Jamaica, VT | 494-498 Goodaleville Road

Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey table, foosball table and corn hole, Sonos entertainment system, and high-speed Wi-Fi and digital cable service. Top of the line WOLF Stove and appliances. 4 years of STRONG rental value. This House checks every box. This is the premier house in the area. Huge owners closet. You have so many options here.

11 Round Tree Road, Winhall, VT 05340 A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and kitchenette. Wonderful staircase leading to the second floor. Great open living space and bedrooms throughout including a useful loft with bathroom. Quality metal roof sheds snow easily. A must-see property at Stratton.

4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and retreat while keeping the mountain and year-round recreation within easy reach. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with a gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, a high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a 1BR apartment with SMEG appliances, in-unit laundry, and a private hot tub. Below are heated storage and a screened porch. The restored barn offers parking and an EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and a welcoming front porch complement the peaceful setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Listing agent is related to seller. See neighboring property MLS #5101689.

Built and thoughtfully expanded by its original owners, this substantial Winhall residence offers the scale and comfort of a true year-round home in a location made for four-season Vermont living. Set on 5.02 acres, the property stands apart for its broad, level, cleared grounds, an uncommon and highly usable setting just minutes from the Stratton Access Road. Inside, 3,644 square feet, four bedrooms, four 3/4 baths, and multiple living areas provide room to gather, work, host, and retreat. The bright formal living room features hardwood floors, detailed millwork, and a classic wood-burning fireplace. The expansive family room addition brings warm mountain character with exposed beams, rich woodwork, abundant windows, radiant floor heat, and a dramatic stone fireplace. Directly above, the newer primary suite creates a private retreat, with the addition served by its own Buderus boiler and radiant heating system. A beautifully appointed kitchen connects naturally to indoor and outdoor dining, while an additional sitting room adds even more flexibility. A two-car garage, dedicated workshop, and covered connection to the house make year-round use especially convenient. Once established as a horse property, the open acreage and barn remain ready for a new chapter, whether for equestrian use, vehicle and recreational equipment storage, a workshop, or memorable gatherings. Approximately 15 minutes from Stratton Resort, 12 minutes from Bromley, 19 minutes from Magic Mountain, 15 minutes from Londonderry, and 19 minutes from Manchester, this is far more than a weekend chalet. It is a gracious, versatile Vermont home designed for full-time living and four-season enjoyment.

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 repeat guests who return to experience this special home year after year. Inside, the expansive open-concept living areas were made for gathering after a day on the mountain, while thoughtfully designed private spaces allow everyone room to relax and recharge. Curl up beside one of two fireplaces as the snow falls outside, host movie nights in the impressive 11-foot home theater, or gather in the great room around the 90-inch TV for game day. The lodge experience continues outdoors, where four-season entertaining takes center stage. Grill and dine beneath the stars, soak in the six-person hot tub, unwind in the eight-person sauna, then end the evening around the fire pit surrounded by the peaceful Vermont forest. Every detail has been considered to create a property that feels less like simply a house and more like a destination. There is room for extended family, friends, ski weekends, holidays, and generations of memories—all with the comforts and amenities of a private mountain resort. Whether you're searching for a quintessential Vermont escape to enjoy yourself, a gathering place for family and friends, or a property with an established rental history and repeat clientele, this remarkable lodge offers a combination that is increasingly difficult to find. Arrive, settle in, and experience the Vermont lifestyle exactly as it was meant to be.

Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent renovations include updates to the kitchen and carpeting, creating a move-in ready retreat for all seasons. A spacious wraparound deck with hot tub provides the ideal setting to relax after a day on the slopes. The separate family room, complete with an adjacent full bath, offers excellent flexibility and can easily serve as additional sleeping space for guests. Additional highlights include an attached two-car garage and shuttle service access to Stratton’s ski slopes, winter activities, Stratton Village, shopping, and dining. Active Stratton Sport Center Bond.