28

Stratton Mountain, VT Houses for Sale

Section Image
  • /41

    $8,950,000

    • 6 Beds
    • 10 Baths
    • 13,393 Sq Ft

    370 Fischer Ln, Jamaica, VT 05343

    Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

    Dia Jenks LandVest, Inc/Woodstock

    370 Fischer Ln, Jamaica, VT 05343
  • /60

    $1,825,000

    • 3 Beds
    • 4 Baths
    • 2,872 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! 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, this property delivers! Plus, it's only a 10-minute

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /55

    $2,225,000

    • 4 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    16 Hunter Ridge Rd, Bondville, VT 05340

    Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    16 Hunter Ridge Rd, Bondville, VT 05340
  • /51

    $1,600,000 Open Sat 10AM - 1PM

    • 4 Beds
    • 4.5 Baths
    • 4,541 Sq Ft

    33 Jamie Ln, Bondville, VT 05340

    Exceptional Log Home tucked away in the beautiful Green Mountains of Vermont. Welcome to 33 Jamie Lane a 12 acre sanctuary minutes to Stratton Mountain Resort. This extraordinary property offers true privacy surrounded by woods and nature. Features three finished levels of dramatic living space with floor to ceiling windows , soaring stone fireplace, and cherry floors. Open concept kitchen/dining

    Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

    33 Jamie Ln, Bondville, VT 05340
  • /39

    $2,950,000

    • 8 Beds
    • 8.5 Baths
    • 6,471 Sq Ft

    69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

    This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

    Sara Buckley Josiah Allen Real Estate, Inc.

    69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
  • /43

    $2,500,000

    • 5 Beds
    • 7 Baths
    • 7,625 Sq Ft

    19 Old Town Rd, Bondville, VT 05340

    Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

    Christiane Carroccio TPW Real Estate

    19 Old Town Rd, Bondville, VT 05340
  • /40

    $1,450,000

    • 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
  • /46

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 4,640 Sq Ft

    33 Forest Haunts Rd, Winhall, VT 05340

    Discover Your Vermont Retreat Nestled amidst 20.8 private acres of tranquil woods, this French country manor offers an exceptional opportunity to own a piece of Vermont paradise. Situated near the serene North Branch Ball Mountain Brook, enjoy the soothing sounds of cascading water and the breathtaking beauty of nature. Property Highlights: Prime Location: Just minutes from Stratton Resort for

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    33 Forest Haunts Rd, Winhall, VT 05340
  • /35

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft

    5 Linscott Rd Unit 56, Jamaica, VT 05343

    This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 1⁄2 baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances, new

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    5 Linscott Rd Unit 56, Jamaica, VT 05343
  • /22

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft

    163 Vt Route 30, Winhall, VT 05340

    Charming Restored Post & Beam Home with Commercial Zoning Near Stratton. Discover the perfect blend of rustic charm and modern functionality in this beautifully restored post and beam home ideally situated at the corner of Vermont Route 30 and scenic Kendall Farm Road. Featuring three bedrooms and two full baths, the home offers soaring vaulted ceilings, exposed beams, and an abundance of natural

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    163 Vt Route 30, Winhall, VT 05340
  • /41

    $574,000

    • 3 Beds
    • 3 Baths
    • 2,704 Sq Ft

    4138 W Hill Rd S, Jamaica, VT 05343

    This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

    Patricia Fitzpatrick Skihome Realty

    4138 W Hill Rd S, Jamaica, VT 05343
  • /28

    $749,000

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft

    21 Burnt Hill Rd, Winhall, VT 05341

    Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont!This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    21 Burnt Hill Rd, Winhall, VT 05341
  • /33

    $525,000

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    3 Strattonwald Rd, Winhall, VT 05340

    Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you’ll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Strattonwald Rd, Winhall, VT 05340
  • /60

    $899,000

    • 5 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    42 Blackberry Ln, Jamaica, VT 05343

    Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

    Steve Goldfarb Deerfield Valley Real Estate

    42 Blackberry Ln, Jamaica, VT 05343
  • /38

    $980,000

    • 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

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /26

    $795,000

    • 3 Beds
    • 3 Baths
    • 2,044 Sq Ft

    6 Quarter Mile Rd, Winhall, VT 05340

    AMAZING LOCATION! Walking distance to Stratton Mountain! This home is located on the shuttle route and being offered fully furnished! Walk to the slopes or just take a nice walk around the local trails. Spacious home with ample room for everyone. The open concept kitchen, dining, living room offers cathedral ceilings and woodburning fireplace. French doors leading out to the firepit area for

    Julie Lowe Lowe's Real Estate, LLC

    6 Quarter Mile Rd, Winhall, VT 05340
  • /28

    $825,000

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    6 Roundtree Rd, Winhall, VT 05340

    Prime Stratton location! This charming 4-bedroom, 2-bathroom retreat offers vaulted ceilings, an open-concept living area with a wood burning fireplace, and a private deck and backyard for relaxing after a day on the slopes. With weekend and holiday shuttle service during ski season, plus easy access to Stratton Village’s shops, dining, and year-round activities, it’s the ideal spot to recharge

    Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    6 Roundtree Rd, Winhall, VT 05340
  • /60

    $1,100,000

    • 6 Beds
    • 5 Baths
    • 5,298 Sq Ft

    50 Stratton View Rd, Winhall, VT 05340

    Custom built six-bedroom home on 2 acres with spectacular views of Stratton Mountain. The kitchen has granite countertops and custom cabinets with the dining area nearby with plenty of space to accommodate a large gathering. The living area has a cathedral ceiling with large windows for an abundance of natural light and stunning year-round views of Stratton Mountain, with a lovely stone fireplace

    Mike England Michael England Real Estate

    50 Stratton View Rd, Winhall, VT 05340
  • /30

    $415,000

    • 3 Beds
    • 1 Bath
    • 1,338 Sq Ft

    2779 Pikes Falls Rd, Jamaica, VT 05343

    Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no

    Carrie Mathews Winhall Real Estate

    2779 Pikes Falls Rd, Jamaica, VT 05343
  • /39

    $4,300,000

    • 6 Beds
    • 5 Baths
    • 4,715 Sq Ft

    141 W Ridge Rd, Stratton, VT 05360

    Experience the charm of this renovated, ski-in/ski-out 6-bedroom, 5-bathroom retreat, perched as the second-highest home on Stratton’s iconic Lower Wanderer Ski Trail. Immerse yourself in the rustic elegance of this space, where expansive windows invite breathtaking outdoor views inside. This mountain sanctuary seamlessly combines modern comfort, solar technology, and nature’s serene beauty,

    Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    141 W Ridge Rd, Stratton, VT 05360
  • /31

    $975,000

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft

    73 Cranberry Hill Rd, Winhall, VT 05340

    Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

    Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
  • /26

    $399,000

    • 4 Beds
    • 1.5 Baths
    • 1,344 Sq Ft

    2 Lower Stratton Valley Rd, Winhall, VT 05340

    Welcome to this charming ski chalet situated in close proximity to three major ski resorts and offered fully furnished so you can move right in, unpack, and start enjoying yourself. There's a full bath downstairs to go along with 4 generously sized bedrooms and a 1/2 bath upstairs for guests, creating a cozy and inviting atmosphere that's ideal for apres-ski relaxation or a peaceful retreat

    Mike Masters Four Seasons Sotheby's Int'l Realty

    2 Lower Stratton Valley Rd, Winhall, VT 05340
  • /35

    $649,000

    • 8 Beds
    • 3.5 Baths
    • 2,520 Sq Ft

    405 Vermont 30, Winhall, VT 05340

    Ski Resort Investment Gem! 2-Family Home Near Stratton & BromleyRare investment opportunity in the heart of Vermont's premier ski region. Located on scenic Vermont Route 30, this property offers unparalleled access to both Stratton Mountain Resort and Bromley Mountain Ski Resort. Whether you're looking to live in one unit and rent the other, or convert it to a single-family home, this

    Robin Apps Four Seasons Sotheby's Int'l Realty

    405 Vermont 30, Winhall, VT 05340
  • /60

    $4,495,500

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

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning 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 surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /48

    $2,999,000

    • 6 Beds
    • 6.5 Baths
    • 6,500 Sq Ft

    25 Mountain Haunts Rd, Winhall, VT 05340

    Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

    Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340
  • /50

    $1,050,000

    • 5 Beds
    • 5.5 Baths
    • 4,729 Sq Ft

    83 Benson Fuller Dr, Bondville, VT 05340

    Just an 8-minute drive to Stratton, 83 Benson Fuller Drive sits atop the beautiful Forest Farms neighborhood, offering both serenity and convenience. This meticulously updated home is ready for you to move in and enjoy the best of Vermont living. Nestled on a quiet dirt road, it’s perfect for morning and evening strolls with the dog before or after a day on the slopes.Inside, this

    Christiane Carroccio TPW Real Estate

    83 Benson Fuller Dr, Bondville, VT 05340
  • /51

    $5,999,000

    • 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.

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    454 Mountain Rd, Stratton, VT 05155
  • /40

    $1,975,000

    • 4 Beds
    • 4 Baths
    • 4,270 Sq Ft

    14 Old Ridge Rd, Winhall, VT 05155

    This mountain home is beautifully furnished with a refined design that perfectly balances comfort and style, offering a seamless move-in ready experience. Located in the sought-after High Meadow neighborhood, this four bedroom, four bathroom property sits high on a perch, with clear views of Stratton’s trails, and a view of Bromley from the front of the house. Rebuilt in 2023/2024, the home is

    Christiane Carroccio TPW Real Estate

    14 Old Ridge Rd, Winhall, VT 05155
How to Buy a Home How to Finance a Home How to Sell a Home