Jamaica, VT Homes

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  $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
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  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • House for Rent

  67 Vermont Route 100, Jamaica, VT 05155

  Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  67 Vermont Route 100, Jamaica, VT 05155
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  $125,000 Sold Dec 11, 2025

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343

  • Land
  • 1.51 Acres
  • $82,781 per Acre

  Last Sold Summary

  • 880 Days On Market

  Last Listing Agent Mike England Michael England Real Estate

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
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  Est $499,370 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  476 Edie Ln, Jamaica, VT 05343

  476 Edie Ln, Jamaica, VT 05343
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  $275,000

  • Land
  • 34.53 Acres
  • $7,964 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  $6,000 per month

  • 5 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • House for Rent

  1138 River Rd, Jamaica, VT 05343

  WINTER MONTHLY RENTAL - $6,000/Month Plus prepaid utilities ($750/month) | Total due in Full Before Occupancy. Spend the winter in the mountains with this spacious and fully updated 5-bedroom, 3-bath home with a cozy loft in scenic Jamaica, VT. Nestled in a quiet wooded setting, this inviting retreat comfortably accommodates up to 12 guests. After a day on the slopes, relax by the fireplace with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1138 River Rd, Jamaica, VT 05343
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  $200,000 Sold Oct 17, 2025

  533 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 2,613 Sq Ft
  • Built 1970

  Last Sold Summary

  • 27% Below List Price
  • $77/SF
  • 25 Days On Market

  Last Listing Agent Mike England Michael England Real Estate

  533 Pratt Bridge Rd, Jamaica, VT 05343
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  Est $444,513 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 3,169 Sq Ft

  3796 Vt Route 30, Jamaica, VT 05343

  3796 Vt Route 30, Jamaica, VT 05343
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  /11

  $495,000

  • Land
  • 68.89 Acres
  • $7,185 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  $2,500 per month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  4591 Vermont 30, Jamaica, VT 05343

  ITS NOT TOO LATE.. SNOW IS JUST STARTING TO FLY..This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen,

  Wilkie Bushby TPW Real Estate

  4591 Vermont 30, Jamaica, VT 05343
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  /23

  $249,000 Sold Jan 10, 2025

  106 Vermont 30 Unit Property 3, Jamaica, VT 05359

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Built 2021

  Last Sold Summary

  • 29% Below List Price
  • $194/SF
  • 187 Days On Market

  Last Listing Agent Joe Castaluccio Winhall Real Estate

  106 Vermont 30 Unit Property 3, Jamaica, VT 05359
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  Est $412,391 Not Listed For Sale

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

  3996 Vt Route 30, Jamaica, VT 05343

  3996 Vt Route 30, Jamaica, VT 05343
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  $195,000

  • Land
  • 15.27 Acres
  • $12,770 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  $1,300,000 Sold Jul 31, 2025

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

  • Land
  • 591 Acres
  • $2,200 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 136 Days On Market

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

  0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
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  Est $297,321 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  3790 S Hill Rd, Jamaica, VT 05343

  3790 S Hill Rd, Jamaica, VT 05343
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  $650,000

  • Land
  • 51.93 Acres
  • $12,517 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
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  $887,000 Sold Oct 17, 2025

  460 Stratton Gate Rd, Jamaica, VT 05343

  • 4 Beds
  • 3 Baths
  • 3,155 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Below List Price
  • $281/SF
  • 12 Days On Market

  Last Listing Agent Helen Nault

  460 Stratton Gate Rd, Jamaica, VT 05343
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  /18

  Est $580,751 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  155 Pratt Bridge Rd, Jamaica, VT 05343

  155 Pratt Bridge Rd, Jamaica, VT 05343
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  $315,000 Under Contract

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

  4410 Pikes Falls Rd, Jamaica, VT 05343

  This charming cabin in the woods is the perfect retreat for those seeking adventure and tranquility alike. Surrounded by 10.7 acres of forest, it offers a cozy haven just a short walk from the breathtaking Pikes Falls and is 5 minutes to Stratton Mountain, ideal for skiing enthusiasts during the winter months. In warmer weather, the nearby trails beckon hikers and mountain bikers to explore the

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  4410 Pikes Falls Rd, Jamaica, VT 05343
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  $245,000 Sold Nov 14, 2025

  8365 Vermont 30, Jamaica, VT 05343

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Below List Price
  • $324/SF
  • 0 Days On Market

  Last Listing Agent TG Glazer Winhall Real Estate

  8365 Vermont 30, Jamaica, VT 05343
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  Est $928,879 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,197 Sq Ft

  1223 Cole Pond Rd, Jamaica, VT 05343

  1223 Cole Pond Rd, Jamaica, VT 05343
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  $435,000

  • 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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  $510,000 Sold Jun 05, 2025

  5600 Pikes Falls Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1977

  Last Sold Summary

  • 24% Below List Price
  • $350/SF
  • 170 Days On Market

  Current Estimated Value $640,211

  Last Listing Agent Jamie Wylie Stratton Real Estate

  5600 Pikes Falls Rd, Jamaica, VT 05343
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  Est $477,514 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 848 Sq Ft

  1706 Vt Route 30, Jamaica, VT 05343

  1706 Vt Route 30, Jamaica, VT 05343
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  $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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  $785,000 Sold Nov 21, 2025

  202 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1966

  Last Sold Summary

  • 1% Below List Price
  • $280/SF
  • 28 Days On Market

  Last Listing Agent Geralyn Donohue Engel & Völkers Okemo

  202 Pratt Bridge Rd, Jamaica, VT 05343
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  Est $259,206 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 956 Sq Ft

  192 Howe Farm Rd, Jamaica, VT 05343

  192 Howe Farm Rd, Jamaica, VT 05343
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  $1,250,000

  • Land
  • 108 Acres
  • $11,574 per Acre

  585 Pleasant Valley Rd, Jamaica, VT 05343

  108 Acres of Pristine Land For Sale – 2 Miles to Stratton Sun Bowl with Panoramic ViewsA rare opportunity to own ~108 acres of stunning land with sweeping views of Stratton’s Sun Bowl and Mount Snow. Just 2 miles to the Sun Bowl base and 15 minutes to Mount Snow, this Jamaica, VT property (on the Stratton line) offers unmatched privacy, no zoning restrictions, and incredible

  Britt Wohler

  585 Pleasant Valley Rd, Jamaica, VT 05343
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  $170,000 Sold Nov 07, 2025

  440 Edie Ln, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1971

  Last Sold Summary

  • 19% Below List Price
  • $81/SF
  • 16 Days On Market

  Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

  440 Edie Ln, Jamaica, VT 05343
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  Est $343,815 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  60 River Rd, Jamaica, VT 05343

  60 River Rd, Jamaica, VT 05343
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  $165,000

  • Land
  • 1.2 Acres
  • $137,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  $64,000 Sold Sep 29, 2025

  2080 Vermont 30, Jamaica, VT 05343

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $68/SF
  • 5 Days On Market

  Last Listing Agent TG Glazer Winhall Real Estate

  2080 Vermont 30, Jamaica, VT 05343
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  Not Listed For Sale

  • 8 Beds
  • 6 Baths
  • 4,600 Sq Ft

  498 Goodaleville Rd, South Londonderry, VT 05155

  498 Goodaleville Rd, South Londonderry, VT 05155
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  $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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  $338,000 Sold May 16, 2025

  6217 Vt Route 30, Jamaica, VT 05343

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $261/SF
  • 100 Days On Market

  Current Estimated Value $347,118

  Last Listing Agent Trent Stephens Wohler Realty Group

  6217 Vt Route 30, Jamaica, VT 05343
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  Est $648,148 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 768 Sq Ft

  886 Dalewood Rd, Jamaica, VT 05343

  886 Dalewood Rd, Jamaica, VT 05343
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  $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
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  $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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  Est $304,037 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,122 Sq Ft

  80 Henderson Rd, Jamaica, VT 05343

  80 Henderson Rd, Jamaica, VT 05343
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  $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

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