Windham, VT Classified Ad Listings

Dover Rd. Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that y...

Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished with a heated in-ground pool (2025), hot tub, barrel sauna, Level 2 EV charger and rooftop solar. Open great room with stone wood-burning fireplace and indoor swing, open kitchen and dining, walkout lower level with wet bar and...

52 Fishing Access Rd. Lakefront Living Meets Mountain Adventure on Lake Rescue Located just minutes from Okemo Mountain, this home offers a rare opportunity to own a property that masterfully bridges the best of Vermont's lake and ski seasons. Whether you are seeking a premier lakefront retreat or a cozy mountain lodge, this home is designed to deliver the perfect four-season lifestyle. The int...

180 High Meadow Road. Single Family Home for sale in Winhall, VT for $1,500,000 with 5 bedrooms and 4 full baths. This 4,173 square foot home was built in 1987 on a lot size of 1.. First Chair Lair: a proven, turnkey Stratton rental on High Meadow, on the complimentary winter-weekend Stratton shuttle route and about 5 minutes to the base. Two-story great room with brick wood-burning fireplace a...

691 Indian Paint Brush Road # E-13R and E-14R. Lots and Land for sale in Winhall, VT for $500,000. The lot size is 2.48.. Build your Stratton estate on the golf course. Two adjoining High Meadow building lots (E-13R and E-14R, 2.48 surveyed acres) that abut the Stratton golf course, with Stratton public water and sewer available and shared driveway access in place. High Meadow covenants protect...

112 Merrill St. This sweet Cape is the perfect place to start your homeownership journey or to simplify your lifestyle with comfortable, easy living. The main level features an inviting open-concept kitchen, dining, and living area, creating a bright and functional space for everyday living and entertaining. Upstairs, you'll find two cozy bedrooms that offer privacy away from the general living...

Location is everything, and this quintessential Vermont retreat delivers. Tucked at the end of a private cul-de-sac just above the upper entrance to Mount Snow, this turn-key residence offers a rare combination of seclusion plus easy mountain and snowmobile trail access. The flat, private lot is built for year-round entertaining, complete with a covered front porch, expansive back deck, hot tub...

Howe Farm Rd. Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound, ...

5735 VT Route 11. What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate? You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market! Sellers are motivated due to having already relocate...

19 Lawridge Hts. Beautifully renovated farmhouse offering the perfect blend of timeless New England charm and modern convenience. Situated on a private, low-maintenance lot with both town water and sewer, this inviting home is just a short stroll to Main Street's shops and restaurants and only three minutes from Okemo Mountain Resort. The heart of the home is the spectacular oversized great roo...

Build your Stratton estate on the golf course. Two adjoining High Meadow building lots (E-13R and E-14R, 2.48 surveyed acres) that abut the Stratton golf course, with Stratton public water and sewer available and shared driveway access in place. High Meadow covenants protect the neighborhood (single-family, 2,000 sf minimum). Mountain views from the area; minutes to the Stratton base and on the...

318/320 Qtr I Jackson Gore Inn. Welcome to this 1 BR lockout with a secluded, private and wooded view with a slight glimpse of the pool off your deck! This unit is located in the south wing with close proximity to the outdoor pool and owners lockers. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2 fixed Queen beds, Queen sleep sofa, Queen wall bed, full kitchen, 2 full bathro...

725 Route 63 Unit 1. This charming 1-bedroom, 3/4-bath apartment blends fresh updates with classic New England character. This beautifully renovated post and beam barn features exposed beams and plenty of natural light, updated kitchen featuring white cabinetry, generous counter space, and stainless steel appliances. The open living area offers ample room to create a comfortable living and dini...

165 High Meadow Road. Single Family Home for sale in Winhall, VT for $2,250,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,034 square foot home was built in 1988 on a lot size of 1.08.. Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished with a heated in-ground pool (...

165 Stone Hollow Road. Single Family Home for sale in Londonderry, VT for $699,000 with 4 bedrooms and 2 full baths, 1 half bath. This 3,959 square foot home was built in 1993 on a lot size of 1.. Welcome to an extraordinary Southern Vermont property where Vermont living meets year-round recreation and relaxation. Located a mile from the center of Londonderry this spacious 4-bedroom, 3-bath hom...

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A rare opportunity to acquire a fully occupied, well-maintained mixed-use property in one of Chester s most recognizable village locations. The front portion of the building is leased as professional office space for $5,000 per month, with the commercial tenant responsible for heat and electricity. The tenant has expressed interest in entering into a significantly longer-term lease, with the le...

21 Crescent St APT 2. Updated 1-Bedroom Apartment First Floor | Springfield, VTBeautifully updated 1-bedroom, 1-bath first-floor apartment in Springfield, Vermont. This apartment offers modern upgrades, efficient systems, and convenient amenities in a well-maintained building.Apartment Features:\n* Updated 1-bedroom, 1-bath layout\n* First-floor location\n* New stainless-steel fridge with ice-m...

395 School Marm Lane. Single Family Home for sale in Townshend, VT for $774,000 with 3 bedrooms and 2 full baths, 1 half bath. This 3,334 square foot home was built in 2010 on a lot size of 5.3.. Tucked into the beautiful hills of Townshend, Vermont is a truly special property, offered to the market for the first time. Beautifully crafted in the timeless tradition of timber-frame construction, ...

311 Dover Rd. This charming 3 bedroom, 1 bath Vermont home is full of personality, character, and vintage charm, offering inviting spaces both inside and out! Situated on 1 acre, with part of the land offering direct frontage on the Rock River, you'll enjoy your own little summer time paradise. Inside, warm wood floors, and unique architectural details give the home a character all its own. Wit...