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$515,000
2 Beds ⋅ 1 Baths
Welcome to Collins Pond Cottage -- a private, character-filled year-round waterfront retreat offering 150 feet of frontage on scenic Collins Pond. This charming 2-bedroom, 1,275 sq ft cottage captures the very best of Maine lake living, where mornings begin with coffee on the private dock as eagles soar overhead and evenings are spent gathered around the stunning stone fireplace on the expansive waterside deck. Inside, warm wood finishes and natural light create an inviting atmosphere throughout the open-concept living space. Thoughtfully designed to showcase the beauty of the waterfront setting, the home features a galley-style kitchen with a gas stove and a spacious living room highlighted by a dramatic wall of windows overlooking the pond and a cozy gas fireplace. A newly renovated bathroom with a luxury shower completes the main level. Upstairs, the waterfront primary bedroom offers its own private balcony -- the perfect spot to start or end the day surrounded by peaceful water views. A second bedroom/den provides flexible space for guests, a home office, or quiet retreat. Outdoor enthusiasts will love the endless four-season recreation right from the property, including kayaking, canoeing, sailing, paddleboarding, fishing, ice fishing, and skating. Hiking, biking, and skiing are all nearby, making this an ideal getaway or full-time residence year-round. Conveniently located just 5 minutes from North Windham, you'll enjoy easy access to shopping, restaurants, and local attractions, while vibrant Portland is only 30 minutes away with its renowned dining scene, local breweries, arts, shopping, Casco Bay access, and iconic working waterfront. The property has also been enjoyed as a successful Airbnb with a strong rental history and 98- 5-star reviews, offering exceptional investment potential alongside unforgettable personal enjoyment. Open House Saturday, May 9th, 12-2pm

42 Emerson Dr, Windham

Listing courtesy of The Maine Real Estate Group.

Selling Office: Samonas Realty.

$510,000
4 Beds ⋅ 2 Baths
Set on a dead-end road, this well-cared-for 4-bedroom, 2-bath home combines character, comfort, and versatility. Unique built-ins provide both charm and functionality, while the inviting layout offers space for a variety of needs. Step outside to enjoy the yard and patio, creating opportunities for outdoor entertaining, recreation, or relaxation. A custom-built shed offers excellent storage for tools, equipment, and seasonal items. A special property with distinctive features and lasting appeal. Open house Saturday 6/6 11am-1pm

2 Homestead Ln, Windham

Listing courtesy of Duston Leddy Real Estate.

Selling Office: A Team Realty.

$510,000
3 Beds ⋅ 3 Baths
Lots to see in this beautiful, well maintained 3 Bedroom, 2.5 bath home which boasts 2252 sf of living space, including a huge Bonus Room above the garage. The home sits on 1.87 acres of land. This home offers plenty of privacy on a private road yet is just 5 minutes from North Windham, shopping and many restaurants. The home has a New Roof (2021) and an Entire House Stand by Generator. The home also offers direct access to several walking trails including trails leading to Donnabeth Lippman Park, Chaffin Pond and the Little Sebago Lake Boat Launch. Open House Sunday July 27 11:00-1:00

20 Cameron Ln, Windham

Listing courtesy of Cumberland County Realty.

Selling Office: Coldwell Banker Realty.

$510,000
3 Beds ⋅ 2 Baths
Welcome to 91 Vista Drive in Windham, a well-maintained Highland Lake property offering water views and not one, but two deeded rights of way to the lake. Ideally situated one back from the water, this home gives you the best of lake living without the waterfront taxes. The sellers have meticulously cared for and thoughtfully improved the property over the years. In 2014, the home was lifted and a full partially finished basement was added, creating excellent bonus space, storage, and flexibility. In 2020, a spacious primary suite addition was completed featuring an en suite bath and walk-in closet. Enjoy entertaining on the large composite deck just off the living room, perfect for gatherings with family and friends. Additional improvements include a gutter system with French drains running beneath the paved driveway into the drainage ditch for added water management peace of mind, as well as a fresh air return system designed to provide pristine indoor air quality throughout the home. The pellet stove provides an extremely energy-efficient primary heat source, helping keep utilities low during Maine winters. Situated on a generously sized former double lot with ample yard space for pets, recreation, or gardening. An attached one-bay garage provides excellent storage for a boat, convertible, or lake toys. Conveniently located just minutes from North Windham amenities, including restaurants, shopping, grocery stores, coffee shops, and easy access to Portland, this home offers the perfect balance of lake life and everyday convenience. Whether you are looking for a year-round residence or a seasonal getaway, this Highland Lake home offers comfort, functionality, and access to one of Windham's most desirable lakes.

91 Vista Dr, Windham

Listing courtesy of Keller Williams Realty.

Selling Office: RE/MAX Shoreline.

$510,000
3 Beds ⋅ 3 Baths
This brand new 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. Move right in and make your dream of owning a brand new home come true!

12 Shepherd Ln Unit 6, Windham

Listing courtesy of RE/MAX By The Bay.

Selling Office: Sebago to the Sea Realty LLC.

$505,000
3 Beds ⋅ 1 Baths
Enjoy the ease of single-level living in this well-maintained 3-bedroom ranch-style home in a convenient Windham location! Built in 2016, this property offers modern comfort and thoughtful design throughout. Step inside to an inviting open-concept layout featuring beautiful wood floors that flow seamlessly through the kitchen, dining, and living areas - perfect for both everyday living and entertaining. The updated kitchen serves as the heart of the home, offering both style and functionality. Stay cool in the summer and warm all winter long with efficient heat pumps for heating and cooling - plus backup propane heat - the best of both worlds in Maine! The large daylight, walk-out basement presents excellent potential for future expansion - ideal for a home office, gym, recreation space, workspace or future living space! Outside, enjoy a nicely maintained yard and great sense of neighborhood living. An automatic generator provides added peace of mind in all seasons. Discover this fantastic location close to Windham's lakes and just a short drive to Portland. Seller will review all offers Friday April 3 at 3:00 PM

10 Twoey Dr, Windham

Listing courtesy of Demetria Real Estate.

Selling Office: Keller Williams Realty.

$502,500
4 Beds ⋅ 3 Baths
Welcome to 19 Moss Road, a completely remodeled four bedroom, three bathroom home complete with a two car garage, office space, and large family room. Here, you will enjoy your privacy and quiet on more than two acres, with plenty of space to entertain and enjoy the outdoors. The home is conveniently located not far from motorsports trails and public lake access on Sebago Lake and others. And there is more space than meets the eye - this home has ample space that can fit a variety of needs, with the convenience of a first-floor bedroom and first-floor bathroom, plus plenty of space for working from home, hobbies, or entertaining. The home features a primary bedroom with an in-suite bathroom, a large family room on the second floor, as well as an office space on the first floor. The home is conveniently located fifteen minutes from the center of Windham, and twenty minutes from exit 48 of I-95. You will be close to city and town conveniences but also enjoy your privacy as this home is at the very end of the road on 2.5 forested acres.

19 Moss Rd, Windham

Listing courtesy of Coldwell Banker Realty. 207-967-9900

Selling Office: NextHome NorthEast Realty.

$500,000
2 Baths
Low maintenance and income producing, this well maintained 2 unit property offers a smart addition to any investment portfolio, or a great opportunity to owner occupy and offset your mortgage with rental income. Recent upgrades include conversion to natural gas with a new boiler installed in 2023, along with a durable metal roof, updated siding for easy long term upkeep, and heat pumps in both units for efficient heating and cooling. The property features a 1 bedroom 1 bath unit and a 2 bedroom 1 bath unit, providing flexibility for both investors and owner occupants. Ideally located with convenient access to local amenities and an easy commute to Portland, this is a turnkey opportunity in a desirable Windham location. Also listed as Residential MLS #1659671

8 Lamb St, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Home At Last Realty.

$500,000
3 Beds ⋅ 2 Baths
If you're looking for a cozy Cape-style home, look no further! This charming property offers 2,334 sq. ft. of living space, including 633 sq. ft. in a daylight walk-out basement, perfect for additional living, recreation, or guest space. The home features 3 bedrooms and 1.5 baths, providing a comfortable and functional layout. A detached heated two-car garage includes unfinished space above, offering great potential for future expansion such as a studio, home office or game room, with access via an exterior rear stairway. Enjoy outdoor living with a spacious 20' x 16' deck overlooking the backyard, ideal for entertaining and family gatherings, or relax on the 20' x 8' covered porch, perfect for enjoying the outdoors in any weather. Two additional sheds provide ample storage space for tools, equipment, or seasonal items. Conveniently located just 10 minutes from Westbrook, Gorham, and North Windham, and only 20 minutes to the Portland Jetport, this home offers both comfort and accessibility. Don't miss the opportunity to make this wonderful property your new home!

26 Depot St, Windham

Listing courtesy of RE/MAX Shoreline.

Selling Office: Excellence Realty.

$499,900
3 Beds ⋅ 2 Baths
Welcome to 20 Shepherd Lane, a newly completed home offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

20 Shepherd Ln, Windham

Listing courtesy of RE/MAX By The Bay.

Selling Office: Legacy Properties Sotheby's International Realty.

$499,000
2 Beds ⋅ 3 Baths
Rare Sebago Lakefront Property! Don't miss this rare opportunity to own a beachfront home on the shores of stunning Sebago Lake with approximately 300 feet of private, sandy shoreline. This exceptional property offers breathtaking sunsets and panoramic views of Sebago Lake and Mount Washington. The home offers an updated kitchen with brand-new stainless steel appliances, modern cabinets and solid surface counter tops. Refreshed bathrooms feature modern vanities, fixtures, walk-in shower and tub/shower enclosure. Two large bedrooms with ensuite baths provide plenty of space, comfort and convenience. Additional interior improvements include new flooring, fresh paint, and updated lighting throughout, creating a comfortable blend of modern finishes and classic lakeside charm. Enjoy easy access to private community amenities including tennis, basketball, and pickleball courts, along with an expansive dock and a deeded mooring, ideal for boating, swimming, kayaking, and fishing. Year-round enjoyment continues through the winter months with ice fishing, snowshoeing, snowmobiling and peaceful lakefront living. Conveniently located near Windham Center, Point Sebago Golf Resort, area ski resorts, and just a short drive to Portland's Old Port and the Maine coastline. This property is well suited for year-round residence, seasonal getaways, or investment opportunity. Strong association finances have kept fees flat for the past three years and cover more than most associations, including exterior building maintenance, roofs, siding, water, septic, trash removal, plowing/shoveling, lawn care, dock, and tennis court, with no added assessments for over 10 years. Come experience all that this Sebago Lake community has to offer!

1112 Roosevelt Trl Unit 8, Windham

Listing courtesy of Keller Williams Realty.

Selling Office: Breakwater Realty Group, LLC.

$496,350
3 Beds ⋅ 3 Baths
Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from currently under construction.

4 Dolley Farm Rd Unit 2, Windham

Listing courtesy of The Flaherty Group.

Selling Office: Coldwell Banker Realty.

$495,000
3 Beds ⋅ 2 Baths
Move right in! Set on a peaceful, wooded lot, 8 Environmental Way offers the perfect balance of privacy and convenience, just 30 minutes from downtown Portland. Thoughtful updates, including a new roof and whole-house generator, provide peace of mind, while deer, birdsong, and surrounding nature create your own private retreat just minutes from shopping, restaurants, schools, and Sebago Lake recreation. Inside, the three-level layout is both functional and inviting. The open kitchen, dining, and family room flow seamlessly together, highlighted by a cozy propane stove and views of the natural landscape. Upstairs are three bedrooms, including a spacious primary suite with two closets and a private bath, plus a second full bathroom. The finished lower level offers flexible space for a media room, home office, gym, or playroom. Storage is abundant with a double-door pantry, generous closets throughout, and a large two-car garage. For added confidence, a pre-listing home inspection has been completed, and a past water test report will be available to interested buyers.

8 Environmental Way, Windham

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com

Selling Office: Maine Real Estate Experts.

$494,900
3 Beds ⋅ 2 Baths
Welcome to 9 Shepherd Lane, a newly completed home offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Move right in and make your dream of owning a brand new home come true!

9 Shepherd Ln Unit 13, Windham

Listing courtesy of RE/MAX By The Bay.

Selling Office: Allied Real Estate.

$490,000
2 Beds ⋅ 2 Baths
This ranch style home is the only stand alone condo presently available in Windham. Built in 2018, it still has that brand new feeling. Aquatic Way is conveniently located just south of the North Windham strip, close to all the shopping and recreational activities offered by the Sebago Lake region, and an easy commute into Greater Portland. This ranch style condo offers single floor living with 1240sqft of comfort, an open floor plan, featuring a fully applianced kitchen with high end finishes, a living room, two large bedrooms, two baths, a laundry and lots of storage space. Large windows provide for a lot of light and wonderful views of the brook and wildlife. (Including two eagles who have made this area their home as well). Not enough?? This condo also has an additional 750sqft finished in the walkout basement. It is presently used as an office and a game room, but ready for your ideas! The condo is heated by clean and efficient natural gas, but also has Heat Pumps for cooling and alternative heat. The home also has an attached garage with direct entry to the living area.

7 Aquatic Way Unit 7, Windham

Listing courtesy of Plowman Realty Group.

Selling Office: Landing Real Estate.

$490,000
4 Beds ⋅ 2 Baths
Welcome to this freshly updated Cape-style home conveniently located in Windham. Step inside to find a bright and modern interior featuring a brand-new kitchen with stainless steel appliances, quartz countertops, and updated cabinetry — perfect for cooking and entertaining. This spacious home offers four bedrooms and one and a half baths, providing flexibility for families, guests, or a home office. The flowing layout combines charm and functionality with fresh finishes throughout. Move-in ready and beautifully refreshed, this home is ready for its next chapter. Don't miss your chance to make it yours!

39 Varney Mill Rd, Windham

Listing courtesy of Maine Real Estate Experts.

Selling Office: RE/MAX Shoreline.

$487,500
3 Beds ⋅ 3 Baths
Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from currently under construction.

24 Dolley Farm Rd Unit 11, Windham

Listing courtesy of The Flaherty Group.

Selling Office: King + Miller Real Estate.

$487,500
3 Beds ⋅ 3 Baths
Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Harvest style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear deck extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunset -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities.

16 Dolley Farm Rd Unit 7, Windham

Listing courtesy of The Flaherty Group.

Selling Office: Hearth & Key Realty.

$485,000
4 Beds ⋅ 2 Baths
Welcome to your private retreat! This charming 3-bedroom, 1-bathroom ranch has been renovated with a brand-new interior! Nestled on a quiet, dead-end street surrounded by woods, this home offers tranquility and privacy. The daylight basement includes a spacious 1-bedroom in-law apartment, perfect for guests or rental income, while also having space still available to finish. Experience the best of both worlds - modern updates and a serene natural setting. Explore the easily accessible walking tails, or the convenience of the great restaurants all within minutes of your front door.

7 Primer Way, Windham

Listing courtesy of Plowman Realty Group.

Selling Office: Landing Real Estate.

$485,000
2 Beds ⋅ 1 Baths
This home is nestled in a peaceful Highland Lake community. Bathed in sunlight with direct water views from the deck and access to the shared neighborhood ROW, this inviting property offers the perfect balance of comfort, sensibility, and access to year-round recreation. Inside you will find an open cathedral ceiling in the main space, and a welcoming interior filled with natural sunlight spilling from several windows and skylights. The home's layout is thoughtfully designed, offering wide doors on the entry level to store larger items or to use the basement as a workshop. There is a seamless flow between the kitchen, dining, and living spaces. Outside, notice the Solar Panels that gather the suns energy, which translates to an incredilbly low electric bill! Set on a level corner lot, with a firepit, shed and garden, this home sits steps away from the Lake. Imagine morning coffee on the deck breathng in the fresh Maine air, or afternoon kayak ride or a refreshing swim. Spend your evenings unwinding under the stars. This home has a 3 bedroom Septic system, for future expansion possibilities. This house has an unexpected surprize in that it has Public Water. Heat pumps and a woodstove heat the home very comfortably as it is well insulated. Energy expenses are low because of the Solar panels. (Solar Panels are leased) The Lowell Preserve with miles of hiking and biking trails is a half a mile from this home. Shopping, and dining are close by, but not at the expense of tranquility. Exit 53 in Falmouth is just 10 minutes away, making this East Windham home an easy commute to Falmouth and Portland. Whether you're looking for a year-round residence, a vacation getaway, or an investment opportunity, 54 Lower Beach Road is a place where lasting memories are made. Pre-listing inspection report available.

54 Lower Beach Rd, Windham

Listing courtesy of Rockstar Real Estate.

Selling Office: Maine Real Estate Co.

$484,000
3 Beds ⋅ 3 Baths
Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from currently under construction.

22 Dolley Farm Rd Unit 10, Windham

Listing courtesy of The Flaherty Group.

Selling Office: Tim Dunham Realty.

$481,000
3 Beds ⋅ 3 Baths
Now Building!! Be in this Spring. Dolley Farm, Windham's NEWEST condominium community offering modern design in a peaceful, thoughtfully planned setting with shared open space and a neighborhood playground. The Sunrise style townhouse features a well-designed open floor plan ideal for today's lifestyle. The spacious kitchen includes a center island and pantry and flows seamlessly into the dining and living areas--perfect for everyday living and entertaining. A rear patio extends your living space outdoors, ideal for summer meals, grilling, or relaxing with a good book. Upstairs, the primary suite offers a private retreat with an en-suite bath. Two additional bedrooms and a second full bath provide flexibility for guests or family. A second-floor flex space creates the perfect spot for a desk, reading nook, or study area, and the second-level laundry room adds everyday convenience. The full unfinished basement offers generous storage and the opportunity to create additional finished space for a future family room, gym, or flex area. Dolley Farm offers two distinct floor plans -- the Harvest and the Sunrise -- allowing buyers to choose the layout that best fits their needs. With early summer occupancy available, you can settle in and enjoy the season right away. Ideally located with easy access to Windham Center, Westbrook, and Portland, Dolley Farm combines neighborhood living with everyday convenience in one of Southern Maine's most desirable communities. Several other units to choose from currently under construction.

18 Dolley Farm Rd Unit 8, Windham

Listing courtesy of The Flaherty Group.

Selling Office: Coastal Pine Real Estate, LLC.

$480,000
3 Beds ⋅ 2 Baths
Contemporary chalet with open-concept living. Offering a perfect blend of style, comfort, and convenience. This 3-bedroom, 2-bath home boasts soaring cathedral ceilings and an airy, sun-filled living space that invites you to relax and entertain with ease. The second-floor primary suite features its own private bath, creating a peaceful retreat, while the spacious family room provides plenty of space for gatherings. Set on 1.35 acres, the property is framed by lush green lawns, charming rock walls, and vibrant gardens that create a picturesque New England backdrop. Located near the Windham/Westbrook line, you'll enjoy easy access to local shops, dining, and commuting routes—while still feeling tucked away in your own private oasis. Whether you're seeking a year-round residence or a stylish getaway, this home delivers the perfect combination of modern comfort and natural beauty.

1 Alweber Rd, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: NextHome Experience.

$479,800
3 Beds ⋅ 2 Baths
Tastefully updated, move in ready split level that sits way back from Tandberg Trail. The home has everything buyers are looking for: 3/4 bedrooms with two full baths and an oversized two car garage. Natural gas and public water add to the convivence of owning this well cared for home. There is a private back yard, yet the home is close to everything Windham and the lakes region has to offer. Open House 8/30 10am -12pm

214 Tandberg Trl, Windham

Listing courtesy of NextHome NorthEast Realty.

Selling Office: Maine Real Estate Co.

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

8 Dolley Farm Rd Unit 4, Windham

Listing courtesy of The Flaherty Group.

Selling Office: FIV Realty Co Maine, LLC.

$476,000
3 Beds ⋅ 2 Baths
Welcome to your own private slice of Maine paradise! Nestled on 11.71 acres of pristine, wooded land in desirable Windham, this stunning log cabin offers the perfect blend of rustic charm and modern convenience. Step inside this beautifully maintained 3-bedroom, 2-full-bath home and be captivated by the timeless appeal of log cabin construction. The interior has been tastefully updated and features a fresh coat of paint on the exterior, ensuring a warm and inviting atmosphere from the moment you arrive. The true magic of this property lies in its connection to the outdoors. A massive wrap-around deck provides an ideal space for entertaining, enjoying your morning coffee, or simply soaking in the serene natural surroundings. The front of the home also boasts a charming covered porch, perfect for relaxing on a summer evening. The deck is thoughtfully designed and ready for your above-ground pool installation, making it a breeze to create your own personal oasis. This is more than just a home; it's a lifestyle. While you'll feel miles away from the hustle and bustle, you're only minutes from everything you need. Enjoy easy access to major routes including I-95 and I-295, putting you within a short drive of Portland, Brunswick, and Windham. Explore the natural beauty of the area with Sebago Lake and countless hiking trails just a stone's throw away. Plus, you're never far from shopping, dining, and all the amenities you desire. This is a rare opportunity to own a private nature retreat that's still close to it all. Don't miss your chance to experience the best of Maine living. Schedule your private showing today! Showings start Friday 8/21/2025 at 8:00 am.

31 Snowy Ridge Rd, Windham

Listing courtesy of CENTURY 21 Advantage.

Selling Office: Keller Williams Realty.

$475,000
3 Beds ⋅ 1 Baths
A must see! Set on a level, fenced corner lot with mature landscaping, this charming three-bedroom Cape offers a warm blend of comfort and New England character. The bright kitchen—featuring a new stovetop and refrigerator—opens to a sunny dining area and an inviting living room just around the corner. A first-floor bedroom, two spacious upstairs bedrooms, and a cozy nook for work or reading provide flexible living options, while an additional family room on the entry level adds versatility. Classic cedar shakes, hardwood floors, and vinyl windows enhance the home's timeless appeal. Step outside to a freshly painted deck overlooking a private, tree-lined yard—perfect for gatherings or quiet mornings. A walk-out bonus room, storage area, and attached garage complete the package. Ideally located just 10 minutes from Sebago Lake and under an hour from Maine's ski country, the home offers four-season recreation close to schools, shops, gyms, and the scenic trails of Brookhaven and Ditch Brook.

16 Brookhaven Dr, Windham

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com

Selling Office: Saco Valley Real Estate.

$475,000
3 Beds ⋅ 2 Baths
Welcome to this inviting 3-bedroom ranch in Windham, offering the perfect combination of comfortable one-level living and access to one of the area's hidden gems. Enjoy deeded water access to beautiful Pettingill Pond, where you can spend your days kayaking, fishing, swimming, or simply taking in the peaceful surroundings.

11 Bates Ln, Windham

Listing courtesy of Town & Shore Real Estate. 207-773-0262

Selling Office: Maine Real Estate Co.

$475,000
3 Beds ⋅ 2 Baths
Welcome to 37 Dakota Drive in Windham, a beautifully updated and renovated 3 to 4 bedroom home tucked into a quiet neighborhood setting while still being just minutes to all that Windham has to provide . This move in ready property combines comfort, style, and functionality with thoughtful improvements throughout. Inside, you will find a bright and inviting layout featuring updated finishes, refreshed living spaces, and a warm, comfortable feel from the moment you walk through the door. The flexible floor plan offers the potential for 3 to 4 bedrooms, making it ideal for growing families, guests, a home office, or additional living space needs. The kitchen offers great flow for everyday living and entertaining, while the spacious rooms throughout the home provide both comfort and versatility. The home sits on a nicely sized lot with a private backyard surrounded by trees, creating a peaceful outdoor setting to relax, entertain, or enjoy Maine's seasons. A large deck overlooks the backyard space, and the daylight lower level offers excellent potential for additional finished living area, recreation space, or storage. Located in a desirable Windham neighborhood, 37 Dakota Drive offers the perfect balance of privacy and convenience with nearby shopping, restaurants, schools, lakes, and easy access to Portland. If you have been searching for an updated home that has been well cared for and is truly move in ready, this is one you will not want to miss.

37 Dakota Dr, Windham

Listing courtesy of Benchmark Real Estate.

Selling Office: EXP 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!

32 Dolley Farm Rd Unit 14, Windham

Listing courtesy of The Flaherty Group.

Selling Office: Coastal Pine Real Estate, LLC.

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