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$650,000
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION TO BE BUILT: Experience the best of lakeside living with this stunning new construction opportunity. This thoughtfully designed 3-bedroom, 2-bath home offers modern finishes, open-concept living, and the rare chance to personalize the home to fit your lifestyle. Nestled in a peaceful, scenic setting, the property includes two deeded access points to the lake, making it easy to enjoy swimming, kayaking, fishing, or simply taking in the tranquil waterfront surroundings. Surrounded by nature and nearby trails, this location offers the perfect balance of outdoor recreation and everyday comfort. The home can be customized, with additional options available such as a garage, daylight basement, expanded living space, and other upgrades to create your ideal home. Enjoy the serenity of lake life while remaining just 20 minutes from Portland, offering convenient access to shopping, dining, entertainment, and major commuting routes. Whether you're looking for a year-round residence or a peaceful retreat, this modern new construction home is a unique opportunity to build the lifestyle you've been dreaming of.

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

$949,000
5 Beds ⋅ 4 Baths
Welcome to Windemere, one of Sebago Lake's most sought-after lakefront communities, where timeless craftsmanship, exceptional amenities, and the Maine lake lifestyle come together. This custom-built Colonial offers 3,555 square feet of beautifully finished living space with a thoughtfully designed floor plan that balances elegance, comfort, and flexibility. The home features five bedrooms and three and a half bathrooms, including spacious primary suites on both the first and second floors, making it ideal for multi-generational living or hosting family and guests. Hardwood flooring, quartz countertops, a gas fireplace, a dedicated home office, and both formal and informal living spaces provide the perfect setting for everyday living and entertaining alike. Above the attached garage, a finished bonus space complete with a kitchenette offers endless possibilities as an in-law suite, guest quarters, recreation room, or private retreat. Outside, enjoy the privacy of the beautifully landscaped backyard from the expansive patio while taking in seasonal views of Sebago Lake. A new roof installed in 2024 provides added peace of mind for years to come. As a resident of Windemere, you'll enjoy exclusive access to outstanding community amenities, including a 700-foot sandy beach on Sebago Lake with breathtaking mountain and sunset views, a private boat launch, boat slips (subject to availability), tennis and pickleball courts, canoe and kayak storage, and beautifully maintained common areas. Located just minutes from downtown Windham, this home offers the rare opportunity to enjoy spacious luxury living in one of Southern Maine's premier lake communities. With In-law apartment, it could be used as a 6 bedroom but note septic system is designed for four bedrooms.

35 Woldbrook Dr, Windham

Listing courtesy of Portside Real Estate Group.

$949,900
3 Beds ⋅ 3 Baths
Nestled on an extraordinary 16-acre estate in the heart of Windham, this one-of-a-kind farmhouse masterfully blends timeless New England charm with exceptional modern amenities. Surrounded by breathtaking stone walls, spectacular perennial gardens, and stunning custom hardscaping, the property offers an unparalleled setting of beauty, privacy, and tranquility. At the heart of the home is a dream chef's kitchen, thoughtfully designed for both everyday living and entertaining. Featuring gleaming granite countertops, stainless steel appliances, and a coveted Wolf gas range, this impressive space is as functional as it is beautiful. The home offers three spacious bedrooms and two-and-a-half baths, with inviting living spaces that embrace the surrounding landscape. Relax year-round in the passive solar sunroom, unwind on the spacious screened porch, or entertain on the deck before soaking in the hot tub beneath the stars. Additional highlights include a three-car garage, a garden shed, and an expansive third-floor attic with incredible potential to create additional finished living space, whether you envision a home office, studio, guest suite, or recreation room. Every inch of this remarkable property reflects thoughtful craftsmanship and pride of ownership. From the magnificent gardens to the picturesque stonework and peaceful acreage, this is a rare opportunity to own a truly exceptional country estate--offering the perfect balance of elegance, comfort, and natural beauty, just minutes from all that Windham has to offer. This home has even been pre-inspected for the buyer's convenience. Seller Concessions Available. For a video walk-thru go to YouTube and enter the property address.

605 River Rd, Windham

Listing courtesy of Keller Williams Realty.

$499,000
3 Beds ⋅ 2 Baths
Tucked away on a peaceful, wooded lot, 8 Environmental Way has had many thoughtful updates including a new roof and whole house generator! This home has the perfect balance of privacy and convenience, just about 30 minutes from downtown Portland. Wake up to birdsong, watch deer wander through the yard, and enjoy the feeling of your own nature retreat, all while being just minutes from shopping, restaurants, schools, and Sebago Lake recreation. Inside, the thoughtful three level layout offers the best of both worlds. The main living spaces flow seamlessly together with an open kitchen, dining, and family room with a propane stove and natural landscape outside drawing nature in. Separate levels provide privacy when it's time to unwind. Upstairs, you'll find three bedrooms, including a spacious primary suite with its own en suite bathroom, plus a second full shared bathroom off the hallway. The finished lower level adds valuable flex space and is currently set up as a gaming room, making it perfect for a media room, home office, gym, or bonus space. For added peace of mind, a pre-listing home inspection has already been completed, and a water test report will be provided to interested buyers.

8 Environmental Way, Windham

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com
$599,000
3 Beds ⋅ 3 Baths
This beautiful 3-bedroom, 2.5-bath home will have you celebrating your good luck! Life in this serenely situated Windham neighborhood strikes a perfect balance of comfort, convenience & idyllic charm. Inside, a seamless layout, hardwood floors, lofty ceilings, and mood-boosting natural light await. The kitchen's granite countertops, stainless steel appliances, gas stove, island with storage + seating, and large pantry will inspire every home chef. Open access to the dining area makes for easy chatting while cooking. Beautiful windows and a gas fireplace preside over the living room. A half bath with laundry rounds out the main floor. You'll love retreating to the primary suite upstairs, where peaceful nature views and a private bath create the perfect place to unwind. Two additional second-floor bedrooms and a full bath mean there's room for everyone. Opportunity abounds for entertainment, work, or play in the finished basement. Nature lovers & wildlife watchers will adore this tranquil, tree-lined spot, be it from the front porch, back deck, or around a campfire in the backyard. Evening strolls & bike rides are a breeze in the welcoming, walkable neighborhood. The attached 2-car garage adds everyday ease. North Windham's endless amenities mean you need not leave the bounds of town for a thing. Sebago Lake's public beach is a mere 5-minute drive away. This home will have you singing the praises of a life well-lived - a must-see! Showings begin Friday 7/31 OPEN HOUSE Sunday Aug 2nd 11-1

77 Harvest Hill Rd, Windham

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com
$1,179,900
4 Beds ⋅ 3 Baths
Luxury meets timeless craftsmanship in this exceptional new construction home, privately nestled on 1.84 wooded acres. Offering 4 bedrooms and 2.5 baths, every space has been thoughtfully designed with elevated finishes, abundant natural light, and a seamless blend of elegance and comfort. The heart of the home is a stunning gourmet kitchen featuring custom cabinetry, premium finishes, an expansive walk-in pantry, and an inviting layout perfect for everyday living or entertaining. The spacious living area is anchored by a beautiful gas fireplace, while oversized windows frame the natural surroundings and flood the home with light. Throughout the home, you'll find gorgeous white oak radiant-heated floors, custom tile, and meticulous craftsmanship at every turn. An extended garage provides generous room for vehicles, storage, or a workshop. Outside, the welcoming farmer's porch and stone walkway create timeless curb appeal, while the wooded setting offers exceptional privacy and a peaceful retreat. Combining sophisticated design, modern efficiency with heat pumps, and high-end custom finishes throughout, this is a rare opportunity to own a truly stunning home where quality is evident in every detail.

108 Highland Cliff Rd, Windham

Listing courtesy of Landmark Realty.

$474,000
3 Beds ⋅ 3 Baths
New model completed and available for sale! Come see why so may have chosen Dolley Farm Condominiums for their new home! Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With completed units available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from. Common area pavilion and playground, and a short distance to Shaw Park and the Sebago to Sea trail. Pet friendly!

2 Dolley Farm Rd Unit 1, Windham

Listing courtesy of The Flaherty Group.

$299,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully maintained and inviting two-bedroom condo, ideally located in the heart of Windham. Enjoy the convenience of being just minutes from shopping, restaurants, and everyday amenities while tucked away in a peaceful setting. The first floor features an open-concept layout with a spacious living room, kitchen, and dining area--perfect for both everyday living and entertaining. Just off the dining area, step onto the newer deck, an ideal spot to enjoy your morning coffee, dine outdoors, or unwind after a long day. Upstairs, you'll find two generously sized bedrooms with cathedral ceilings that create a bright and airy feel, along with a full bathroom. The finished walk-out basement offers valuable additional living space that can easily serve as a third bedroom, home office, fitness room, or family room, with direct access to the private backyard. Conveniently located near Sebago Lake and just a short drive to Portland, this move-in-ready condo offers the perfect blend of comfort, functionality, and location. Don't miss your opportunity to make this wonderful property your new home! Open house Saturday, August 1 from 10:30am to 12:00pm.

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

$529,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully updated home in one of Windham's most desirable neighborhoods, where timeless charm, quality craftsmanship, and an exceptional location come together. From the moment you arrive, you'll appreciate the meticulously maintained landscaping featuring mature trees and stunning perennial gardens that provide vibrant blooms throughout the growing season, creating incredible curb appeal and a picturesque setting you'll enjoy year after year. Inside, pride of ownership shines throughout. Refinished hardwood floors, new flooring in the upstairs bedrooms, and new basement flooring create a fresh, cohesive feel, while the bright kitchen features a new window and new appliances. New electrical outlets, fixtures, and recessed lighting installed by Simply Electric LLC add a stylish, modern touch. Additional improvements include a beautiful new front porch, board and batten detailing on the garage, select new cedar shakes, and a professionally cleaned and inspected chimney, reflecting the exceptional care this home has received. The private backyard is equally impressive, surrounded by mature landscaping and colorful flower gardens that bloom throughout the seasons, creating the perfect setting to relax, entertain, or simply enjoy Maine's natural beauty. Perfectly situated just minutes from downtown Windham, you'll enjoy convenient access to shopping, local restaurants, entertainment, and everyday amenities. Portland is only 15 minutes away, while Sebago Lake's public boat launch is approximately 10 minutes from your doorstep, making it easy to enjoy boating, fishing, swimming, and all that Southern Maine has to give. Thoughtfully updated and truly move-in ready, this exceptional property offers the perfect blend of elegance, comfort, and convenience in one of Windham's most sought-after communities.

12 Arcadia Dr, Windham

Listing courtesy of Real Broker.

$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.

$599,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully private and tucked-away retreat, gracefully situated on 1.29 acres of peaceful countryside. Offering 3 spacious bedrooms, 1.5 bathrooms, and a 1-car garage, this charming home provides the perfect blend of comfort, privacy, and convenience. Surrounded by the beauty of a serene rural setting, you can enjoy the tranquility of nature while remaining just moments from public beaches, boat launches, shopping centers, and local restaurants, all while being only 25 minutes from Portland. Outside, you'll find a lovely area ready for your dream garden, along with an existing chicken coop awaiting its next flock, creating the perfect opportunity to embrace a simple and rewarding homestead lifestyle. Whether you're spending a day on the water, enjoying nearby amenities, gathering fresh eggs in the morning, or simply relaxing in your own private oasis, this exceptional property offers the lifestyle you've been searching for.

7 Hall Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$699,000
3 Beds ⋅ 3 Baths
NEWLY PRICED!! Nature beckons you in the popular Lakes Region! Nestled on 2 acres, this meticulously maintained home offers approximately 2,875 square feet of light-filled living space. A beautiful stone fireplace with woodstove insert takes center stage on the main level featuring hardwood floors, a den/home office and eat-in kitchen area with granite peninsula, stainless steel appliances and maple cabinets! There's easy access to the well built, heavy duty deck overlooking a wooded, private fenced-in yard. Down the hall is a cozy laundry room, full bath and 2 spacious bedrooms. The primary suite tucked in the rear corner, features a tile shower and walk-in closet providing a comfortable and serene environment. The possibilities are endless in the lower-level family room with storage closet, full bath and mudroom. Walk-out access to the custom cedar hot tub provides a luxurious and relaxing experience! The whole-house generator ensures uninterrupted power, and heat pumps on each level provide added comfort throughout each season. A magnificent wildflower garden adds natural beauty and charm to the surroundings of this move-in ready home, minutes from area amenities and bustling North Windham! A home warranty provides peace of mind for this special oasis, just 35 minutes to the Portland Jetport. What are you waiting for?

20 Cross Ridge Dr, Windham

Listing courtesy of Coldwell Banker Realty. 207-773-1990
$499,900
3 Beds ⋅ 2 Baths
Do NOT miss this well maintained colonial style home in Windham on nearly 2-acres! From your recently paved driveway, step inside and find a kitchen that's open to the dining area, and living room around the corner. Kitchen features newer flooring, counters, sink, and stainless steel appliances! Dining area has a sliding door that leads to a rear deck (freshly painted) that over looks your private back yard. First floor also offers wood flooring in the living room, bonus room that could be used as an office, and first floor laundry. Upstairs find another full bathroom and 3-large bedrooms, including a primary with a massive walk-in closet. Basement has great storage and if you need more, there's a shed! Property abuts East Windham Conservation Area land that secures your privacy. Enjoy exploring trails right from your back yard! Only 25-minutes to Portland and minutes to lakes

11 Bruschi Rd, Windham

Listing courtesy of Coldwell Banker Realty. 207-282-5988
$625,000
4 Beds ⋅ 3 Baths
Charming, antique 3 bedroom 1.5 bath New England Farmhouse with an additional 1 level, 1 bedroom, 1 bath In-Law apartment attached. Huge barn, pottery/artist studio, beautifully landscaped, pastoral 3.3 acre lot with gardens, flowers, blueberries, veggies and mature trees offered for the first time in 31 years. This classic home with modern accommodations has integrity and flexibility, it's just waiting for your design. Thoughtful and practical updates and upgrades made throughout the ownership. Lovingly maintained and enjoyed. Enchanting spaces inside and out. The farmhouse boasts a large, eat-in kitchen with a pantry and laundry room adjacent. Beautiful antique cast iron stove. Formal dining room and a 1st floor bedroom with a sizable dressing room/closet. Large, newer French doors lead to a sweet side deck overlooking green trees and fields. New roof on the main home 2024 as well as a heat pump for heating and cooling in 2023. The expansive mudroom separates the In-Law apartment from the farmhouse. In-Law apartment with its own deck was added in 1995. Perfect for personal, family use or for additional income. New roof on the apartment 2023, heat pump in apartment installed 2025. The barn and the back woodstock was used as the owner's pottery studio and wood fired kiln. A stunning piece of structural history, with tons of storage and space for your passions or practical uses. This truly special property offers a solid, warm and practical home on positively cinematic farm land. Tucked away from the hustle and bustle but only minutes away from walking trails and Windham Center for shopping, services, entertainment and dining. Less than 15 minutes to the Maine Turnpike, less than 30 minutes to Portland. Make this historic gem your own bucolic, rural paradise.

305 Windham Center Rd, Windham

Listing courtesy of Portside Real Estate Group.

$419,900
3 Beds ⋅ 2 Baths
Move right into this well-maintained home, perfectly situated on a semi-private lot surrounded by mature greenery. Enjoy deeded right-of-way access to Pettingill Pond for swimming, kayaking, or simply relaxing by the water, all while being just one mile from Windham's shopping, dining, and everyday conveniences. Inside, the daylight basement with a cozy pellet stove offers flexible living space, while the deck just off the kitchen is perfect for grilling, entertaining, or enjoying your morning coffee. A second full bathroom adds extra convenience, making this move-in-ready home an ideal blend of comfort, privacy, and location.

33 Spear Ave, Windham

Listing courtesy of Coastal Pine Real Estate, LLC.

$450,000
3 Beds ⋅ 2 Baths
Welcome to 14 Pope Road in Windham--a place that just feels like home the moment you pull in. Set on 1.7 acres, there's plenty of room to spread out, with a bright, sunny backyard that's perfect for summer nights, backyard games, or letting pets roam free in the fully fenced yard. The barn and shed give you all the extra space you need for storage, hobbies, or projects you've been meaning to start. Bring your ideas to make it yours! Upstairs, you'll find 3 bedrooms and 1 bathroom with a layout that's easy to live in and make your own. Downstairs is an half bath with laundry and an open kitchen and living room with a door directly to the backyard. A charming covered porch off two of the bedrooms is the perfect spot to curl up with a book. A two car attached garage opens directly into a hallway to stow away shoes and coats. Sellers installed a new well and a new furnace in 2025. You'll love the location--close to Portland for an easy commute, but tucked into a great area of Windham. Property is being sold AS IS. Sellers are motivated to move on to their next chapter!

14 Pope Rd, Windham

Listing courtesy of Maine Real Estate Experts.

$649,000
2 Beds ⋅ 3 Baths
Timeless charm meets lakeside living at this beautifully restored 1920 bungalow just steps from Big Sebago Lake. Rich in character and thoughtfully updated, this 2-bedroom, 2.5-bath home offers nearly 2,000 square feet of inviting living space with original details blended seamlessly with modern comfort. The warm and welcoming interior features a classic wood-burning fireplace, two comfortable living areas, a charming period-style kitchen, and two bedrooms with additional living space that's perfect for family and guests. Step outside to the spacious, west-facing deck where you'll enjoy breathtaking sunsets over Big Sebago Lake. Spend your days taking advantage of deeded access to the lake through the shared right of way directly across the road, offering an ideal setting for swimming, boating, and making lasting summer memories. Tucked away on a quiet dead-end private road, this well-landscaped property also features a new roof installed in 2025, adding peace of mind for years to come. Conveniently located near shopping, golf, and all the amenities of the Lakes Region, this exceptional home is equally suited as a year-round residence or a quintessential Maine getaway.

25 Lake Ave, Windham

Listing courtesy of Keller Williams Realty.

$589,000
3 Beds ⋅ 2 Baths
Nestled on a beautifully maintained 2.4-acre lot in Windham, Maine, this charming Cape-style home, built in 2006, features 1,547 square feet of comfortable living space with 3 bedrooms and 2 full bathrooms. The property combines country charm with modern conveniences in a peaceful setting surrounded by nature. Enter through the attached garage into a welcoming mudroom finished with warm knotty pine, creating a functional and inviting transition into the home. An oil-fired forced hot water boiler provides efficient, dependable heat throughout the seasons. The outdoor space is thoughtfully designed for gardening, recreation, and relaxation. Beautiful landscaping includes established blueberry, raspberry, and blackberry bushes, a large vegetable garden, and colorful sunflower plantings. A private nature trail leads to Baker Brook, creating a serene backdrop for enjoying the outdoors. Spend summer days by the above-ground swimming pool, unwind in the hot tub, or gather around the fire pit on cool Maine evenings. A chicken coop and an additional outbuilding provide excellent space for hobby farming, storage, or workshop use. Conveniently located near Windham's shopping, dining, schools, lakes, and recreational amenities, this well-maintained property combines the privacy of country living with easy access to everyday conveniences.

7 Mancini Rd, Windham

Listing courtesy of Landing Real Estate.

$719,000
3 Beds ⋅ 3 Baths
Welcome to ''The Tree House'', where every window frames a view of nature. Set on nearly 10 private acres, this beautifully renovated oversized ranch has been thoughtfully updated throughout with exceptional attention to detail. Designed for easy single-level living, the home features hardwood floors, solid wood doors, high-end glass door knobs, 35-inch hallways and doorways, a spacious primary suite with a private bath, first floor laundry, and a beautifully appointed kitchen with a gas range. The finished lower level includes a bonus room with a kitchenette, offering excellent flexibility for guests, extended family, or additional living space. The heated barn features its own oil tank, a professional-grade Kellogg air compressor, loft storage with a pull-down ladder, and ample workspace. Additional highlights include abundant electrical outlets, an exterior hot and cold water spigot, and the pride of ownership that comes with only one previous owner. Located just minutes from Windham Center, lakes, and an easy commute to Portland, this property offers the perfect blend of privacy and convenience. The nearly 10-acre parcel also offers potential for two buildable lots behind the existing home (subject to municipal approvals), with access possible via a new road or an extension of the existing driveway. A remarkable transformation inside and out, this is a place you will not want to miss.

21 Land Of Nod Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$659,000
3 Beds ⋅ 3 Baths
'AMAZING HOUSE, LOT, LOCATION & VALUE' This is the property you've been searching for with the perfect combination of everything you are looking for!! This beautifully cared for newer home has bright spacious rooms with an awesome plan that is both comfortable and versatile. Nestled on one of the prettiest lots in a very desirable small neighborhood with a dead end and gorgeous sun-drenched setting, this home features a 3 bedroom, 2.5 bath open concept design, nice bright kitchen with island and stainless steel appliances, very large pantry, maple floors, slider to deck and great yard areas, front to back living room with gas fireplace, master bedroom with double sinks & tiled shower, huge finished room over the garage adding tremendous versatility to adapt to your specific needs, efficient gas heat, 3 heat pumps for heat & cooling, full farmers porch, and a superior lot & location that is most convenient to everything!!! DON'T DELAY & SEE IT AS SOON AS POSSIBLE!!

13 Maysens Way, Windham

Listing courtesy of Maine Realty 2000.

$875,000
4 Baths
4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built in 2003, the main house offers nearly 2800sqft, 4+ bedrooms, 2.5 baths, a spacious loft with pool table, and a fully finished basement. High-quality Andersen windows fill the home with natural light, while warm wood finishes and generous living spaces create an inviting, comfortable atmosphere. Savor the heart of the home with custom birch cabinetry, Corian counters, a roomy island, and ample storage for all of your culinary needs. Keep your toes warm all winter long with the luxury of radiant heat floors beneath every step. Enjoy peaceful surroundings, abundant wildlife, and endless opportunities to relax. Nestled on 4.26 acres of impeccably maintained and manicured, park-like grounds, this property invites you to enjoy the serene beauty and a picturesque setting right at your doorstep. A preliminary inspection indicates that the lot may possibly be subdivided, allowing the potential of building an additional rental property or a guest house for family and friends. Unwind on the 8'x24' farmer's porch or entertain guests on the 10'x20' rear deck. The oversized 24'x32' heated two car garage provides ample storage for vehicles, tools, and recreational equipment. Above the garage is a legal efficiency apartment with 1 bedroom, 1 bath, offers excellent rental income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. Additional property updates include a 26KW whole house automatic generator installed in 2022 powering the home, garage, and apartment; heat pumps installed in 2020: a full exterior re-stain completed in 2022; a new house roof installed in 2023: and the driveway resealed in 2026. Most furnishings are negotiable, and most appliances are less than 10 years old. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$875,000
4 Beds ⋅ 3 Baths
4.26 ACRES (potentially sub-dividable) WITH INCOME PRODUCING EFFICIENCY APARTMENT! Built in 2003, the main house offers nearly 2800sqft, 4+ bedrooms, 2.5 baths, a spacious loft with pool table, and a fully finished basement. High-quality Andersen windows fill the home with natural light, while warm wood finishes and generous living spaces create an inviting, comfortable atmosphere. Savor the heart of the home with custom birch cabinetry, Corian counters, a roomy island, and ample storage for all of your culinary needs. Keep your toes warm all winter long with the luxury of radiant heat floors beneath every step. Enjoy peaceful surroundings, abundant wildlife, and endless opportunities to relax. Nestled on 4.26 acres of impeccably maintained and manicured, park-like grounds, this property invites you to enjoy the serene beauty and a picturesque setting right at your doorstep. A preliminary inspection indicates that the lot may possibly be subdivided, allowing the potential of building an additional rental property or a guest house for family and friends. Unwind on the 8'x24' farmer's porch or entertain guests on the 10'x20' rear deck. The oversized 24'x32' heated two car garage provides ample storage for vehicles, tools, and recreational equipment. Above the garage is a legal efficiency apartment with 1 bedroom, 1 bath, offers excellent rental income. Apartment features a small kitchen, washer and dryer, and private entrance separate from the garage. Additional property updates include a 26KW whole house automatic generator installed in 2022 powering the home, garage, and apartment; heat pumps installed in 2020: a full exterior re-stain completed in 2022; a new house roof installed in 2023: and the driveway resealed in 2026. Most furnishings are negotiable, and most appliances are less than 10 years old. Whether you're seeking a full-time residence or a private getaway, this Maine Cedar Log Home delivers exceptional space, comfort, and privacy.

27 Independence Dr, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$549,900
3 Beds ⋅ 2 Baths
Welcome to this charming 3-bedroom, 2-bath Cape offering a bright, open-concept layout designed for comfortable living and effortless entertaining. Features include a convenient first-floor bedroom, hardwood floors, a daylight basement with expansion potential, an office/bonus/bedroom and a stunning oversized new deck--perfect for hosting family and friends or simply relaxing outdoors. Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is just minutes from Tassel Top Park and its private beach access on beautiful Sebago Lake and a short drive to the shops of North Windham. Enjoy the perfect balance of neighborhood living and convenience, with the city of Portland, the Maine Turnpike, and the beauty of the lakes region all within a 20-minute drive. Don't miss this exceptional opportunity to own a home in one of Windham's most sought-after locations. Schedule your private showing today before it's gone!

115 Harvest Hill Rd, Windham

Listing courtesy of Landmark Realty.

$875,000
4 Beds ⋅ 3 Baths
Welcome to this stunning custom-built 4-bedroom (3 bedroom septic) home nestled in one of Windham's most desirable neighborhoods. Perfectly situated just 15 minutes from Portland and 15 minutes from North Windham's shopping, dining and recreation. This property offers the ideal blend of convenience and peaceful living. Designed with both comfort and entertaining in mind, the home features an open-concept layout with spacious living areas, creating a seamless flow throughout the main level. Enjoy the flexibility of two separate living spaces. One room on first floor may be used as a play room, office, media room or the possibility of a first floor bedroom. The finished bonus room above the garage is a standout feature, complete with wet bar and endless possibilities. Thoughtfully crafted with quality finishes and attention to detail, this newer custom home offers modern living in an exceptional neighborhood setting. Whether you're enjoying quiet evenings at home or taking advantage or the nearby amenities and easy Portland commute, this property truly has it all. FULL HOUSE AUTOMATIC GENERATOR!!!

24 Leonards Way, Windham

Listing courtesy of Portside Real Estate Group.

$189,900
Back line on a small trout brook with trees, most of the lot is beautiful fields. Nice level loamy lot.

40 Highland Cliff Rd, Windham

Listing courtesy of Butts Commercial Brokers.

$339,900
1 Beds ⋅ 1 Baths
New Price! Investor, builder, developers, home buyers! Exceptional opportunity on highly popular Roosevelt Trail with flexible Residential (RM) zoning, offering potential for limited business use, a home occupation, or multi-unit development. This neat, clean, and sun-drenched property sits on a spacious 0.56-acre lot with 137 feet of prime road frontage. An asset for immediate expansion or development is the existing two-bedroom septic system already on site. The property features a turnkey, updated 1-bedroom home with a modernized heating system and convenient downstairs laundry--perfect for immediate rental income while you plan your build. Capitalize on the large open backyard, a 1+ car garage, and two powered storage sheds. Explore the possibilities under the town's RM land use ordinance. Owner-occupants looking for a business-ready property, savvy investors, and builders--take notice!

549 Roosevelt Trl, Windham

Listing courtesy of Pine Tree Realty of Maine.

$1,199,000
6 Beds ⋅ 5 Baths
Luxury, Serenity, and Versatility Near Highland Lake Immerse yourself in a masterfully executed, 'down-to-the-studs' remodel (completed 2023) marrying organic warmth with modern sophistication. Infused with rich wood tones, textured accent walls, and a curated, boho-chic palette, this striking 6BR/5BA estate feels less like a house and more like a private sanctuary. Designed for seamless entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites--one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations offer ultimate convenience. Flexible Guest Wing / Income Suite: Accessed via an indoor breezeway or a private outdoor entrance, the space above the 3-car garage features 2 bedrooms, 2 bathrooms, and a full second kitchen. This brilliant layout is perfect for multi-generational living, or entirely closed off as a premium rental income suite. Outdoor Oasis & Lifestyle: Sited on a generous, tranquil lot, the property echoes the privacy of the wooded road leading to it. Step onto multiple 'treehouse' decks to take in the canopy, or explore the greenhouse shed and cedar spa awaiting your creative touches. Additional interior flex rooms easily accommodate a fitness studio, remote offices, a theater, or a playroom. Best of all, this private retreat includes deeded right-of-way access down the road to beautiful Highland Lake for swimming, kayaking, and summer recreation. Photos are beautiful, but the texture, scale, and soul of this remarkable home must be exper

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$39,000
AFFORDABLE WATER ACCESS ! This lot is Non Buildable, however can accommodate a camper or single wide trailer. It has an Easement Deed with Consolidated Communications to have a small equipment building on the property. Consolidated Communications pays all annual taxes. The property has ROW access to Highland Lake.

1 Vista Dr, Windham

Listing courtesy of Cumberland County Realty.

$1,199,000
5 Baths
Luxury, Serenity, and Versatility Near Highland Lake Immerse yourself in a masterfully executed, 'down-to-the-studs' remodel (completed 2023) marrying organic warmth with modern sophistication. Infused with rich wood tones, textured accent walls, and a curated, boho-chic palette, this striking 6BR/5BA estate feels less like a house and more like a private sanctuary. Designed for seamless entertaining, the open layout boasts bespoke details at every turn. The chef's kitchen features Brazilian quartzite, handmade custom cabinetry, and designer fixtures. Gathering spaces are abundant, with two distinct living areas inviting you to cozy up by a wood stove or a new propane fireplace. The main residence offers rare dual first-floor primary suites--one flanking each side of the home. Luxury details include custom tile showers, built-in nightstands, and powered blinds regulating the sun-drenched rooms. For hosting, a speakeasy-style bar serves as the perfect retreat, while 3 separate laundry locations offer ultimate convenience. Flexible Guest Wing / Income Suite: Accessed via an indoor breezeway or a private outdoor entrance, the space above the 3-car garage features 2 bedrooms, 2 bathrooms, and a full second kitchen. This brilliant layout is perfect for multi-generational living, or entirely closed off as a premium rental income suite. Outdoor Oasis & Lifestyle: Sited on a generous, tranquil lot, the property echoes the privacy of the wooded road leading to it. Step onto multiple 'treehouse' decks to take in the canopy, or explore the greenhouse shed and cedar spa awaiting your creative touches. Additional interior flex rooms easily accommodate a fitness studio, remote offices, a theater, or a playroom. Best of all, this private retreat includes deeded right-of-way access down the road to beautiful Highland Lake for swimming, kayaking, and summer recreation. Photos are beautiful, but the texture, scale, and soul of this remarkable home must be exper

44 Johnson Rd, Windham

Listing courtesy of Beacon Realty.

$479,000
3 Beds ⋅ 3 Baths
New model completed and available for sale! Come see why so may have chosen Dolley Farm Condominiums for their new home! Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an ensuite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With completed units available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from. Common area pavilion and playground, and a short distance to Shaw Park and the Sebago to Sea trail. Pet friendly!

6 Dolley Farm Rd Unit 3, Windham

Listing courtesy of The Flaherty Group.

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