Winhall, VT | 33 Old Ridge Road

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.

Stratton Mountain Club AVAILABLE to the purchaser of this exceptional Stratton Resort Residence in High Meadow! This home's design and fit and finish creates the mountain ambiance you look for:Commanding Riverstone Fireplace, Wood accents, Cathedral Ceilings, Wide Pine Floors, an open floorplan with Gourmet Stainless Steel Kitchen and Dining. A lower level family room and game room with 2nd fireplace and entertaining space. Whether it's gathering with friends for apres ski after a day on the slopes or cozying up with family around the fireplaces, you'll experience the lifestyle you look for in a year round retreat. Four Bedrooms/4.5 baths with multiple suites on three levels offers privacy and spacious accommodation. Pull into your oversized heated garage with mudroom entry. Situated on a one acre lot to take in an abundance of sunlight and winter views. Beautifully maintained and turnkey.Resort shuttle stops at your driveway, sports center bond available. All the amenities of the resort are available to you. This location is ideal for summer, fall and winter activities:The Stratton Golf Course and Mountain Biking, Summer Concerts and Fall Foliage from the Gondola, First tracks and crisp mountain mornings. And when you tire of mountain activities, you are just a short drive to Manchester and all the area has to offer, Restaurants, the Manchester Music Festival , and Professional Summer Theatre in Weston and Dorset. Hiking, biking, golf, ski, snowboard, snowshoe and snowmobiling... It's all here for you. A rare offering!

Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling that masterfully blends industrial strength with warm, natural aesthetics. Its bold, dark-bronze standing seam metal exterior provides a sleek, low-maintenance finish that stands out against the lush Vermont landscape. The upper-level living space features a massive wall of glass that opens onto a spacious deck, offering a one-of-a-kind vantage point to enjoy your morning coffee while scouting the ski conditions across the valley. Complementing the living quarters, the ground floor offers high-clearance multi-functional space, perfect for a professional-grade workshop, gear room, or housing a full fleet of UTVs and mountain bikes. Beyond the residence, the land has been transformed into a premier recreational paradise. You can navigate professionally designed and carved mountain bike trails that wind through the expansive 23.5-acre forest. Below the main house, a vast, rolling meadow leads to a custom stone firepit area—the ultimate destination for après-bike gatherings under the stars. Located just minutes from Stratton Mountain Resort, this estate offers a rare combination of architectural sophistication and private access to the best of the Vermont outdoors. This property is also primed for future expansion and the creation of a grander mountain estate. The septic system was specifically built to accommodate a new five-bedroom house, and comprehensive plans are available for viewing for the proposed home. Representing the very best of the Vermont lifestyle, this offering provides both a turnkey adventure hub and a ready-to-build canvas for your dream residence.

Selling very close to the assessed value of $1,126,100!!! This 2026 town assessment just made this property a REAL DEAL because the Owner wants 1,200,000. This property can be sold furnished or unfurnished with closing before the ski season is here. 6 bedrooms and 3.5 bathrooms to accommodate your family and guests. Enjoy 2 primary suites with attached baths and one is on the main floor. Walk in closets for the primary bedrooms and a mini split on the 3rd floor primary for air conditioning in the hottest months. There's also a sweet porch off the 3rd floor that feels like a tree house. 3 real wood fireplaces to cozy up to. A chef's kitchen at the heart of this home with big open spaces for large groups to gather. There's a gas grill connected to the house line just outside the kitchen slider doors. It's covered too! Porches surround this entire home for you to enjoy nature without leaving the house. The corner lot is a very short distance to the Stratton Gondola. Fireworks at the mountain can be enjoyed from the porch or yard. This real estate investment is worth a look in person. Stratton is also close the shopping outlet town of Manchester, theatre and restaurants in Dorset and Bromley Mtn. Driveway can fit 10 cars and 2 more in the garage.

Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast, this propery has the features you look for in a Resort Residence, 5 bedrooms (which includes a spacious and private primary suite wing), 4 updated bathrooms, a spacious media room that opens to a patio with hot tub and fire pit. The galley kitchen opens to a dining room and all with ease to entertaining and apres ski. This location is prime for winter ski and snowboarding as well as an incredible mountain biking trail system during the summer and fall. Hike, bike, golf and enjoy incredible year round activities. Very few homes become available in the North Brookwood neighborhood. Don't miss an opportunity to create your own mountain lifestyle in this great resort location.

Discover this truly exceptional Vermont Mountain Retreat just seven miles from Stratton Mountain, perfectly located for four-season living! Boasting an inviting open layout great for spending time together, southern exposure and an abundance of natural light this beautifully renovated home has been updated in a sophisticated Vermont rustic style with all the comforts. Enjoy the Luxurious primary suite with its own gas fireplace and sitting area with southern views, 3 additional ensuite bedrooms plus a Bonus room, and a large Family Room. A spacious mudroom entry provides plenty of storage and the private office makes it easy to work while you are here. Eight interior mini splits provide year-round comfort, while a two-car garage with EV charger adds modern convenience. Step outside and experience your own Private Resort. With a stunning in-ground pool, expansive patio areas, and bubbling hot tub, all surrounded by beautifully designed landscaping by Mark Wright. Private and peaceful yet wonderfully close to Stratton, Bromley, and Magic Mountains, this is an extraordinary Vermont escape designed for memorable weekends and truly exceptional mountain living.