Windham Real Estate

Welcome to Windham, Maine – a hidden gem nestled in the heart of Cumberland County. Known for its stunning natural beauty and vibrant community spirit, Windham offers a perfect blend of rural charm and modern conveniences, making it an ideal place to call home.

Windham is renowned for its picturesque landscapes, featuring serene lakes, rolling hills, and lush woodlands. The town is a haven for outdoor enthusiasts, with a plethora of recreational activities available year-round. Enjoy kayaking or fishing on the tranquil Sebago Lake, or explore the extensive trail systems for hiking, biking, and snowmobiling. The nearby Presumpscot River also offers opportunities for scenic walks and wildlife observation.

Families will appreciate Windham’s strong sense of community and excellent school system, fostering a nurturing environment for children. The town boasts a variety of local shops, restaurants, and parks, providing residents with a charming, small-town atmosphere while still being conveniently close to the bustling city of Portland, just a short drive away.

Windham hosts a range of community events throughout the year, from farmers' markets to seasonal festivals, ensuring that there’s always something happening to bring neighbors together. Whether you’re looking to settle down in a peaceful neighborhood or seeking an active lifestyle, Windham has something for everyone.

With its friendly ambiance, stunning scenery, and ample amenities, Windham, Maine, is not just a place to live – it’s a place to thrive. Explore the possibilities of making this delightful town your new home!

Newest Listings in Windham

$650,000

3 Beds ⋅ 2 Baths

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

78 Lakeside Dr, Windham

Listing courtesy of Engel & Volkers Portsmouth.

$949,000

5 Beds ⋅ 4 Baths

Just a short ~0.3-mile walk or less than a one-minute drive to Windemere's private sandy beach on Sebago Lake, this exceptional custom Colonial offers the perfect blend of luxury, craftsmanship, and the Maine lake lifestyle. Welcome to Windemere, one of Sebago Lake's most sought-after private lakefront communities. Offering 3,555 square feet of beautifully finished living space, this custom-built home features a thoughtfully designed floor plan with five bedrooms and three and a half bathrooms, including spacious primary suites on both the first and second floors, making it ideal for multi-generational living or hosting guests. Hardwood floors, quartz countertops, a gas fireplace, a dedicated home office, and both formal and informal living spaces provide comfort and flexibility for everyday living and entertaining. Above the attached two-car garage, a finished bonus space complete with a kitchenette offers endless possibilities as an in-law suite, guest quarters, recreation room, home office, or private retreat. Outside, relax on the expansive patio overlooking the beautifully landscaped backyard while enjoying seasonal views of Sebago Lake. A new roof installed in 2024 provides added peace of mind. Windemere residents enjoy exclusive access to outstanding amenities, including a private boat launch, boat slips (subject to availability), tennis and pickleball courts, canoe and kayak storage, and beautifully maintained common areas with breathtaking mountain and sunset views. The community's private sandy beach offers the perfect place to swim, relax, or spend the day enjoying everything Sebago Lake has to offer. Just minutes from downtown Windham, this home offers the rare opportunity to enjoy spacious luxury living in one of Southern Maine's premier lake communities. The finished bonus space provides the flexibility to function as a sixth bedroom; however, buyers should note that the septic system is designed for four bedrooms.

35 Woldbrook Dr, Windham

Listing courtesy of Portside Real Estate Group.

$575,000

3 Beds ⋅ 3 Baths

Move-in ready and thoughtfully designed, this exceptional Colonial in sought-after Belvedere Estates offers the perfect blend of style, comfort, and efficiency. 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 to make it your home!

36 Belvedere Dr, Windham

Listing courtesy of Keller Williams Realty.

$489,500

3 Beds ⋅ 1 Baths

Welcome to 47 Running Brook Road, a beautifully renovated three-bedroom ranch offering move-in-ready comfort, an oversized wooded lot, and deeded access to approximately 1,500 feet of shared Collins Pond shoreline and park area. Inside, the main level has been thoughtfully transformed with an open and inviting layout, refinished hardwood floors, fresh paint, new doors and trim, and updated lighting throughout. The completely remodeled kitchen features new cabinetry, granite countertops, a farmhouse sink, tile backsplash, stainless appliances, and modern black hardware. The renovated full bath includes a tiled shower, double vanity, new fixtures, and updated plumbing. All three bedrooms are generously sized, and the spacious living room offers plenty of room to relax around the woodstove. The finished lower-level recreation room provides additional flexible living space, while the unfinished portion of the basement offers excellent storage and utility space. Major improvements completed since 2025 include Anderson windows, new exterior doors, a new oil boiler, a new heat pump water heater, a new chimney liner and cap, updated outlets and switches, new flooring, refreshed landscaping, fencing, and extensive tree clearing. Outside, enjoy a private backyard setting with multiple deck areas, a gazebo, storage shed, and a gorgeous, wooded section of the lot. Deeded rights provide access to the shared Collins Pond park area, where residents can enjoy kayaking, paddleboarding, fishing, swimming, and the lake lifestyle without the cost and maintenance of direct waterfront ownership. With extensive renovations, updated systems, flexible living space, and deeded pond access, this home offers a rare combination of comfort, recreation, and peace of mind.

47 Running Brook Rd, Windham

Listing courtesy of Keller Williams Realty.

$949,900

3 Beds ⋅ 3 Baths

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

605 River Rd, Windham

Listing courtesy of Keller Williams Realty.

$499,000

3 Beds ⋅ 2 Baths

OPEN HOUSE THIS SATURDAY: 9-10:30AM! Tucked away on a peaceful, wooded lot, 8 Environmental Way has had many thoughtful updates including a new roof and whole house generator! This home has the perfect balance of privacy and convenience, just about 30 minutes from downtown Portland. Wake up to birdsong, watch deer wander through the yard, and enjoy the feeling of your own nature retreat, all while being just minutes from shopping, restaurants, schools, and Sebago Lake recreation. Inside, the thoughtful three level layout offers the best of both worlds. The main living spaces flow seamlessly together with an open kitchen, dining, and family room with a propane stove and natural landscape outside drawing nature in. Separate levels provide privacy when it's time to unwind. Upstairs, you'll find three bedrooms, including a spacious primary suite with its own en suite bathroom, plus a second full shared bathroom off the hallway. The finished lower level adds valuable flex space and is currently set up as a gaming room, making it perfect for a media room, home office, gym, or bonus space. For added peace of mind, a pre-listing home inspection has already been completed, and a water test report will be provided to interested buyers.

8 Environmental Way, Windham

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

$599,000

3 Beds ⋅ 3 Baths

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

77 Harvest Hill Rd, Windham

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com

$1,179,900

4 Beds ⋅ 3 Baths

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

108 Highland Cliff Rd, Windham

Listing courtesy of Landmark Realty.

$75,000

3 Beds ⋅ 2 Baths

One-level living in a well-kept 55+ community! This single wide provides an easy layout with the kitchen open to the dining area, great for everyday living or having people over. The primary suite comes with its own half bath, and you've got a dedicated laundry room and mudroom for all the stuff that usually ends up piled by the door. Outside, the yard is landscaped and there's a shed for extra storage. Just a short drive to everything Windham has to provide, shopping, restaurants, the lake. Additionally, this home has all new appliances, that are only about a year old! Low-maintenance, move-in ready, and priced to sell.

42 Robin Ln, Windham

Listing courtesy of Keller Williams Realty.

$474,000

3 Beds ⋅ 3 Baths

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

2 Dolley Farm Rd Unit 1, Windham

Listing courtesy of The Flaherty Group.

$509,000

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.

$299,000

2 Beds ⋅ 2 Baths

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

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

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