaceful surroundings. Additional features include a whole-house generator and a new septic system installed in 2025. With flexible living spaces, a convenient first-floor primary suite, and inviting outdoor areas, 14 Rocklinn Drive offers plenty of room to gather, relax, and enjoy life at home.

14 Rocklinn Dr, Windham

Listing courtesy of Keller Williams Realty.

98 Vista Dr, Windham
$799,950
4 Beds ⋅ 3 Baths
Rare 4-season Highland Lake offering—a newly built, turnkey 4-bedroom waterfront home with 3 full baths and beautiful lake views. Live year-round with exceptional energy efficiency/performance, a solar system and low-maintenance exterior for stress-free living. Skylights, tongue and groove pine accents and exposed beams add character to the interior. The lake becomes part of everyday life, whether you're cooking breakfast, reading on the covered porch, or waking up to the sparkle of the water from your bedroom. From the excitement of your own waterfrontage, go for a swim, paddle, boat ride or ice fish. Cozy up by the wood stove on cool fall nights. A gradual sandy entry leads to 43 feet of privately owned waterfront with space for a dock and boat, plus an additional 40 feet of shared sandy waterfront access—all just 15 minutes from Portland. Open House Sunday, 10/4, 1-3 PM.

98 Vista Dr, Windham

Listing courtesy of Keller Williams Realty.

23 Fall Ridge Rd, Windham
$799,900
3 Beds ⋅ 2 Baths
Looking for single-level living without giving up space or privacy? This 2020-built ranch offers three bedrooms, two full baths and over 2,000 square feet on approximately two acres in Windham. Vaulted ceilings and wood floors carry through the open kitchen, dining and living area, with a fireplace that anchors the space. The kitchen features white cabinets, stainless steel appliances and a large island with seating, giving you room to cook, gather and entertain without being separated from the conversation. Just off the dining area, a bright sunroom overlooks the backyard and surrounding trees. The primary bedroom includes its own full bathroom, and first-floor laundry means your everyday living stays on one level. Two additional bedrooms and a second full bath provide room for guests or a home office. Enjoy your morning coffee on the covered front porch, spend time in the spacious yard, and appreciate the convenience of an attached two-car garage and paved driveway. A full unfinished basement adds plenty of storage. If a newer ranch with an open layout and room around you is on your list, this one deserves a look.

23 Fall Ridge Rd, Windham

Listing courtesy of Plowman Realty Group.

22 Daybreak Ln Unit 11, Windham
$799,000
3 Beds ⋅ 3 Baths
NEW CONSTRUCTION CONDO NOW AVAILABLE FOR 2026 OCCUPANCY - MUST SEE ONE OF A KIND DEVELOPMENT! Welcome to The Cove at Highland Lake: where low maintenance lake-life meets Portland-proximate convenience! The Freeport floorplan, our largest single level 2 Bed/2 Bath floor plan comes standard with 1340+/- sq ft, a large open concept living area with a spacious kitchen, soft-close cabinetry, Energy Efficient LED Lighting & Appliances. 22 Daybreak features a floor to ceiling Gas Fireplace feature, Upgraded Cafe Appliance Package, Light & Bright Granite and Quartz Countertops, Finished Basement with an additional bed and full bath, and 9Ft ceiling height! Custom tiled showers, spa like bath fixtures, and cathedral ceilings ensure your condo is well appointed and beaming with natural light. 18 x 12 (approximate) Primary Suite with double vanity bath and a walk-in closet. The Freeport also boasts a large front porch and an oversized single stall attached garage with extra room for storage. Community Amenities to Include: Tennis & Pickle Ball court, two-level clubhouse with fitness center, full kitchen and function/meeting space, private access to the 53 acre parcel with over 6000 feet of nature trails, 585 feet of lake front to carry in kayaks, canoes and paddle boards, plus a community maintained dock. Located JUST 10 MILES from Downtown Portland, residents will enjoy UNBEATABLE proximity to top rated health care and hospitals, Maine's finest dining and endless entertainment options. Have you ever imagined a life immersed in nature full of boating, skiing, golf, shopping, dining, sports & activity clubs, and LOW MAINTENANCE? The way 55+ life should be can be found here in The Cove at Highland Lake!

22 Daybreak Ln Unit 11, Windham

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

6 Barbara Win Ln, Windham
$786,000
3 Baths
Highlights: Master Suite - Expansive primary bedroom with full private bath and a spacious walk-in closet Gourmet Kitchen - Designed for the home chef and perfect for gatherings Separate 1-Bedroom In-Law Unit / Apartment - Ideal for guests, multigenerational living, or rental income Daylight Finished Basement - Bright, usable living space with natural light Two 2-Car Garages (one attached) - Both fully heated one with radiant floor heat and the other has a Modine heating system for year-round comfort Backyard Patio - Perfect for outdoor entertaining and relaxation 2 Acres - Private setting with room to enjoy nature and outdoor activities This rare offering combines comfort, functionality, and privacy in one outstanding package. The separate in-law unit, dual heated garages, and finished daylight basement provide flexibility few homes can match. Don't miss this unique opportunity. Schedule your private showing today, don't delay.

6 Barbara Win Ln, Windham

Listing courtesy of EXP Realty.

6 Barbara Win Ln, Windham
$786,000
3 Beds ⋅ 3 Baths
Stunning Private Estate Home with In-Law Suite - 2 Acres of Privacy. Welcome to this exceptional property offering the perfect blend of luxury living and versatile space. Nestled on a generous 2-acre lot, this home features a gourmet kitchen ideal for entertaining, three spacious bedrooms, and a private 1-bedroom in-law apartment/unit completely separate from the main house. Highlights: Master Suite - Expansive primary bedroom with full private bath and a spacious walk-in closet Gourmet Kitchen - Designed for the home chef and perfect for gatherings Separate 1-Bedroom In-Law Unit / Apartment - Ideal for guests, multigenerational living, or rental income Daylight Finished Basement - Bright, usable living space with natural light Two 2-Car Garages (one attached) - Both fully heated one with radiant floor heat and the other has a Modine heating system for year-round comfort Backyard Patio - Perfect for outdoor entertaining and relaxation 2 Acres - Private setting with room to enjoy nature and outdoor activities This rare offering combines comfort, functionality, and privacy in one outstanding package. The separate in-law unit, dual heated garages, and finished daylight basement provide flexibility few homes can match. Don't miss this unique opportunity! Contact us today to schedule your private showing.

6 Barbara Win Ln, Windham

Listing courtesy of EXP Realty.

32 Pennywhistle Dr, Windham
$775,000
3 Beds ⋅ 3 Baths
This stunning home is bathed in natural light and beautifully appointed. As you enter the front door you will find a 2 story foyer and living room which flows into the dining room and to the large open kitchen with dining area overlooking the back yard and cabinets galore. The 1st floor also offers a sunken den/office with built ins, a powder room with laundry, and mudroom leading to the heated garage. Up the bright open stairway to a spacious loft that can be a study or exercise area and leads to the primary suite with a recently completed bath offering a soaking tub and a large custom shower. There are 2 additional bedrooms and guest bath. The lower level offers a walk out partially finished daylight basement with sliders leading to the back yard. An expansive, fully fenced, a 0.7-acre yard surrounded by 34 acres of preserve on 2 sides. Conveniently located 8 miles from Portland, 5 miles from Gorham or Windham centers. This home offers much of the best of Southern Maine, with high efficiency gas heat as well as a heat pump for year round comfort.

32 Pennywhistle Dr, Windham

Listing courtesy of Keller Williams Realty.

2 Victoria Ln, Windham
$775,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully maintained Colonial nestled in a family-friendly neighborhood! From the moment you arrive, you'll appreciate the inviting curb appeal, well-landscaped grounds, freshly painted exterior, Trex front porch, and stamped concrete walkway. The open-concept main level offers an ideal layout for everyday living and entertaining. The living room features a cozy fireplace with Brazilian teak hardwood floors and flows seamlessly into the dining area and spacious kitchen, complete with plenty of workspace. A charming coffee bar adds an extra touch of convenience. The large mudroom provides excellent storage and space. Upstairs, the primary suite offers hardwood flooring and a private bath, while additional bedrooms provide plenty of space for family and guests. Step outside to enjoy the newer deck, overlooking a wonderfully private backyard--perfect for relaxing, entertaining, or enjoying your morning coffee. Thoughtfully cared for and move-in ready, this home offers the space, comfort, and privacy you've been looking for in a desirable Windham location. A must-see!

2 Victoria Ln, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

56 Webb Rd, Windham
$769,000
3 Beds ⋅ 2 Baths
Imagine coming home to a beautifully crafted custom ranch designed for effortless single-level living. This to-be-built home offers three bedrooms, two bathrooms, and an attached two-car garage. A welcoming covered front porch opens to a defined foyer and a spacious open living area, where cathedral ceilings create a bright, expansive setting in the living room and kitchen. The kitchen will impress with 42-inch upper cabinets, elegant crown molding, and durable quartz countertops. Engineered hardwood flooring will flow seamlessly through the main living spaces and every bedroom. A comfortable primary suite, two additional bedrooms, and thoughtful details throughout make this new-construction home an exceptional place to settle in and enjoy.

56 Webb Rd, Windham

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

Hall Rd, Windham
$749,900
Build your dream home--or explore the potential for future development--on this exceptional 8.85-acre parcel in desirable Windham. Situated on a paved, town-maintained side street, this expansive property offers a rare combination of privacy, convenience, and natural beauty. With over 400 feet of owned frontage along the scenic Pleasant River, you'll enjoy a picturesque setting perfect for relaxing and enjoying the outdoors. Conveniently located near local schools, popular running and walking trails, shopping, and some of the area's favorite restaurants, this property offers easy access to all that Windham has to offer. The generous acreage may offer subdivision potential, subject to town approvals and applicable ordinances, making it an attractive opportunity for builders, investors, or those looking to create a family compound. Whether you're envisioning a private waterfront retreat or considering future development possibilities, this unique property is full of potential.

Hall Rd, Windham

Listing courtesy of Dream Home Realty LLC.

8 Hazel Dr, Windham
$699,900
3 Beds ⋅ 3 Baths
Built in 2019, this beautiful ranch showcases quality craftsmanship by MGM Builders, with thoughtful design and attention to detail to offer both comfort and functionality. The home offers two welcoming entry points, including a covered front porch with direct access to the living area and a convenient mudroom off the garage. The mudroom features closets to neatly store coats, shoes, and other everyday essentials. From the front entry, step into the open-concept kitchen, dining, and living area. The living room features a gas fireplace surrounded by built-in shelving and cabinetry, creating an attractive focal point while providing additional storage and display space. Heat pumps provide efficient heating and cooling for year-round comfort. The spacious eat-in kitchen is designed for both everyday living and entertaining, featuring a large island, quartz countertops, stainless steel appliances, and white cabinetry with under cabinet lighting. A generously sized pantry provides additional storage. Conveniently located just off the kitchen are a half bath and a separate laundry room. The primary suite is tucked away at the back of the home, offering a quiet and private retreat. The full primary bath features double sinks, radiant-heated tile flooring, and a tiled shower. On the opposite end of the home, two additional bedrooms share a second full bath, complete with radiant-heated flooring and a towel warmer. The full basement offers excellent potential for future family room, home gym, or hobby area. Enjoy relaxing evenings on the backyard patio, accessed through the dining area. Additional features include a lawn irrigation system, whole-house generator, and security system. Located in Green Acres, one of Windham's desirable subdivisions, this home offers shared access to the Pleasant River, with +/-1,400 feet of shared river frontage. Conveniently situated near local schools, shopping, restaurants, and the greater Portland area, this home is a must see!

8 Hazel Dr, Windham

Listing courtesy of The Maine Real Estate Experience.

21 Land Of Nod Rd, Windham
$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.

25 Daybreak Ln Unit 8, Windham
$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

18 Daybreak Ln Unit 13, Windham
$689,000
2 Beds ⋅ 2 Baths
NEW CONSTRUCTION CONDOS - MUST SEE LAKEFRONT DEVELOPMENT! Welcome to The Cove at Highland Lake: where low maintenance lake-life meets Portland-proximate convenience! The Freeport model, our largest single level 2 Bed/2 Bath floor plan comes standard with 1340+/- sq ft of living area, a large open concept living area with a spacious kitchen, soft-close cabinetry, Energy Efficient LED Lighting & Appliances. Buyers may add Gas Fireplace, up to 1000SF Finished Basement with 9Ft ceiling height, and a long list of other custom elements! Cathedral ceilings and skylights ensure your condo is beaming with natural light. Appointed with two large bedrooms including an 18 x 12 (approximate) Primary Suite with double vanity bath and a walk-in closet. The Freeport also boasts a large front porch and an oversized single stall attached garage with extra room for storage. Community Amenities to Include: Tennis & Pickle Ball court, two-level clubhouse with fitness center, full kitchen and function/meeting space, private access to the 53 acre parcel with over 6000 feet of nature trails, 585 feet of lake front to carry in kayaks, canoes and paddle boards, plus a community maintained dock. Located JUST 10 MILES from Downtown Portland, residents will enjoy UNBEATABLE proximity to top rated health care and hospitals, Maine's finest dining and endless entertainment options. Have you ever imagined a life immersed in nature full of boating, skiing, golf, shopping, dining, sports & activity clubs, and LOW MAINTENANCE? The way 55+ life should be can be found here in The Cove at Highland Lake! Reserve now and for a limited time you may choose your homes finishes.

18 Daybreak Ln Unit 13, Windham

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

630 Roosevelt Trl Unit 1, Windham
$689,000
Prime commercial opportunity with outstanding exposure and ample parking! This stylish, modern office building offers excellent signage visibility along high-traffic Route 302 and flexible C-1 zoning that allows for a variety of uses. With 14 parking spaces and two separate entrances, the building is well-suited for owner occupancy with tenant income. The first level features a welcoming reception area, conference room with gas fireplace, kitchenette, private office with its own entrance, and an ADA-compliant half bath. The second floor includes five offices and a full bathroom. A full basement with double-door access from the parking lot provides excellent loading, storage, or future expansion potential. Built in 2017, the property features modern systems including central air conditioning, a full security system, and irrigation. The association covers plowing and landscaping, making this an attractive, low-maintenance investment. Don't miss the opportunity to elevate your business in this highly visible, turnkey location.

630 Roosevelt Trl Unit 1, Windham

Listing courtesy of Signature Homes Real Estate Group.

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