Stratton, VT Classified Ad Listings

68 Green Peak Orch S. Welcome to Green Peak Orchard in Dorset, Vermont, where timeless architecture and exceptional craftsmanship define this custom Greek Revival residence on 9.9 private acres. Surrounded by mature landscaping, stone walls, and slate terraces, this remarkable home blends classic New England elegance with modern comfort. Designed with meticulous attention to detail, the home fe...

66 Upper Oak Hill Rd. 180 degrees +/- views, end of the road, top of the hill privacy. 12 acres,4 beds,2 baths,brick,beams,built-ins,custom features,screen room, bonus space! A combination increasingly difficult to find, especially minutes from Newfane Village, Rock River, Brattleboro, vibrant arts community, farm-to-table dining, local galleries, garden shops, farm markets, outdoor recreation ...

9 Mountain Acres Rd. Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installe...

47 Purintan Rd Unit A109. 94 Private Mountainside Acres with Residence: Create Your Vermont Estate. Discover a rare opportunity to own a substantial private estate in Southern Vermont with approximately 94 acres offering the space, privacy, and flexibility to create something truly your own. Originally a livestock farm, with several stone walls and a spring-fed pond nearby. Explore nature at it...

177 Old Tavern Rd. Renovated in 2024, this timber frame sits on 5.75 pastoral acres. This property offers sunrise views, beautiful sun all day and a peaceful setting with pond on a quiet country road. The house has 4 bedrooms, 3 full baths, and an office. Wide plank original pine floors, open timber frame concept and all new baths with heated floors. Custom white oak cabinets in the kitchen and...

564 Goodaleville Rd. Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. ...

679 Burrington Hill Rd. OLD BARN. NEW LUXURY. YOUR PRIVATE SOUTHERN VERMONT ESCAPE. There's something special about a home that feels completely different from anything else-and this beautifully transformed barn conversion is exactly that. Originally an old barn, this stunning 3-bedroom, 2.5-bath home has been thoughtfully reimagined with sophisticated modern finishes, an inviting open-concept ...

8 Winhall Station Rd. Welcome to 8 Winhall Station Road in South Londonderry, a well-located three-bedroom, two-full-bath Vermont home offering convenient access to some of Southern Vermont's best year-round recreation. Several major ski resorts are within easy driving distance, along with nearby hiking trails, campgrounds, swimming, biking, and countless opportunities to enjoy the Green Mounta...

1 Frog Holw. Nestled in a convenient Lower Chimney Hill location, this charming country saltbox offers classic Vermont character, cozy comfort, and access to the many benefits of the Chimney Hill community. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace, the home provides a warm and inviting atmosphere for year-round enjoyment. Recent updates, including ...

4427 W Hill Rd S. A true Vermont lodge in every sense-warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with re...

123 Nichols Rd. HIGH-QUALITY NEW CONSTRUCTION | 123 Nichols Hill Road, Peru, Vermont Rarely does an opportunity like this come to market in Peru, Vermont, a brand new, high-quality, luxury residence offering the perfect combination of refined construction, privacy, expansive mountain views, a private pond, and a beautifully renovated guest house. The main residence was thoughtfully designed for...

88 Windward S. Beautifully maintained contemporary home on 3.62 private acres with elevated westerly views of Mt. Equinox and spectacular sunsets. Designed by renown architect Deborah Berke, Dean of the Yale School of Architecture, this light-filled home offers the ease of main-level living with a first-floor primary suite, laundry, bright office, den with custom built-ins, and spacious living ...

67 Castle Hill Rd. Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham's boat launch and beach areas - trul...

231 VT Route 100. Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL and MOUND SEPTIC SYSTEM just installed in August 2026. Updated elec...

1871 W Hill Rd. Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Tucked away at the end of a private drive on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of comfort and Vermont charm. With four separate sleeping areas, there's plenty of space. The first-floor primary suite provides a private retreat with its own ensuite ...

52 North Rd. Located on a corner lot in the lower section of Chimney Hill, this 4-bedroom, 2-bath home offers 1,856 square feet of living space and a great opportunity for buyers looking to refresh, personalize, and add value. Set on 0.69 acres, the property provides a comfortable amount of outdoor space without the burden of extensive maintenance. The two-story layout is well-suited for full-t...

52 Ruth Way. Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living roo...

123 High Top Rd. Build your Vermont retreat on this oversized lot in Section B of Chimney Hill! A recent perc test indicates suitability for a three-bedroom single-family home, offering a great starting point for your plans. Enjoy full access to Chimney Hill's amenities, including indoor and outdoor pools, a hot tub, tennis and pickleball courts, basketball, an arcade, and a trail system for hi...

High Peak 158/160 Way Lot 3. A opportunity to own this.50-acre double lot in the High Peak Development, offering a double lot for your Vermont getaway. Ideally situated adjacent to the Haystack Golf Course, this parcel provides the perfect mountain convenience. Just a short drive to Mount Snow**, The Hermitage Club, and all the year-round recreation the Deerfield Valley is known for, this prope...

000F-320 Bourbon Run. This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Brom...