Stratton, VT Classified Ad Listings

291 Springhill Rd. Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the chan...

16 Sawmill Road. Single Family Home for sale in Stratton, VT for $3,900,000 with 5 bedrooms and 4 full baths. This 5,080 square foot home was built in 2002 on a lot size of 1.16.. Location, luxury, and the best of Stratton Mountain living! Just steps from Stratton Village and The Stratton Club, this exceptional mountain retreat offers convenience, privacy, and timeless Vermont charm, with the a...

777 McCooey Dr. Set back from a quiet country road in Manchester, Vermont, this spacious Federal farmhouse style home offers a wonderful blend of comfort, privacy and Vermont charm. The classic white exterior with its attached red barn creates a welcoming first impression, while the home's thoughtful design provides plenty of space for everyday living, entertaining and enjoying the peaceful sur...

23 Shincracker Way. Set among the treetops with sweeping views spanning multiple states, this Rod Williams designed classic is a sprawling 5300+ sq ft, 6 bed, 4 bath with attached 2 car garage, capturing everything there is to love about a Vermont ski retreat. Situated on 3 acres bordering community land, the property enjoys an elevated setting, exceptional privacy, expansive views including th...

318 North St. Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, sing...

7 Lightning Ledge Way. Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxe...

640 Cross Rd. An exceptional opportunity to establish a private Vermont estate on approximately 61.36 acres, offering stunning panoramic views of Stratton and Bromley Mountains and located a short drive from Magic Mountain. The site is fully prepared for construction, with utilities, services, and a gravel road in place, an approved septic permit for a 5-bedroom residence with building plans an...

21 Lawrence Davis Dr. NEW 2025 MANUFACTURED HOME ON 1.4 ACRES IN WILMINGTON! Enjoy the perfect blend of privacy, convenience, and value in this immaculate 3-bedroom, 2-bath double-wide manufactured home offering approximately 1,300 square feet of comfortable one-level living. Set on 1.4+/- acres on a quiet dead-end road, this property offers a peaceful setting while remaining just a short drive...

9282 VT Route 100. This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman...

2 Bromley Ln. Charming 4-bedroom, 1.5 bathroom house on private lane in desirable North Bennington, steps from Bennington College and a short walk to the Village center's restaurants, library, and shops. The home's first floor features an updated eat-in kitchen with granite countertops, dining room, living room with fireplace, half bath, and study with built-in bookcases, as well as a sun room ...

40 Kelleher Rd. Where Vermont Living Feels Effortless Dorset Home, Guest Cottage, Pond and Mountain Views Settle into the beauty of Dorset with a property that feels like a true Vermont retreat. This lovingly maintained offering pairs a welcoming main residence with a separate one-bedroom cottage, 4.5 acres of open land, a private pond, and beautiful views creating a rare opportunity to enjoy s...

197 Bromley Brook Rd. A classic Vermont setting, mountain views, and a home designed for comfortable living come together in this inviting Manchester property. Set on a level, beautifully usable lot, the home offers a peaceful retreat while keeping Bromley, Magic, and Stratton close at hand. The kitchen and dining areas are filled with natural light, with large windows bringing the surrounding ...

14 Vaughn Farm Rd Unit 1. Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-bu...

36 Woffenden Rd. Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land ar...

662 Howe Farm Rd. Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, ad...

392 Powderhorn Rd. Set on two private acres in Manchester, this 4-bedroom, 2.5-bath Colonial combines classic character with thoughtful updates. Wide-plank pine floors, abundant natural light, and generously proportioned rooms define the interiors. The main level includes a spacious living room with a stone fireplace, a formal dining room, and an eat-in kitchen. An adjoining flexible space offe...

B Prospect St. A rare opportunity to own 38 stunning acres in the heart of Manchester Village, offering the perfect balance of seclusion, natural beauty, and convenience. A long, winding serpentine driveway gracefully leads to a beautifully manicured and ready-to-build homesite, creating a dramatic and private approach. Thoughtfully improved with underground power brought directly to the buildi...

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...