16

Winhall, VT Houses for Sale

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  • /34

    $579,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,455 Sq Ft

    4 Pearl Buck Dr, Winhall, VT 05340

    Just minutes from the slopes of Stratton Mountain Resort, this four-bedroom, two-bath home offers an easy four-season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time, offering a

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    4 Pearl Buck Dr, Winhall, VT 05340
  • /50

    $975,000

    • 4 Beds
    • 4 Baths
    • 4,184 Sq Ft

    520 Moose Hollow Rd, Winhall, VT 05340

    This custom-built contemporary home was designed with large gatherings of family and friends in mind, offering a spacious layout and plenty of room to relax and entertain. You can’t beat the location - just minutes to Manchester, Bromley, and Stratton, and nestled in the heart of year-round recreation. The private setting has views of Bromley’s trails and is bordered by the National Forest. This

    Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    520 Moose Hollow Rd, Winhall, VT 05340
  • /29

    $1,200,000

    • 1 Bath
    • 950 Sq Ft

    109 Winhall Hollow Rd, Winhall, VT 05340

    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

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    109 Winhall Hollow Rd, Winhall, VT 05340
  • /33

    $1,399,999

    • 6 Beds
    • 4 Baths
    • 3,800 Sq Ft

    121 High Meadow Rd, Winhall, VT 05340

    Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

    Ralph Harvey Listwithfreedom.com

    121 High Meadow Rd, Winhall, VT 05340
  • /60

    $979,000

    • 4 Beds
    • 3.5 Baths
    • 5,248 Sq Ft

    41-43 Cranberry Hill Rd, Winhall, VT 05340

    This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

    Jamie Luke TPW Real Estate

    41-43 Cranberry Hill Rd, Winhall, VT 05340
  • /37

    $829,000

    • 4 Beds
    • 3 Baths
    • 2,797 Sq Ft

    13 Betty Johnson Ln, Bondville, VT 05340

    Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    13 Betty Johnson Ln, Bondville, VT 05340
  • /50

    $750,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    57 Pearl Buck Dr Unit 33, Bondville, VT 05340

    WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    57 Pearl Buck Dr Unit 33, Bondville, VT 05340
  • /41

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,031 Sq Ft

    7 Roundtree Rd, Winhall, VT 05340

    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

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    7 Roundtree Rd, Winhall, VT 05340
  • /55

    $995,000

    • 5 Beds
    • 4.5 Baths
    • 2,321 Sq Ft

    24 N Branch Rd, Winhall, VT 05340

    Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite-

    Kim Morgan-Wohler Wohler Realty Group

    24 N Branch Rd, Winhall, VT 05340
  • /40

    $1,150,000

    • 5 Beds
    • 3.5 Baths
    • 4,017 Sq Ft

    11 Founders Hill Rd, Winhall, VT 05360

    Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    11 Founders Hill Rd, Winhall, VT 05360
  • /45

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,200 Sq Ft

    9 Lower Taylor Hill Rd, Winhall, VT 05340

    Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

    Timothy Mich Doddridge Stratton Real Estate

    9 Lower Taylor Hill Rd, Winhall, VT 05340
  • /22

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340

    Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping. Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can easily

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
  • /59

    $2,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    23 Valley View Rd, Winhall, VT 05340

    Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

    Kim Morgan-Wohler Wohler Realty Group

    23 Valley View Rd, Winhall, VT 05340
  • /38

    $860,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Jamaica, VT 05343

    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

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /50

    $4,999,000

    • 6 Beds
    • 7.5 Baths
    • 8,720 Sq Ft

    454 Mountain Rd, Stratton, VT 05155

    Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication. A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace. Expansive

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    454 Mountain Rd, Stratton, VT 05155
  • /11

    $2,425,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, Winhall, VT 05340

Why Live in Winhall

Winhall, located in southwestern Vermont, is a mountain town surrounded by ski resorts such as Bromley, Stratton, and Magic Mountain, making it a hub for outdoor recreation year-round. Residents enjoy alpine skiing, hiking the Long Trail, camping in Green Mountain National Forest, and fishing in Gale Meadows Wildlife Management Area. The town features a variety of home styles, including A-frame chalets, luxury New Traditional constructions, and simple cabins, with properties ranging from small acreages to expansive lots. Condos near Stratton Mountain Ski Resort offer additional housing options. Winhall Market and Workhorse Cafe provide local dining and shopping, while nearby Manchester offers more retail choices. The annual Bondville Fair, Vermont's oldest, celebrates rural traditions with quilt making, produce judging, carnival rides, and livestock pulls. Families in Winhall benefit from the state's school choice system, with highly rated Stratton Mountain School serving grades 7-12. The town has a low crime risk compared to the national average. State Route 30 connects Winhall to regional hubs, and Albany International Airport is about 70 miles away. Mud season can affect travel on dirt roads, coinciding with maple sugaring season, adding a unique aspect to life in Winhall.

Home Trends in Winhall, VT

Housing Trends

Median Sale Price
$717,500
Median Single Family Sale Price
$963,007
Median Townhouse Sale Price
$537,500
Median 2 Bedroom Sale Price
$265,000
Average Price Per Sq Ft
$391
Number of Homes for Sale
22
Last 12 months Home Sales
49
Months of Supply
5.40
Median List Price
$795,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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