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Winhall, VT Homes for Sale

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  • 18 Old Snow Valley Rd, Winhall, VT 05340
    18 Old Snow Valley Rd, Winhall, VT 05340
    18 Old Snow Valley Rd, Winhall, VT 05340
    /39

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,040 Sq Ft

    18 Old Snow Valley Rd, Winhall, VT 05340

    ***Open House Sunday 9/6/26 11:00-1:00***Charming, comfortable, and ideally situated, this expanded 3-bedroom, 2-bath A-frame captures the essence of a Vermont retreat. Perfectly located just 6 minutes to Bromley, 8 minutes to Manchester Center, and aprox 15 minutes to Stratton Mountain, endless mountain recreation and dining are right at your doorstep.A spacious enclosed porch doubles as

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    18 Old Snow Valley Rd, Winhall, VT 05340
  • 20 W Branch Rd, Winhall, VT 05340
    20 W Branch Rd, Winhall, VT 05340
    20 W Branch Rd, Winhall, VT 05340
    /43

    $1,050,000

    • 4 Beds
    • 4 Baths
    • 2,380 Sq Ft

    20 W Branch Rd, Winhall, VT 05340

    Escape to the mountains and enjoy everything Stratton, Vermont has to offer in this fabulous 4 bedroom, 4 bath contemporary home, ideally located on a private cul-de-sac in the heart of Stratton Resort. Designed for gathering with family and friends, the home features a spacious open floor plan with a cathedral-ceiling living room, wood-burning fireplace, open kitchen and dining area, and plenty

    MaryKate Grey Stratton Real Estate

    20 W Branch Rd, Winhall, VT 05340
  • 7 Wood Rock Rd, Winhall, VT 05340
    7 Wood Rock Rd, Winhall, VT 05340
    7 Wood Rock Rd, Winhall, VT 05340
    /26

    $749,000

    • 3 Beds
    • 2 Baths
    • 976 Sq Ft

    7 Wood Rock Rd, Winhall, VT 05340

    A rare Stratton ownership opportunity with exceptional amenities and possibilities. The purchase presents an opportunity for the buyer to bypass the Stratton Mountain Club waiting list, subject to Club approval and payment of all associated fees.. Also included with the property is an active Stratton Mountain Homeowner Membership Bond, with the buyer responsible for the applicable transfer

    Jamie Wylie Stratton Real Estate

    7 Wood Rock Rd, Winhall, VT 05340
  • 144 High Meadow Rd, Winhall, VT 05340
    144 High Meadow Rd, Winhall, VT 05340
    144 High Meadow Rd, Winhall, VT 05340
    /46

    $1,599,000

    • 6 Beds
    • 5.5 Baths
    • 5,568 Sq Ft

    144 High Meadow Rd, Winhall, VT 05340

    Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

    Kim Morgan-Wohler Wohler Realty Group

    144 High Meadow Rd, Winhall, VT 05340
  • 36 Beaver St, Bondville, VT 05340
    36 Beaver St, Bondville, VT 05340
    36 Beaver St, Bondville, VT 05340
    /60

    $1,650,000

    • 3 Beds
    • 4 Baths
    • 5,072 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage,

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • 27 Mountain View Rd, Winhall, VT 05360
    27 Mountain View Rd, Winhall, VT 05360
    27 Mountain View Rd, Winhall, VT 05360
    /54

    $1,895,000

    $95K PRICE DROP
    • 6 Beds
    • 6.5 Baths
    • 5,896 Sq Ft

    27 Mountain View Rd, Winhall, VT 05360

    Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere.Designed for gathering, the

    Jamie Wylie Stratton Real Estate

    27 Mountain View Rd, Winhall, VT 05360
  • 33 Stone Lodge Rd, Winhall, VT 05340
    33 Stone Lodge Rd, Winhall, VT 05340
    33 Stone Lodge Rd, Winhall, VT 05340
    /58

    $2,399,000

    New Construction $26K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    33 Stone Lodge Rd, Winhall, VT 05340

    Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views . Just minutes to Stratton Mountain'sTrails and move in ready, no detail has been overlooked with superior craftsmanship, energy efficiency and contemporary design. The handcrafted Timber Frame great room , defined by cathedral ceilings, wood burning stone hearth and expansive windows,

    Kim Morgan-Wohler Wohler Realty Group

    33 Stone Lodge Rd, Winhall, VT 05340
  • 3 Kimball Hill Rd Unit 1, Winhall, VT 05340
    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
    /22

    $425,000

    • 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

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
  • 59 Garden Loop Rd, Winhall, VT 05340
    59 Garden Loop Rd, Winhall, VT 05340
    59 Garden Loop Rd, Winhall, VT 05340
    /60

    $2,500,000

    New Construction $450K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    LABOR DAY WEEKEND BEGINS WITH A HUGE PRICE CHANGE! - Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • 6 Old Ridge Rd, Winhall, VT 05340
    6 Old Ridge Rd, Winhall, VT 05340
    6 Old Ridge Rd, Winhall, VT 05340
    /40

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 4,453 Sq Ft

    6 Old Ridge Rd, Winhall, VT 05340

    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,

    Trent Stephens Wohler Realty Group

    6 Old Ridge Rd, Winhall, VT 05340
  • 4.1 Pearl Buck Dr, Winhall, VT 05340
    4.1 Pearl Buck Dr, Winhall, VT 05340
    4.1 Pearl Buck Dr, Winhall, VT 05340
    /12

    $450,000

    • Land
    • 10.26 Acres
    • $43,860 per Acre

    4.1 Pearl Buck Dr, Winhall, VT 05340

    One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

    Kim Morgan-Wohler Wohler Realty Group

    4.1 Pearl Buck Dr, Winhall, VT 05340
  • 0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
    /38

    $375,000

    • Land
    • 1.23 Acres
    • $304,878 per Acre

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

    Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

    Kim Morgan-Wohler Wohler Realty Group

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
  • 121 High Meadow Rd, Winhall, VT 05340
    121 High Meadow Rd, Winhall, VT 05340
    121 High Meadow 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
  • 57 Pearl Buck Dr, Bondville, VT 05340
    57 Pearl Buck Dr, Bondville, VT 05340
    57 Pearl Buck Dr, Bondville, VT 05340
    /23

    $695,000

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

    57 Pearl Buck Dr, Bondville, VT 05340

    Perched high on Pearl Buck Drive, this distinctive Vermont home is all about location—and the scenery is truly exceptional. Sweeping mountain vistas capture both Stratton and Bromley, creating a dramatic backdrop in every season, from autumn color and snow-covered peaks to long summer sunsets. The road also carries a special local connection to Pearl S. Buck, the Pulitzer- and Nobel Prize-winning

    Carrie Mathews Winhall Real Estate

    57 Pearl Buck Dr, Bondville, VT 05340
  • 248 French Hollow Rd, Winhall, VT 05340
    248 French Hollow Rd, Winhall, VT 05340
    248 French Hollow Rd, Winhall, VT 05340
    /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • 11 Founders Hill Rd, Winhall, VT 05360
    11 Founders Hill Rd, Winhall, VT 05360
    11 Founders Hill Rd, Winhall, VT 05360
    /25

    $1,200,000

    Open House 10/10
    • 6 Beds
    • 3.5 Baths
    • 4,017 Sq Ft

    11 Founders Hill Rd, Winhall, VT 05360

    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

    Derek Greene Derek Greene

    11 Founders Hill Rd, Winhall, VT 05360
  • 148 Vt Route 30, Winhall, VT 05340
    148 Vt Route 30, Winhall, VT 05340
    148 Vt Route 30, Winhall, VT 05340
    /10

    $190,000

    • Land
    • 3.8 Acres
    • $50,000 per Acre

    148 Vt Route 30, Winhall, VT 05340

    This exceptional 3.8-acre, partially-cleared Winhall lot offers potentially unobstructed views of Stratton mountain, and is permitted for a 4BR home perched at the top of the lot's slope. Nestled in pines, spruces, birches and maple trees, this private Vermont retreat offers an enviable sense of seclusion and natural beauty away from it all, yet with easy proximity to four seasons of fun

    Jamie Luke TPW Real Estate

    148 Vt Route 30, Winhall, VT 05340
  • C-4 Ridge Rd Unit C-4, Winhall, VT 05340
    C-4 Ridge Rd Unit C-4, Winhall, VT 05340
    C-4 Ridge Rd Unit C-4, Winhall, VT 05340
    /26

    $825,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    C-4 Ridge Rd Unit C-4, Winhall, VT 05340
  • 23 Loop Rd Unit 10, Bondville, VT 05340
    23 Loop Rd Unit 10, Bondville, VT 05340
    23 Loop Rd Unit 10, Bondville, VT 05340
    /40

    $595,000

    $20K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    23 Loop Rd Unit 10, Bondville, VT 05340

    Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    23 Loop Rd Unit 10, Bondville, VT 05340
  • G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340
    G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340
    G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340
    /12

    $679,000

    • 3 Beds
    • 3 Baths
    • 1,830 Sq Ft

    G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340

    This 3-bedroom,3-bathroom, Tri-level Piper Ridge "Tunbridge" Townhome/Condo has a full facing view of the face of Stratton Mountain. It is basically in original condition. It is completely empty and the interior has just been completely painted. The family is aware that some upgrades will be required to accommodate new owner's taste. The listed price of $679,000-below assessment- {$757,600} -

    Eric Nathan Nathan Auction & Real Estate Inc.

    G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340
  • 19 Winhall Condo Rd Unit 4, Winhall, VT 05340
    19 Winhall Condo Rd Unit 4, Winhall, VT 05340
    19 Winhall Condo Rd Unit 4, Winhall, VT 05340
    /34

    $345,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    19 Winhall Condo Rd Unit 4, Winhall, VT 05340

    Tucked at the end of a quiet back road less than one mile from the Stratton Access Road, The Winhall Condos offer a peaceful mountain retreat with convenient access to both Stratton and Manchester. This updated 2-bedroom, 2-bath residence features an open-concept kitchen, living, and dining area, two elevated decks, and beautiful views of Stratton Mountain. Offered furnished and ready to enjoy,

    Cheyanne Pugliese

    19 Winhall Condo Rd Unit 4, Winhall, VT 05340
  • 0 Wall St, Winhall, VT 05340
    0 Wall St, Winhall, VT 05340
    0 Wall St, Winhall, VT 05340
    /9

    $374,900

    • Land
    • 2.31 Acres
    • $162,294 per Acre

    0 Wall St, Winhall, VT 05340

    Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

    Cheyanne Pugliese

    0 Wall St, Winhall, VT 05340
  • 25 Benson Fuller Dr, Bondville, VT 05340
    25 Benson Fuller Dr, Bondville, VT 05340
    25 Benson Fuller Dr, Bondville, VT 05340
    /38

    $795,000

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

    25 Benson Fuller Dr, Bondville, VT 05340

    Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Bondville, VT 05340
  • 109 Winhall Hollow Rd, Winhall, VT 05340
    109 Winhall Hollow Rd, Winhall, VT 05340
    109 Winhall Hollow Rd, Winhall, VT 05340
    /31

    $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
  • 72 Benson Fuller Dr, Winhall, VT 05340
    72 Benson Fuller Dr, Winhall, VT 05340
    72 Benson Fuller Dr, Winhall, VT 05340
    /32

    $765,000

    • 3 Beds
    • 3 Baths
    • 2,322 Sq Ft

    72 Benson Fuller Dr, Winhall, VT 05340

    Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the

    Christine Chovan

    72 Benson Fuller Dr, Winhall, VT 05340
  • 1 Beaver St, Bondville, VT 05340
    1 Beaver St, Bondville, VT 05340
    1 Beaver St, Bondville, VT 05340
    /38

    $605,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,288 Sq Ft

    1 Beaver St, Bondville, VT 05340

    Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

    Carrie Mathews Winhall Real Estate

    1 Beaver St, Bondville, VT 05340
  • 11 W Round Rd, Winhall, VT 05340
    11 W Round Rd, Winhall, VT 05340
    11 W Round Rd, Winhall, VT 05340
    /40

    $1,325,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    11 W Round Rd, Winhall, VT 05340

    11 Round Tree Road, Winhall, VT 05340A 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

    Andrew King Stratton Real Estate

    11 W Round Rd, Winhall, VT 05340
  • 0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
    /12

    $150,000

    $25K PRICE DROP
    • Land
    • 2.26 Acres
    • $66,372 per Acre

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

    Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
  • 16B Bromley Knolls Rd Unit B, Winhall, VT 05340
    16B Bromley Knolls Rd Unit B, Winhall, VT 05340
    16B Bromley Knolls Rd Unit B, Winhall, VT 05340
    /20

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,225 Sq Ft

    16B Bromley Knolls Rd Unit B, Winhall, VT 05340

    TURN-KEY VERMONT MOUNTAIN RETREAT JUST MINUTES FROM BROMLEY & STRATTON!Beautifully renovated in 2021, this fully furnished 3-bedroom, 2-bath condominium offers the perfect combination of Vermont charm, modern comfort, and year-round recreation. Located just one minute from Bromley Mountain and approximately ten minutes from Stratton, this property is ideally situated for skiing, hiking,

    Jason Saphire www.HomeZu.com

    16B Bromley Knolls Rd Unit B, Winhall, VT 05340
  • 7 Roundtree Rd, Winhall, VT 05340
    7 Roundtree Rd, Winhall, VT 05340
    7 Roundtree Rd, Winhall, VT 05340
    /41

    $910,000

    $40K PRICE DROP
    • 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
  • 33 Burnt Hill Ln, Winhall, VT 05340
    33 Burnt Hill Ln, Winhall, VT 05340
    33 Burnt Hill Ln, Winhall, VT 05340
    /26

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    33 Burnt Hill Ln, Winhall, VT 05340

    Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded acres, this three bedroom, two bath mountain home combines privacy and Vermont character with access to the Strattonwald swimming pond and beach, tennis courts and winter shuttle service to Stratton.Inside, natural wood,

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    33 Burnt Hill Ln, Winhall, VT 05340
  • 159 Winhall Hollow Rd, Bondville, VT 05340
    159 Winhall Hollow Rd, Bondville, VT 05340
    159 Winhall Hollow Rd, Bondville, VT 05340
    /60

    $5,575,000

    • 7 Beds
    • 9.5 Baths
    • 9,915 Sq Ft

    159 Winhall Hollow Rd, Bondville, VT 05340

    Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of

    Kim Morgan-Wohler Wohler Realty Group

    159 Winhall Hollow Rd, Bondville, VT 05340
  • 0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
    /15

    $825,000

    • Land
    • 77.6 Acres
    • $10,631 per Acre

    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

    Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

    Trent Stephens Wohler Realty Group

    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
  • Lot 3 Route 11 30, Winhall, VT 05340
    Lot 3 Route 11 30, Winhall, VT 05340
    Lot 3 Route 11 30, Winhall, VT 05340
    /15

    $115,000

    $30K PRICE DROP
    • Land
    • 2.9 Acres
    • $39,655 per Acre

    Lot 3 Route 11 30, Winhall, VT 05340

    Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

    Laura Beckwith Josiah Allen Real Estate, Inc.

    Lot 3 Route 11 30, Winhall, VT 05340
  • 0 Stratton Gardens Rd Unit 35, Winhall, VT 05340
    0 Stratton Gardens Rd Unit 35, Winhall, VT 05340
    0 Stratton Gardens Rd Unit 35, Winhall, VT 05340
    /11

    $240,000

    • Land
    • 10.06 Acres
    • $23,857 per Acre

    0 Stratton Gardens Rd Unit 35, Winhall, VT 05340

    This expansive building lot, situated just off the Stratton Access Road, offers breathtaking views of Bromley Mountain, presenting an ideal opportunity to construct your dream home in the picturesque setting of Stratton, Vermont. The property is designated for a five-bedroom residence, with the necessary State Waste permit (WW-2-1972-14) already in place, ensuring a smooth development process.

    Mike England Michael England Real Estate

    0 Stratton Gardens Rd Unit 35, Winhall, VT 05340
  • 0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340
    0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340
    0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340
    /7

    $108,000

    • Land
    • 1 Acre
    • $108,000 per Acre

    0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340

    Discover the opportunity to create your own Vermont getaway on this beautiful 1-acre parcel on Sylvan Ridge Road in Winhall. Ideally situated between Stratton Mountain and Bromley Mountain, this location offers easy access to some of Southern Vermont's best year-round recreation. In winter, enjoy skiing and snowboarding at nearby Stratton and Bromley. During spring summer and fall, the area comes

    David Shehadi Josiah Allen Real Estate, Inc.

    0 Sylvan Ridge Rd Unit 5106244, Winhall, VT 05340
  • 56 Lower Taylor Hill Rd, Winhall, VT 05340
    56 Lower Taylor Hill Rd, Winhall, VT 05340
    56 Lower Taylor Hill Rd, Winhall, VT 05340
    /14

    $450,000

    $50K PRICE DROP
    • Land
    • 21.2 Acres
    • $21,226 per Acre

    56 Lower Taylor Hill Rd, Winhall, VT 05340

    Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    56 Lower Taylor Hill Rd, Winhall, VT 05340
  • 75 Sylvan Ridge Rd, Winhall, VT 05340
    75 Sylvan Ridge Rd, Winhall, VT 05340
    75 Sylvan Ridge Rd, Winhall, VT 05340
    /15

    $115,000

    • Land
    • 1 Acre
    • $115,000 per Acre

    75 Sylvan Ridge Rd, Winhall, VT 05340

    Your Vermont adventure starts here. This 0.90 - acre parcel offers a fantastic location between Stratton, Bromley, and Magic Mountains, with easy access to the year round recreation, dining, and shopping of Manchester. The current owner cleared and leveled the building site and excavated and built a driveway. There is a Waste Water Permit for a 4 bedroom home in place. Electric service is readily

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    75 Sylvan Ridge Rd, Winhall, VT 05340
  • Lot #4 Margeaux Ln, Stratton, VT 05155
    Lot #4 Margeaux Ln, Stratton, VT 05155
    Lot #4 Margeaux Ln, Stratton, VT 05155
    /5

    $375,000

    $90K PRICE DROP
    • Land
    • 5.54 Acres
    • $67,690 per Acre

    Lot #4 Margeaux Ln, Stratton, VT 05155

    Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    Lot #4 Margeaux Ln, Stratton, VT 05155
  • 6 Snowflake Ln, Winhall, VT 05255
    6 Snowflake Ln, Winhall, VT 05255
    6 Snowflake Ln, Winhall, VT 05255
    /29

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,633 Sq Ft

    6 Snowflake Ln, Winhall, VT 05255

    This picture perfect energy conscience geo-thermal (saves big on heating or AC) and electric vehicle friendly, well maintained log home is offered fully furnished! The great room has a large brick gas fireplace, vaulted ceiling and warm wood floors - a place to put your feet up after a day on the slopes. There is a spacious dining area off the mudroom/entryway and an updated kitchen with

    Laura Beckwith Josiah Allen Real Estate, Inc.

    6 Snowflake Ln, Winhall, VT 05255

Showing Results 1 - 40, Page 1 of 2

Vermont Bennington County

Real Estate & Homes for Sale in Winhall, VT

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.

Learn more about living in Winhall

Winhall, VT Home Prices

Winhall, VT
Median Home Price
$799,000
Median Sale Price
$776,250
+20% YoY
Avg. Price per Square Foot
$416
Median Single Family Price
$947,000
Median Townhouse Price
$600,000
Median Condo Price
$697,500
Total Active Listings
53 listings
Market Conditions
4 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Winhall, VT?
Homes for sale in Winhall, VT have an average home price of $997,978.
How many homes have sold over the last 12 months in Winhall, VT?
70 homes have sold in Winhall, VT over the last 12 months.
What is the average household income in Winhall, VT?
The average household income in Winhall, VT is $95K.
What are the most popular zip codes in Winhall, VT?
The most popular zip codes in Winhall, VT include 05340, 05343, 05360, 05155 and 05152.
How much do you need to make to afford a house in Winhall?
The median home price in Winhall is $799,000. If you put a 20% down payment of $159,800 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $4,230 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $181K a year to afford the median home price in Winhall. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winhall is $95K.
How are the schools in Winhall, VT?
Winhall, VT has highly rated public and private schools. Some of the best schools in Winhall based on Niche Grades are Stratton Mountain School, Sunderland Elementary School and Jamaica Village School. Browse all the schools in Winhall, VT to learn more.
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