Windham Homes with Trees/Woods View

Welcome to Windham, Maine, a picturesque town nestled in the heart of Cumberland County, where the beauty of nature meets the warmth of community living. Known for its stunning landscapes, Windham offers a unique blend of suburban tranquility and easy access to urban amenities. With its charming downtown area, vibrant local businesses, and a plethora of outdoor recreational opportunities, Windham is the perfect place to call home.

One of the standout features of homes in Windham is their breathtaking views of trees and wooded landscapes. Imagine waking up each morning to the soothing sights and sounds of nature right outside your window. Many properties in this area boast expansive views of lush forests and serene woodlands, providing a peaceful retreat from the hustle and bustle of daily life. Whether you enjoy sipping your morning coffee on a sun-drenched deck or hosting gatherings in your backyard surrounded by towering trees, these homes offer a slice of paradise.

Windham is also known for its outdoor activities, from hiking and biking trails to beautiful lakes perfect for fishing and boating. The community is family-friendly, with excellent schools and parks that foster a sense of belonging. With a variety of homes available, including charming single-family residences and modern townhouses, there’s something for everyone in Windham.

Experience the perfect blend of nature and community in Windham, Maine, where your dream home with a view of trees and woods awaits. Discover the joys of living in this enchanting town, where every day feels like a getaway in your own backyard.

Newest Windham Homes with Trees/Woods View

$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.

$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.

$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.

$625,000

3 Beds ⋅ 3 Baths

Beautiful contemporary cape with 1st floor primary suite! At the end of a cul-de-sac, in a quiet neighborhood, with the 5-acre community common space along the backside of the property, 14 Abenaki Drive is a peaceful retreat. Everyday conveniences and four-season recreation are close at hand. North Windham's shops, groceries, restaurants, and attractions like Seacoast Adventure are a short drive away, while Dundee Park's river beach, Lippman Park's trails and playground, and the Mountain Division Trail invite easy walks, bikes, and paddles. Sebago Lake and Little Sebago are nearby for swimming and boating, and Portland is only about twenty minutes down the road. North and South travel are at your doorstep! Enjoy small-town Maine charm and city access, gorgeous mornings and star filled nights from the deck off the dining room, or sweet summer days in the private back yard. If you are cozy to home, or delight in travel, this solidly built home will become your paradise. Check out the unique, 10 ft ceilings in the daylight walk-out basement. Find plenty of storage space. This house has it all. See it soon! OPEN HOUSE Sunday 9/6/2026 from 11:00 am - 1:00 pm

14 Abenaki Dr, Windham

Listing courtesy of EXP Realty.

$389,000

3 Beds ⋅ 1 Baths

Welcome to 229 Tandberg Trail, where comfort, convenience, and opportunity come together in Maine's beautiful Lakes Region. This inviting ranch-style home offers easy one-level living in a desirable neighborhood, just minutes from shopping, restaurants, schools, lakes, parks, walking trails, and other everyday conveniences. Inside, you'll be greeted by a spacious open-concept living room, dining area, and kitchen, highlighted by soaring cathedral ceilings that create a bright and welcoming atmosphere. The layout is comfortable, functional, and move in ready! Outside, the generous yard offers plenty of room to relax, entertain, garden, or simply enjoy the outdoors. Adding a privacy fence could further enhance the backyard, creating an even more secluded outdoor retreat. Whether you're searching for your first home, looking to simplify your lifestyle, or seeking a property in one of Southern Maine's most sought-after areas, this home offers an excellent opportunity to make it your own. Some of the photos for this listing have been virtually staged. This home features a new heating system,hot water heater & 200-amp breaker panel-all new August 2026! The property card identifies the home as a 1.5- bath property. The toilet in the half bath was removed by the seller; however,the existing plumbing remains in place, allowing for a toilet to be reinstalled. Showings begin Saturday September 5th 2026. Open house on Sunday Sept 6th 11am-2pm.

229 Tandberg Trl, Windham

Listing courtesy of Plowman Realty Group.

$649,999

3 Beds ⋅ 2 Baths

Welcome to 51 Gambo Road in Windham, where peaceful waterfront living meets everyday convenience. Set along 144 feet of privately owned Presumpscot River frontage, this unique property offers a rare opportunity to enjoy nature right outside your door while remaining close to shopping, dining, walking trails, golf, beaches, fishing, kayaking, and canoeing. This 3 bedroom 2 bathroom home offers over 2400 total square feet and has seen numerous thoughtful renovations, including a newly renovated kitchen, bathroom, and basement. Enjoy your mornings on the screened-in front porch, then spend your afternoons by the river before unwinding in the hot tub or sauna. An outdoor patio and fire pit create the perfect setting for evenings with friends and family. Private riverfront, modern updates, endless recreation, and unmatched tranquility. Come experience 51 Gambo Road, and discover a home that feels like a getaway, without giving up the convenience of being close to most everything!

51 Gambo Rd, Windham

Listing courtesy of Landing Real Estate.

$550,000

3 Beds ⋅ 3 Baths

Brand New Home with ROW access to Highland Lake! Experience Maine living in this move-in-ready custom home set on .47 acres. Offering 1,664 sq. ft., 3 bedrooms, and 2.5 baths. The thoughtfully designed floor plan features a first-floor primary suite with walk-in closet and en-suite bath with tiled shower. The beautifully appointed kitchen showcases an oversized island with quartz countertops, while first-floor laundry adds everyday convenience. All three Bedrooms have walk-in closets for plenty of storage. Step outside to an extra-large deck, perfect for entertaining, summer gatherings, and relaxing while enjoying the Maine outdoors. Modern craftsmanship, refined finishes, and easy access to Highland Lake create the perfect setting for elevated four-season lake living. Taxes shown are land only, TBD, call town of Windham. **Directions are tricky with GPS- Be sure to come down Albion Rd to Swan Rd, Vista Dr, to Birdsong- other routes will take you on rough roads ****Be sure to see interior tour video!- https://youtu.be/T_KmdYtGVFM

16 Birdsong Ln, Windham

Listing courtesy of RE/MAX Coastal.

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