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Stratton Mountain, VT Houses for Sale

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  • /38

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,115 Sq Ft

    367 Stratton Gate Rd, Jamaica, VT 05343

    Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

    Agent Photo

    Alison Cummings

    Cummings & Co

    367 Stratton Gate Rd, Jamaica, VT 05343
  • /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
  • /13

    $2,525,000

    New Construction $100K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    FULLY FINISHED-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 comfort and performance,

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, Winhall, VT 05340
  • /55

    $2,850,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    JULY 23 - Significant new price change today! - 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 laundry

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop 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
  • /52

    $1,997,000

    • 4 Beds
    • 4.5 Baths
    • 3,631 Sq Ft

    14 Talon Dr, Stratton, VT 05360

    Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    14 Talon Dr, Stratton, VT 05360
  • /60

    $3,995,000

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /38

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft

    564 Goodaleville Rd, Jamaica, VT 05343

    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

    Cheyanne Pugliese

    564 Goodaleville Rd, Jamaica, VT 05343
  • /57

    $850,000

    • 5 Beds
    • 4 Baths
    • 3,218 Sq Ft

    4880 Pikes Falls Rd, Jamaica, VT 05343

    Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

    Mike England Michael England Real Estate

    4880 Pikes Falls Rd, Jamaica, VT 05343
  • /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
  • /22

    $595,000

    • 4 Beds
    • 2 Baths
    • 1,430 Sq Ft

    9 Mountain Acres Rd, Jamaica, VT 05343

    Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

    Carrie Mathews Winhall Real Estate

    9 Mountain Acres Rd, Jamaica, VT 05343
  • /25

    $1,200,000

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

    11 Founders Hill Rd, Winhall, VT 05360

    Located .25 of a mile from the Stratton Mtn Gondola, Village and Resort. Corner lot with mature, professionally planned landscaping to enjoy all year. New roof and skylights were installed in 2024. One large expansion to the whole side of the house, all 3 levels, was 30 years ago. Lovingly maintained but needs a new kitchen floor and floor refinishing of the hard woods. Recently the bamboo

    Derek Greene Derek Greene

    11 Founders Hill Rd, Winhall, VT 05360
  • /32

    $849,000

    • 4 Beds
    • 3.5 Baths
    • 2,878 Sq Ft

    32 Benson Fuller Dr, Bondville, VT 05340

    Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    32 Benson Fuller Dr, Bondville, VT 05340
  • /60

    $8,200,000

    • 6 Beds
    • 10 Baths
    • 10,763 Sq Ft

    557 Trager Rd, Jamaica, VT 05343

    Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

    Kim Morgan-Wohler Wohler Realty Group

    557 Trager Rd, Jamaica, VT 05343
  • /47

    $1,140,000

    $60K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,193 Sq Ft

    70 Hunter Ln, Jamaica, VT 05343

    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

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    70 Hunter Ln, Jamaica, VT 05343
  • /60

    $1,160,000

    • 5 Beds
    • 4 Baths
    • 3,664 Sq Ft

    82 N Brookwood Rd, Stratton, VT 05360

    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,

    Kim Morgan-Wohler Wohler Realty Group

    82 N Brookwood Rd, Stratton, VT 05360
  • /47

    $1,450,000

    • 5 Beds
    • 4 Baths
    • 2,974 Sq Ft

    494-498 Goodaleville Rd, Jamaica, VT 05343

    10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit

    Cheyanne Pugliese

    494-498 Goodaleville Rd, Jamaica, VT 05343
  • /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
  • /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
  • /38

    $775,000

    • 4 Beds
    • 4 Baths
    • 3,520 Sq Ft

    12 Stratton Ridge Rd, Winhall, VT 05340

    First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

    Carrie Mathews Winhall Real Estate

    12 Stratton Ridge 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
  • /38

    $625,000

    • 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
  • /22

    $430,000

    • 5 Beds
    • 2 Baths
    • 1,664 Sq Ft

    13 Golden Triangle Rd, Winhall, VT 05340

    The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

    Mike England Michael England Real Estate

    13 Golden Triangle Rd, Winhall, VT 05340
  • /53

    $4,500,000

    • 5 Beds
    • 5.5 Baths
    • 5,700 Sq Ft

    24 Sawmill Rd, Stratton, VT 05360

    Experience the ultimate Stratton Mountain lifestyle from this exceptional ski home, perfectly positioned in one of the resort's most coveted locations. Offering the rare advantage of deeded access to Stratton's impeccably groomed ski trail, this extraordinary property places world-class skiing just steps from your front door—an amenity few homes can claim and even fewer can match.Designed for

    Carrie Mathews Winhall Real Estate

    24 Sawmill Rd, Stratton, VT 05360
  • /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
  • /44

    $1,475,000

    • 2 Beds
    • 2 Baths
    • 1,601 Sq Ft

    691 Black Bear Rd, Jamaica, VT 05343

    A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying

    Carrie Mathews Winhall Real Estate

    691 Black Bear Rd, Jamaica, VT 05343
  • /59

    $2,350,000

    • 5 Beds
    • 3.5 Baths
    • 4,752 Sq Ft

    6 Sunset Ridge Rd, Winhall, VT 05340

    Set within the exclusive High Meadow community, one of Stratton's most prestigious mountain enclaves, 6 Sunset Ridge is an extraordinary resort residence of post and beam architecture & impeccable craftsmanship. Positioned to capture sweeping views of Stratton Mountain, this exceptional residence offers an unparalleled lifestyle in one of Stratton's most sought-after luxury neighborhoods. From

    Kim Morgan-Wohler Wohler Realty Group

    6 Sunset Ridge Rd, Winhall, VT 05340
  • /51

    $5,100,000

    • 10 Beds
    • 9.5 Baths
    • 6,648 Sq Ft

    15 Sawmill Rd, Stratton, VT 05155

    Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

    Kim Morgan-Wohler Wohler Realty Group

    15 Sawmill Rd, Stratton, VT 05155
  • /59

    $949,000

    $30K PRICE DROP
    • 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
  • /48

    $629,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,329 Sq Ft

    774 Stratton Arlington Rd, Stratton, VT 05360

    Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    774 Stratton Arlington Rd, Stratton, VT 05360
  • /54

    $1,990,000

    • 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 lower

    Jamie Wylie Stratton Real Estate

    27 Mountain View Rd, Winhall, VT 05360
  • /47

    $1,225,000

    • 4 Beds
    • 3 Baths
    • 3,357 Sq Ft

    153 High Meadow Rd, Winhall, VT 05340

    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

    Britt Wohler

    153 High Meadow Rd, Winhall, VT 05340
  • /37

    $839,000

    • 5 Beds
    • 4.5 Baths
    • 3,840 Sq Ft

    42 Blackberry Ln, Jamaica, VT 05343

    Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but

    Cheyanne Pugliese

    42 Blackberry Ln, Jamaica, VT 05343
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