Windham Real Estate

Welcome to Windham, Maine – a charming town nestled in the heart of Cumberland County that beautifully blends the tranquility of rural living with the convenience of modern amenities. Known for its picturesque landscapes, Windham offers a perfect escape for those seeking a serene lifestyle without sacrificing access to urban conveniences.

With a population of around 18,000 residents, Windham is a close-knit community that prides itself on its friendly atmosphere and strong local spirit. The town is characterized by its stunning natural beauty, featuring lush forests, pristine lakes, and an abundance of outdoor recreational opportunities. Whether you enjoy hiking, fishing, or simply taking in the fresh Maine air, Windham has something for everyone.

Windham is also home to a vibrant downtown area that boasts delightful shops, restaurants, and local businesses, making it easy to support the community while enjoying a variety of dining and shopping experiences. The town hosts numerous events throughout the year, including farmers' markets and seasonal festivals, which foster a sense of togetherness among residents.

Families will appreciate Windham's excellent school system, which is dedicated to providing quality education and fostering a supportive environment for children. The town's proximity to Portland – just a short drive away – means that residents can easily access the cultural, culinary, and entertainment offerings of Maine's largest city while returning home to the peace and quiet of Windham.

If you're considering a move to a place that combines scenic beauty, community spirit, and convenience, Windham, Maine, may just be the perfect fit for you. Come discover the charm that awaits in this delightful town!

Newest Listings in Windham

$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

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.

$347,900

2 Beds ⋅ 2 Baths

Welcome home to Windham Hill Woods, where comfort, convenience, and community come together! This beautifully maintained 2-bedroom, 1.5-bath townhouse offers bright, inviting living spaces and a versatile third-floor loft that's perfect for a home office, guest space, workout room, or cozy retreat. The open layout creates an easy flow for everyday living, while the private back deck provides the ideal spot to unwind and enjoy the peaceful surroundings. The full basement offers plenty of extra storage, giving you all the space you need to stay organized. Best of all, the association takes care of lawn maintenance, snow removal, and exterior upkeep, allowing you to enjoy a truly low-maintenance lifestyle. Windham Hill Woods is known for its outstanding amenities and welcoming community. Spend summer days at the in-ground pool, gather with neighbors in the community garden or gazebo, and enjoy the basketball and pickle ball courts just steps from your door. Conveniently located just minutes from North Windham's shopping, dining, and everyday conveniences, with easy access to the Sebago Lakes Region and only about 25 minutes to Portland, this home offers the perfect balance of recreation, relaxation, and accessibility. Whether you're looking for your first home, a place to simplify your lifestyle, or a move-in-ready property in one of Windham's most desirable communities, this townhouse is one you won't want to miss!

22 Turkey Trail, Unit 22, Windham

Listing courtesy of Dream Home Realty LLC.

$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, July 25th from 10-12!

26 Whites Bridge Rd Unit 26, Windham

Listing courtesy of Signature Homes Real Estate Group.

$529,000

4 Beds ⋅ 2 Baths

Welcome to this beautifully updated home in one of Windham's most desirable neighborhoods, where timeless charm, quality craftsmanship, and an exceptional location come together. From the moment you arrive, you'll appreciate the meticulously maintained landscaping featuring mature trees and stunning perennial gardens that provide vibrant blooms throughout the growing season, creating incredible curb appeal and a picturesque setting you'll enjoy year after year. Inside, pride of ownership shines throughout. Refinished hardwood floors, new flooring in the upstairs bedrooms, and new basement flooring create a fresh, cohesive feel, while the bright kitchen features a new window and new appliances. New electrical outlets, fixtures, and recessed lighting installed by Simply Electric LLC add a stylish, modern touch. Additional improvements include a beautiful new front porch, board and batten detailing on the garage, select new cedar shakes, and a professionally cleaned and inspected chimney, reflecting the exceptional care this home has received. The private backyard is equally impressive, surrounded by mature landscaping and colorful flower gardens that bloom throughout the seasons, creating the perfect setting to relax, entertain, or simply enjoy Maine's natural beauty. Perfectly situated just minutes from downtown Windham, you'll enjoy convenient access to shopping, local restaurants, entertainment, and everyday amenities. Portland is only 15 minutes away, while Sebago Lake's public boat launch is approximately 10 minutes from your doorstep, making it easy to enjoy boating, fishing, swimming, and all that Southern Maine has to give. Thoughtfully updated and truly move-in ready, this exceptional property offers the perfect blend of elegance, comfort, and convenience in one of Windham's most sought-after communities.

12 Arcadia Dr, Windham

Listing courtesy of Real Broker.

$689,000

Prime commercial opportunity with outstanding exposure and ample parking! This stylish, modern office building offers excellent signage visibility along high-traffic Route 302 and flexible C-1 zoning that allows for a variety of uses. With 14 parking spaces and two separate entrances, the building is well-suited for owner occupancy with tenant income. The first level features a welcoming reception area, conference room with gas fireplace, kitchenette, private office with its own entrance, and an ADA-compliant half bath. The second floor includes five offices and a full bathroom. A full basement with double-door access from the parking lot provides excellent loading, storage, or future expansion potential. Built in 2017, the property features modern systems including central air conditioning, a full security system, and irrigation. The association covers plowing and landscaping, making this an attractive, low-maintenance investment. Don't miss the opportunity to elevate your business in this highly visible, turnkey location.

630 Roosevelt Trl Unit 1, Windham

Listing courtesy of Signature Homes Real Estate Group.

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