Winhall, VT | 45 Benson Fuller Drive

Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views. Upstairs, you'll find two bedrooms and a separate office, sharing a full bath. The property also includes a two-car garage with a convenient studio apartment and private bath, ideal for guests. Enjoy direct access to the water with a unique floating dock, perfect for kayaks, paddle-boards, and simply taking in the magnificent scenery. This home is designed to accommodate a life of both leisure and adventure.

A rare opportunity in Long Trail House, this corner residence has been thoughtfully reimagined from two separate units into a spacious, fully renovated retreat designed for flexible living. The expanded layout now includes multiple sleeping areas and a den/office, offering versatility for guests or remote work. Natural light fills the home thanks to its corner position, while open living space flows seamlessly to an extended outdoor footprint with both a full-length deck and covered porches. The oversized primary suite stands out with its private fireplace, walk-in closet, direct deck access, and a beautifully finished bath featuring double vanities and a large shower. The kitchen has been enlarged and upgraded with granite countertops, stainless appliances, and a substantial island that anchors the space for gathering and entertaining. Located across the street from Stratton's snowfront, lifts, Village shops, and restaurants, this residence offers exceptional access without the need to drive. Long Trail House amenities included heated underground parking, private owner storage, a year-round heated pool, sauna, multiple hot tubs, and a welcoming hearth room. Discounted access to the Stratton Training and Fitness Center is also available. Contact us for more information or to schedule a private showing.

Experience ultimate year-round luxury in this tastefully renovated townhome at Slopeside, featuring convenient trail access. Perfectly blending comfort and convenience, this inviting mountain retreat features an updated kitchen and baths, a cozy wood-burning fireplace, and mini-splits for efficient summer cooling. The spacious layout offers three bedrooms plus a private loft complete with its own 3/4 bath. There is plenty of room to relax after a day on the trails, or you can step down into the sunken hot tub on the recently updated deck. Leave the keys behind, its exceptional location offers easy walking access to village shops, dining, and the in-ground pool for the ultimate hassle-free mountain getaway.

Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes, this property offers the best of Stratton living in every season. Step inside to find a spacious, light-filled interior with clean contemporary lines, warm natural materials, and an inviting open layout ideal for gathering with family and friends. Large windows bring the outdoors in, while generous living spaces provide plenty of room to relax after a day on the mountain. With four well-appointed bedrooms, this home comfortably accommodates guests and offers flexible space for work, play, or quiet retreat. Outside, the expansive 1.37-acre lot delivers the privacy and peaceful surroundings you expect from a mountain home, including a covered deck with a hot tub and grill to be able to enjoy year round, all while keeping you close to the heart of the resort. Whether you’re seeking a year-round getaway, a winter ski home, or a property with excellent rental potential, 7 Roundtree Road delivers contemporary style, convenience, and Stratton Mountain charm in one exceptional package.

Shred Shack: the portfolio's workhorse. A post-and-beam Stratton ski house with mountain views on 2.2 private acres, about 6 minutes to the base. Soaring timber great room with stone wood-burning fireplace and indoor swing, knotty-pine kitchen with bar seating, big farm-table dining, wrap-around deck with hot tub, indoor barrel sauna, outdoor fireplace and Level 2 EV charger. 4 bedrooms (bunk room with lounge), 3 full baths, solar with battery backup. INCOME: $118,675 gross in 2025; $132,292 trailing 12 months; about $45,000 in confirmed future bookings on the books (11 stays). Ski-season revenue has run $53-58K per winter. Featured on FOX Weather through a Vrbo partnership. PORTFOLIO FOR SALE: This property is one of five 42 North properties in Winhall offered individually or together (four turnkey short-term rentals + the Indian Paint Brush building lot; ~$560K combined trailing-12-month gross rental revenue). Ask about package pricing. Listing broker is a principal and beneficial owner of the selling entity. Potential tax advantages for STR buyers (non-passive treatment, cost segregation, bonus depreciation) - consult your tax advisor. Revenue figures are gross rental revenue excluding taxes, before expenses; unaudited; past results do not guarantee future results.

This tastefully renovated 4-bedroom, 4-bathroom townhome is the mountain getaway you’ve been waiting for. The coveted end unit boasts an open, airy layout and new oversized windows in the kitchen and living room. The result is a space flooded with natural light, offering private, wooded views right from the couch. Just one mile from the Village, you can skip the parking hassle with the convenient weekend and holiday shuttle. After a day of adventure, unwind in your turnkey sanctuary by the wood-burning fireplace. As an owner at Styles Brook you have access to a clubhouse, a paddle/pickleball court, and a seasonal in-ground heated pool for the warmer months. Just a short walk to the Stratton Fitness Center, bond available to purchase. Offered fully furnished for an effortless escape.

Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a spacious kitchen, dining area, and expansive living room centered around a cozy fireplace—perfect for unwinding after a day on the slopes. Designed for active outdoor living, the home features a dedicated ski room right inside the entry from the attached two-car garage to keep your gear organized and dry. Upstairs, comfortable bedrooms offer plenty of space for guests and a fun-filled loft complete with pool and foosball tables. The finished lower level functions as a private second primary suite with generous storage. Outside, year-round enjoyment continues with a covered hot tub and a dedicated fire pit for cool mountain evenings. Offered furnished, this property is ready for immediate use as an alpine getaway or turn-key primary residence.

Unmatched Comfort and Convenience at Stratton's Ober Tal - trailside property Discover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Next to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village. Close enough to swing back for a quick lunch, this condo lets you make the most of your mountain time. After a day on the mountain, unwind by the wood-burning fireplace in the family room, or gather for meals in the large dining area, featuring a second wood-burning fireplace. Step outside to relax on the oversized deck with distant views of Bromley Mountain. Designed for entertaining, the spacious chef’s kitchen is well-equipped for group cooking, with thoughtful amenities like double ovens, a microwave, two dishwashers, a prep sink, and a wine fridge. Gather around the long granite island with seating for five, where everyone can join in the fun or simply relax while dinner is prepared. With plenty of room for everyone, this condo features four bedrooms (one with bunk beds and trundle) plus an office with an additional full-sized Murphy bed, providing a flexible fifth bedroom. Two full bathrooms ensure comfort and privacy for all. The large, rustic wood-paneled mudroom offers generous storage for ski gear, complete with a boot bench and a full-size washer and dryer to keep everything ready for the next day.

Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no matter the weather. Or you can relax in the hot tub after a long day and even enjoy the sounds of a local waterfall located just a short walk from the doorstep. A 1-bedroom apartment with a separate entrance gives this home more flexibility for family and friends to stay for extended visits. The two-car garage provides space for all the outdoor gear you could need to explore the Vermont wilderness year-round. This home has all you need to enjoy all the Vermont has to offer.

Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but contains a new addition from the 21st allowing you & your family to have space. The home has high ceilings, hand-hewn beams, classic woodwork, a wood-burning stove, and walls of windows that bring in warmth & light. The addition includes a grand primary suite with soaring ceilings, views over the land, walk-in closet, large tiled bathroom with a tiled shower, powerful jet tub, and double vanity. With 5 total bedrooms, 4.5 baths, 2 living spaces, and 3 bonus rooms, there is space to host or work from this 3,840SqFt home. The expansive kitchen contains large countertops with space for seating as well as a window covered breakfast nook. The butler’s pantry, complete with a wet bar, makes entertaining easy. Sit by the stove while snow falls across the pasture and enjoy your snow-globe like winter scene, complete with a great sledding hill right outside. On warm days, open the sliders to the brick patio, or to the back deck to grill, pick berries in the garden, walk the orchard trail, or watch the leaves change during the seasons. The home is located near the town of Manchester, ski mountains (Stratton, Bromley, and Mount Snow), excellent golf courses, & local renowned dining at Honeypie, River & Rye and Solo Farm & Table within easy reach. Bradley International Airport is 2 hours away, Boston is 3, and New York City is 4. This is a home you can enjoy now. One whose location, scale, and enchanting views provide the foundation to create your dream oasis. You deserve to enjoy the Vermont life you have been dreaming of, and make this home and timeless setting part of your family’s legacy.

78 Middle Ridge Road, #407, Stratton Resort, Stratton, Vt 05155 Founders Lodge is located on the Village Common, a masterfully planned neighborhood at Stratton Mountain Resort. Leave your car in the underground heated garage and walk to the Village Shops, restaurants and ski lifts! Soak in the over sized hot tub after a fun day on the slopes. Family friendly location with a skating pond and fire pit on the Village Common. Ski locker and owner’s storage cages. Founders Lodge has a workout room, game room and a large hearth room for gathering.

Hilltop Hideaway: a bright saltbox retreat in Forest Farms, 5-10 minutes to Stratton. Cathedral glass-gable loft with brick fireplace, two more wood-burning fireplaces including the main living room, open kitchen and dining, three en-suite bedrooms plus a bunk room, hot tub and a stone fire-pit patio in the trees. Solar-equipped. INCOME: $61,063 gross in 2025; $64,121 trailing 12 months; about $14,000 in confirmed future bookings on the books (6 stays). Upside for an owner-operator or a buyer who wants a part-time personal ski house that pays much of its own carry. PORTFOLIO FOR SALE: This property is one of five 42 North properties in Winhall offered individually or together (four turnkey short-term rentals + the Indian Paint Brush building lot; ~$560K combined trailing-12-month gross rental revenue). Ask about package pricing. Listing broker is a principal and beneficial owner of the selling entity. Potential tax advantages for STR buyers (non-passive treatment, cost segregation, bonus depreciation) - consult your tax advisor. Revenue figures are gross rental revenue excluding taxes, before expenses; unaudited; past results do not guarantee future results.