52

Homes for Sale in 05343

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  • /60

    $549,000

    • 4 Beds
    • 4 Baths
    • 3,075 Sq Ft

    24 Mowrey Rd, Jamaica, VT 05343

    Already operating as a successful short-term rental, 24 Mowrey Road offers the space, setting, and amenities buyers are looking for in a Southern Vermont getaway. Set on 2.3 acres along a town-maintained dead-end road, this spacious 4-bedroom, 4-bath home is positioned between Stratton and Mount Snow, with easy access to year-round recreation. Inside, the open great room creates an inviting

    Erica Reynolds Southern Vermont Realty Group

    24 Mowrey Rd, Jamaica, VT 05343
  • /5

    $995,000

    • Land
    • 130 Acres
    • $7,654 per Acre

    0 Forrester Rd Unit 5110773, Jamaica, VT 05360

    130 acre tract, this parcel backs up to over 1100 additional acres of Green Mountain National Forest lands. This private setting is less than 3 miles to Stratton Mountain Resort. Being subdivided off a larger 200+ acre parcel. Overhead power currently existing on premise, multiple drilled wells also already on premise and there will be access to this and other lots via existing road/driveway

    Chris Lowe Lowe's Real Estate, LLC

    0 Forrester Rd Unit 5110773, Jamaica, VT 05360
  • /18

    $799,000

    • Land
    • 67 Acres
    • $11,925 per Acre

    0 Forrester Rd Unit 5110766, Jamaica, VT 05360

    Own this large 67 acre tract of land just minutes to Stratton Mountain Resort with direct access to Forrester Pond. This parcel backs up to over 1100 additional acres of Green Mountain National Forest. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Being subdivided off a larger 200+ acre parcel. Power existing on current right of

    Chris Lowe Lowe's Real Estate, LLC

    0 Forrester Rd Unit 5110766, Jamaica, VT 05360
  • /3

    $250,000

    • Land
    • 4 Acres
    • $62,500 per Acre

    0 Forrester Rd Unit 5110757, Jamaica, VT 05360

    Lot 4 IS 4 acres! This private setting is less than 3 miles to Stratton Mountain Resort with easy access in the no zoning town of Jamaica. Five Bedroom Existing State Issued Wastewater Permit WW-2-2200 along with survey already in place for this lot. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this wooded lot. Residential and

    Chris Lowe Lowe's Real Estate, LLC

    0 Forrester Rd Unit 5110757, Jamaica, VT 05360
  • /19

    $425,000

    Open House 10/10
    • 2 Beds
    • 2.5 Baths
    • 1,257 Sq Ft

    190 Depot St, Jamaica, VT 05343

    Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for every season and

    Carrie Mathews Winhall Real Estate

    190 Depot St, Jamaica, VT 05343
  • /9

    $500,000

    • Land
    • 20.2 Acres
    • $24,752 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    West Hill Road is situated prominently on a mountainside, offering breathtaking views that stretch across the valley to the north, with clearing there will be scenic beauty of the area. This property presents an exceptional opportunity for individuals looking to construct their dream home or a private compound, with an abundance of possibilities limited only by one's imagination. Located just

    Mike England Michael England Real Estate

    0 W Hill Rd, Jamaica, VT 05343
  • /22

    $190,000

    • Land
    • 30.1 Acres
    • $6,312 per Acre

    S Jamaica Parcels – Unit 2, Jamaica, VT 05343

    Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. Schoolhouse Road is a private road, with maintenance split among all parties on the road. A

    Thom Milke Fountains Land

    S Jamaica Parcels – Unit 2, Jamaica, VT 05343
  • /11

    $120,000

    • Land
    • 10.2 Acres
    • $11,765 per Acre

    S Jamaica Parcels - Unit 1, Jamaica, VT 05343

    Parcel 1 is a 10-acre building site located on South Hill Road. A grass-covered access road leads from the street to a flat area just off the road, an ideal spot for a future home. Along the entire road frontage, except for the access driveway, an old stone wall runs the length of the property, lending charm and excellent curb appeal to any home built here.Beyond the potential building

    Thom Milke Fountains Land

    S Jamaica Parcels - Unit 1, Jamaica, VT 05343
  • /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
  • /30

    $995,000

    • 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
  • /16

    $975,000

    • Land
    • 235.3 Acres
    • $4,144 per Acre

    00 Pratt Bridge Rd, Jamaica, VT 05343

    Enjoy Vermont in all the seasons!! This land has a number of options! With 235 acres to call your own! Build somewhere on the property. A stream runs through for your enjoyment! Part of the West River Trail passes through as well. Harvest timber from this lot and make some $$. Pratt Bridge Road is a close drive to Stratton, Magic or Bromley in the winter and enjoy spring, summer and fall

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    00 Pratt Bridge Rd, Jamaica, VT 05343
  • /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
  • /60

    $2,430,000

    $270K PRICE DROP
    • 9 Beds
    • 7 Baths
    • 4,996 Sq Ft

    494-564 Goodaleville Rd, Jamaica, VT 05343

    TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern

    Cheyanne Pugliese

    494-564 Goodaleville Rd, Jamaica, VT 05343
  • /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
  • /35

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,359 Sq Ft

    116 Teacher Rd, Jamaica, VT 05343

    Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time

    Carrie Mathews Winhall Real Estate

    116 Teacher Rd, Jamaica, VT 05343
  • /20

    $190,000

    • Land
    • 30.1 Acres
    • $6,312 per Acre

    0 Schoolhouse Rd, Jamaica, VT 05343

    Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. A weathered stone wall is found along the entire length of the road frontage, hinting at the land's

    Thom Milke Fountains Land Inc.

    0 Schoolhouse Rd, Jamaica, VT 05343
  • /11

    $120,000

    • Land
    • 10.2 Acres
    • $11,765 per Acre

    0 S Hill Rd, Jamaica, VT 05343

    The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home.Parcel I is a 10-acre building site located on

    Thom Milke Fountains Land Inc.

    0 S Hill Rd, Jamaica, VT 05343
  • /4

    $299,000

    • Land
    • 57.76 Acres
    • $5,177 per Acre

    0 Vt Route 100 S Unit 5103450, Jamaica, VT 05343

    Discover the possibilities with this exceptional 57+ acre parcel in the Town of Jamaica, Vermont, where no local zoning provides incredible flexibility for your vision. Ideally located just minutes from Stratton Mountain, Mount Snow, and within easy reach of Bromley, Magic Mountain, Manchester, and Brattleboro, this property offers the perfect balance of privacy, recreation, and convenience.

    Julie Lowe Lowe's Real Estate, LLC

    0 Vt Route 100 S Unit 5103450, Jamaica, VT 05343
  • /8

    $585,000

    • Land
    • 91.6 Acres
    • $6,386 per Acre

    0 Water St Unit 5102573, Jamaica, VT 05343

    A rare opportunity to own over 91 private acres just a short walk from the charming Village of Jamaica. Tucked away off a private right-of-way, this remarkable parcel offers the perfect balance of peaceful seclusion and convenient access to local shops, dining, and community events.The property features a beautiful mix of mature forest, gently rolling terrain, and serene natural surroundings.

    Carrie Mathews Winhall Real Estate

    0 Water St Unit 5102573, Jamaica, VT 05343
  • /42

    $1,115,000

    $135K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft

    564 Goodaleville Rd, Jamaica, VT 05343

    Set along a quiet back road on the Winhall River, 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

    Cheyanne Pugliese

    564 Goodaleville Rd, Jamaica, VT 05343
  • /53

    $1,315,000

    $135K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,974 Sq Ft

    494-498 Goodaleville Rd, Jamaica, VT 05343

    4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and

    Cheyanne Pugliese

    494-498 Goodaleville Rd, Jamaica, VT 05343
  • /44

    $136,000

    • Land
    • 14 Acres
    • $9,714 per Acre

    182 Partridge Ln, Jamaica, VT 05343

    Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a

    Jessica Landers Barrett and Valley Associates Inc.

    182 Partridge Ln, Jamaica, VT 05343
  • /25

    $219,000

    • Land
    • 16.9 Acres
    • $12,959 per Acre

    00 Howe Farm Rd, Jamaica, VT 05343

    Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound,

    Patrice Schneider Southern Vermont Realty Group

    00 Howe Farm Rd, Jamaica, VT 05343
  • /19

    $63,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    2022 Route 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 Route 30, Jamaica, VT 05343
  • /28

    $480,000

    • 5 Beds
    • 2 Baths
    • 2,194 Sq Ft

    3327 Route 30, Jamaica, VT 05343

    Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and

    Carrie Mathews Winhall Real Estate

    3327 Route 30, Jamaica, VT 05343
  • /40

    $1,500,000

    • 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
  • /27

    $140,000

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft

    2074 Vt Rt 30, Jamaica, VT 05343

    Some places stop time. River's Edge is one of them.Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin

    Mike England Michael England Real Estate

    2074 Vt Rt 30, Jamaica, VT 05343
  • /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

    $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
  • /44

    $1,475,000

    Open House 10/10
    • 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
  • /39

    $799,000

    $40K PRICE DROP
    • 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
  • /22

    $85,000

    $1K PRICE DROP
    • Land
    • 6.2 Acres
    • $13,710 per Acre

    1297 River Rd, Jamaica, VT 05343

    Unique! Do you love to camp? swim? fish?.....this may be it for you....Over2000 feet of West River frontage with electric on site and just offpavement and at the intersection of 2 major access road to skiing andrecreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping

    Christine Lewis Brattleboro Area Realty

    1297 River Rd, Jamaica, VT 05343
  • /37

    $1,295,000

    $20K PRICE INCREASE
    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    4427 W Hill Rd S, Jamaica, VT 05343

    A true Vermont lodge in every sense—warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who

    Carrie Mathews Winhall Real Estate

    4427 W Hill Rd S, Jamaica, VT 05343
  • /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
  • /57

    $825,000

    $25K PRICE DROP
    • 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
  • /18

    $1,450,000

    • Land
    • 201.4 Acres
    • $7,200 per Acre

    0 Forrester Rd Unit 5082418, Jamaica, VT 05360

    Own this large tract of land, over 200 acres that abuts over 1100 additional acres of Green Mountain National Forest. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Currently only 18 of the 200 acres is gravel pit and being reclaimed and closed out on this property. See the Vermont Land Use Permit 2W1316 online for further

    Chris Lowe Lowe's Real Estate, LLC

    0 Forrester Rd Unit 5082418, Jamaica, VT 05360
  • /51

    $420,000

    $105K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft

    57 Oak Ln, Jamaica, VT 05343

    This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

    Mike England Michael England Real Estate

    57 Oak Ln, Jamaica, VT 05343
  • /9

    $195,000

    • Land
    • 1.2 Acres
    • $162,500 per Acre

    4769 Pikes Falls Rd, Jamaica, VT 05143

    This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

    Rachel Febbie EXP Realty

    4769 Pikes Falls Rd, Jamaica, VT 05143
  • /49

    $500,000

    • Land
    • 71 Acres
    • $7,042 per Acre

    00 Turkey Mountain Rd, Jamaica, VT 05343

    Escape to your own private 71-acre Vermont retreat, offering exceptional privacy and possibility plus access to nearby ski mountain villages. Tucked at the end of a town-maintained dead-end road and bordered on two sides by over 1,000 acres of conservation land, this property promises unmatched peace and lasting protection. Only 20 minutes to either Mt. Snow or Stratton, with over 3,300 feet of

    Jessica Landers Barrett and Valley Associates Inc.

    00 Turkey Mountain Rd, Jamaica, VT 05343
  • /13

    $120,000

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

    8559 Vt Route 30, Jamaica, VT 05343

    Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

    TG Glazer Winhall Real Estate

    8559 Vt Route 30, Jamaica, VT 05343

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