Properties Near 109 Winhall Hollow Road Winhall, VT

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.

Beautifully renovated in 2023, this 4-bedroom, 2-1/2 bathroom contemporary sits on 1.47 wooded acres with a sweeping circular driveway and genuine privacy — while still being on the Stratton shuttle route and just minutes from the base lodge on foot. The interior renovation was done right. Radiant heat floors run through the living room and kitchen, with two wood-burning fireplaces anchoring the main living spaces. The kitchen is built for serious use: Top of the line Wolf and Miele appliances, marble countertops and a layout that opens directly to the dining area and forest views. Vaulted wood-plank ceilings and oversized windows keep the spaces light and connected to the setting without trying too hard. The bedroom layout works well for groups or families — three bedrooms across the main levels plus a top-floor primary suite with loft, two full baths with heated floors and a half bath on the entry level. The two-car heated garage with an electric car charger handles gear and vehicles whether you’re coming off the mountain or heading into the fall foliage season. Mechanicals include mini-split cooling, baseboard and radiant heat, community water and septic. Electric roof electric cables were installed for ice protection while security cameras cover the exterior. Walk to the shuttle. Drive to the village in minutes. Own it year-round or use it as the mountain house it was built to be. Your Vermont chapter starts here. Reach out for a private tour.

OPEN HOUSE SATURDAY 8/1 FROM 3PM-5PM | 10 MINUTES TO STRATTON RESORT | 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. Just 10 minutes from Stratton Mountain Resort and less than a mile from Honeypie Restaurant and Rawsonville Market, the location offers easy access to the mountain, local favorites, and everything the area has to offer. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while quality construction and thoughtful details are evident throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for-full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property available 494-498 Goodaleville Road - MLS#5101688.

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.

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.

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.

Welcome to this beautifully maintained top-floor Rising Bear condominium, where you’ll enjoy stunning views of Stratton Mountain and the Commons Pond from nearly every room. The soaring cathedral ceilings and abundant natural light create a bright, open feel, while the spacious loft overlooking the living area offers a great spot for relaxing, gathering, or extra sleeping space. The living room is warm and inviting, centered around a stone-faced gas fireplace perfect for cozy evenings after a day on the slopes. Recent updates, including refreshed countertops, updated lighting, and a high-quality audio/visual system, add modern comfort while keeping the home’s classic mountain charm. The layout is both practical and comfortable, with a primary suite on the main level and an additional en-suite bedroom, bunk room, and loft upstairs ideal for hosting family and friends while still offering privacy. Owners also benefit from excellent amenities, including two heated underground parking spaces, private ski lockers, a year-round heated pool, outdoor hot tubs, and a sauna. With its beautiful views, thoughtful updates, and move-in-ready condition, this is a wonderful opportunity to enjoy life at Stratton Mountain.

Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community . Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces highlighted by two fireplaces, creating a warm and inviting atmosphere. A bonus room is an art studio to expand your creative senses. Large windows capture the natural beauty of the surroundings, while a wraparound deck extends the living space outdoors—ideal for entertaining or simply enjoying the peaceful setting. The property is uniquely enhanced by two beautiful private ponds, And an abundance of perennial gardens, offering a serene and picturesque backdrop. Relax in the outdoor hot tub after a day on the slopes. Enjoy Highland Forests private beach access to Cole Pond, This grassy space with a dock is perfect for swimming, kayaking, and quiet enjoyment. Outdoor enthusiasts will appreciate the nearby Hiking and Snowshoe trail access, making this an ideal four-season retreat. Whether you're seeking a full-time residence or a Vermont getaway, this home delivers a rare combination of space, setting, and proximity to one of Southern Vermont’s premier resorts.

Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering, relaxing, and enjoying all four seasons in Vermont. Recent exterior improvements have significantly enhanced the home’s appearance and overall exterior presentation. Extensive work included reconstruction and upgrading of major exterior sections, along with new windows, roofing, trim, upgraded siding, exterior refinishing, and fresh paint. Complemented by a standing seam metal roof and updated exterior detailing, the home now offers a refreshed mountain exterior with a warm and inviting presence. Inside, the layout is exceptionally functional and inviting. The main level features an open kitchen, dining area, and vaulted living room with fireplace, along with a sunroom, screened porch, stone patio, and private primary suite. A mudroom with half bath off the attached two-car garage adds convenience for ski season and everyday living. Upstairs offers three additional bedrooms, a full bath with double vanity, and an airy loft overlook. The finished walkout lower level is built for entertaining and flexible living, featuring a spacious family room with wood stove and sliders, custom bar area, guest bedroom and bath, additional half bath, laundry, utility areas, and wide hallways throughout. Located just minutes from the slopes, golf course, village, and shuttle access, this is a rare opportunity to own a substantial Stratton mountain home with significant exterior improvements already completed, while still offering the chance to bring your own vision and style to the interior spaces.

Nestled on 10 private acres just off the Stratton Mountain Access Road, 65 Lower Taylor Hill Road offers a rare opportunity to own a beautifully renovated Vermont retreat ideally positioned between Stratton Mountain Resort and the area's endless four-season recreation. Surrounded by mature woodlands and exceptional privacy, this property offers a three-bedroom, three-bath main house along with a charming bunk house. The home combines refined craftsmanship, modern amenities, and timeless mountain charm. The thoughtfully redesigned interior is highlighted by a dramatic entryway featuring soaring ceilings with exposed beams and beautiful sight lines to the original great room and spacious dining area surrounded by spectacular forest views. French doors from the great room flow onto an expansive covered deck providing sweeping views of the gorgeous mountain surroundings – the perfect place to begin or end the day. Grounding the entry are heated slate tile floors and a convenient mudroom. The stunning all-new custom kitchen features hardwood shaker-style cabinetry, crown molding, elegant slate countertops and professional-grade stainless steel Café appliances. The first-floor master suite includes custom wardrobes and large French doors leading to a private deck. The private en-suite bath features heated slate tile floors, walk-in tile shower, and Kohler finishes. Completing the main floor is a full bath with spacious walk-in tile shower and heated floors. The sunny second floor features two large bedrooms and loft area. The full bath also boasts heated slate tile floors as well as a curved basin tub, and Kohler finishes. The finished basement area includes family space and an adjacent laundry room with new full-sized washer and dryer. The “family favorite” bunk house provides a rustic studio-style flex space with kitchen, full bath, living area, and a roomy loft. Beautiful French doors provide treetop views and lead to a private outdoor sitting area.