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Jamaica, VT Homes for Sale

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  • /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
  • /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
  • /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

    $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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

Why Live in Jamaica

Jamaica, Vermont, located in Windham County, is a small town known for its natural beauty and outdoor recreational opportunities. The town features mountainous terrain, lush vegetation, and water features, drawing both permanent and seasonal residents. Jamaica State Park, with nearly 800 acres, offers access points for anglers, swimmers, and boaters along the West River. Popular hiking destinations include Hamilton Falls, one of Vermont's tallest waterfalls. The Green Mountains to the west host major winter sports destinations like Stratton Mountain Resort and Bromley Mountain Ski Resort, offering activities such as skiing, mountain biking, and pickleball. Housing in Jamaica ranges from early 1800s farmhouses to modern A-frame chalets and cabins, with median single-family home prices around $500,000. The village cores of Jamaica and East Jamaica feature late 1800s to early 1900s folk-style homes. Jamaica Village School and Townshend Village School are highly rated, serving prekindergarten and kindergarten through fifth grade, respectively. Local events include Old Home Day, fostering community spirit with historical reenactments, craft vendors, and live music. Residents can find small businesses and dining options along State Route 30, with more diverse shopping and dining available 20 miles away in Manchester. The town is prone to flooding in low-lying areas along the West River, but the community is known for its resilience. The nearest major airport is Albany International Airport, approximately 80 miles away.

Frequently Asked Questions

What is the average home price in Jamaica, VT?
Homes for sale in Jamaica, VT have an average home price of $742,035.
Are home prices dropping in Jamaica?
Yes, home prices in Jamaica are down 18% in the last 12 months.
How many homes have sold over the last 12 months in Jamaica, VT?
26 homes have sold in Jamaica, VT over the last 12 months.
What are the most popular zip codes in Jamaica, VT?
The most popular zip codes in Jamaica, VT include 05343, 05359, 05155, 05148 and 05340.
How much do you need to make to afford a house in Jamaica?
The median home price in Jamaica is $534,500. If you put a 20% down payment of $106,900 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $2,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K a year to afford the median home price in Jamaica. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Jamaica, VT?
Jamaica, VT has highly rated public and private schools. Some of the best schools in Jamaica based on Niche Grades are Stratton Mountain School, Jamaica Village School and Townshend Village School. Browse all the schools in Jamaica, VT to learn more.

Home Trends in Jamaica, VT

Housing Trends

Median Sale Price
$461,500
Median Single Family Sale Price
$520,000
Median 2 Bedroom Sale Price
$190,000
Average Price Per Sq Ft
$310
Number of Homes for Sale
16
Last 12 months Home Sales
26
Months of Supply
7.40
Median List Price
$534,500
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-7%
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