Windham Real Estate

Welcome to Windham, Maine – a picturesque town nestled in the heart of Cumberland County. Known for its breathtaking natural beauty and vibrant community spirit, Windham is a hidden gem that offers the perfect blend of rural charm and modern convenience. With its stunning lakes, lush forests, and scenic views, residents and visitors alike are drawn to the area's outdoor recreational opportunities, including hiking, fishing, and boating.

Windham boasts a rich history, with roots dating back to the 18th century. Today, it thrives as a welcoming community that values both tradition and progress. The town is home to a variety of local shops, delightful eateries, and community events that foster a strong sense of belonging. The annual Windham Summerfest is a highlight, bringing together families and friends for a celebration of local culture, food, and fun.

Education is a cornerstone of the Windham community, with highly-rated schools that prioritize student success and engagement. Families will appreciate the safe, friendly neighborhoods that make Windham an ideal place to raise children.

For those commuting to nearby Portland or seeking a tranquil retreat from city life, Windham offers easy access to major roadways while maintaining its serene atmosphere. Whether you’re looking for a cozy home or an expansive property, Windham’s real estate market has something for everyone.

Embrace the charm of Windham, Maine, where community, nature, and opportunity come together to create a truly enchanting place to call home. Discover your new beginning in this captivating town!

Newest Listings in Windham

$375,000

2 Beds ⋅ 2 Baths

Beautifully updated and well-maintained home in a desirable Windham location! This move-in-ready property offers a thoughtfully improved interior with modern updates throughout, reflecting pride of ownership at every turn. The home features a bright, welcoming layout with comfortable living spaces ideal for both everyday living and entertaining. Recent updates enhance both style and functionality, while ongoing maintenance provides peace of mind for the next owner. Enjoy the meticulously landscaped grounds that create a welcoming outdoor setting and enhance the home's curb appeal. The lower level offers excellent potential and is ready for your personal touch, providing an opportunity to expand the home's finished living space with updated areas for a recreation room, home office, gym, guest space, or additional living area. Set in a quiet neighborhood yet conveniently located near shopping, schools, lakes, and commuter routes, this home offers the perfect blend of comfort, convenience, and value. A wonderful opportunity to own a turnkey Windham home with room to grow--don't miss it! Offer Deadline by 5 p.m. today, August 5th!

60 Forbes Ln, Windham

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$399,000

3 Beds ⋅ 1 Baths

Welcome to 38 Lantern Lane, a three bedroom Cape in a quiet Windham neighborhood near Highland Lake. The kitchen was fully updated in 2022. Granite counters, a deep stainless farmhouse sink, subway tile backsplash, and new stainless appliances. The butcher block island adds counter space and can be moved. The kitchen and dining area are connected to each other and flow through to the living room, where there is a propane fireplace. Hardwood floors run throughout. The home has been well maintained. The roofing has been replaced, the interior is freshly painted, and there is a generator with hookup for the winter storms. The lot is sunny with woods along the back, and the garden beds are framed and fenced. The covered farmer's porch runs across the front of the house and is a quiet place to sit and take in the nature that surrounds the property. There are walking trails and a playground near the East Windham Fire Station, biking trails nearby, and I-95 at exit 53 is about ten minutes away. Loons, owls, and deer are just some of the sights and sounds of nature that surround the property. Showings start August 7.

38 Lantern Ln, Windham

Listing courtesy of EXP Realty.

$525,000

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.

$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

6 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 six 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. 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

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

$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.

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