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$470,000
2 Beds ⋅ 2 Baths
Great Opportunity, Motivated Sellers, In An Amazing Windham Location!! Welcome to 26 Marshall Valley Road. This 2 bedroom, 2 bath split level cape has a ton of charm. The open concept living room with wood wrapped beams, and a wood stove, along with the formal dining room both have spacious cathedral ceilings. Next you go to the well lit kitchen with island and granite tops throughout, that leads you into the very sunny breakfast nook!! The dining room and breakfast nook are joined together by a huge covered wrap around farmers porch, perfect for entertaining and enjoying the country setting. Upstairs there are 2 good size bedrooms and 2 baths. This includes a large primary bedroom with private bath, and walk in closet. The 2nd floor hallway is set up beautifully for a sitting area (with overlook to below), and an office nook. The daylight basement comes complete with a partially finished section on one half, (perfect for a family room), and an oversized 2 car garage under on the other half. The land is the perfect country setting, with plenty of privacy and room to entertain. There's even a brook towards the back of the property. All Conveniently located off of Highland Cliff Rd. A very private lot, but close to everything including the Turnpike. This Property Is A Must See!!!

26 Marshall Valley Rd, Windham

Listing courtesy of Getty Real Estate Services, LLC.

Selling Office: Keller Williams Realty.

$469,000
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!

20 Dolley Farm Rd Unit 9, Windham

Listing courtesy of The Flaherty Group.

Selling Office: Keller Williams Realty.

$469,000
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.

10 Dolley Farm Rd Unit 5, Windham

Listing courtesy of The Flaherty Group.

Selling Office: The Flaherty Group.

$460,000
3 Beds ⋅ 1 Baths
You'll love this contemporary Ranch-style home ideally located in South Windham, offering easy access to Portland, Interstate 295, and the Maine Turnpike. Designed with comfort and functionality in mind, the thoughtfully laid-out open floor plan features a welcoming front living room that flows seamlessly into the dining area and kitchen—perfect for everyday living and entertaining alike. The main level offers two bedrooms and a full bathroom, while the daylight walkout basement provides valuable additional living space. The lower level includes a third bedroom, a versatile bonus room, an unfinished future bathroom, and a dedicated storage and laundry area. Set on a generous 3.62-acre lot, this property strikes the perfect balance between convenience and privacy. With worry-free public water, you'll enjoy both accessibility and peace of mind. Spend summer evenings gathered around the firepit, taking in views of the wooded edge, surrounding nature, and abundant wildlife—your own private retreat just minutes from local amenities.

236 Main St, Windham

Listing courtesy of PO-GO REALTY.

Selling Office: Keller Williams Realty.

$450,000
3 Beds ⋅ 1 Baths
Recently remodeled yet full of charm, this beautiful 3-bedroom home perfectly blends character with modern updates. From the moment you step inside, you'll appreciate the warmth of hardwood floors, spacious bedrooms, and thoughtful finishes throughout. The updated kitchen features granite countertops, stainless steel appliances, and a layout ideal for both everyday living and entertaining. A cozy gas fireplace anchors the living space, creating the perfect spot to relax and unwind. Need extra space? The bonus room offers flexibility for a home office, playroom, or guest area. Outside, you'll find a detached barn with additional storage above--perfect for hobbies, equipment, or future potential. Set on a large yard, there's plenty of room to enjoy the outdoors while still being conveniently located just minutes to town and the turnpike for an easy commute. This is the perfect opportunity to enjoy modern comfort without sacrificing the charm of a classic home.

34 Smith Rd, Windham

Listing courtesy of A Team Realty.

Selling Office: Keller Williams Realty.

$450,000
3 Beds ⋅ 2 Baths
Ready to unlock equity? This expansive Windham home is located only minutes to Portland in an established neighborhood on a public road. Full of potential, this property is ideal for investors, builders, or handy buyers looking for their next project. This home offers a flexible and expansive floor plan with a comfortable flow just waiting for a glow up vision. Upstairs, you'll find a bright, spacious kitchen and dining area with direct access to a private deck overlooking the huge backyard. An open living room provides plenty of space to gather. The lower level offers two bonus rooms, a home office with it's own entry and a large family room with built in storage. The attached 30x30 heated garage is a stand out feature complete with workbench, hot & cold water and a working whole house vacuum used for detailing cars. Above there is 900ft of finished living space with a full bathroom and own entry. Set on over an acre, the property features a beautiful yard that wraps from the front, around the side, and into a large, private backyard filled with natural light. Be prepared for whatever Maine sends your way with a whole house Generac generator. Being sold as-is and ready to move into.

9 Haven Rd, Windham

Listing courtesy of Locations Real Estate Group LLC.

Selling Office: Maine Real Estate Co.

$450,000
3 Beds ⋅ 2 Baths
Welcome to 93 Woodland Road, Windham--a well-maintained 3-bedroom, 2-bath Cape Cod set on 2.05 acres in Woodland Estates. The home offers 1,170 sq ft of finished living space with warm pine floors, an updated kitchen, and comfortable living and dining areas designed for everyday functionality. A major value-add is the attached 2-car garage with unfinished space above, providing excellent potential for additional living space--ideal for a primary suite, bonus room, home office, or in-law setup. The garage adds even more flexibility for storage, workshop use, or hobbies. The wooded lot offers privacy while still being conveniently located near Windham's Route 302 corridor, providing easy access to shopping, dining, and daily amenities. A strong opportunity for buyers looking for a solid home with room to grow.

93 Woodland Rd, Windham

Listing courtesy of Coldwell Banker Realty. 207-282-5988

Selling Office: A Team Realty.

$440,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1 bathroom home features many recent updates, including a newer furnace, roof, vinyl siding, windows, decks, and appliances--giving peace of mind and modern convenience. Enjoy the outdoors from the updated decks overlooking Black Brook, perfect for relaxing and taking in the natural surroundings. Located across the street from Black Brook Preserve, featuring over 100 acres of rolling hills, mature trees, brooks, abundant wildlife and plant life. Outdoor enthusiasts will love the nearby trail network ideal for hiking, running, snowshoeing, cross-country skiing, and snowmobiling. This move-in ready home offers a wonderful balance of updated living and access to year-round recreation!

265 Windham Center Rd, Windham

Listing courtesy of Coldwell Banker Realty. 207-773-1990

Selling Office: Portside Real Estate Group.

$435,000
2 Beds ⋅ 2 Baths
Welcome to 186 Falmouth Rd in Windham Maine, a warm and inviting log cabin that blends rustic charm with everyday convenience. This well maintained two bedroom two bath home offers approximately 1,800 square feet of living space and sits on just under four private acres, providing room to relax while still being close to everything you need. Inside, the natural character of the log construction creates a cozy and welcoming atmosphere throughout. Exposed wood, comfortable living spaces, and a functional layout make this home ideal for everyday living or entertaining. With two full bathrooms and flexible living areas, the home easily adapts to a variety of lifestyles whether you are looking for a primary residence, a getaway, or space to work from home. Outside, the nearly four acre lot offers privacy and opportunity while remaining minutes from hiking trails, lakes, shopping, dining, and major commuter routes. You get the feeling of peaceful country living without giving up convenience. Located in Windham, this property is a great fit for anyone who values outdoor recreation, space, and the timeless appeal of a true Maine log cabin. A rare opportunity in a highly accessible location that offers the best of both worlds.

186 Falmouth Rd, Windham

Listing courtesy of Landing Real Estate.

Selling Office: Locations Real Estate Group LLC.

$432,000
3 Beds ⋅ 2 Baths
Welcome to 14 Pope Road in Windham--a place that just feels like home the moment you pull in. Set on 1.7 acres, there's plenty of room to spread out, with a bright, sunny backyard that's perfect for summer nights, backyard games, or letting pets roam free in the fully fenced yard. The barn and shed give you all the extra space you need for storage, hobbies, or projects you've been meaning to start. Farm land zoning allows you to have a horse or goats. Bring your ideas to make it yours! Upstairs, you'll find 3 bedrooms and 1 bathroom with a layout that's easy to live in and make your own. Downstairs is an half bath with laundry and an open kitchen and living room with a door directly to the backyard. A charming covered porch off two of the bedrooms is the perfect spot to curl up with a book. A two car attached garage opens directly into a hallway to stow away shoes and coats. Sellers installed a new well and a new furnace in 2025. You'll love the location--close to Portland for an easy commute, but tucked into a great area of Windham. Property is being sold AS IS. Sellers are motivated to move on to their next chapter!

14 Pope Rd, Windham

Listing courtesy of Maine Real Estate Experts.

Selling Office: Down To Earth Real Estate.

$430,000
3 Beds ⋅ 1 Baths
Welcome home to this beautifully renovated 3 bedroom Cape, where modern style meets convenience. Completely updated in 2023, this move-in ready home offers the perfect blend of comfort, functionality, and peace of mind; all in a convenient Windham location with easy access to shopping, dining, schools, and commuting routes. Step inside to discover a bright, open main living area that flows seamlessly into the stunning kitchen, featuring crisp white cabinetry, granite countertops, stainless steel appliances, subway tile backsplash, and abundant storage. The thoughtfully designed floor plan includes two bedrooms and a full bath on the first floor, making one level living an easy option, while the two spacious rooms upstairs offers flexibility as a private primary suite, guest space, or home office. Outside, enjoy a large detached shed, paved driveway, and a spacious yard with room to garden, entertain, or simply relax. Whether you're searching for your first home, looking to downsize without compromising on space, or simply want a turnkey property in a desirable Windham setting, this home is ready to welcome you.

62 Ward Rd, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Hearth & Key Realty.

$430,000
2 Beds ⋅ 1 Baths
Welcome to 244 Falmouth Road in Windham! This 2-bedroom, 1-bath split-level home, built in 2003, offers comfort and charm on a generous 2.75-acre lot. Inside, you'll find wood floors, a bright and inviting layout, and solid systems for peace of mind. Step outside onto the large composite deck, perfect for entertaining or simply enjoying views of the private yard surrounded by woods. The oversized 2 car attached garage and daylight walkout basement allows for many uses or future expansion. Ideally located conveniently to Windham Center, Westbrook, Highland Lake and Little Sebago Lake, this property combines convenience and recreation with space to spread out and enjoy Maine living at its best.

244 Falmouth Rd, Windham

Listing courtesy of RE/MAX Shoreline.

Selling Office: RE/MAX Shoreline.

$425,000
2 Beds ⋅ 2 Baths
Easy living starts here. Set in one of Windham's sought-after 55+ communities, this thoughtfully upgraded 2-bedroom, 2-bath condo offers a low-maintenance lifestyle without sacrificing comfort or style. The layout is bright, open, and designed for everyday ease. The kitchen stands out with granite counters, stainless appliances, a center island perfect for gathering, and plenty of pantry space, all opening into a light-filled living area with vaulted ceilings. From there, step out to the back deck--an ideal spot for morning coffee or unwinding at the end of the day. The primary bedroom includes a walk-in closet and private feel, while the second bedroom can flex to fit your needs--guest space, office, or cozy den. Downstairs, the basement gives you even more options for hobbies, workouts, or a quiet retreat, plus space for storage or future expansion. You'll also appreciate the attached one-car garage with direct entry, efficient heat pump for year-round comfort, and a long list of upgrades including plantation shutters, updated fixtures, gutters, and more. With a community garden nearby and quick access to the Lakes Region, outdoor recreation, and local amenities, this location makes it easy to stay active--or simply relax and enjoy the surroundings. If you're looking for a move-in-ready home with the right mix of convenience and quality, this one checks all the boxes.

11 Unity Ln Unit 11, Windham

Listing courtesy of Signature Homes Real Estate Group, LLC.

Selling Office: Signature Homes Real Estate Group, LLC.

$415,000
3 Beds ⋅ 2 Baths
Surrounded by mature trees on a private wooded lot, this inviting Cape offers the space, flexibility, and setting that so many buyers are looking for in Windham. Inside, you'll find a thoughtful layout with three bedrooms and two full bathrooms, including a first-floor bedroom and full bath; ideal for guests, one-level living, or a home office. Upstairs, two generously sized bedrooms share a second full bathroom, while the hallway features a walk-in closet for additional storage. Natural light fills the home, creating warm and inviting living spaces you'll enjoy year-round. The spacious first-floor bonus room offers endless possibilities, whether you're looking for a family room, home gym, playroom, or office. The living room provides a cozy place to unwind, while the kitchen offers ample cabinet space, overlooks the backyard, and flows seamlessly into the dining room for easy everyday living and entertaining. Outside, you'll appreciate the privacy this setting provides, all while being just minutes from North Windham's shopping, restaurants, schools, Sebago Lake, and countless year-round recreational opportunities. An attached garage, paved driveway, and generous yard complete the property, offering plenty of room to relax, entertain, or simply enjoy the peaceful surroundings. If you've been searching for a home that combines privacy, a flexible floor plan, and a convenient Windham location, this is one you won't want to miss.

8 Dutton Hill Rd, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Legacy Properties Sotheby's International Realty.

$415,000
4 Beds ⋅ 2 Baths
Affordable homes in Windham are getting harder to find, and this one is a great opportunity to get into the Southern Maine market without stretching your budget. This 4 bedroom, 1.5 bath home offers plenty of space, including finished bonus space in the basement that works well for a second living area, playroom, or home office. The home has solid bones and is completely move-in ready, with the chance to add your own style over time with some light cosmetic updates. Outside, you'll find a great backyard space with a beautiful deck that's perfect for summer evenings, plus a shed for extra storage. The location makes everyday living easy. It's just minutes to grocery stores, restaurants, and shopping along Route 302, with quick access to lakes, outdoor recreation, and an easy drive toward Portland for commuting. It's a smart option for buyers who want a comfortable home now with the chance to build equity over time, something that's becoming harder to find in Southern Maine.

192 Varney Mill Rd, Windham

Listing courtesy of Hearth & Key Realty. 2074404066

Selling Office: Landvest, Inc..

$410,000
3 Beds ⋅ 1 Baths
This solid 3-bedroom, 1-bath ranch offers the ease and comfort of one-floor living in a quiet neighborhood setting. The well-designed open-concept living room, dining area, and kitchen with breakfast bar create a welcoming space for everyday living and entertaining, while still providing definition between each area. Well maintained and filled with natural light, the home opens to a deck overlooking a sizable, level backyard complete with a storage shed--an ideal setting for gardening, recreation, or simply enjoying the outdoors. A Kohler generator provides added peace of mind, while the spacious basement offers excellent storage and future potential. Located just minutes from the conveniences of Windham's vibrant town center, this property also enjoys easy access to some of Maine's most cherished outdoor recreation, including lakes, ponds, trails, and mountains. Portland is just 15 miles away, making commuting and city amenities easily accessible. Well priced and full of opportunity, this home offers strong value. With a few thoughtful cosmetic updates, it could truly shine.

15 Birchwood Ave, Windham

Listing courtesy of Portside Real Estate Group.

Selling Office: Coldwell Banker Realty.

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