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$599,000

Set on 1.84 acres in a desirable Windham location, this 3-bedroom, 2-bath split-level offers space, privacy, and plenty of potential to make it your own. Tucked away on a dead-end road and situated across from a former apple farm, the property enjoys a peaceful setting while still being convenient to everything Windham has to offer. An added bonus is direct access to the rail trail right from the property, perfect for walking, biking, and enjoying the outdoors. Inside, hardwood flooring runs throughout much of the main level, while a spacious sunroom and wood-burning stove add warmth and character. Step outside onto the deck overlooking the private backyard, offering a wonderful setting to relax, entertain, or simply enjoy the surrounding natural landscape. The finished lower level provides additional living space with flexibility for a family room, home office, gym, or more, and a two-car garage offers added convenience and storage. Ready for your personal touches and updates, this home presents an exciting opportunity to create something truly your own in one of Windham’s most desirable communities. With nearly two acres, a peaceful setting, and a versatile layout, there is so much potential to make this property shine.

3 Beds ⋅ 2 Baths ⋅ 5108856 MLS

Set on 1.84 acres in a desirable Windham location, this 3-bedroom, 2-bath split-level offers space, privacy, and plenty of potential to make it your own. Tucked away on a dead-end road and situated across from a former apple farm, the property enjoys a peaceful setting while still being convenient to everything Windham has to offer. An added bonus is direct access to the rail trail right from the property, perfect for walking, biking, and enjoying the outdoors. Inside, hardwood flooring runs throughout much of the main level, while a spacious sunroom and wood-burning stove add warmth and character. Step outside onto the deck overlooking the private backyard, offering a wonderful setting to relax, entertain, or simply enjoy the surrounding natural landscape. The finished lower level provides additional living space with flexibility for a family room, home office, gym, or more, and a two-car garage offers added convenience and storage. Ready for your personal touches and updates, this home presents an exciting opportunity to create something truly your own in one of Windham’s most desirable communities. With nearly two acres, a peaceful setting, and a versatile layout, there is so much potential to make this property shine.

36 Governor Dinsmore Rd, Windham

$1,175,000

Set on a quiet street in Windham's sought-after Wood Meadow Estates, this DiPietro Homes Colonial is genuinely turnkey, with nothing left to do but move in. Offering 4 bedrooms, 3.5 baths, approximately 3,188 square feet, and a first-floor office on a private 0.53-acre lot, it pairs the ease of newer construction with custom finishes and indoor-outdoor living ready to enjoy. The home lives beautifully, with an open layout where daily life and entertaining unfold with equal ease, showcasing stained hardwood floors, crown molding, wainscoting, and a cathedral-ceilinged entry with a turned staircase. At its heart, a stunning eat-in kitchen features custom Cabico cabinetry, quartz counters, a large center island, Jenn-Air appliances with a six-burner gas range, a walk-in pantry, and glass-front uppers with integrated lighting, opening to a family room anchored by a gas fireplace with stone surround. A French-doored office, wainscoted dining room, half bath, and mudroom-to-laundry layout complete the first floor. Upstairs, the primary suite offers a cathedral ceiling, walk-in closet, and spa-inspired bath with dual vanities, a soaking tub, and glass-enclosed shower. Three additional bedrooms, one with a private bath, flex easily as guest rooms, office, or fitness space, with another full bath nearby. Outdoors is built for entertaining and unwinding alike: a composite deck with motorized awning, a stone paver patio with built-in firepit, and a hot tub, all within a fully fenced backyard. Full basement with windows, bulkhead access, and expansion potential.Twilight open house Fri 9/11, 5-7 PM; also Sat 9/12 & Sun 9/13, 12-2 PM. No showings prior.

4 Beds ⋅ 4 Baths ⋅ 5107701 MLS

Set on a quiet street in Windham's sought-after Wood Meadow Estates, this DiPietro Homes Colonial is genuinely turnkey, with nothing left to do but move in. Offering 4 bedrooms, 3.5 baths, approximately 3,188 square feet, and a first-floor office on a private 0.53-acre lot, it pairs the ease of newer construction with custom finishes and indoor-outdoor living ready to enjoy. The home lives beautifully, with an open layout where daily life and entertaining unfold with equal ease, showcasing stained hardwood floors, crown molding, wainscoting, and a cathedral-ceilinged entry with a turned staircase. At its heart, a stunning eat-in kitchen features custom Cabico cabinetry, quartz counters, a large center island, Jenn-Air appliances with a six-burner gas range, a walk-in pantry, and glass-front uppers with integrated lighting, opening to a family room anchored by a gas fireplace with stone surround. A French-doored office, wainscoted dining room, half bath, and mudroom-to-laundry layout complete the first floor. Upstairs, the primary suite offers a cathedral ceiling, walk-in closet, and spa-inspired bath with dual vanities, a soaking tub, and glass-enclosed shower. Three additional bedrooms, one with a private bath, flex easily as guest rooms, office, or fitness space, with another full bath nearby. Outdoors is built for entertaining and unwinding alike: a composite deck with motorized awning, a stone paver patio with built-in firepit, and a hot tub, all within a fully fenced backyard. Full basement with windows, bulkhead access, and expansion potential.Twilight open house Fri 9/11, 5-7 PM; also Sat 9/12 & Sun 9/13, 12-2 PM. No showings prior.

28 Settlers Ridge Rd, Windham

$375,000

In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here.

4 Beds ⋅ 2 Baths ⋅ 5099541 MLS

In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here.

715 Chase Rd, Windham

$825,000

**OFFER DEADLINE SET FOR MONDAY AT 12 NOON** Offered for the very first time since custom built 30 years ago, this extraordinary Windham estate is a rare opportunity to own a property that has been well loved for and thoughtfully enhanced over decades. Perched on 3.13 private acres, this unique Colonial offers 3 bedrooms, 2.5 baths, and welcomes you with timeless New England charm, highlighted by a distinctive two-story turret and wraparound porch featuring intricate arch detailing. The professionally manicured grounds just create the truly storybook setting. Inside, you'll discover one of the home's most remarkable features; a stunning peninsula saltwater aquarium that serves as a living centerpiece at the heart of the home! Designed with an automated filtration system for minimal upkeep, you'll enjoy all of the beauty and tranquility of a thriving reef ecosystem including a variety of stunning bright specialty fish and coral, with little more than just feeding them each evening! Step outside and relax beneath the retractable awning on the spacious 20' x 14' deck. Then, stroll among mature specimen plantings throughout including rare Japanese Maple tree varieties. While you experience your own private retreat, a cascading waterfall into two picturesque koi ponds creates a peaceful soundtrack to everyday life. As if that wasn't an impressive list of features, the abutting hiking/walking trails of Deer Leap with unfiltered views of and private access to Rock Pond beyond the property line, are additional experiences you're privy to with this home! A partially finished lower level, 2 car garage, front & back yard irrigation system, and a standby generator add to the year round comfort and peace of mind. Properties like this are rarely available... a home where architecture, nature, and lifestyle come together to create something truly special; a living destination! Seller to find suitable housing.

3 Beds ⋅ 3 Baths ⋅ 5094260 MLS

**OFFER DEADLINE SET FOR MONDAY AT 12 NOON** Offered for the very first time since custom built 30 years ago, this extraordinary Windham estate is a rare opportunity to own a property that has been well loved for and thoughtfully enhanced over decades. Perched on 3.13 private acres, this unique Colonial offers 3 bedrooms, 2.5 baths, and welcomes you with timeless New England charm, highlighted by a distinctive two-story turret and wraparound porch featuring intricate arch detailing. The professionally manicured grounds just create the truly storybook setting. Inside, you'll discover one of the home's most remarkable features; a stunning peninsula saltwater aquarium that serves as a living centerpiece at the heart of the home! Designed with an automated filtration system for minimal upkeep, you'll enjoy all of the beauty and tranquility of a thriving reef ecosystem including a variety of stunning bright specialty fish and coral, with little more than just feeding them each evening! Step outside and relax beneath the retractable awning on the spacious 20' x 14' deck. Then, stroll among mature specimen plantings throughout including rare Japanese Maple tree varieties. While you experience your own private retreat, a cascading waterfall into two picturesque koi ponds creates a peaceful soundtrack to everyday life. As if that wasn't an impressive list of features, the abutting hiking/walking trails of Deer Leap with unfiltered views of and private access to Rock Pond beyond the property line, are additional experiences you're privy to with this home! A partially finished lower level, 2 car garage, front & back yard irrigation system, and a standby generator add to the year round comfort and peace of mind. Properties like this are rarely available... a home where architecture, nature, and lifestyle come together to create something truly special; a living destination! Seller to find suitable housing.

76 Marblehead Rd, Windham

$1,450,000

Welcome to this beautifully maintained home that combines comfort, style, and functionality. Featuring spacious living areas filled with natural light, this residence offers an open and inviting floor plan perfect for both everyday living and entertaining. The modern kitchen boasts ample cabinetry, quality appliances, and generous counter space, flowing seamlessly into the dining, sunroom and family rooms. The home includes generously sized bedrooms, including a relaxing primary suite with a private bath and walk-in closet. Thoughtful updates and well-appointed finishes throughout create a warm and welcoming atmosphere. Outside, enjoy a beautifully landscaped yard with plenty of space for outdoor gatherings, gardening, or simply relaxing. Conveniently located near schools, shopping, dining, this property offers the perfect blend of privacy and accessibility. Move-in ready and full of charm, this home is an exceptional opportunity for anyone seeking comfort, convenience, and lasting value. Showings begin June 4, 2026.

4 Beds ⋅ 3 Baths ⋅ 5092176 MLS

Welcome to this beautifully maintained home that combines comfort, style, and functionality. Featuring spacious living areas filled with natural light, this residence offers an open and inviting floor plan perfect for both everyday living and entertaining. The modern kitchen boasts ample cabinetry, quality appliances, and generous counter space, flowing seamlessly into the dining, sunroom and family rooms. The home includes generously sized bedrooms, including a relaxing primary suite with a private bath and walk-in closet. Thoughtful updates and well-appointed finishes throughout create a warm and welcoming atmosphere. Outside, enjoy a beautifully landscaped yard with plenty of space for outdoor gatherings, gardening, or simply relaxing. Conveniently located near schools, shopping, dining, this property offers the perfect blend of privacy and accessibility. Move-in ready and full of charm, this home is an exceptional opportunity for anyone seeking comfort, convenience, and lasting value. Showings begin June 4, 2026.

3 Aberdeen St, Windham