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Homes for Sale in 05343

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  • /26

    $325,000

    • 2 Beds
    • 2 Baths
    • 976 Sq Ft

    9047 Vermont 30, Jamaica, VT 05155

    “The Yellow Sweetie” offers a rare blend of charm, convenience, and proven income potential. This stylish country-meets-shabby-chic retreat has been a high-income producing rental for many years, making it an excellent opportunity for investment, year-round living, or a Vermont vacation retreat.Ideally located near the base of Stratton Mountain, the property sits just one minute from the

    Carrie Mathews Winhall Real Estate

    9047 Vermont 30, Jamaica, VT 05155
  • /29

    $449,000 Open Sun 11AM - 12:30PM

    • 4 Beds
    • 1 Bath
    • 1,730 Sq Ft

    83 Depot St, Jamaica, VT 05343

    Step back in time while enjoying modern comforts in this lovingly restored 1800s riverfront farmhouse with attached barn, set in the heart of Southern Vermont. Rich with historic character, the home features original wide pine floors, plaster walls, a slate roof, and classic architectural lines that reflect Vermont’s timeless heritage.The private backyard borders the West River, offering a

    Carrie Mathews Winhall Real Estate

    83 Depot St, Jamaica, VT 05343
  • /39

    $849,000

    • 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
  • /15

    $500,000

    • Land
    • 21.2 Acres
    • $23,585 per Acre

    56 Lower Taylor Hill Rd, Winhall, VT 05340

    A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    56 Lower Taylor Hill Rd, Winhall, VT 05340
  • /21

    $379,000

    • Land
    • 12.05 Acres
    • $31,452 per Acre

    101 Catherine Rd, Jamaica, VT 05343

    Discover 12 scenic acres close to Stratton Mountain Resort with sweeping mountain views and endless potential. This unique property features a charming small treehouse and two Jamaica cottage structures set on permanent foundations ready to be finished. Cabin would be perfect for income producing tiny homes, storage, creative space, or future development. An active septic permit is already in

    Jamie Wylie Stratton Real Estate

    101 Catherine Rd, Jamaica, VT 05343
  • /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
  • /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
  • /8

    $175,000

    • Land
    • 2.26 Acres
    • $77,434 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-Shuttle service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water permit in place for a 4 bedroom home.

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

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
  • /28

    $57,000

    • 2 Beds
    • 1 Bath
    • 844 Sq Ft

    2036 Vermont 30, Jamaica, VT 05343

    A cozy base for days spent enjoying Vermont country life warmed by a cozy wood stove and enjoying countless meals prepared together in the upgraded cherry and tile kitchen. Property has direct access to the West River. a nice deck to sit on in the back and a nice sitting platform overlooking river. Two bedroom one bath mobile home. Six months occupancy per year. New tenants must be approved by

    Mike England Michael England Real Estate

    2036 Vermont 30, Jamaica, VT 05343
  • /16

    $139,000

    • Land
    • 1.62 Acres
    • $85,802 per Acre

    0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

    wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

    Mike England Michael England Real Estate

    0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
  • /35

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    5 Linscott Rd, Jamaica, VT 05343

    PRICE ADJUSTMENT This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half 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

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    5 Linscott Rd, Jamaica, VT 05343
  • /3

    $625,000

    • 4 Beds
    • 1.5 Baths
    • 2,764 Sq Ft

    768 Vt Route 30, Jamaica, VT 05343

    Large farmhouse with 15.78 acres, metal roof, easy access to multiple ski resorts. Four bedrooms, one and a half baths. Large front and back yard, level with some fencing. Will need notice to show.

    Julie Lowe Lowe's Real Estate, LLC

    768 Vt Route 30, Jamaica, VT 05343
  • /46

    $660,000

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft

    9 Pond View Rd Unit 9, Winhall, VT 05340

    Exceptional Renovation and Prime Intervale Location on the Pond . Beautiful upscale kitchen that opens to a wonderful great room with wood burning fireplace, cathedral ceiling, a spacious dining area and new deck with steps to the outdoors and pond. Tasteful details of this highly desirable floor plan with three bedrooms/3 baths that includes two bedrooms ensuite and a loft. The loft features

    Kim Morgan-Wohler Wohler Realty Group

    9 Pond View Rd Unit 9, Winhall, VT 05340
  • /14

    $210,000

    • Land
    • 35 Acres
    • $6,000 per Acre

    00 Vermont Route 100, Jamaica, VT 05343

    Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

    Patrice Schneider Southern Vermont Realty Group

    00 Vermont Route 100, Jamaica, VT 05343
  • /60

    $849,000

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

    42 Blackberry Ln, Jamaica, VT 05343

    Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

    MaryKate Grey Stratton Real Estate

    42 Blackberry Ln, Jamaica, VT 05343
  • /39

    $890,000

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

    4880 Pikes Falls Rd, Jamaica, VT 05343

    This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    4880 Pikes Falls Rd, Jamaica, VT 05343
  • /9

    $185,000

    • Land
    • 8 Acres
    • $23,125 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /38

    $1,600,000

    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    4427 W Hill Rd S, Jamaica, VT 05343

    One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

    Carrie Mathews Winhall Real Estate

    4427 W Hill Rd S, Jamaica, VT 05343
  • /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
  • /24

    $225,000

    • 1 Bed
    • 1 Bath
    • 265 Sq Ft

    2053 Pikes Falls Rd, Jamaica, VT 05343

    A unique tiny house offering contemporary, Vermont farmhouse luxury in the Green Mountains. Featured on A & E's Living Smaller!This is tiny house vacation living at its finest. The house offers a full kitchen with four-burner gas stove and oven, farmhouse sink, butcher-block countertops, electric fireplace, AC, 40” Smart TV, Starlink WiFi, small soaking bathtub with shower. The bedroom loft

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    2053 Pikes Falls Rd, Jamaica, VT 05343
  • /15

    $530,000

    • Land
    • 30 Acres
    • $17,667 per Acre

    00 W Hill Rd S, Jamaica, VT 05343

    Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

    Jacki Murano Southern Vermont Realty Group

    00 W Hill Rd S, Jamaica, VT 05343
  • /32

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    4106 Vt Route 30, Jamaica, VT 05343

    Built in 1840, this charming home has long been a part of Jamaica’s rich history. Thoughtfully updated for modern living, it features a brand-new septic system, a renovated kitchen with granite countertops, and spacious rooms filled with natural light. Perfectly located just a short walk to town and Jamaica State Park, and only 10 miles from Stratton’s lifts, this property offers the ideal blend

    Carrie Mathews Winhall Real Estate

    4106 Vt Route 30, Jamaica, VT 05343
  • /19

    $63,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    2022 Vermont 30, Jamaica, VT 05343

    Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both!Stratton is just 20

    Carrie Mathews Winhall Real Estate

    2022 Vermont 30, Jamaica, VT 05343
  • /44

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 4,193 Sq Ft

    70 Hunter Ln, Jamaica, VT 05343

    Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    70 Hunter Ln, Jamaica, VT 05343
  • /30

    $1,040,000

    • 5 Beds
    • 4.5 Baths
    • 3,363 Sq Ft

    1189 Cole Pond Rd, Jamaica, VT 05343

    Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1189 Cole Pond Rd, Jamaica, VT 05343
  • /17

    $2,495,000

    • Land
    • 2.36 Acres
    • $1,057,203 per Acre

    4 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Lot #4

    Andrew King Stratton Real Estate

    4 Gold Medal Cir, Stratton, VT 05343
  • /40

    $1,695,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /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

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /6

    $239,000

    • Land
    • 1.57 Acres
    • $152,229 per Acre

    2 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Find

    Andrew King Stratton Real Estate

    2 Gold Medal Cir, Stratton, VT 05343
  • /29

    $190,000

    • 2 Beds
    • 1 Bath
    • 844 Sq Ft

    8577 Vermont 30 Unit H, Jamaica, VT 05343

    Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed Condo featuring 2 bedrooms, 1 full bathroom with washer and dryer and updated appliances. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Stratton Access Road and within easy reach of Jamaica State Park and the West River. Ideal

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

    8577 Vermont 30 Unit H, Jamaica, VT 05343
  • /6

    $470,000

    • Land
    • 6.93 Acres
    • $67,821 per Acre

    lot#2 Margeaux Ln, Stratton, VT 05155

    This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    lot#2 Margeaux Ln, Stratton, VT 05155
  • /5

    $440,000

    • Land
    • 5.54 Acres
    • $79,422 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
  • /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
  • /13

    $120,000

    • Land
    • 4.68 Acres
    • $25,641 per Acre

    8559 Vt Route 30, Jamaica, VT 05343

    Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

    TG Glazer Winhall Real Estate

    8559 Vt Route 30, Jamaica, VT 05343
  • /56

    $2,999,000

    • 6 Beds
    • 6.5 Baths
    • 6,650 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
  • /35

    $2,399,000

    • 4 Beds
    • 4.5 Baths
    • 3,569 Sq Ft

    662 Howe Farm Rd, Jamaica, VT 05343

    Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    662 Howe Farm Rd, Jamaica, VT 05343
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