Properties Near 30 Upper Woods and Water Road Winhall, VT

Great location, flexible living, and room for everyone! Featuring a massive private in-law suite with bonus room PLUS THREE additional bonus rooms in the main home — yes, THREE! Whether you need guest space, home offices, hobby rooms, or overflow sleeping areas, this Vermont property gives you options. Offered for the first time since it was built in 1986 and lovingly enjoyed by the same family ever since, this home was designed for gathering, flexibility, and making lifelong Vermont memories. The main level features true single-floor living with an open floor plan, vaulted ceilings, and abundant natural light. The spacious primary suite is thoughtfully separated from the guest bedrooms and includes two walk-in closets, a soaking tub, and standing shower. Two additional bedrooms, a family room, laundry room, and powder room provide comfortable everyday living. A large rear deck expands the living space outdoors and offers a peaceful setting to relax or entertain. T The finished lower level adds exceptional flexibility with another family room, full bath, and three (3!) bonus rooms ideal for guests, office space, hobbies or overflow sleeping areas. A separate 1-bed, 1-bath in-law suite with private entrance includes its own large kitchen, huge dining/living area, BONUS room with w/d, and cozy wood stove. Ideal for multi-generational living, guests, or rental income potential. Live in one space and rent the other, or host the entire family under one roof. Perfectly situated in Winhall on a very private 0.96-acre lot with a storage shed, this property offers easy access to some of Southern Vermont’s best four-season destinations—just 5 minutes to Bromley Mountain, 15 minutes to Stratton Resort, and 15 minutes to Manchester Center for shopping, dining, and entertainment. A rare opportunity in a prime Vermont location with room for everyone. Home will conveyed furnished minus some personal items. Pictures of in-law suite available upon request.

Come take a look at this charming Cape-style home set on nearly 4 acres, offering river frontage and beautiful mountain views. Bring your fishing pole or a canoe and head down to the river or relax and enjoy the sunshine on your own private beach as the water flows by. Inside, the home features an open-concept living and dining area, along with a first-floor primary suite for added convenience. Upstairs, you’ll find two additional bedrooms and a full bathroom. The finished basement provides a versatile multipurpose room and a dedicated office space—perfect for working from home or extra living area. Step outside to enjoy the covered deck during warm summer months, ideal for gathering with family and friends. The property also includes a small storage shed for your outdoor equipment. Sold furnished. All measurements are approximate.

"COME TAKE A PEEK, IT'S JUST ACROSS THE CREEK.....Enjoy an inviting front porch to unwind and breathe in the serene surroundings! Unwind and take in the lovely mountain views, all set on the scenic Tom River in East Dorset! Charming saltbox style (1982 circa), the design is open living spaces with abundant light through out... As an added bonus this property boasts an over sized two car garage and a pole barn with easy access and plenty of room for setting up games and activities..host holiday get-together in a rustic, welcoming setting. Make your family memories here! This is indeed a rare opportunity!

LOCATION, LOCATION: Privately set just moments from Manchester’s dining, shopping, golf, year-round recreation, and easy access to Bromley and Stratton, this thoughtfully updated 5-bedroom, 2-bath Cape offers 2,050 sq ft on 0.48 acres—ideal as a primary home, Vermont retreat, or long-term investment. Move-in ready and beautifully maintained, the home balances a peaceful setting with exceptional proximity to town. The kitchen is both refined and functional, featuring stainless steel appliances, granite counters, a deep farmhouse sink, and solid hickory cabinetry, opening easily into the expansive dining and living area with a wood-burning fireplace for warmth and gathering. Hardwood floors run throughout the main level, while windows frame the surrounding greenery and seasonal Vermont landscape. The main level offers a private bedroom, generous den or home office, full bath, mudroom with accessible washer & dryer, plenty of storage, and a covered porch perfect for quiet mornings or après-ski evenings. Upstairs, a spacious primary bedroom is joined by additional bedrooms and a second full bath, creating flexible accommodations for guests, family, or work-from-home needs. With its desirable Manchester location, thoughtful updates, two-car garage, and well-balanced layout, 1649 East Manchester Road is a compelling year-round home defined by comfort, convenience, and enduring Vermont appeal.

Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest—a daily reminder that some of Southern Vermont’s best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain living. The main living area is designed to showcase the spectacular scenery, with large windows that frame the surrounding mountains and fill the space with natural light. A wood-burning fireplace anchors the living room, creating the perfect spot to gather after a day on the slopes. Clean architectural lines, warm materials, and thoughtful updates give the home a contemporary yet welcoming feel throughout. Several upgrades and renovations provide comfort and efficiency for years to come. The property also includes a carport, providing convenient covered parking so you won’t have to clear snow off your car after a Vermont snowfall, along with space for skis and all the gear that comes with an active mountain lifestyle. Perfectly located just minutes from Bromley Mountain and a short drive to Stratton Resort, this home is ideally positioned for year-round recreation—from skiing and snowboarding in winter to hiking, biking, and golf in the warmer months. An added benefit of this property, if you opt to join, is that a Bromley Bond is available, providing driveway plowing, and garbage pickup services. Whether you are seeking a full-time residence or a retreat, this unique mountain home offers style, views, and an unbeatable Southern Vermont location. Closing to occur on or after June 15. The buyer may elect to close earlier and allow the seller to rent the property back until June 15. This property will transfer unfurnished.

Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski Access Escape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure. Fully self-sufficient with solar power and propane generator backup, the home features an updated kitchen with new appliances, a new sliding door to the side yard, and a refreshed mudroom with wood accents and tile flooring. Being sold fully furnished! Enjoy quiet mornings in the gazebo, work on projects in the shed workshop, and explore your private land year-round. Whether you're seeking a full-time off-grid lifestyle, a weekend ski getaway, or a nature lover’s escape, this property delivers peace, privacy, and four-season recreation. Your mountain cabin dream is here—just minutes from the slopes!

Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace. The middle level offers three generously sized bedrooms that comfortably accommodate queen and king beds. On the ground floor, you’ll find an expansive bonus room and a private office that can easily be converted into an additional sleeping area. Ample storage is found throughout the home, including a large utility room with washer and dryer and a secure storage closet, a dedicated outdoor gear closet, and additional exterior storage. Firewood stays dry and ready under the private carport just steps from your door. Community amenities have recently been redone and include a pool, tennis courts, and basketball court—all set against the backdrop of beautiful mountain views.

Set on over half an acre in the heart of East Dorset Village, this newly renovated three-bedroom, two-bath bungalow blends modern upgrades with cozy charm—and even includes a peaceful brook running through the property. Recent upgrades include completely new kitchen and bathrooms and fresh interior paint throughout. The open-concept layout creates a bright, connected space that’s perfect for both everyday living and entertaining. Hardwood floors add character and charm. The main level also features an inviting mudroom/laundry room, bedroom, and full bath. A bonus office/sunroom offers the flexibility to work from home or to create a quiet retreat. The primary suite, complete with walk-in closet and ensuite bathroom, is located on the second floor, along with a third bedroom. The oversized detached two-car garage has new overhead doors and electric openers, a solid concrete floor, and plenty of extra space for storage, gear, or hobbies. Exterior improvements include updated roofing and new retaining wall. Low-maintenance vinyl siding makes exterior upkeep simple. Step outside to enjoy the covered porch overlooking the yard and gentle brook - a perfect place to relax and unwind.