1,395

Jamaica, VT Homes

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  • /2

    $2,500

    $13K PRICE DROP Under Contract
    • Land
    • 7,840 Sq Ft
    • $13,889 per Acre

    0 Clayton Ln Unit 5094564, Jamaica, VT 05343

    This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the towns registered voters, the select, Board cannot just sell the property,

    Carrie Mathews Winhall Real Estate

    0 Clayton Ln Unit 5094564, Jamaica, VT 05343
  • /42

    $499,000

    Sold Aug 29, 2025

    168 Howard Rd, Jamaica, VT 05343

    • 4 Beds
    • 2.5 Baths
    • 1,986 Sq Ft
    • Built 1970

    Last Sold Summary

    • $251/SF
    • 21 Days On Market

    Current Estimated Value $505,239

    Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

    168 Howard Rd, Jamaica, VT 05343
    • /23

      Not Listed For Sale

      106 Vermont 30 Unit Property 3, Jamaica, VT 05359

      • 3 Beds
      • 2 Baths
      • 1,286 Sq Ft
      • Built 2021
      106 Vermont 30 Unit Property 3, Jamaica, VT 05359

      Last Sold Summary

      • 187 Days On Market

      Last Listing Agent Joe Castaluccio Winhall Real Estate

  • /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 seamless

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1189 Cole Pond Rd, Jamaica, VT 05343
  • /54

    $586,750

    Sold Apr 30, 2026

    98 Gleason Farm Ln, Jamaica, VT 05343

    • 3 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 1990

    Last Sold Summary

    • 8% Below List Price
    • $217/SF
    • 6 Days On Market

    Current Estimated Value $593,907

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    98 Gleason Farm Ln, Jamaica, VT 05343
    • /29

      Est $517,255

      Not Listed For Sale

      139 Worden Rd, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 2,139 Sq Ft
      • Built 1984
      139 Worden Rd, Jamaica, VT 05343

      Last Sold Summary

      • 130 Days On Market

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /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
    • /40

      Not Listed For Sale

      926 Dalewood Rd, Jamaica, VT 05343

      • 3 Beds
      • 2 Baths
      • 1,165 Sq Ft
      • Built 1996
      926 Dalewood Rd, Jamaica, VT 05343

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Mike England Michael England Real Estate

  • /2

    $50,000

    Under Contract
    • Land
    • 28 Acres
    • $1,786 per Acre

    non Pikes Falls Rd, Jamaica, VT 05343

    This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5%

    Carrie Mathews Winhall Real Estate

    non Pikes Falls Rd, Jamaica, VT 05343
    • /34

      Est $445,074

      Not Listed For Sale

      162 Upper Bear Ln Unit C-19, Jamaica, VT 05343

      • 3 Beds
      • 3 Baths
      • 1,425 Sq Ft
      • Built 1985
      162 Upper Bear Ln Unit C-19, Jamaica, VT 05343

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  • /35

    $2,399,000

    $100K PRICE DROP
    • 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
    • /15

      Not Listed For Sale

      000 Rose Ln, Londonderry, VT 05148

      000 Rose Ln, Londonderry, VT 05148

      Last Sold Summary

      • 440 Days On Market

      Last Listing Agent Rachel Febbie EXP Realty

  • /28

    $57,000

    $6K PRICE DROP
    • 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
    • /6

      Est $147,511

      Not Listed For Sale

      122 Blackberry Ln Unit 7, Jamaica, VT 05343

      122 Blackberry Ln Unit 7, Jamaica, VT 05343

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Helen Nault

  • /13

    $139,000

    Under Contract
    • Land
    • 5 Acres
    • $27,800 per Acre

    14 Sugar Lot Ln, Jamaica, VT 05343

    Nestled in the heart of Jamaica, this pristine wooded lot offers a quintessential Vermont building canvas where privacy meets accessibility. As you pull off the quiet road onto the roughed-in driveway, you are immediately enveloped by a mature hardwoods that leads directly to a cleared homesite. This dedicated building envelope allows you to drive your car right to the center of your future

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    14 Sugar Lot Ln, Jamaica, VT 05343
    • /17

      Est $303,858

      Not Listed For Sale

      35 Copeland Ln, Jamaica, VT 05343

      • 2 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1976
      35 Copeland Ln, Jamaica, VT 05343

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  • /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
    • /40

      Est $669,707

      Not Listed For Sale

      747 Cole Pond Rd, Jamaica, VT 05343

      • 3 Beds
      • 3.5 Baths
      • 2,126 Sq Ft
      • Built 1989
      747 Cole Pond Rd, Jamaica, VT 05343

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Lee Brown Four Seasons Sotheby's Int'l Realty

  • /39

    $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
    • /14

      Est $273,738

      Not Listed For Sale

      259 Howe Farm Rd, Jamaica, VT 05343

      • 2 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1965
      259 Howe Farm Rd, Jamaica, VT 05343

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Robert Sabol Wohler Realty Group

  • /34

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,296 Sq Ft

    170 River Rd, Jamaica, VT 05343

    Charming cape style modular home set on a beautiful, level 3.67 acre parcel. The expansive yard is framed by a stunning mountain backdrop that gives the entire property a peaceful, protected feel. Inside, you’ll find a bright and welcoming three bedroom, one and a half bath layout with plenty of natural light and comfortable living spaces. Mudroom entryway offers nice closet space and washer

    Julie Lowe Lowe's Real Estate, LLC

    170 River Rd, Jamaica, VT 05343
    • /22

      Est $304,520

      Not Listed For Sale

      1308 Turkey Mountain Rd, Jamaica, VT 05343

      • 1 Bed
      • Built 2015
      1308 Turkey Mountain Rd, Jamaica, VT 05343

      Last Sold Summary

      • 237 Days On Market

      Last Listing Agent Susan LeCours Barrett & Valley Assoc. Inc

  • /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

      Est $485,263

      Not Listed For Sale

      411 Stratton Gate Rd, Jamaica, VT 05343

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 1987
      411 Stratton Gate Rd, Jamaica, VT 05343

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

  • /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
    • /39

      Est $530,752

      Not Listed For Sale

      201 Pratt Bridge Rd, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 1,814 Sq Ft
      • Built 1968
      201 Pratt Bridge Rd, Jamaica, VT 05343

      Last Sold Summary

      • 140 Days On Market

      Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

    • /40

      Not Listed For Sale

      200 Forrester Rd, Jamaica, VT 05360

      • 3 Beds
      • 2 Baths
      • 1,354 Sq Ft
      • Built 1977
      200 Forrester Rd, Jamaica, VT 05360

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    • /23

      Not Listed For Sale

      2014 Vt Route 30, Jamaica, VT 05343

      • 3 Beds
      • 1 Bath
      • 840 Sq Ft
      • Built 1975
      2014 Vt Route 30, Jamaica, VT 05343

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Carrie Mathews Winhall Real Estate

    • /27

      Est $518,362

      Not Listed For Sale

      88 Peter's Ln, Wardsboro, VT 05355

      • 4 Beds
      • 2.5 Baths
      • 2,688 Sq Ft
      • Built 2004
      88 Peter's Ln, Wardsboro, VT 05355

      Last Sold Summary

      • 153 Days On Market

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    • /26

      Est $359,606

      Not Listed For Sale

      195 Stratton Gate Rd, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 1,350 Sq Ft
      • Built 1973
      195 Stratton Gate Rd, Jamaica, VT 05343

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Mike England Michael England Real Estate

    • /3

      Not Listed For Sale

      00 Blackberry Ln, Jamaica, VT 05343

      00 Blackberry Ln, Jamaica, VT 05343

      Last Sold Summary

      • 130 Days On Market

      Last Listing Agent Britt Wohler

    • /16

      Not Listed For Sale

      Lot E-2 Stratton Gate Rd, Jamaica, VT 05343

      Lot E-2 Stratton Gate Rd, Jamaica, VT 05343

      Last Sold Summary

      • 272 Days On Market

      Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    • /30

      Not Listed For Sale

      180 Vermont Route 100, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 2,348 Sq Ft
      • Built 1850
      180 Vermont Route 100, Jamaica, VT 05343

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent John Sobel Four Seasons Sotheby's Int'l Realty

    • /22

      Est $246,641

      Not Listed For Sale

      118 Pineapple Hill Ln, Jamaica, VT 05343

      • 5 Beds
      • 2 Baths
      • 1,036 Sq Ft
      • Built 1964
      118 Pineapple Hill Ln, Jamaica, VT 05343

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent John Morrison John W. Morrison Real Estate

    • /35

      Not Listed For Sale

      83 Benson Fuller Dr Unit Stocker Acres Lot 14, Jamaica, VT 05343

      • 5 Beds
      • 5.5 Baths
      • 3,359 Sq Ft
      • Built 2005
      83 Benson Fuller Dr Unit Stocker Acres Lot 14, Jamaica, VT 05343

      Last Sold Summary

      • 134 Days On Market

      Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

    • /10

      Not Listed For Sale

      144 Tony's Ln, Jamaica, VT 05343

      • 1 Bed
      • 1 Bath
      • 356 Sq Ft
      • Built 2007
      144 Tony's Ln, Jamaica, VT 05343

      Last Sold Summary

      • 210 Days On Market

      Last Listing Agent Mike England Michael England Real Estate

    • /32

      Not Listed For Sale

      4491 W Jamaica Rd, Jamaica, VT 05343

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1980
      4491 W Jamaica Rd, Jamaica, VT 05343

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Britt Wohler

    • /24

      Not Listed For Sale

      5807 Pikes Falls Rd, Stratton, VT 05360

      • 1 Bed
      • 1 Bath
      • 476 Sq Ft
      • Built 1965
      5807 Pikes Falls Rd, Stratton, VT 05360

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent TG Glazer Winhall Real Estate

    • /29

      Not Listed For Sale

      12 Jamie Ln, Jamaica, VT 05343

      • 4 Beds
      • 3.5 Baths
      • 3,084 Sq Ft
      • Built 2003
      12 Jamie Ln, Jamaica, VT 05343

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

    • /38

      Not Listed For Sale

      3883 Vermont 30, Townshend, VT 05353

      • 3 Beds
      • 2 Baths
      • 1,760 Sq Ft
      • Built 1930
      3883 Vermont 30, Townshend, VT 05353

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

Showing Results 121 - 160, Page 4 of 18

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