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

$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

5 Beds ⋅ 4 Baths

Welcome to Windemere, one of Sebago Lake's most sought-after lakefront communities, where timeless craftsmanship, exceptional amenities, and the Maine lake lifestyle come together. This custom-built Colonial offers 3,555 square feet of beautifully finished living space with a thoughtfully designed floor plan that balances elegance, comfort, and flexibility. The home features five 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 family and guests. Hardwood flooring, quartz countertops, a gas fireplace, a dedicated home office, and both formal and informal living spaces provide the perfect setting for everyday living and entertaining alike. Above the attached garage, a finished bonus space complete with a kitchenette offers endless possibilities as an in-law suite, guest quarters, recreation room, or private retreat. Outside, enjoy the privacy of the beautifully landscaped backyard from the expansive patio while taking in seasonal views of Sebago Lake. A new roof installed in 2024 provides added peace of mind for years to come. As a resident of Windemere, you'll enjoy exclusive access to outstanding community amenities, including a 700-foot sandy beach on Sebago Lake with breathtaking mountain and sunset views, a private boat launch, boat slips (subject to availability), tennis and pickleball courts, canoe and kayak storage, and beautifully maintained common areas. Located 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. With In-law apartment, it could be used as a 6 bedroom but note septic system is designed for four bedrooms.

35 Woldbrook Dr, Windham

Listing courtesy of Portside Real Estate Group.

$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.

$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.

$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, August 1 from 10:30am to 12:00pm.

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.

$475,000

3 Beds ⋅ 1 Baths

Enjoy the best of both worlds with this charming 3-bedroom ranch featuring a 1-car garage, nestled in a peaceful rural setting in Windham while remaining just minutes from shopping, restaurants, and local businesses. The open-concept layout offers a spacious feel, highlighted by hardwood floors and a large front-to-back living room that's perfect for relaxing or entertaining. The primary bedroom provides a comfortable retreat, while city water and a spacious deck add to the home's convenience and appeal. Outside, you'll find two driveways, offering plenty of parking and flexibility. The property also presents future potential, with the town indicating it may be eligible for conversion to a duplex. Buyers are encouraged to perform their own due diligence to verify all zoning and conversion possibilities. Whether you're looking for a comfortable single-family home or an investment opportunity with expansion potential, this property is worth a look!

439 Falmouth Rd, Windham

Listing courtesy of Dream Home Realty LLC.

$599,000

3 Beds ⋅ 2 Baths

Welcome to this beautifully private and tucked-away retreat, gracefully situated on 1.29 acres of peaceful countryside. Offering 3 spacious bedrooms, 1.5 bathrooms, and a 1-car garage, this charming home provides the perfect blend of comfort, privacy, and convenience. Surrounded by the beauty of a serene rural setting, you can enjoy the tranquility of nature while remaining just moments from public beaches, boat launches, shopping centers, and local restaurants, all while being only 25 minutes from Portland. Outside, you'll find a lovely area ready for your dream garden, along with an existing chicken coop awaiting its next flock, creating the perfect opportunity to embrace a simple and rewarding homestead lifestyle. Whether you're spending a day on the water, enjoying nearby amenities, gathering fresh eggs in the morning, or simply relaxing in your own private oasis, this exceptional property offers the lifestyle you've been searching for.

7 Hall Rd, Windham

Listing courtesy of Coldwell Banker Team Real Estate.

$699,000

3 Beds ⋅ 3 Baths

NEWLY PRICED!! Nature beckons you in the popular Lakes Region! Nestled on 2 acres, this meticulously maintained home offers approximately 2,875 square feet of light-filled living space. A beautiful stone fireplace with woodstove insert takes center stage on the main level featuring hardwood floors, a den/home office and eat-in kitchen area with granite peninsula, stainless steel appliances and maple cabinets! There's easy access to the well built, heavy duty deck overlooking a wooded, private fenced-in yard. Down the hall is a cozy laundry room, full bath and 2 spacious bedrooms. The primary suite tucked in the rear corner, features a tile shower and walk-in closet providing a comfortable and serene environment. The possibilities are endless in the lower-level family room with storage closet, full bath and mudroom. Walk-out access to the custom cedar hot tub provides a luxurious and relaxing experience! The whole-house generator ensures uninterrupted power, and heat pumps on each level provide added comfort throughout each season. A magnificent wildflower garden adds natural beauty and charm to the surroundings of this move-in ready home, minutes from area amenities and bustling North Windham! A home warranty provides peace of mind for this special oasis, just 35 minutes to the Portland Jetport. What are you waiting for?

20 Cross Ridge Dr, Windham

Listing courtesy of Coldwell Banker Realty. 207-773-1990

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