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$489,000
3 Beds ⋅ 2 Baths
Full of classic New England charm, this 3-bedroom home offers generous living space and a flexible floor plan on a .46 acre corner lot. The updated kitchen features a large center island, new appliances, ample cabinet space, and an inviting layout for everyday living. Original hardwood floors, fireplaces, built-ins, exposed beams, and other period details add warmth and character throughout. Recent improvements include all new windows, updated electrical, freshly paved driveway and new leach field, providing peace of mind while preserving the home's historic appeal. Multiple living and dining areas provide room to gather, work, or relax, and the attached two-car garage adds everyday convenience. Located close to shopping, restaurants, and outdoor recreation, this home offers the space, character, and flexibility to suit a variety of lifestyles.

1 Marigold Ln, Windham

Listing courtesy of RE/MAX By The Bay.

$484,000
3 Beds ⋅ 3 Baths
Move in Ready! Come see why so many have chosen Dolley Farm Condominiums for their new home! 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, while a rear patio extends your living space outdoors. 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. With completed units available, you can settle in and enjoy now! Pet friendly and short walk to Sebago to Sea trail and Shaw Park!

26 Dolley Farm Rd Unit 12, Windham

Listing courtesy of The Flaherty Group.

$479,900
3 Beds ⋅ 2 Baths
Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$479,900
3 Beds ⋅ 2 Baths
Welcome to 6 Shepherd Lane, offering a blend of classic charm and modern convenience. This sun-drenched Cape-style residence features 3 bedrooms, 2 full baths, and over 1,600 square feet of thoughtfully designed living space, set in a peaceful neighborhood just minutes from local amenities. Step onto the inviting farmer's porch and into a bright, open-concept first floor where the living, dining, and kitchen areas flow seamlessly together. The kitchen features quartz countertops, a center island with excellent drawer storage, and new appliances. The first floor also offers a flexible den or office, a full bath, laundry hookup, and a functional mudroom entry. Upstairs includes three bedrooms, including a spacious primary with a walk-in closet, along with a second full bath. Enjoy wooded views from the back deck, while the full daylight basement provides great potential for storage, hobbies, or future finishing. A walking trail at the end of the street adds to the quiet setting. Conveniently located near shopping, town services, and recreational opportunities, this home offers both comfort and accessibility. Make your dream of owning a brand new home come true!

6 Shepherd Ln Unit 3, Windham

Listing courtesy of RE/MAX By The Bay.

$479,000
3 Beds ⋅ 3 Baths
Come see why so many have chosen Dolley Farm Condominiums for their new home! 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, while a rear patio extends your living space outdoors. 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. With completed units available, you can settle in and enjoy now! Pet friendly and short walk to Sebago to Sea trail and Shaw Park!

6 Dolley Farm Rd Unit 3, Windham

Listing courtesy of The Flaherty Group.

$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.

$474,000
3 Beds ⋅ 3 Baths
"Come see why so many have chosen Dolley Farm Condominiums for their new home! 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, while a rear patio extends your living space outdoors. 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. With completed units available, you can settle in and enjoy now! Pet friendly!"

1 Dolley Farm Rd Unit 15, Windham

Listing courtesy of The Flaherty Group.

$465,000
3 Beds ⋅ 2 Baths
Welcome to 129 Forbes Lane! Set on nearly half an acre in an established Windham neighborhood, this classic and well built Cape offers a 1st floor bonus room which was designed as a primary bedroom and 3 second level bedrooms! 2 full bathrooms have been beautifully updated recently, and approximately 1,888 square feet of living space on the 1st and 2nd floor with room to expand. A full bathroom on both the first and second levels provides added convenience and flexibility. Inside, there is hardwood flooring and a gas fireplace, a wood burning stove in the partially finished basement to add warmth and character. This traditional floor plan offers plenty of room to make the home your own. Additional features include a large and bright vaulted ceiling sun room with radiant flooring and it's own wood burning stove, attached oversized and spacious garage with overhead storage, partially finished basement space offers great potential with a laundry room, unfinished attic storage, a generous rear deck, large patio, and a storage shed. Enjoy a generous yard and a convenient location near Windham's shops, restaurants, schools, and outdoor recreation, with Little Sebago Lake approximately 10 minutes away. This property presents a wonderful opportunity to create a home tailored to your style and needs.

129 Forbes Ln, Windham

Listing courtesy of Elevate Maine Realty.

$459,900
4 Beds ⋅ 2 Baths
Your Maine waterfront opportunity is knocking. This 2005 built Contemporary located on Collins Pond with over 200 feet of water frontage was just pulled from Auction and has been reduced. Boasting a Single Family home with attached apartment and over 3,000 square feet of previous finished space the possibilities are endless. Images in this listing have been virtually staged.

14 Emerson Dr, Windham

Listing courtesy of Excellence Realty.

$457,000
3 Beds ⋅ 2 Baths
Welcome to 8 Port Drive, Unit 8, a well-maintained Windham condo offering comfort, convenience, and access to Collins Pond. Tucked into a quiet setting close to North Windham's shops, restaurants, and everyday essentials, this home combines a relaxed atmosphere with convenient access to Portland and Big Sebago's public boat launch. Enjoy the ease of single-floor living, with the main level providing the spaces you need for everyday comfort. An additional upstairs room offers flexibility for a bedroom, den, workout space, or bonus room, giving you extra room to suit your needs. Thoughtful updates include a new roof in 2024, a new washer and dryer in 2025, and a Trex deck added in November 2025. A kitchen backsplash, blinds and curtains, and a Ring Doorbell add practical touches throughout. Step outside to enjoy the deck, an inviting spot for morning coffee or relaxing at the end of the day. The attached garage provides convenient parking and additional storage. A small condominium association handles exterior maintenance and septic, with weekly trash pickup adding to the convenience. Spend less time on outdoor upkeep and more time enjoying the surrounding lakes, nearby dining, shopping, and everything the area has to offer. With Collins Pond access, convenient single-floor living, flexible bonus space, and proximity to both the Sebago Lake region and Portland, 8 Port Drive, Unit 8 offers a comfortable home base in a convenient Windham location.

8 Port Dr Unit 8, Windham

Listing courtesy of Real Broker.

$450,000
Beautiful 17.8+/- acre parcel, tucked back just off Route 302 for privacy and a true country feel. With approximately 1,400 feet of owned water frontage on the Pleasant River, this property is surrounded by woods and open fields, offering a natural setting that feels worlds away while still being close to local conveniences. The land offers a range of possibilities, whether you envision building a private single-family home with room to roam, creating a small farm or homestead, or exploring the potential for further division with town approval. With its scenic beauty, generous acreage, and river frontage, this is a rare opportunity to create a lifestyle connected to the land.

28b Harriett Ave, Windham

Listing courtesy of A Team Realty.

$450,000
3 Beds ⋅ 1 Baths
Tucked away just one block from the shores of Highland Lake sits 2 Abbadaba, a home reimagined from the studs up with an unwavering commitment to quality and longevity. Though its structure carries decades of history, a total 2023 rebuild effectively gave this residence a brand-new life. Every wall was opened and major systems replaced, including brand-new wiring, plumbing, insulation, windows, doors, and heating. Stepping inside through the mudroom entry, high-end touches shine—from custom tongue-and-groove pine on the ceiling to durable LVP flooring throughout. The main level flows naturally from a bright living area into a kitchen featuring white shaker cabinets, solid granite countertops, and modern appliances. A full custom bathroom and a flexible spare room complete the ground floor. Upstairs, three cozy bedrooms make clever use of the classic sloped roofline. Outdoors, a detached two-car garage provides abundant storage for lake gear. Walk just down the street to public access on Highland Lake, a 640-acre haven for boating and fishing. Perfect as a year-round home, summer retreat, or short-term rental, this total rebuild offers modern peace of mind in a prime location. Distant water views from most upstairs windows!

2 Abbadaba Ln, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. (207)749-4699
$450,000
This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 2 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

1 Derringer Dr, Windham

Listing courtesy of Kre Brokerage Group.

$450,000
This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 2 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

1 Derringer Dr, Windham

Listing courtesy of Kre Brokerage Group.

$450,000
3 Beds ⋅ 2 Baths
Tucked in South Windham, an area experiencing exciting momentum as part of the town's ongoing Little Falls/South Windham Villages revitalization plan, this classic 1900 New Englander has been freshly painted from top to bottom and is ready to welcome its next chapter. Wood floors carry you through a sun-filled first floor, where the kitchen, dining room, and living room flow together with ease -- the living room anchored by a cozy wood stove for those crisp Maine evenings. Upstairs, three bedrooms -- including a comfortable primary suite -- share a second full bath, while first-floor laundry keeps everyday living simple. With 2 full baths total and thoughtful updates throughout, this home is in truly move-in ready condition. Step outside and the possibilities open up. A level, beautifully landscaped 0.69-acre lot offers a patio and firepit made for gathering, plus a detached 2-car garage for storage and hobbies alike. And for buyers thinking ahead, the property's high-density VC zoning may allow for future expansion, subject to town approval -- a rare bonus as the surrounding village center continues to grow and attract new investment. Rounding out the package: double-pane windows, a storm door, central vacuum, public water and sewer, and an air radon mitigation system already installed -- the practical details taken care of, so you can focus on making it home. Located between Westbrook and the lakes region, and just steps from a village on the rise, 65 High Street offers the character of a century-old home with real upside for the future.

65 High St, Windham

Listing courtesy of The Flaherty Group.

$450,000
2 Beds ⋅ 1 Baths
Don't miss this opportunity to own a year-round, two-bedroom cottage on beautiful Sebago Lake! Located in a five-member association, this property includes its own deep-water boat slip, making it ideal for boating enthusiasts. The renovation has already begun, as shown in the photos, giving the next owner a head start on creating their perfect lakeside retreat. The seller has decided to move on before completing the project, creating an excellent opportunity to add your own style and finishing touches. Enjoy the level common waterfront area featuring picnic tables, a fire pit, and plenty of space to relax and gather with family and friends. With a reduced list price, this cottage offers outstanding value and endless potential. Bring your vision and make this Sebago Lake getaway your own!

14 Family Cir Unit 2, Windham

Listing courtesy of Real Estate 2000 ME/NH.

$450,000
Discover the potential of this 4.59-acre parcel, perfectly situated in an area zoned for enterprise development—offering endless possibilities for commercial, industrial, or mixed-use projects. This prime location provides excellent accessibility and visibility, ideal for future growth. The lot is cleared and ready for your vision. Don't miss this chance to create something extraordinary in a thriving area!

Lot 10 Enterprise, Windham

Listing courtesy of A Team Realty.

$449,900
3 Beds ⋅ 3 Baths
Like new without the new price, this three-year-old condo has just been freshly painted and professionally cleaned. Move in ready and affordable. Spacious open floor plan with high-end cabinets/ Granite counters and an oversized deck make this a wonderful place to call home. This small (6 total units) association will keep condo fees low and allow for input on association rules. Three large bedroom, big closets and full basement make this home perfect for so many living situations including work from home. If you are looking for a comfortable and affordable place to call home, you have found it. Special financing maybe available for qualified buyers. Open House 9/13 10-12

12 Voyager Ln Unit 12, Windham

Listing courtesy of Maine Values Real Estate.

$445,000
Large 9.4 +/-acre tract with 908' frontage meets the dimensional standards for up to four lots, each requiring minimum 200' frontage and 1.84 acres. Great opportunity for a home builder to construct several homes or a buyer to build his/her home and split off the remainder for multiple lots. Tavern Hill is a private road with a homeowners association. A nearly six acre lot with 200' frontage in Tavern Hill sold this spring.

Tavern Hl, Windham

Listing courtesy of EXP Realty.

$435,000
1 Beds ⋅ 1 Baths
If you've been searching for a true, easy-living Maine camp feel with modern comfort, you've found it! 12 Getaway Road in Windham checks every box. Nestled right on the quiet Little Duck Pond, this charming, updated cottage offers peaceful waterfront living with the unbeatable convenience of an easy-access Windham location. Inside, the fresh space centers around the amazing views and a beautiful stone fireplace. This cottage has been beautifully updated with a new kitchen, bath, flooring and pine shiplap throughout. Enjoy this private, quaint cottage on a clean 35 +/- acre pond that is home to largemouth bass, perch, pickerel, etc. Kayak, paddle, swim or launch your motorized boat right from your front yard.

12 Getaway Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$429,000
2 Beds ⋅ 1 Baths
Welcome to this charming ranch tucked away on a spacious lot with a quaint private backyard. Enjoy the bright sunroom, cozy living room and eat in kitchen. The spacious two-car detached garage offers a finished room and extra storage, while the outdoor shed provides even more flexibility. A wonderful one floor home with plenty of charm, privacy, and space to enjoy!

156 Albion Rd, Windham

Listing courtesy of Swan Real Estate.

$429,000
3 Beds ⋅ 2 Baths
Welcome Home! This meticulously maintained 2 or 3 bedroom townhouse offers an open floor plan with numerous amenities and upgrades including a freshly painted interior, custom design kitchen with granite counter tops and stainless appliances. Plus recently added modern comforts like the high efficiency heat pumps for climate control and a standby generator hook up. The high ceilings and large windows flood the space with natural light. There are 2 full baths and both have been upgraded. The 2nd floor bath was totally redone with a custom shower and glass door. The full basement offers plenty of storage while the large bonus room offers plenty of flexible uses including a home office, family room or 3rd bedroom. In addition to the large amount of living space there is a private deck and patio ideal for enjoying the outdoors relaxing or entertaining. while backing up to common green space for added privacy. This unit is part of a well-run association located in a peaceful neighborhood with easy access to local walking trails and outdoor recreation while being just minutes to local shopping centers, grocery stores, and popular local restaurants. Its also an Convenient commuting distance to downtown Portland. Don't miss this stunning, value priced and move in ready townhouse!

54 Provost Dr Unit 54, Windham

Listing courtesy of Keller Williams Realty.

$425,000
2 Beds ⋅ 1 Baths

12 Birchwood Ave, Windham

Listing courtesy of Century 21 North East.

$400,000
4 Beds ⋅ 2 Baths
Located in one of Windham Center's established neighborhoods, this 4-bedroom, 2-bath Cape offers comfortable living in a location that's hard to beat. The classic floor plan includes a convenient breezeway connecting the home to the attached two-car garage, while the private 0.35-acre lot provides space to relax, garden, or entertain outdoors. Enjoy being just minutes from North Windham's shopping, restaurants, grocery stores, and everyday conveniences, with easy access to Sebago Lake for boating, swimming, fishing, and year-round recreation. Nearby parks, trails, golf courses, and outdoor attractions make it easy to enjoy the best of Maine's Lakes Region, while Portland is an easy commute for work, dining, and entertainment. Whether you're looking for your next home or a place to enjoy everything Windham has to offer, 25 Abby Road combines neighborhood living with an exceptional location.

25 Abby Rd, Windham

Listing courtesy of Meservier & Associates.

$399,900
The parcel has water stubbed at the road and a gravel curb cut already installed. Ideal location for manufacturing, private warehousing and high bay boat storage.

99 Enterprise Dr, Windham

Listing courtesy of Butts Commercial Brokers.

$385,000
1 Beds ⋅ 1 Baths
Nestled along the peaceful shores of Pettingill Pond, 12 Shore Road in Windham, Maine has the perfect blend of classic lakeside charm and modern comfort. This inviting property boasts stunning water views, direct access to the pond, and a serene setting ideal for both year-round living and seasonal escapes. Inside, you'll find a bright and welcoming layout with large windows that fill the home with natural light and showcase the surrounding beauty. The open-concept living and dining areas create an easy flow for entertaining, while the kitchen provides ample space for preparing meals after a day on the water. Need more space, you will be pleased to find that this property also has a bunkhouse, perfect for overnight guests. Step outside to enjoy your private slice of Maine's natural beauty--whether it's morning coffee overlooking the water, afternoons spent boating or swimming, or evenings around the firepit under the stars. The property offers convenient pond access, making it easy to embrace the full waterfront lifestyle. Located just a short drive from local shops, restaurants, and all of Windhams amenities. This home combines tranquility with accessibility. Whether you're looking for a permanent residence, a vacation getaway, or an investment opportunity, 12 Shore Road is a rare chance to own a piece of Maine's sought-after waterfront living.

12 Shore Rd, Windham

Listing courtesy of Rockstar Real Estate.

$375,000
3 Beds ⋅ 1 Baths
RECENT PRICE IMPROVEMENT! Welcome to 229 Tandberg Trail, where comfort, convenience, and opportunity come together in Maine's beautiful Lakes Region. This inviting ranch-style home offers easy one-level living in a desirable neighborhood, just minutes from shopping, restaurants, schools, lakes, parks, walking trails, and other everyday conveniences. Inside, you'll be greeted by a spacious open-concept living room, dining area, and kitchen, highlighted by soaring cathedral ceilings that create a bright and welcoming atmosphere. The layout is comfortable, functional, and move in ready! Outside, the generous yard offers plenty of room to relax, entertain, garden, or simply enjoy the outdoors. Adding a privacy fence could further enhance the backyard, creating an even more secluded outdoor retreat. Whether you're searching for your first home, looking to simplify your lifestyle, or seeking a property in one of Southern Maine's most sought-after areas, this home offers an excellent opportunity to make it your own. Some of the photos for this listing have been virtually staged. This home features a new heating system,hot water heater & 200-amp breaker panel-all new August 2026! The property card identifies the home as a 1.5- bath property. The toilet in the half bath was removed by the seller; however,the existing plumbing remains in place, allowing for a toilet to be reinstalled.Open house on Saturday Sept 26th 10-12pm

229 Tandberg Trl, Windham

Listing courtesy of Plowman Realty Group.

$350,000
This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 1 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

2 Vintage Dr, Windham

Listing courtesy of Kre Brokerage Group.

$350,000
This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 1 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

2 Vintage Dr, Windham

Listing courtesy of Kre Brokerage Group.

$339,900
2 Beds ⋅ 2 Baths
Welcome to Windham Hill Woods, a well-established and desirable condominium community offering an exceptional combination of convenience, amenities and value. Ideally located on the south side of downtown Windham, this townhouse-style condo provides easy access to shopping, dining and area amenities while helping you avoid much of the traffic congestion found farther north. Inside, the thoughtfully designed floor plan offers comfortable living across three levels. The first floor features a granite kitchen, inviting living room with hardwood flooring, convenient half bath and a sliding glass door leading to your private deck overlooking the wooded edge. Upstairs, you'll find a spacious primary bedroom, second bedroom and full bathroom. Continue to the third-floor loft, an especially versatile space that works beautifully as a home office, reading area, hobby space or flex room. A full basement provides excellent storage and includes the convenience of an in-unit washer and dryer. The $300 monthly association fee includes water and sewer, adding to the overall value and ease of ownership. Windham Hill Woods offers an in-ground pool, pickleball court, sidewalks and generous open space. The association is also pet friendly, making this an inviting community for a variety of lifestyles. Whether you're looking to simplify your lifestyle, make your first home purchase or find a convenient Maine getaway, 23 Meagans Way offers the space, amenities and location to make condo living easy and enjoyable.

23 Meagans Way Unit 12, Windham

Listing courtesy of PO-GO REALTY.

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