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$635,000
3 Beds ⋅ 3 Baths
Welcome to 32 Carriage Hill Drive. This beautiful 1 owner home has been lovingly cared for and updated to keep up with the times. Set on just under an acre, this picture perfect colonial is positioned perfectly at the top of the hill and faces out overlooking common space. Everywhere you look there are flowers in bloom in every season flanking all the special spots in the yard. Step inside where multiple options for heating and cooling will ensure your comfort year round. The breezeway area is a great spot to shake off the day and step into the updated kitchen where the dining area leads to the 3-season porch. Having company? a full dining room can accommodate all your special guests. Work at home or can't make the stairs? a first floor room perfect for your needs. Outfitted nicely with hardwood and fresh paint the entire first floor leaves nothing to be desired. The second Floor features a Primary suite with bath and walk-in closet and two additional generously sized bedrooms. Still not enough? Expansion Possibilities Over the Garage or in the dry Basement!

32 Carriage Hill Dr, Windham

Listing courtesy of RE/MAX Coastal.

$629,900
Large ranch with so much to provide. Over 3200 sq ft of finished living space. Kitchen is open to the living room and dining area, great layout for entertaining. Kitchen Includes new cabinets, granite countertop and appliances. New plumbing fixtures, cabinet and countertop in the first floor bathroom with laundry shoot. Epoxy floor recently installed in basement. Massive 780 sq ft primary suite features jetted tub, separate shower and 2 large walk-in closets. Large laundry room with wrap-around work counter. Relax and enjoy your favorite drink in the comfort of the screened porch. Two large rock walls enhance the beauty of this property located only a few minutes to North Windham's business district. This property sits on nearly 2 acres, plenty of room to savor the outdoors. For those with an entrepreneurial spirit, you can set up your business in the basement with your advertising sign on Rte 302. Property is located in Windham's C-3 zoning (see town ordinance for the types of businesses allowed). The opportunities are extensive. Member of selling LLC holds a Maine Associate Brokers license.

5 Foster Flds, Windham

Listing courtesy of Regency Realty Group.

$629,900
3 Beds ⋅ 3 Baths
Large ranch with so much to provide. Over 3200 sq ft of finished living space. Kitchen is open to the living room and dining area, great layout for entertaining. Kitchen Includes new cabinets, granite countertop and appliances. New plumbing fixtures, cabinet and countertop in the first floor bathroom with laundry shoot. Epoxy floor recently installed in basement. Massive 780 sq ft primary suite features jetted tub, separate shower and 2 large walk-in closets. Large laundry room with wrap-around work counter. Relax and enjoy your favorite drink in the comfort of the screened porch. Two large rock walls enhance the beauty of this property located only a few minutes to North Windham's business district. This property sits on nearly 2 acres, plenty of room to savor the outdoors. For those with an entrepreneurial spirit, you can set up your business in the basement with your advertising sign on Rte 302. Property is located in Windham's C-3 zoning (see town ordinance for the types of businesses allowed). The opportunities are extensive. Member of selling LLC holds a Maine Associate Brokers license.

5 Foster Flds, Windham

Listing courtesy of Regency Realty Group.

$629,000
4 Beds ⋅ 3 Baths
NEW PRICE—NOW OFFERED AT $629,000! If you have been waiting for the right combination of space, privacy, location, and value in Windham, this home is it! Come and check it out! First time on the market by its original owner, this 2006 Colonial offers four bedrooms, 2½ baths, a bonus room, an attached two-car garage, and 1.17 wooded acres. With hardwood flooring, a versatile floor plan, and plenty of room to spread out, the home is move-in ready and well suited to today's lifestyles. The kitchen is open to the dining room and a comfortable den with a pellet stove, creating a warm and inviting everyday living space. A separate living room gives you even more flexibility for entertaining, relaxing, or simply enjoying some quiet time. Upstairs, the primary bedroom includes its own full bath. Three additional bedrooms and a bonus room offer options for a home office, playroom, exercise room, hobby space, or whatever best fits your needs. The attached two-car garage provides direct entry to the main level, as well as convenient separate access to the second floor. Practical Maine features include hot-water baseboard heat, two oil tanks, a pellet stove, and a whole-house generator for added comfort and peace of mind. The private backyard is surrounded by woods and offers space to garden, entertain, play, or unwind. Enjoy summer barbecues on the spacious deck or relax in the hot tub at the end of the day. The location makes it easy to get just about anywhere. Routes 302 and 202 are nearby, with convenient access to North Windham's shopping and amenities, Sebago Lake, I-95, and Portland. Four bedrooms, multiple living spaces, a bonus room, a two-car garage, a generator, and a private wooded setting—now offered at $629,000. Come take another look and see how much this Windham home has to offer!

16 Pheasant Ridge Dr, Windham

Listing courtesy of Maine Real Estate Experts. YvonneSellsMaine@gmail.com
$625,000
3 Beds ⋅ 3 Baths
Beautiful contemporary cape with 1st floor primary suite! At the end of a cul-de-sac, in a quiet neighborhood, with the 5-acre community common space along the backside of the property, 14 Abenaki Drive is a peaceful retreat. Everyday conveniences and four-season recreation are close at hand. North Windham's shops, groceries, restaurants, and attractions like Seacoast Adventure are a short drive away, while Dundee Park's river beach, Lippman Park's trails and playground, and the Mountain Division Trail invite easy walks, bikes, and paddles. Sebago Lake and Little Sebago are nearby for swimming and boating, and Portland is only about twenty minutes down the road. North and South travel are at your doorstep! Enjoy small-town Maine charm and city access, gorgeous mornings and star filled nights from the deck off the dining room, or sweet summer days in the private back yard. If you are cozy to home, or delight in travel, this solidly built home will become your paradise. Check out the unique, 10 ft ceilings in the daylight walk-out basement. Find plenty of storage space. This house has it all. See it soon!

14 Abenaki Dr, Windham

Listing courtesy of EXP Realty.

$616,000
3 Beds ⋅ 3 Baths
*Back on the market - no fault of seller or property* This is your opportunity to enjoy and reap the rewards of this charming, antique 3 bedroom 1.5 bath New England Farmhouse with an additional 1 level, 1 bedroom, 1 bath In-Law apartment attached. Huge barn, w/work space/pottery studio, beautifully landscaped, pastoral 3.3 acre lot with gardens, flowers, blueberries, veggies and mature trees offered for the first time in 31 years. This classic home with modern accommodations has integrity and flexibility, it's just waiting for your design. Thoughtful and practical updates and upgrades made throughout the ownership. Lovingly maintained and enjoyed. Enchanting spaces inside and out. The farmhouse boasts a large, eat-in kitchen with a pantry and laundry room adjacent. Beautiful antique cast iron stove. Formal dining room and a 1st floor bedroom with a sizable dressing room/closet. Large, newer French doors lead to a sweet side deck overlooking green trees and fields. New roof on the main home 2024 as well as a heat pump for heating and cooling in 2023. The expansive mudroom separates the In-Law apartment from the farmhouse. In-Law apartment with its own deck was added in 1995. Perfect for personal, family use or for additional income. New roof on the apartment 2023, heat pump in apartment installed 2025. The barn and the back woodstock was used as the owner's pottery studio and wood fired kiln. A stunning piece of structural history, with tons of storage and space for your passions or practical uses. This truly special property offers a solid, warm and practical home on positively cinematic farm land. Tucked away from the hustle and bustle but only minutes away from walking trails and Windham Center for shopping, services, entertainment and dining. Less than 15 minutes to the Maine Turnpike, less than 30 minutes to Portland. Make this historic gem your own bucolic, rural paradise.

305 Windham Center Rd, Windham

Listing courtesy of Portside Real Estate Group.

$614,900
3 Beds ⋅ 3 Baths
Built in 2019 and thoughtfully designed for today's lifestyle, this move-in ready Colonial offers the perfect balance of modern comfort, privacy, and convenience. Situated on a private 1.17-acre lot in the desirable Riverside Ridge neighborhood, this home provides a peaceful setting while remaining just minutes from shopping, restaurants, schools, the Maine Turnpike, and a short drive to the recreational opportunities of Sebago Lake. Designed with both everyday living and entertaining in mind, the open-concept main level features an eat-in kitchen with granite countertops, a center island, pantry, and seamless flow into the dining and living areas. In addition to the reported living area, the home features a fully finished and heated bonus room above the attached two-car garage, offering exceptional flexibility as a home office, media room, game room, fitness area, playroom, or guest retreat. Upstairs, the spacious primary suite offers a private bath and walk-in closet, while two additional bedrooms and second-floor laundry add comfort and convenience. Enjoy your morning coffee on the inviting front porch or unwind on the private rear deck overlooking the spacious backyard. Additional highlights include an attached two-car garage with direct entry, generator hookup, on-demand hot water, and an unfinished walk-out basement offering abundant storage or outstanding potential for future finished living space. Whether you're looking for newer construction, modern finishes, flexible living space, low-maintenance ownership, or a convenient location close to both everyday amenities and Maine's lakes region, 3 Lieutenants Drive offers an exceptional opportunity to enjoy the very best of Windham living.

3 Lieutenants Dr, Windham

Listing courtesy of Meservier & Associates.

$599,000
4 Beds ⋅ 2 Baths
Set near the end of a quiet cul-de-sac, 23 Tate Lane offers approximately 2,400 square feet of flexible living space on 1.16 acres in a remarkably convenient Windham location. The Cape-style home features four bedrooms, two full baths and an attached two-car garage with direct entry. Inside, the sunny eat-in kitchen connects naturally with comfortable living and dining spaces. One of the home's standout features is the expansive, light-filled bonus room above the garage--ideal as a family room, game room, home office, fitness space or guest area. First-floor laundry, a newer heating system and a full unfinished basement with abundant storage add everyday practicality. Outside, a spacious composite deck overlooks the large, open backyard, where a seasonal stream and small bridge add character to the setting. There is plenty of room to entertain, garden, play or simply relax and enjoy the view. Located nearly across the street from Windham High School and its athletic fields, the property is also just minutes from shopping, restaurants, schools and everyday conveniences. With generous living space, a versatile floor plan and a location that makes daily life easier, 23 Tate Lane is ready for its next chapter.

23 Tate Ln, Windham

Listing courtesy of Keller Williams Realty.

$599,000
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION TO BE BUILT: Experience the best of lakeside living with this stunning new construction opportunity. This thoughtfully designed 3-bedroom, 2-bath home offers modern finishes, open-concept living, and the rare chance to personalize the home to fit your lifestyle. Nestled in a peaceful, scenic setting, the property includes two deeded access points to the lake, making it easy to enjoy swimming, kayaking, fishing, or simply taking in the tranquil waterfront surroundings. Surrounded by nature and nearby trails, this location offers the perfect balance of outdoor recreation and everyday comfort. The home can be customized, with additional options available such as a garage, daylight basement, expanded living space, and other upgrades to create your ideal home. Enjoy the serenity of lake life while remaining just 20 minutes from Portland, offering convenient access to shopping, dining, entertainment, and major commuting routes. Whether you're looking for a year-round residence or a peaceful retreat, this modern new construction home is a unique opportunity to build the lifestyle you've been dreaming of.

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

$579,000
4 Beds ⋅ 3 Baths
Historic circa-1900 farmhouse on 4 acres of fields and forest in a desirable rural Windham location, adjacent to Bumbleroot Organic Farm and minutes to Westbrook and Gorham. Filled with vintage character and potential, the home features abundant custom cabinetry in the kitchen, dining, and office spaces; a separate bedroom suite with soaking tub and walk-in closet; and a sunroom overlooking a fenced garden, open field, and woods. A 1,200-square-foot post-and-beam barn provides outstanding possibilities for a workshop, studio, storage, animals, or hobby use. A rare chance to restore, reimagine, and make this remarkable property your own.

180 Highland Cliff Rd, Windham

Listing courtesy of A Team Realty.

$579,000
2 Baths
Two Family building situated on a 0.69 acre lot. Sewer to be connected at Towns expense in the near future. Many development options for this site.

705 Roosevelt Trl, Windham

Listing courtesy of Allied Real Estate.

$575,000
3 Beds ⋅ 2 Baths
If you've been searching for a prime location and space to entertain, you've found it! Welcome to your own backyard oasis in one of Windham's most desirable areas. Designed for hosting and everyday living, this 3-bedroom, 2-bathroom home features an above ground pool, hot tub, tiki bar, and expansive fenced in outdoor space ready for gatherings all year long. The large concrete pad currently used for grilling, is easily converted to a basketball court providing plenty of room for recreation. A second outbuilding has been transformed into an insulated, heated home gym giving you a dedicated workout space just steps from the house. Inside, you'll find floor to ceiling updates including a large kitchen, oversized living room with sliding glass doors to the backyard, spacious bedrooms, and the private primary bedroom with en-suite bath. The finished lower level adds even more living and entertainment space with your own movie theater, and two bonus rooms currently used for air hockey and poker nights. The spacious two-car garage gives you ample room for vehicles, gear, and storage, and provides direct entry to the living area, and the bar and hot tub. Whether you're enjoying summer by the pool, working out from home, movie nights, football Sundays, or simply looking for more space without sacrificing location, this property delivers a lifestyle that's surely hard to find. Conveniently located for easy access to Portland, Sebago, and the Lakes Region, it's an ideal investment or year-round home for work, play, and everything in between.

483 Falmouth Rd, Windham

Listing courtesy of EXP Realty.

$569,000
4 Beds ⋅ 2 Baths
Opportunity meets versatility at 5 Cliff Drive in Windham. Set on a spacious 1.84-acre lot, in The C3 Zone, this property offers more than 2,000 square feet of living space, a flexible floor plan, and is set up with an ADU (check with the town for specifics) with a tenant already in place. The upper level offers generous living spaces and plenty of opportunity for a new owner to make it their own. While ready for some updating and personal touches, the property's layout, setting, and additional spaces provide an excellent foundation for creating something truly special. A standout feature is the walkout lower-level with a kitchenette and its own bathroom and entrance coupled with separation from the main living areas, this space offers tremendous flexibility for future possibilities; multigenerational living, extended-stay guests, or supplemental income. There's even more potential to explore. Above the attached garage is additional unfinished space that may offer an opportunity for future expansion--perhaps a home office, studio, bonus room, or additional finished space, subject to necessary approvals. For folks looking for a property they can improve and grow into over time, the possibilities here are particularly appealing. Outside, nearly two acres provide room to enjoy the Maine seasons, complemented by established outdoor spaces, stonework, a large deck and patio areas. The attached heated garage and additional outbuilding add valuable storage and functionality. Conveniently located near Windham's shopping, dining, recreation, and everyday amenities, 5 Cliff Drive presents an exciting opportunity for a buyer who sees the possibilities. With acreage, flexible living space, expansion potential, Commercial possibilities, and room to add value, this is a property ready for its new owner!

5 Cliff Dr, Windham

Listing courtesy of Rockstar Real Estate.

$565,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully private and tucked-away retreat, gracefully situated on 1.29 acres of peaceful countryside. Offering 3 spacious bedrooms, 1.5 bathrooms, and a 1-car garage, this charming home provides the perfect blend of comfort, privacy, and convenience. Surrounded by the beauty of a serene rural setting, you can enjoy the tranquility of nature while remaining just moments from public beaches, boat launches, shopping centers, and local restaurants, all while being only 25 minutes from Portland. Outside, you'll find a lovely area ready for your dream garden, along with an existing chicken coop awaiting its next flock, creating the perfect opportunity to embrace a simple and rewarding homestead lifestyle. Whether you're spending a day on the water, enjoying nearby amenities, gathering fresh eggs in the morning, or simply relaxing in your own private oasis, this exceptional property offers the lifestyle you've been searching for.

7 Hall Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$560,000
3 Beds ⋅ 3 Baths
OPEN HOUSE THIS SUNDAY 9/27/26 FROM 11:30 TO 1:00. Don't miss this property with a recent price adjustment. Rarely seen on the market right now, large rooms, attention to details with upgrades AND a standalone condo with a two-car garage and full basement and low monthly fee of $70.00 for common area maintenance and insurance. From the moment you enter, you'll appreciate the bright, open floor plan, quality craftsmanship, and beautiful hardwood flooring that flows throughout both levels of the home. At the heart of the home is an inviting kitchen featuring granite countertops, a spacious center island, stainless steel appliances, and abundant cabinetry--creating the ideal space for everyday living, meal preparation, and entertaining. The kitchen opens into the welcoming living area highlighted by a custom feature wall with a contemporary fireplace, creating stylish space. Exit through the sliding glass doors to a generous deck overlooking a level backyard, offering plenty of room for summer barbecues, morning coffee, or evenings with family and friends. The second level is designed for comfort, featuring an expansive primary suite complete with 2 walk-in closets and a beautifully finished ensuite bath with granite-topped vanity and tile flooring. Two additional generously sized bedrooms, all with hardwood floors, share a full bath. Also located on the second-floor is the laundry room adding to everyday convenience. The full daylight basement presents outstanding possibilities for future finishing, whether you envision a recreation room, fitness area, home office, or additional living space, while still leaving ample room for storage. An attached two-car garage provides additional space for vehicles, tools, and outdoor equipment. Built with efficiency in mind, this home offers the comfort of natural gas heating. This property is ready for you

36 Belvedere Dr, Windham

Listing courtesy of Keller Williams Realty.

$549,000
3 Beds ⋅ 2 Baths
Welcome to 513 Falmouth Rd in Windham, Maine! Move-in ready and freshly refreshed, this 3-bedroom home offers comfort, space, and plenty of storage for today's lifestyle. The interior features fresh new paint, giving the home a clean and inviting feel. Recent updates include new flooring in the primary bedroom, common bathroom, and basement. Outside, enjoy a large, fenced-in backyard with plenty of room for entertaining, gardening, recreation, or simply relaxing. A shed provides additional storage for outdoor equipment and tools. For those needing extra parking, storage, or workspace, this property offers an attached 2-car garage plus a detached 2-car garage, providing an impressive amount of space for vehicles, hobbies, equipment, or a workshop. Located in desirable Windham, this property combines recent updates, generous outdoor space, and exceptional garage capacity. Whether you're a first-time buyer, growing household, or simply looking for a home with room for vehicles and projects, This Home is ready for its next owner! Come see all this home has to offer.

513 Falmouth Rd, Windham

Listing courtesy of The Maine Real Estate Experience.

$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.

$545,000
3 Beds ⋅ 2 Baths
This home sparkles! Immaculate and is ready for it's next owner. Beautiful landscaping, raised bed garden and a private back yard tucked away. in a great neighborhood on the Windham, Raymond town line. Public water, town maintained road and close to shopping. Five minutes from a Big Sebago beach. Open floorplan and great deck off of dining area. Perfect for summer grilling. Newer heat pump to keep things cool on those warmer days and nights.

111 Harvest Hill Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$545,000
3 Beds ⋅ 2 Baths
Seller financing incentive available! With an acceptable offer, seller is willing to contribute up to two points toward a buyer's interest rate buydown. Set on 2.5 acres in a peaceful Windham setting, this three-bedroom, two-full-bath home offers privacy, space, and everyday convenience while remaining close to everything the area has to offer. Built in 2006, the home features a comfortable and functional layout with an open-concept kitchen and dining area flowing into the living room, creating an easy space for everyday living and gathering. A welcoming sitting room provides an additional place to relax, while first-floor laundry adds to the home's practical layout. Outside, there's plenty of space to enjoy the property throughout Maine's seasons. Spend summer days by the pool and cooler evenings relaxing in the hot tub, which conveys with the property. Keep chickens in the existing coop, or take advantage of the additional outbuilding for storage, hobbies, equipment, or projects. Mature raspberry and blackberry bushes offer seasonal berries right from the yard, while a beautiful magnolia tree, lilacs, and an Oriental apple tree add established character and seasonal color to the property. With 2.5 acres and only two neighboring homes along the road, the property offers a sense of privacy without feeling isolated. Located just off Falmouth Road, the home strikes a great balance between a quieter setting and convenient access to town. Windham's shopping, restaurants, and everyday amenities are just a short drive away, while Portland is also within easy reach. With acreage, privacy, a pool, hot tub, useful outbuildings, and a convenient location, this property offers plenty of opportunity to make it your own.

7 Mancini Rd, Windham

Listing courtesy of Landing Real Estate.

$529,000
3 Beds ⋅ 3 Baths
Welcome to 1 Morgan Ln, a charming 3-bedroom, 2-bath home set on nearly 2 private acres in Windham. The home is thoughtfully laid out for convenient first-floor living, offering ease and functionality for everyday life. Enjoy the space and privacy of a generous lot while still being conveniently located for an easy commute to Portland and surrounding areas. A wonderful opportunity to enjoy peaceful living with the convenience of nearby amenities.

1 Morgan Ln, Windham

Listing courtesy of Tim Dunham Realty. 207-729-7297
$525,000
The business currently at the location is not for sale, just the building and the grounds. The current tenant has a lease expiring on 7-1-2027 which will be transferred to the new owner. The monthly lease payment is $2500, triple net. Situated in a high traffic area with unmatched visibility. Make this location the home for your new business or franchise.

14 Heathwood Dr, Windham

Listing courtesy of Big Bear Real Estate Company.

$523,999
4 Beds ⋅ 2 Baths
Welcome to this beautifully maintained, move-in ready home in a highly desirable Windham location. Set back from the road with a spacious driveway, oversized two-car garage, and private backyard, this property combines comfort, privacy, and convenience. The recently renovated kitchen flows seamlessly into the updated living room, creating a bright and inviting space for everyday living and entertaining. Fresh paint throughout enhances the clean, modern feel, while the brand-new laundry room adds both style and functionality. With 3-4 bedrooms and two full bathrooms, the flexible floor plan provides a variety of possibilities, including guest accommodations, a home office, hobby space, or additional living areas. Natural gas and public water add to the convenience of ownership. Outside, enjoy the privacy of the backyard along with a generous driveway providing ample parking for multiple vehicles or recreational equipment. Located just minutes from Sebago Lake, local beaches, boating, hiking trails, shopping, dining, and everything the Windham area and the Lakes Region have to enjoy, this home features thoughtful updates, a functional layout, and an exceptional location. Don't miss the opportunity to make this beautifully updated property your next home.

214 Tandberg Trl, Windham

Listing courtesy of Maine Real Estate Co.

$520,000
4 Beds ⋅ 2 Baths
Welcome home to this spacious 4-bedroom, 1.5-bath residence with over 2,000 square feet of living space and plenty of room to accommodate today's lifestyle. With traditional living spaces, a comfortable layout, and generous room sizes, this home provides an inviting backdrop for both everyday living and entertaining. The main living areas give a classic feel with plenty of flexibility for formal gatherings, relaxed evenings, a home office, or additional living space. Four well-proportioned bedrooms provide room for family, guests, hobbies, or work-from-home needs, while the 1.5 baths add convenience to the thoughtful floor plan. One of the highlights of the property is the expansive backyard. Step out onto the back deck and enjoy views of the pool and spacious yard, creating a wonderful setting for summer entertaining, outdoor meals, weekend gatherings, or quiet afternoons at home. The generous outdoor space offers endless possibilities for recreation, gardening, and enjoying time outdoors. Conveniently located near local shopping and dining, this home makes it easy to enjoy nearby amenities while still offering a private and spacious retreat. If you're looking for a home with room to grow, inviting traditional living spaces, and an exceptional backyard setting, this property is ready to welcome you home.

15 Gromble Way, Windham

Listing courtesy of Maine Real Estate Co.

$520,000
3 Beds ⋅ 2 Baths
Welcome to this adorable Colonial offering 3 bedrooms, 1.5 baths and a bright, open concept with 9' high ceilings. Recent updates include all new windows and doors, flooring on 1st level and 2nd floor hallway and a Vermont Casting woodstove for an additional source of heat. Enjoy the seasonal views of the Western Mountains and amazing sunsets from your front windows or sitting outside in your Adirondack chairs sipping your morning coffee. You will understand why its named, ''Harvest'' Hill Rd on this natural piece of property with the likes of strawberries, blackberries, blueberries, witch hazel and mint! Located in Sebago Heights, one of Windham's most desirable neighborhoods, this home is 5 minutes to both Little Sebago Lake and Big Sebago Lake boat launches and a quick walk or bike ride to the private beachfront of Tassel Top on Sebago Lake. The shops and grocery stores are 7 minutes away as well as minutes from Chipman's Farm Stand and Good Life Market! You are nestled away, yet 20 minutes from the Maine Turnpike, 30 minutes to downtown Portland (South) and 45 min - 1 hr (North) from Pleasant Mountain and Sunday River Ski Resort. Don't miss out on this little piece of heaven and check it out with a private tour today! Seller is willing to give concessions to Buyer at closing.

104 Harvest Hill Rd, Windham

Listing courtesy of www.HomeZu.com. 877-249-5478
$510,000
3 Beds ⋅ 3 Baths
This brand new Cottonwood Colonial home offers a blend of thoughtfully designed living spaces set in a peaceful neighborhood just minutes from local amenities. Enjoy the sunny exposure and spacious open floor plan. The kitchen features quartz countertops, a center island, and new appliances. The first floor also offers a functional mudroom and a great back deck. Upstairs includes a primary suite with walk-in closet, two additional bedrooms, a second full bathroom, and laundry hook-ups. 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!

2 Shepherd Ln Unit 1, Windham

Listing courtesy of RE/MAX By The Bay.

$500,000
3 Beds ⋅ 2 Baths
BIG SKY VIEWS. FRESH DESIGN. Maine Living at its best! This light filled 3-bed Windham home delivers the space, style, and a setting you have been waiting for. The crisp interior features a striking kitchen with white cabinetry, stainless steel appliances, granite counters, and an open flow into the dining and living areas. Bright bedrooms, modern baths, 1st floor laundry, and warm wood floors make everyday living feel effortless. Full basement offers plenty of storgae space. Spend hours on a welcoming covered porch or rear deck, and take in the peaceful surroundings. Enjoy Highland Lake and Sebago Lake adventures, local trails, dining, and easy access to Portland. Schedule a private tour or join us at one of the Open Houses. Open House 1: Wednesday 9/23 @ 4:30-6pm Open House 2: Sunday 9/27 @ 10-11:30am

4 Captain Thomas Dr, Windham

Listing courtesy of Real Broker. 207-317-6464
$499,900
3 Beds ⋅ 1 Baths
Offered for the first time in over 30 years, this charming 3 bedroom, 1 bathroom home with 1,331 square feet of living space sits on a private 0.41 acre lot tucked away on a quiet dead end road. Surrounded by mature greenery, fruit trees, and flowering shrubs, the setting provides a peaceful retreat with classic curb appeal highlighted by a red cedar shake exterior and a circular style paved driveway offering ample parking. Inside, the bright living area features original hardwood floors, abundant natural light, and a cozy brick fireplace that adds warmth and character. The home extends its living space outdoors with an expansive elevated rear deck spanning the width of the house, ideal for dining and entertaining, along with a covered lower level walkout patio perfect for relaxing in the shade. The finished lower level includes a spacious recreation room with wood paneling, ideal for a game room or home theater, and comes complete with a pool table. A dedicated workshop area offers built in benches, cabinetry, and pegboard storage, making it perfect for hobbies or projects. Enjoy deeded lake access just across the road via a shared right of way, offering easy opportunities for swimming, boating, and enjoying summer days by the water. This estate sale is being sold as is, presenting a wonderful opportunity to make this well loved home your own.

29 Lake Ave, Windham

Listing courtesy of Redfin Corporation.

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

22 Montgomery Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$499,000
3 Beds ⋅ 2 Baths
Welcome to this well-maintained 3-bedroom, 1.5-bath home nestled on over 2 acres in a quiet Windham neighborhood, yet conveniently located close to all that the area has to provide. The home features a spacious two-car garage beneath the two-story residence. Step inside to a generous open-concept living, kitchen, and dining area, creating a comfortable space for everyday living and entertaining. Just off the main living area are a full bathroom, separate laundry area, and first-floor bedroom. From the kitchen, step out onto the large back deck and enjoy the peaceful natural setting and surrounding woods. Upstairs, you'll find two generously sized bedrooms and a convenient half bath. Outside, enjoy the privacy of over 2 acres, with quiet roads for leisurely walks and trails throughout the property. A wonderful location just minutes from in-town Windham and approximately 20 minutes to Westbrook. Don't miss the opportunity to make this peaceful property your new home! Open house Thursday, September 24th from 4:00 pm - 6:00 pm!

29 Riverside Rdg, Windham

Listing courtesy of Signature Homes Real Estate Group.

$499,000
3 Beds ⋅ 3 Baths
Brand New Home with ROW access to Highland Lake! Experience Maine living in this move-in-ready custom home set on .47 acres. Offering 1,664 sq. ft., 3 bedrooms, and 2.5 baths. The thoughtfully designed floor plan features a first-floor primary suite with walk-in closet and en-suite bath with tiled shower. The beautifully appointed kitchen showcases an oversized island with quartz countertops, while first-floor laundry adds everyday convenience. All three Bedrooms have walk-in closets for plenty of storage. Step outside to an extra-large deck, perfect for entertaining, summer gatherings, and relaxing while enjoying the Maine outdoors. Modern craftsmanship, refined finishes, and easy access to Highland Lake create the perfect setting for elevated four-season lake living. Taxes shown are land only, TBD, call town of Windham. **Directions are tricky with GPS- Be sure to come down Albion Rd to Swan Rd, Vista Dr, to Birdsong- other routes will take you on rough roads ****Be sure to see interior tour video!- https://youtu.be/T_KmdYtGVFM

16 Birdsong Ln, Windham

Listing courtesy of RE/MAX Coastal.

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