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

$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.

$1,425,000

5 Beds ⋅ 3 Baths

Set on more than 100 feet of private sandy beach frontage on Little Sebago Lake, this completely renovated lake house offers a turn-key opportunity that rarely comes to market. The main home features five bedrooms and three full bathrooms, including a primary suite on the first floor. The stunning living room boasts cathedral ceilings with exposed beams, solar powered skylights, a floor-to-ceiling stone fireplace, and unobstructed views of the lake. Inside the kitchen you'll find all new stainless steel appliances including a gas range with a chef's hood, expansive cabinetry, and oversized windows. Outside, the 24x36 two car garage contains a work area and even more finished space above with a private deck overlooking the water. Entertaining here is effortless- the private dock and float provide boat, paddleboard, and swimming access just steps from the house, and sunsets can be enjoyed from the sprawling stone firepit. No detail was overlooked in this tasteful renovation; a new waterproof basement, drilled well, heat pumps, electrical, and roof are just some of the upgrades that make this home so special. This lakefront sanctuary is your opportunity to create memories in one of Maine's most exceptional settings.

112 Sabbady Point Rd, Windham

Listing courtesy of Legacy Properties Sotheby's International Realty.

$585,000

3 Beds ⋅ 3 Baths

This home feels tucked away from it all without being far from anything. Set off a private road with mature trees, classic stone walls, and thoughtfully landscaped grounds, it offers a sense of privacy that can be hard to find. Inside, the layout is open, bright, and easy to live in, with a first-floor kitchen, dining, and living area that feels connected and comfortable. A mudroom and separate office or playroom add flexibility, while the daylight walkout basement offers even more space and future potential. Upstairs, the primary suite features its own bath and walk-in closet, complemented by two additional bedrooms, a second full bath, and a separate laundry space. Outside, the large front porch, back deck, and fire pit area make it easy to relax. Peaceful and private, yet still close to town and the turnpike, this home offers a rare balance of seclusion and convenience.

74 Tavern Hl, Windham

Listing courtesy of A Team Realty.

$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 Saturday 09-12-2026 from 11am - 12:30pm.

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! Open Houses Saturday 9/12 10:00am-12:noon. Sunday 9/13 1:30-3:00pm.

96 Percy Hawkes Rd, Windham

Listing courtesy of RE/MAX Shoreline.

$415,000

3 Beds ⋅ 2 Baths

Indoor and outdoor living at it's best! Come see this great little cottage with water access on the shores of Pettingill Pond. This 3 bedroom 2 bath year round home has been thoughtfully updated and remodeled for ease of living. It features a thoughtfully designed new kitchen with modern features and artistic touches which leads to a giant deck perfect for entertaining. The 2 updated bathrooms and unique layout provides for separate and cozy spaces perfect for when guests arrive or house sharing. Every space feels fresh and ready for its new owner. Major improvements including a new roof and exterior stain have been completed recently so you can just bring your kayak and paddle and get on the water without the worry.

5 Shore Rd, Windham

Listing courtesy of RE/MAX Coastal.

$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.

$450,000

This is an incredible opportunity for a multitude of business uses. The C-1 Zoning allows for many commercial uses. High visibility and directly located in front of a 30 unit residential townhouse development with an adjacent 24 occupied residential units. Lot 2 is also available. Lot((s) are available for sale, for ground lease, or, Seller will consider a build to suit.

1 Derringer Dr, Windham

Listing courtesy of Kre Brokerage Group.

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