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$499,000

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

3 Beds ⋅ 2 Baths ⋅ 5108371 MLS

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

756 Birch Hill Rd, Windham

$2,800,000

UNFORGETTABLE LUXURY | Distinctive, sophisticated and designed to leave a lasting impression, this exceptional custom Colonial by renowned builder DiPietro Homes offers 6,000+ sq. ft. of beautifully appointed living space. Thoughtfully enhanced with on-trend updates and improvements, this remarkable home blends exceptional craftsmanship with a fresh, elevated style for today's luxury lifestyle. From the moment you enter, custom millwork and impressive architectural details set this home apart. At the heart of the home, the stunning family room features a coffered ceiling and wood-burning fireplace, opening seamlessly to a showstopping chef's kitchen designed for both everyday living and effortless entertaining. Full-size refrigerator and freezer, generous workspace and a Butler's Pantry complement this thoughtfully designed space. An elegant dining room, private office and functional mudroom complete the main level. Upstairs, the luxurious primary suite is an unforgettable retreat with its own fireplace and spa-inspired bath featuring a soaking tub and steam shower. With 4 bedrooms, 5 bathrooms, a bonus room and a finished lower level offering a recreation room, full kitchen, built-ins and bath, there is exceptional space and versatility throughout. Outside, your private backyard awaits, complete with an in-ground saltwater pool with waterfall and a covered seating area perfect for relaxing, entertaining and enjoying summer days outdoors. Conveniently located near I-93, schools, shopping and community amenities, with Boston approximately 45 minutes away. A truly unforgettable home where luxury, comfort and exceptional design come together.

4 Beds ⋅ 6 Baths ⋅ 5104676 MLS

UNFORGETTABLE LUXURY | Distinctive, sophisticated and designed to leave a lasting impression, this exceptional custom Colonial by renowned builder DiPietro Homes offers 6,000+ sq. ft. of beautifully appointed living space. Thoughtfully enhanced with on-trend updates and improvements, this remarkable home blends exceptional craftsmanship with a fresh, elevated style for today's luxury lifestyle. From the moment you enter, custom millwork and impressive architectural details set this home apart. At the heart of the home, the stunning family room features a coffered ceiling and wood-burning fireplace, opening seamlessly to a showstopping chef's kitchen designed for both everyday living and effortless entertaining. Full-size refrigerator and freezer, generous workspace and a Butler's Pantry complement this thoughtfully designed space. An elegant dining room, private office and functional mudroom complete the main level. Upstairs, the luxurious primary suite is an unforgettable retreat with its own fireplace and spa-inspired bath featuring a soaking tub and steam shower. With 4 bedrooms, 5 bathrooms, a bonus room and a finished lower level offering a recreation room, full kitchen, built-ins and bath, there is exceptional space and versatility throughout. Outside, your private backyard awaits, complete with an in-ground saltwater pool with waterfall and a covered seating area perfect for relaxing, entertaining and enjoying summer days outdoors. Conveniently located near I-93, schools, shopping and community amenities, with Boston approximately 45 minutes away. A truly unforgettable home where luxury, comfort and exceptional design come together.

17 Bennington Rd, Windham

$1,050,000

Where Every Day Feels Like a Getaway with stunning views of Cobbetts Pond in Windham, NH. Morning light spills across the water as you step onto your private balcony, coffee in hand, watching the lake wake up for the day. By afternoon, you're out on the boat. By evening, you're gathered under the covered porch as the sun drops over the shoreline. This is more than a beautifully renovated home. It's a place where everyday life feels like a getaway. The main living spaces reimagined from top to bottom; every detail here reflects lasting quality and timeless design. At the heart of the home, a lovely seating area open to the upper level, an open-concept gourmet kitchen that flows into the sun room and a generous gathering space in the lower level with a wet bar set the stage for entertaining. The first floor primary suite is a peaceful retreat with a spa-inspired bath and a new slider out to the deck, added to enjoy those lake views. Set on a corner lot, two levels of expansive Trex decking overlooking the lake, beautifully landscaped grounds, and a newly added three-season sunroom to relax through every season. Deeded waterfront ownership brings a private sandy beach, boat launch, kayak storage, and an opportunity for future dock space, making the lake a natural extension of the front yard. ALL NEW: roof, siding, windows, doors, plumbing, electrical wiring, HVAC runs, insulation, whole-house generator, whole-house water system and MORE! Every major investment has already been made. Whether you're hosting friends and family, launching the kayak for an afternoon on the water, or simply taking in the view, this is a home built for lasting memories. Located in highly desirable Windham, NH, you'll enjoy award-winning schools, nearby golf courses, walking trails, and convenient access to Tuscan Village with its outstanding shopping, restaurants, and year-round events, all while remaining close to Rte 93 for an easy commute . Life is simply better at the lake.

2 Beds ⋅ 4 Baths ⋅ 5101174 MLS

Where Every Day Feels Like a Getaway with stunning views of Cobbetts Pond in Windham, NH. Morning light spills across the water as you step onto your private balcony, coffee in hand, watching the lake wake up for the day. By afternoon, you're out on the boat. By evening, you're gathered under the covered porch as the sun drops over the shoreline. This is more than a beautifully renovated home. It's a place where everyday life feels like a getaway. The main living spaces reimagined from top to bottom; every detail here reflects lasting quality and timeless design. At the heart of the home, a lovely seating area open to the upper level, an open-concept gourmet kitchen that flows into the sun room and a generous gathering space in the lower level with a wet bar set the stage for entertaining. The first floor primary suite is a peaceful retreat with a spa-inspired bath and a new slider out to the deck, added to enjoy those lake views. Set on a corner lot, two levels of expansive Trex decking overlooking the lake, beautifully landscaped grounds, and a newly added three-season sunroom to relax through every season. Deeded waterfront ownership brings a private sandy beach, boat launch, kayak storage, and an opportunity for future dock space, making the lake a natural extension of the front yard. ALL NEW: roof, siding, windows, doors, plumbing, electrical wiring, HVAC runs, insulation, whole-house generator, whole-house water system and MORE! Every major investment has already been made. Whether you're hosting friends and family, launching the kayak for an afternoon on the water, or simply taking in the view, this is a home built for lasting memories. Located in highly desirable Windham, NH, you'll enjoy award-winning schools, nearby golf courses, walking trails, and convenient access to Tuscan Village with its outstanding shopping, restaurants, and year-round events, all while remaining close to Rte 93 for an easy commute . Life is simply better at the lake.

2 Fox St, Windham

$1,500,000

Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering 4 spacious bedrooms and a beautifully appointed walk-out lower-level in-law suite, this remarkable home blends sophistication, comfort, and versatility. A grand two-story foyer welcomes you into a home showcasing impeccable craftsmanship, classic architecture, and custom millwork throughout. The thoughtfully designed floor plan features a private home office, elegant formal dining room, and an inviting family room centered around a stunning fireplace. The expansive chef's kitchen flows seamlessly into the main living areas, creating the ideal space for everyday living and entertaining. It is equipped with a custom cabinet-front refrigerator, plus an additional stainless steel refrigerator offering expanded refrigerated storage. Just beyond, a sun-filled four-season room overlooks the private backyard and opens to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room features custom millwork, a built-in bar, and the perfect setting for entertaining. Designed with both luxury and practicality in mind, the home offers central air conditioning throughout, while strategically placed mini-split systems provide individualized comfort and energy-efficient climate control in frequently occupied spaces. The luxurious primary suite features a spa-inspired bath, while the additional bedrooms are generously sized. The walk-out lower level offers a complete in-law suite with its own living space, ideal for multigenerational living, guests, or an au pair. Outside, the expansive composite deck overlooks a spectacular gunite inground pool surrounded by professionally designed landscaping, creating exceptional privacy. A classic farmer's porch completes this extraordinary property, where timeless architecture, refined finishes, and effortless indoor-outdoor living come together.

4 Beds ⋅ 4 Baths ⋅ 5099575 MLS

Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering 4 spacious bedrooms and a beautifully appointed walk-out lower-level in-law suite, this remarkable home blends sophistication, comfort, and versatility. A grand two-story foyer welcomes you into a home showcasing impeccable craftsmanship, classic architecture, and custom millwork throughout. The thoughtfully designed floor plan features a private home office, elegant formal dining room, and an inviting family room centered around a stunning fireplace. The expansive chef's kitchen flows seamlessly into the main living areas, creating the ideal space for everyday living and entertaining. It is equipped with a custom cabinet-front refrigerator, plus an additional stainless steel refrigerator offering expanded refrigerated storage. Just beyond, a sun-filled four-season room overlooks the private backyard and opens to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room features custom millwork, a built-in bar, and the perfect setting for entertaining. Designed with both luxury and practicality in mind, the home offers central air conditioning throughout, while strategically placed mini-split systems provide individualized comfort and energy-efficient climate control in frequently occupied spaces. The luxurious primary suite features a spa-inspired bath, while the additional bedrooms are generously sized. The walk-out lower level offers a complete in-law suite with its own living space, ideal for multigenerational living, guests, or an au pair. Outside, the expansive composite deck overlooks a spectacular gunite inground pool surrounded by professionally designed landscaping, creating exceptional privacy. A classic farmer's porch completes this extraordinary property, where timeless architecture, refined finishes, and effortless indoor-outdoor living come together.

5 Sherwood 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

$799,000

Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. Located within a 20-minute drive to Stratton, Magic, and Bromley, and directly adjacent to the VAST snowmobile trail system, this property offers immediate access to Vermont’s top winter and summer activities.

4 Beds ⋅ 5 Baths ⋅ 5086432 MLS

Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. Located within a 20-minute drive to Stratton, Magic, and Bromley, and directly adjacent to the VAST snowmobile trail system, this property offers immediate access to Vermont’s top winter and summer activities.

1035 Vt Route 121, Windham