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

$849,000

3 Beds ⋅ 3 Baths

NEW CONSTRUCTION CONDO NOW AVAILABLE FOR 2026 OCCUPANCY - MUST SEE ONE OF A KIND DEVELOPMENT! Welcome to The Cove at Highland Lake: where low maintenance lake-life meets Portland-proximate convenience! The Freeport floorplan, our largest single level 2 Bed/2 Bath floor plan comes standard with 1340+/- sq ft, a large open concept living area with a spacious kitchen, soft-close cabinetry, Energy Efficient LED Lighting & Appliances. 22 Daybreak features a floor to ceiling Gas Fireplace feature, Upgraded Cafe Appliance Package, Light & Bright Granite and Quartz Countertops, Finished Basement with an additional bed and full bath, and 9Ft ceiling height! Custom tiled showers, spa like bath fixtures, and cathedral ceilings ensure your condo is well appointed and beaming with natural light. 18 x 12 (approximate) Primary Suite with double vanity bath and a walk-in closet. The Freeport also boasts a large front porch and an oversized single stall attached garage with extra room for storage. Community Amenities to Include: Tennis & Pickle Ball court, two-level clubhouse with fitness center, full kitchen and function/meeting space, private access to the 53 acre parcel with over 6000 feet of nature trails, 585 feet of lake front to carry in kayaks, canoes and paddle boards, plus a community maintained dock. Located JUST 10 MILES from Downtown Portland, residents will enjoy UNBEATABLE proximity to top rated health care and hospitals, Maine's finest dining and endless entertainment options. Have you ever imagined a life immersed in nature full of boating, skiing, golf, shopping, dining, sports & activity clubs, and LOW MAINTENANCE? The way 55+ life should be can be found here in The Cove at Highland Lake!

22 Daybreak Ln Unit 11, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. crystal.chandonnet@verani.com

$649,000

2 Beds ⋅ 3 Baths

14 Daybreak Lane is fully framed and ready for customization. Approximately 8 Weeks from Contract to CO. Welcome to The Cove at Highland Lake! The first of its kind, Gold Cornerstone Award Winning 55+ Lakefront Community nestled on the pristine shores of Highland Lake. The PORTLAND floorplan is the perfect blend of one-level-living with plenty of space for guests and storage. At 1958 SF +/-, this 2 Bedroom 2.5 Bathroom attached condo with generously sized finished basement is an excellent option for those looking to ''rightsize'' into retirement. The Portland offers cathedral ceilings in the main living area, primary bedroom with spacious en suite double vanity bathroom and oversized walk-in closet, plus a guest bathroom with main level laundry. With not one but TWO outdoor composite decks, spacious one level is easy to achieve! But if even more space is needed, you'll enjoy an additional bedroom and bathroom in the finished basement boasting 9ft tall ceiling height. With endless custom finish options and upgrades, owners can select natural stone or quartz countertops, soft-close cabinetry, Age-in-Place safety features, LVP or hardwood flooring, gas or electric fireplace, and energy efficient LED lighting. Community Amenities Include: tennis & pickleball courts, two-level clubhouse with fitness center, full kitchen and function space, plus private access to the 50+ acre parcel with over 6000 feet of nature trails, 500+ feet of lake front to carry in kayaks, canoes and paddleboards, plus a community-maintained dock. Located just 10 miles from downtown Portland, residents will enjoy unbeatable proximity to top rated health care and hospitals, as well as Maine's finest dining and entertainment options. Boating, skiing, golf, shopping, dining, sports & activity clubs... The way 55+ life should be, and you can have it all in The Cove at Highland Lake! Reserve now & for a limited time you may choose your home's finishes!

12 Daybreak Ln Unit 16, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. crystal.chandonnet@verani.com

$635,000

3 Beds ⋅ 3 Baths

Welcome to 32 Carriage Hill Drive. This beautiful 1 owner home has been lovingly cared for and updated to keep up with the times. Set on just under an acre, this picture perfect colonial is positioned perfectly at the top of the hill and faces out overlooking common space. Everywhere you look there are flowers in bloom in every season flanking all the special spots in the yard. Step inside where multiple options for heating and cooling will ensure your comfort year round. The breezeway area is a great spot to shake off the day and step into the updated kitchen where the dining area leads to the 3-season porch. Having company? a full dining room can accommodate all your special guests. Work at home or cant make the stairs? a first floor room perfect for your needs. Outfitted nicely with hardwood and fresh paint the entire first floor leaves nothing to be desired. The second Floor features a Primary suite with bath and walk-in closet and two additional generously sized bedrooms. Still not enough? Expansion Possibilities Over the Garage or in the dry Basement!

32 Carriage Hill Dr, Windham

Listing courtesy of RE/MAX Coastal.

$535,000

4 Beds ⋅ 2 Baths

Welcome home to this spacious 4-bedroom, 1.5-bath residence with over 2,000 square feet of living space and plenty of room to accommodate today's lifestyle. With traditional living spaces, a comfortable layout, and generous room sizes, this home provides an inviting backdrop for both everyday living and entertaining. The main living areas give a classic feel with plenty of flexibility for formal gatherings, relaxed evenings, a home office, or additional living space. Four well-proportioned bedrooms provide room for family, guests, hobbies, or work-from-home needs, while the 1.5 baths add convenience to the thoughtful floor plan. One of the highlights of the property is the expansive backyard. Step out onto the back deck and enjoy views of the pool and spacious yard, creating a wonderful setting for summer entertaining, outdoor meals, weekend gatherings, or quiet afternoons at home. The generous outdoor space offers endless possibilities for recreation, gardening, and enjoying time outdoors. Conveniently located near local shopping and dining, this home makes it easy to enjoy nearby amenities while still offering a private and spacious retreat. If you're looking for a home with room to grow, inviting traditional living spaces, and an exceptional backyard setting, this property is ready to welcome you home.

15 Gromble Way, Windham

Listing courtesy of Maine Real Estate Co.

$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.

$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. Do not wait! Open House Sunday 09-20-2026 from 10:30am - 12pm.

2 Abbadaba Rd, Windham

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty. (207)749-4699

$475,000

3 Beds ⋅ 2 Baths

Welcome to this well-cared-for Cape in a park-like setting, with year-round water views of Highland Lake from the front deck. Enjoy your morning coffee watching the local bald eagles and listening for the loons, and in the evening gather around the fire pit in the flat back yard surrounded by hardwoods that show their colors in the fall. An extensive trail system starts right at the back property line so you can walk, snowshoe, or cross-country ski from your own yard. Inside you will find a spacious mudroom, a kitchen with granite counters, a breakfast nook, and updated appliances, and sun-filled dining and living rooms. A dedicated first-floor office is ready for remote work. Upstairs are three bedrooms and a second-floor laundry, with fresh paint and new carpet throughout. the big-ticket items have already been taken care of: new roof, new attic insulation installed by an Efficiency Maine certified vendor, a new high-efficiency propane boiler and a hybrid electric/heat pump water heater all keeping your heating and hot water costs down. Highland Lake is minutes away for kayaking, paddle boarding, ice skating and ice fishing, and the oversized shed is perfect to store all of those toys. This property offers privacy and plenty of open yard to garden, entertain, and play. Just 3.1 miles to shopping in Windham Center and an easy commute to Portland. Don't miss this one!

96 Percy Hawkes Rd, Windham

Listing courtesy of RE/MAX Shoreline.

$545,000

3 Beds ⋅ 2 Baths

Seller financing incentive available! With an acceptable offer, seller is willing to contribute up to two points toward a buyer's interest rate buydown. Set on 2.5 acres in a peaceful Windham setting, this three-bedroom, two-full-bath home offers privacy, space, and everyday convenience while remaining close to everything the area has to offer. Built in 2006, the home features a comfortable and functional layout with an open-concept kitchen and dining area flowing into the living room, creating an easy space for everyday living and gathering. A welcoming sitting room provides an additional place to relax, while first-floor laundry adds to the home's practical layout. Outside, there's plenty of space to enjoy the property throughout Maine's seasons. Spend summer days by the pool and cooler evenings relaxing in the hot tub, which conveys with the property. Keep chickens in the existing coop, or take advantage of the additional outbuilding for storage, hobbies, equipment, or projects. Mature raspberry and blackberry bushes offer seasonal berries right from the yard, while a beautiful magnolia tree, lilacs, and an Oriental apple tree add established character and seasonal color to the property. With 2.5 acres and only two neighboring homes along the road, the property offers a sense of privacy without feeling isolated. Located just off Falmouth Road, the home strikes a great balance between a quieter setting and convenient access to town. Windham's shopping, restaurants, and everyday amenities are just a short drive away, while Portland is also within easy reach. With acreage, privacy, a pool, hot tub, useful outbuildings, and a convenient location, this property offers plenty of opportunity to make it your own.

7 Mancini Rd, Windham

Listing courtesy of Landing Real Estate.

$629,900

3 Beds ⋅ 3 Baths

Large ranch with so much to provide. Over 3200 sq ft of finished living space. Kitchen is open to the living room and dining area, great layout for entertaining. Kitchen Includes new cabinets, granite countertop and appliances. New plumbing fixtures, cabinet and countertop in the first floor bathroom with laundry shoot. Epoxy floor recently installed in basement. Massive 780 sq ft primary suite features jetted tub, separate shower and 2 large walk-in closets. Large laundry room with wrap-around work counter. Relax and enjoy your favorite drink in the comfort of the screened porch. Two large rock walls enhance the beauty of this property located only a few minutes to North Windham's business district. This property sits on nearly 2 acres, plenty of room to savor the outdoors. For those with an entrepreneurial spirit, you can set up your business in the basement with your advertising sign on Rte 302. Property is located in Windham's C-3 zoning (see town ordinance for the types of businesses allowed). The opportunities are extensive. Member of selling LLC holds a Maine Associate Brokers license.

5 Foster Flds, Windham

Listing courtesy of Regency Realty Group.

$325,000

1 Beds ⋅ 1 Baths

Great little cottage in a fantastic location! In the heart of the lakes region in Windham with views and a ROW to Pettingill Pond, across 302 from The Deckhouse Restaurant and Seacoast Adventure and just a 3 minute drive to Richardsons boat yard in Standish. A 20 minute commute to Portland and a 6 minute drive to the Raymond boat launch on Sebago Lake make this the ultimate home base for all things Maine without breaking the bank. Renovated in 2021 down to the studs with new wiring, plumbing, insulation, sheetrock, heat pump, propane Rinnai heater, and granite kitchen countertops, this gem is ready for you to come and enjoy!

8 Pettingill Rd, Windham

Listing courtesy of Meservier & Associates.

$579,000

4 Beds ⋅ 3 Baths

Historic circa-1900 farmhouse on 4 acres of fields and forest in a desirable rural Windham location, adjacent to Bumbleroot Organic Farm and minutes to Westbrook and Gorham. Filled with vintage character and potential, the home features abundant custom cabinetry in the kitchen, dining, and office spaces; a separate bedroom suite with soaking tub and walk-in closet; and a sunroom overlooking a fenced garden, open field, and woods. A 1,200-square-foot post-and-beam barn provides outstanding possibilities for a workshop, studio, storage, animals, or hobby use. A rare chance to restore, reimagine, and make this remarkable property your own.

180 Highland Cliff Rd, Windham

Listing courtesy of A Team Realty.

$349,900

2 Beds ⋅ 1 Baths

OPEN HOUSE, Saturday 10AM-12PM! Highland Lake doesn't close for the winter. Swim and paddle in July, skate and ice fish in January! At 15 Orchard Rd the lake is yours by deeded right, a short walk down the road. No launch fees, no hunting for parking, no waterfront tax bill. Just a towel, or a sled, and five minutes. The property was originally three lots, so there's room here most homes in this neighborhood don't have — garden, play, park the boat, spread out. Inside: hardwood floors and a kitchen freshly updated with new counters, backsplash, sink, and faucet. Woodstoves in both the kitchen and living room, plus a fireplace and multiple heat sources, so Maine winters are something to enjoy rather than endure. A first-floor bedroom keeps daily life easy, and several additional rooms flex into an office, hobby space, or a landing spot for guests. Septic is designed for three bedrooms; town records currently list the property as a 2-bedroom. Out back, a large shed handles storage with room left for a workbench. Easy commute to Portland. Four seasons of lake living, and a house that's warm through all of them.

15 Orchard Rd, Windham

Listing courtesy of Dream Home Realty LLC.

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