1,395

Jamaica, VT Homes

Section Image
    • /21

      Est $365,452

      Not Listed For Sale

      63 Reynolds Ln, Jamaica, VT 05343

      • 3 Beds
      • 1.5 Baths
      • 1,100 Sq Ft
      • Built 1988
      63 Reynolds Ln, Jamaica, VT 05343

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /48

    $449,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft

    163 Howe Farm Rd, Jamaica, VT 05343

    ***BEST AND HIGHEST DUE BY 6/23/2026 AT 5PM*** Let the sunshine in! This beautifully maintained 3-bedroom, 3-bath home features an open-concept kitchen, living, and dining area centered around a stunning floor-to-ceiling brick fireplace. Cathedral ceilings and abundant windows fill the space with natural light, creating a warm and inviting atmosphere. The spacious primary suite offers a private

    Julie Lowe Lowe's Real Estate, LLC

    163 Howe Farm Rd, Jamaica, VT 05343
  • /55

    $550,000

    Sold Aug 06, 2026

    155 Pratt Bridge Rd, Jamaica, VT 05343

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $275/SF
    • 7 Days On Market

    Current Estimated Value $565,776

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

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

      Not Listed For Sale

      43 Pearl Buck Dr, Jamaica, VT 05343

      • 5 Beds
      • 5 Baths
      • 4,686 Sq Ft
      • Built 1983
      43 Pearl Buck Dr, Jamaica, VT 05343

      Last Sold Summary

      • 116 Days On Market

      Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  • /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
  • /32

    $315,000

    Sold Jul 15, 2026

    29 Pikes Falls Rd, Jamaica, VT 05343

    • 4 Beds
    • 2 Baths
    • 2,520 Sq Ft
    • Built 1863

    Last Sold Summary

    • 10% Below List Price
    • $125/SF
    • 108 Days On Market

    Current Estimated Value $319,500

    Last Listing Agent Carrie Mathews Winhall Real Estate

    29 Pikes Falls Rd, Jamaica, VT 05343
    • /35

      Est $714,269

      Not Listed For Sale

      660 Dalewood Rd, Jamaica, VT 05343

      • 4 Beds
      • 3.5 Baths
      • 1,880 Sq Ft
      • Built 1996
      660 Dalewood Rd, Jamaica, VT 05343

      Last Sold Summary

      • 146 Days On Market

      Last Listing Agent Christopher Cummings Cummings & Co

  • /2

    $45,000

    Under Contract
    • Land
    • 1 Acre
    • $45,000 per Acre

    0 W Hill Rd, 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 W Hill Rd, Jamaica, VT 05343
  • /34

    $510,000

    Sold Jun 18, 2026

    3996 Vermont 30, Jamaica, VT 05343

    • 4 Beds
    • 3 Baths
    • 3,081 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $166/SF
    • 28 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    3996 Vermont 30, Jamaica, VT 05343
    • /26

      Not Listed For Sale

      42 Pine Ln, Jamaica, VT 05359

      • 4 Beds
      • 2 Baths
      • 1,833 Sq Ft
      • Built 1970
      42 Pine Ln, Jamaica, VT 05359

      Last Sold Summary

      • 4 Days On Market

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

  • /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
  • /42

    $775,000

    Sold Dec 17, 2025

    1247 Cole Pond Rd, Jamaica, VT 05343

    • 4 Beds
    • 3 Baths
    • 3,551 Sq Ft
    • Built 1980

    Last Sold Summary

    • 18% Below List Price
    • $218/SF
    • 159 Days On Market

    Current Estimated Value $805,756

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

    1247 Cole Pond Rd, Jamaica, VT 05343
    • /40

      Est $1,718,708

      Not Listed For Sale

      541 Mtn Acres Rd, Jamaica, VT 05343

      • 6 Beds
      • 6.5 Baths
      • 7,426 Sq Ft
      • Built 2018
      541 Mtn Acres Rd, Jamaica, VT 05343

      Last Sold Summary

      • 346 Days On Market

      Last Listing Agent Andrew King Stratton Real Estate

  • /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
  • /15

    $285,000

    Sold Jun 04, 2026

    00 Pratt Bridge Rd, Jamaica, VT 05343

    • Land
    • 30 Acres
    • $9,500 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 11 Days On Market

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    00 Pratt Bridge Rd, Jamaica, VT 05343
    • /31

      Not Listed For Sale

      71 Todd Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 5.5 Baths
      • 3,624 Sq Ft
      • Built 2006
      71 Todd Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 4 Days On Market

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

  • /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
  • /14

    $45,000

    Sold Sep 29, 2025

    2000 Vermont 30, Jamaica, VT 05343

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $72/SF
    • 2 Days On Market

    Last Listing Agent Carrie Mathews Winhall Real Estate

    2000 Vermont 30, Jamaica, VT 05343
    • /5

      Not Listed For Sale

      0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

      0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Edward Jones Josiah Allen Real Estate, Inc.

  • /24

    $189,500

    Pending
    • 2 Beds
    • 1 Bath
    • 893 Sq Ft

    1018 S Hill Rd, Jamaica, VT 05343

    OPEN HOUSE - Sunday 8/2, 1-3 ** BEST AND FINAL DEADLINE - Monday, August 3rd, 5pm. This charming A-frame offers a woodsy Vermont retreat on 2.8 acres on quiet and scenic South Hill Road. Set at the end of a long driveway and perched on a hill, surrounded by mature woods, this 2 bedroom, 1 bath home blends rustic character with a warm, inviting atmosphere. Natural wood flooring and wood features

    Prema Fitzpatrick Real Broker LLC

    1018 S Hill Rd, Jamaica, VT 05343
  • /34

    $520,000

    Sold Sep 11, 2025

    3708 Vermont 30, Jamaica, VT 05343

    • 5 Beds
    • 5 Baths
    • 3,213 Sq Ft
    • Built 1818

    Last Sold Summary

    • $162/SF
    • 5 Days On Market

    Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    3708 Vermont 30, Jamaica, VT 05343
    • /7

      Not Listed For Sale

      0 W Hill Rd S Unit 5021406, Jamaica, VT 05343

      0 W Hill Rd S Unit 5021406, Jamaica, VT 05343

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Thom Milke Fountains Land Inc.

  • /9

    $85,000

    $30K PRICE INCREASE
    • Land
    • 1 Acre
    • $85,000 per Acre

    000F-320 Bourbon Run Rd, Jamaica, VT 05343

    This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Bromley, Magic Mountain, and

    Mike England Michael England Real Estate

    000F-320 Bourbon Run Rd, Jamaica, VT 05343
  • /60

    $480,000

    Sold May 21, 2026

    199 Turkey Mountain Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 2,254 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $213/SF
    • 6 Days On Market

    Current Estimated Value $491,205

    Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

    199 Turkey Mountain Rd, Jamaica, VT 05343
    • /22

      Not Listed For Sale

      8581 Vt Route 30 Unit B, Jamaica, VT 05343

      • 2 Beds
      • 1 Bath
      • 691 Sq Ft
      • Built 1982
      8581 Vt Route 30 Unit B, Jamaica, VT 05343

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  • /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
  • /35

    $630,000

    Sold May 01, 2026

    5 Linscott Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 2,370 Sq Ft
    • Built 1990

    Last Sold Summary

    • 14% Below List Price
    • $266/SF
    • 75 Days On Market

    Last Listing Agent Diana Stugger Four Seasons Sotheby's Int'l Realty

    5 Linscott Rd, Jamaica, VT 05343
    • /32

      Est $279,565

      Not Listed For Sale

      232 Worden Rd, Jamaica, VT 05343

      • 2 Beds
      • 1 Bath
      • 808 Sq Ft
      • Built 1960
      232 Worden Rd, Jamaica, VT 05343

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Jessica Citera Cummings & Co

  • /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
  • /2

    $575,000

    Sold Sep 12, 2025

    14 Nearing Rd, Jamaica, VT 05343

    • 3 Beds
    • 3 Baths
    • 2,064 Sq Ft
    • Built 1990

    Last Sold Summary

    • 12% Below List Price
    • $279/SF
    • 0 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    14 Nearing Rd, Jamaica, VT 05343
    • /10

      Not Listed For Sale

      0 Mowrey Rd Unit 5012138, Jamaica, VT 05343

      0 Mowrey Rd Unit 5012138, Jamaica, VT 05343

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Dan McKenna Cummings & Co

  • /14

    $250,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    270 Castle Hill Rd, Jamaica, VT 05343

    OFFER DEADLINE, MONDAY AUGUST 9TH 2026 5PM. Escape to this charming turnkey cabin nestled in the hills of Southern Vermont, just a short drive from Stratton Mountain. Being sold fully furnished and as is, what you see is what you get, simply bring your personal belongings and start enjoying your mountain retreat! Privately situated on 9.7 wooded acres, this cozy getaway offers the perfect blend

    Julie Lowe Lowe's Real Estate, LLC

    270 Castle Hill Rd, Jamaica, VT 05343
  • /29

    $185,000

    Sold Apr 13, 2026

    8577 Vermont 30 Unit H, Jamaica, VT 05343

    • 2 Beds
    • 1 Bath
    • 844 Sq Ft
    • Built 1982

    Last Sold Summary

    • 10% Below List Price
    • $219/SF
    • 293 Days On Market

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

    8577 Vermont 30 Unit H, Jamaica, VT 05343
    • /36

      Est $374,970

      Not Listed For Sale

      67 Depot St, Jamaica, VT 05343

      • 4 Beds
      • 2.5 Baths
      • 1,961 Sq Ft
      • Built 1815
      67 Depot St, Jamaica, VT 05343

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  • /44

    $1,475,000

    • 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
  • /52

    $450,000

    Sold Jul 23, 2026

    994 W Jamaica Rd, Jamaica, VT 05343

    • 3 Beds
    • 2.5 Baths
    • 1,344 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Below List Price
    • $335/SF
    • 22 Days On Market

    Last Listing Agent Britt Wohler

    994 W Jamaica Rd, Jamaica, VT 05343
    • /27

      Not Listed For Sale

      0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

      0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

      Last Sold Summary

      • 136 Days On Market

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

  • /13

    $99,000

    Under Contract
    • Land
    • 6.4 Acres
    • $15,469 per Acre

    0 Worden Rd Unit 5101763, Jamaica, VT 05343

    Discover the perfect blend of privacy, natural beauty, and convenience with this exceptional 6.4-acre parcel featuring river frontage in the heart of Southern Vermont. Tucked away in a peaceful setting, this unique property offers a rare opportunity to enjoy the serenity of nature while being just a short walk to both Jamaica State Park and the charming Village of Jamaica.Spend your days

    Carrie Mathews Winhall Real Estate

    0 Worden Rd Unit 5101763, Jamaica, VT 05343
  • /22

    $90,000

    Sold Dec 16, 2025

    oos-65-13 Partridge Ln, Jamaica, VT 05343

    • Land
    • 10.4 Acres
    • $8,654 per Acre

    Last Sold Summary

    • 31% Below List Price
    • 99 Days On Market

    Last Listing Agent Mike England Michael England Real Estate

    oos-65-13 Partridge Ln, Jamaica, VT 05343
    • /33

      Est $788,452

      Not Listed For Sale

      366 Stone Hedge Rd Unit 8, Jamaica, VT 05343

      • 3 Beds
      • 2.5 Baths
      • 2,936 Sq Ft
      • Built 2014
      366 Stone Hedge Rd Unit 8, Jamaica, VT 05343

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Helen Nault

Showing Results 81 - 120, Page 3 of 18

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