Jamaica, VT Homes

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  /29

  $750,000 Sold May 12, 2025

  12 Jamie Ln, Jamaica, VT 05343

  • 4 Beds
  • 3.5 Baths
  • 3,084 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $243/SF
  • 82 Days On Market

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

  12 Jamie Ln, Jamaica, VT 05343
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  /40

  Est $547,982 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft

  482 Pratt Bridge Rd, Jamaica, VT 05343

  482 Pratt Bridge Rd, Jamaica, VT 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
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  /37

  $400,000 Sold Oct 02, 2025

  3458 Vt Route 30, Jamaica, VT 05343

  • 6 Beds
  • 2.5 Baths
  • 3,032 Sq Ft
  • Built 1790

  Last Sold Summary

  • 11% Below List Price
  • $132/SF
  • 55 Days On Market

  Current Estimated Value $385,230

  Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

  3458 Vt Route 30, Jamaica, VT 05343
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  /31

  Est $645,845 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,593 Sq Ft

  81 Edie Ln, Jamaica, VT 05343

  81 Edie Ln, Jamaica, VT 05343
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  /50

  $319,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft

  756 Turkey Mountain Rd, Jamaica, VT 05343

  Tucked away on 2.5± mostly level acres with stonewalls and a brook at the edge of the property, this Jamaica, Vermont, Cape offers a rare combination of usable land, privacy, and natural beauty. Inside, the 3-bedroom, 2-bath home offers a sensible, functional floor plan with solid bones and the opportunity to update and personalize over time. First-floor bedroom with a newly refreshed full bath,

  Jacki Murano Southern Vermont Realty Group

  756 Turkey Mountain Rd, Jamaica, VT 05343
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  /29

  $526,000 Sold Aug 08, 2025

  176 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $325/SF
  • 36 Days On Market

  Current Estimated Value $505,446

  Last Listing Agent Carrie Mathews Winhall Real Estate

  176 Pratt Bridge Rd, Jamaica, VT 05343
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  /25

  Est $783,226 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,600 Sq Ft

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  110 Upper Taylor Hill Rd, Jamaica, VT 05343
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  /31

  $435,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  132 Pratt Bridge Rd, Jamaica, VT 05343

  Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
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  /45

  $245,000 Sold Oct 10, 2025

  2277 Vermont 30, Jamaica, VT 05343

  • 3 Beds
  • 1 Bath
  • 1,586 Sq Ft
  • Built 1960

  Last Sold Summary

  • 17% Below List Price
  • $154/SF
  • 71 Days On Market

  Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  2277 Vermont 30, Jamaica, VT 05343
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  /39

  Est $670,500 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  39 Depot St, Jamaica, VT 05343

  39 Depot St, Jamaica, VT 05343
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  /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
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  /22

  $360,000 Sold Jun 20, 2025

  9 Mountain Acres Rd, Jamaica, VT 05343

  • 5 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 112 Days On Market

  Current Estimated Value $356,736

  Last Listing Agent Helen Nault

  9 Mountain Acres Rd, Jamaica, VT 05343
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  /14

  Not Listed For Sale

  0 S Hill Rd, Jamaica, VT 05343

  0 S Hill Rd, Jamaica, VT 05343
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  /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
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  /48

  $645,000 Sold Mar 13, 2025

  418 Diers, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,621 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Above List Price
  • $246/SF
  • 4 Days On Market

  Current Estimated Value $615,940

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

  418 Diers, Jamaica, VT 05343
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  /11

  Est $142,244 Not Listed For Sale

  12 Sugar Lot Ln, Jamaica, VT 05343

  12 Sugar Lot Ln, Jamaica, VT 05343
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  /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
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  /15

  $159,500 Sold May 14, 2025

  000 Rose Ln, Londonderry, VT 05148

  • Land
  • 11.08 Acres
  • $14,395 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 440 Days On Market

  Last Listing Agent Rachel Febbie EXP Realty

  000 Rose Ln, Londonderry, VT 05148
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  /21

  Est $320,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 320 Sq Ft

  1406 Cole Pond Rd, Jamaica, VT 05343

  1406 Cole Pond Rd, Jamaica, VT 05343
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  /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
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  /17

  $215,000 Sold Nov 21, 2025

  5997 Vermont 30, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,387 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Above List Price
  • $155/SF
  • 0 Days On Market

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

  5997 Vermont 30, Jamaica, VT 05343
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  /21

  Est $354,074 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  63 Reynolds Ln, Jamaica, VT 05343

  63 Reynolds Ln, Jamaica, VT 05343
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  /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
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  /31

  $380,000 Sold Dec 11, 2025

  2779 Pikes Falls Rd, Jamaica, VT 05343

  • 3 Beds
  • 1 Bath
  • 1,338 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Below List Price
  • $284/SF
  • 211 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate

  2779 Pikes Falls Rd, Jamaica, VT 05343
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  /26

  Est $486,218 Not Listed For Sale

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

  116 Teacher Rd, Jamaica, VT 05343

  116 Teacher Rd, Jamaica, VT 05343
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  /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
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  /50

  $469,000 Sold Jul 25, 2025

  2194 Mowrey Rd, Jamaica, VT 05343

  • 2 Beds
  • 1.5 Baths
  • 1,346 Sq Ft
  • Built 2003

  Last Sold Summary

  • $348/SF
  • 47 Days On Market

  Current Estimated Value $464,805

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

  2194 Mowrey Rd, Jamaica, VT 05343
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  /35

  Est $645,887 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,880 Sq Ft

  660 Dalewood Rd, Jamaica, VT 05343

  660 Dalewood Rd, Jamaica, VT 05343
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  /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
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  /6

  $45,500 Sold Dec 30, 2025

  0 Route 30 Unit 5048856, Jamaica, VT 05343

  • Land
  • 2.4 Acres
  • $18,958 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 158 Days On Market

  Last Listing Agent Joe Castaluccio Winhall Real Estate

  0 Route 30 Unit 5048856, Jamaica, VT 05343
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  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  42 Pine Ln, Jamaica, VT 05359

  42 Pine Ln, Jamaica, VT 05359
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  /36

  $575,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,033 Sq Ft

  64 Gleason Farm Ln, Jamaica, VT 05343

  Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner,

  Carrie Mathews Winhall Real Estate

  64 Gleason Farm Ln, Jamaica, VT 05343
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  /27

  $530,000 Sold Aug 08, 2025

  69 Chapin Ln, Jamaica, VT 05343

  • 4 Beds
  • 3 Baths
  • 2,052 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $258/SF
  • 135 Days On Market

  Current Estimated Value $538,723

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

  69 Chapin Ln, Jamaica, VT 05343
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  /40

  Est $1,529,728 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 7,426 Sq Ft

  541 Mtn Acres Rd, Jamaica, VT 05343

  541 Mtn Acres Rd, Jamaica, VT 05343
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  /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
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  /54

  $759,000 Sold Aug 08, 2025

  544 Dalewood Rd, Jamaica, VT 05343

  • 5 Beds
  • 4.5 Baths
  • 2,600 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $292/SF
  • 24 Days On Market

  Current Estimated Value $725,795

  Last Listing Agent Rachel Febbie EXP Realty

  544 Dalewood Rd, Jamaica, VT 05343
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  /31

  Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,624 Sq Ft

  71 Todd Hill Rd, Jamaica, VT 05343

  71 Todd Hill Rd, Jamaica, VT 05343
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  /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
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  /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

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

  1247 Cole Pond Rd, Jamaica, VT 05343

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