Properties Near 44 Hilltop Road Winhall, VT

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Enjoy one of the most stunning, unobstructed views of Stratton Mountain and its slopes from this beautifully maintained 5-bedroom, 3-bath home, located on a quiet dead-end road just 3 miles from the lifts. This inviting retreat features a completely renovated kitchen, a new furnace, and comes fully furnished for turnkey enjoyment. Air conditioning throughout ensures comfort year-round—perfect for enjoying all that Vermont has to offer in every season. Outdoor living is a highlight, with a gorgeous screened-in porch and three decks—two recently upgraded with Trex decking—ideal for relaxing or entertaining while taking in the breathtaking scenery. Whether you're seeking a mountain getaway or a spacious year-round residence, this home offers comfort, style, and unbeatable proximity to Stratton’s slopes and outdoor adventures.
Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape. Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for chilly evenings. Cathedral ceilings soar, enhancing the spacious feel. The primary suite is a true sanctuary, boasting a spa-like bathroom with double sinks, a jetted tub, a separate shower, and an expansive walk-in closet. Enjoy private balconies directly from your bedroom, offering stunning vistas and a tranquil spot for morning coffee or evening stargazing. Beyond the living areas, this home offers an array of desirable amenities including a stylish bar, ideal for gatherings, and a dedicated exercise room to maintain your wellness routine. Strategically located, this property offers unparalleled access to outdoor adventures. Just minutes from Stratton Resort, you'll enjoy world-class skiing in winter and championship golf in the warmer months. Experience the best of Vermont living with a perfect blend of luxury, comfort, and convenience. Your Winhall dream home awaits!
Unmatched Comfort and Convenience at Stratton's Ober Tal – Walk to Lift Discover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Just a short walk 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.
OPEN HOUSE SUNDAY OCTOBER 12TH 11:00AM-1:00PM! Escape to the mountains in this enchanting 4 bedroom, 3.5 bath home just moments from Stratton Resort in one of the areas most sought after neighborhoods! Offering classic chalet charm and convenience, this well-appointed home includes winter weekend/holiday shuttle service to the Stratton. After a day on the mountain, enjoy a walk to Stratton Village where you’ll find a variety of shops, and après-ski spots. Rather stay in? Curl up in front of the fire and take in the outdoors from the wall of windows. With its functional layout, open living area, spacious updated kitchen, sunny deck and a premier location, this chalet is the ultimate year round mountain retreat. Property is on Stratton water and sewer, quarterly fee is $228.76. Roads and security fee tbd. Subject to Stratton ROFR.
This beautiful Timber frame home on an 8.1 acre lot is located a few miles from the base of Stratton, Bromley, and Magic Mountain making it a versatile investment. Whether a seasonal prospect or primary home, being next door to Gale Meadow Pond provides a wonderful destination to walk, hike, fish, or just paddle. This home has a private, beautiful yard with its own pond, stream, and firepit just off the deck. Automated whole house generator installed in 2020. Updated kitchen, bathroom, and flooring in 2025. See the recent renovation list. Owner is Vermont licensed real estate agent.
Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s closet—ideal for all your gear. Turnkey and move-in ready, this is the perfect mountain retreat in one of Stratton’s most desirable communities!
In the heart of the Stratton Mountain Village attached to the iconic Clock Tower, Landmark is prime location for all that that the Resort has to offer. This two bedroom floorplan is one of the largest in the community. Ample living and bedroom space as well as a nice separate dining area. Direct mountain views with southern exposure for warm light. Beautifully appointed furniture and ready for immediate occupancy. STRATTON MOUNTAIN CLUB MEMBERSHIP AVAILABLE!
Very unique three bedroom three bathroom in the ever popular Long Trail House community. Originally a studio and two bedroom unit preconstruction, this premiere condominium has been converted into a family retreat. The home was completely renovated a few years back with wood laminate flooring, granite counter tops, new appliances and renovated bathrooms. The studio was turned into a primary suite with gas fireplace and mountain views. Long Trail House offers a year round heated pool, three hot tubs, a sauna and owner storage area. Enjoy the Stratton Mountain views and proximity to all the Resort has to offer. Come home to Vermont!
Your slice of heaven awaits! Leave your worries behind and step into a beautiful Southern Vermont home that's truly turnkey. This well-designed, fully furnished, 3 bedroom, 2.5 bath home on 1.8+/- professionally landscaped acres offers privacy and convenience to the area's premier slopes, trails and natural beauty. The heart of the home is an expansive chef’s kitchen where country cabinetry and stone countertops create a refined haven of sophistication. A three-season screened porch is perfect for curling up with a favorite novel while admiring your tranquil and lush domain. The cottage style dining room features a lovely terrace that overlooks the vibrant perennial gardens. With a high, vaulted natural wood ceiling and woodburning fireplace, the living room creates a sense of spaciousness and warmth for entertaining. The inspired primary ensuite is a true sanctuary replete with a study/nook, powder room, and private, luxurious bath with a deep soaking tub. The lower level, a near-self-sufficient retreat, features two bedrooms, a welcoming mudroom/entry with woodstove, a large living area with 75” TV, stylish bath with tiled shower and a fully-equipped laundry room. Recent improvements include a brand new mini-split system (A/C and heat), full home battery back-up and comprehensive security system. Just 3 miles from Stratton Access Road, 15 minutes to Bromley and Magic Mountains and a scenic hike to Jamaica State Park, this exceptional home is truly a four-season paradise!
Four bedroom, four bathroom Intervale townhouse has all the space you need in a Stratton home. This is the largest Intervale floor plan, with a second living room and wet bar on the lower, walk out floor. The main floor has a mud room entry, living room with wood burning fireplace, and dining room open to kitchen. The primary suite is on the main floor, secondary suite is upstairs, and an additional bedroom and bathroom is upstairs with an office loft. Fourth bedroom and bathroom is on the lowest level. Systems include air conditioning and a new propane boiler. The deck has a door from dining room, and stairs down to the yard for sledding fun. Dedicated parking space in your carport. Intervale at Stratton is a serene townhouse community with skier shuttle access to the base lodge. This unit is offered furnished. Stratton Sports Center bond is current, and transferrable to buyer with buyer paying the transfer fee. The sports and training center has indoor pool, tennis, pickleball, gym, yoga, and more.
Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy family room with a fireplace, an open, airy layout with cathedral ceilings, and a modern kitchen perfect for culinary adventures. With three spacious bedrooms, an office, and a serene primary suite, this home offers both relaxation and style. Don’t miss out on the opportunity to make this exceptional community and beautiful townhouse your new home!
This gorgeous Stratton area townhome is designed for comfort and style, featuring three spacious bedrooms, three baths plus an open loft. Being a Highgate model, it offers a second family room with ample space for relaxation and entertainment, making it perfect for holiday gatherings. The interior of this special home has been freshly painted in October '25 and stunning wide-board pine floors have just been refinished creating a warm, clean and inviting atmosphere. Two cozy fireplaces add charm and warmth during colder months, providing that perfect space to unwind after a day on the slopes. If you are into tuning your own ski/snowboard equipment there is an attached 1 car garage with a workbench! There is a private sports center with an indoor pool, exercise room, squash and tennis courts and game area for the kids. Also the shuttle to Stratton’s slopes allows for residents to come and go with ease. This well sought after Community combines exceptional Vermont living with unlimited recreational opportunities making it a perfect retreat for all to enjoy!
Great opportunity! Your Ultimate Getaway Escape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces. Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf matches below. In the cooler nights of winter, take in the mountain views. As you enter inside you'll find the perfect place to hang your coat and drop your shoes. The open kitchen is perfect for entertaining both inside and out. This house boasts of two inviting living rooms, each features a wood stove for warmth and ambiance—ideal for those chilly winter nights. On the main floor you can entertain in comfort while others enjoy endless fun in the space on the lower level. Everyone is sure to have fun while trying to beat their highest score on a variety of arcade games. Don’t forget the mini golf tournaments! Nestled on a peaceful road, you can take leisurely walks with your dog or explore the nearby surroundings. You are just minutes to the renowned Stratton Ski Resort—perfect for winter sports enthusiasts. This home has everything you need for the ultimate Vermont getaway—peace, fun, and convenience all in one location. Don't miss out on this unique opportunity to make this retreat your home away from home. This property has had an excellent history of rental income.
Escape to your mountain retreat in this spacious 4 bedroom, 4 bath home tucked away in a serene wooden community just minutes away from Stratton Mountain Resort. Perfect for entertaining or relaxing, the home features two cozy wood burning fireplaces that brings warmth and charm throughout the season. Vaulted ceilings in the living room and dining room area provide lots of natural light. Step outside to enjoy the private deck off the back of the house, ideal for gatherings or simply soaking in the privacy and natural beauty that surrounds you. With plenty of room for family and guests, this home offers the perfect blend of comfort, privacy and proximity to year-round adventure.
It’s the Premier Location and commanding views that set this Piper Ridge townhome apart. The stunning unobstructed views are central to the townhomes design, while the southern exposure provides all day sunshine and a light and airy atmosphere. You’ll experience the evening’s magic watching stunning sunsets with the resort lights on full display and will have the premier “front row seats” to Stratton’s fabulous fireworks! Step off your private deck to the expansive level lawn to enjoy a variety of outdoor activities. The spacious and open living areas are designed for entertaining, with a wood burning fireplace providing a welcoming ambiance. The large family room is privately situated. Walk to the Piper Club to relax and enjoy the indoor pool, hot tub, exercise room, sauna, and squash and tennis courts. It’s the ultimate convenience having the winter shuttle stop right at your front door! Piper Ridge townhomes are set on 90 park like acres, with private roads ideal for walking and biking. School choice. Don’t miss this extraordinary opportunity to create your own lasting memories of Vermont.

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