Jamaica, VT Homes

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  /38

  $495,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,115 Sq Ft

  367 Stratton Gate Rd, Jamaica, VT 05343

  Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

  

  Alison Cummings

  Cummings & Co

  367 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  

  /20

  $5,000 Per Month

  • 6 Beds
  • 3 Baths
  • 2,279 Sq Ft
  • House for Rent

  1138 River Rd, Jamaica, VT 05343

  Property Id: 2797610 ****Available for the winter season at $25,000 | $5,000/month for 5 months*** Call for details Escape to the mountains this winter in this spacious and fully updated 6-bedroom, 3-bath home in scenic Jamaica, VT. Set in a peaceful wooded setting, this inviting retreat offers room for the whole crew—sleeping up to 14 comfortably, including a cozy loft, which would

  1138 River Rd, Jamaica, VT 05343
• 

  

  

  /12

  $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
• 

  

  

  /16

  Est $138,997

  Not Listed For Sale

  272 Landman Ln, Jamaica, VT 05343

  • 2 Beds
  • 2 Baths
  • 1,331 Sq Ft
  • Built 1987

  272 Landman Ln, Jamaica, VT 05343

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Mike England Michael England Real Estate
• 

  

  

  /21

  $290,000

  • Land
  • 289.12 Acres
  • $1,003 per Acre

  2817 Lt 22, Jamaica, VT 05343

  Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on

  Zach Jaminet Fountains Land

  2817 Lt 22, Jamaica, VT 05343
• 

  

  /24

  $2,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  776 Old Route 8, Jamaica, VT 05343

  Welcome home to this beautifully renovated 3-bedroom, 2-bath single-family residence nestled on a peaceful 1⁄2-acre lot with direct access to a tranquil brook. This rental comes fully furnished. Blending modern updates with the serenity of nature, this property offers the perfect balance of comfort and outdoor living. Step inside to discover a thoughtfully updated interior featuring bright,

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  776 Old Route 8, Jamaica, VT 05343
• 

  

  /26

  $315,000

  Sold Apr 14, 2026

  9047 Vermont 30, Jamaica, VT 05155

  • 2 Beds
  • 2 Baths
  • 976 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Below List Price
  • $323/SF
  • 20 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate

  9047 Vermont 30, Jamaica, VT 05155
• 

  

  /27

  Est $516,913

  Not Listed For Sale

  69 Chapin Ln, Jamaica, VT 05343

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

  69 Chapin Ln, Jamaica, VT 05343

  Last Sold Summary

  • 135 Days On Market

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

  /2

  $45,000

  Under Contract

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

  0 Edie Ln, 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 Edie Ln, Jamaica, VT 05343
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  /33

  $18,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft
  • House for Rent

  22 Reynolds Ln, Jamaica, VT 05343

  Escape to the mountains and enjoy winter the way it was meant to be experienced. Located just 5.5 miles from Stratton's Sun Bowl, this newly constructed 3-bedroom, 2.5-bath home offers the perfect setting for ski weekends, holiday gatherings, and memorable mountain getaways. Thoughtfully designed with a modern mountain aesthetic, the home features soaring ceilings, warm wood finishes, and

  Cheyanne Pugliese

  22 Reynolds Ln, Jamaica, VT 05343
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  /34

  $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

  Current Estimated Value $233,328

  Last Listing Agent Mike England Michael England Real Estate

  533 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /54

  Est $765,324

  Not Listed For Sale

  544 Dalewood Rd, Jamaica, VT 05343

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

  544 Dalewood Rd, Jamaica, VT 05343

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Rachel Febbie EXP Realty
• 

  /2

  $89,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,902 Sq Ft

  206 Smith Rd, Jamaica, VT 05343

  Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run

  Christine Lewis Brattleboro Area Realty

  206 Smith Rd, Jamaica, VT 05343
• 

  

  /50

  $300,000

  Sold Mar 16, 2026

  756 Turkey Mountain Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft
  • Built 1996

  Last Sold Summary

  • 6% Below List Price
  • $204/SF
  • 19 Days On Market

  Current Estimated Value $307,524

  Last Listing Agent Jacki Murano Southern Vermont Realty Group

  756 Turkey Mountain Rd, Jamaica, VT 05343
• 

  

  /29

  Est $543,453

  Not Listed For Sale

  176 Pratt Bridge Rd, Jamaica, VT 05343

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

  176 Pratt Bridge Rd, Jamaica, VT 05343

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate
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  /12

  $178,000

  $7K PRICE DROP

  • Land
  • 8 Acres
  • $22,250 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
• 

  

  /46

  $299,000

  Sold Jan 22, 2026

  4410 Pikes Falls Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 2,194 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $136/SF
  • 5 Days On Market

  Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  4410 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  /32

  Est $483,343

  Not Listed For Sale

  476 Edie Ln, Jamaica, VT 05343

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • Built 1988

  476 Edie Ln, Jamaica, VT 05343

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate
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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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  /31

  $405,000

  Sold Mar 05, 2026

  132 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft
  • Built 1987

  Last Sold Summary

  • 13% Below List Price
  • $223/SF
  • 140 Days On Market

  Current Estimated Value $426,573

  Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /48

  Est $607,843

  Not Listed For Sale

  418 Diers, Jamaica, VT 05343

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

  418 Diers, Jamaica, VT 05343

  Last Sold Summary

  • 4 Days On Market

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

  

  /38

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,022 Sq Ft

  564 Goodaleville Rd, Jamaica, VT 05343

  10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain

  Cheyanne Pugliese

  564 Goodaleville Rd, Jamaica, VT 05343
• 

  

  /30

  $1,000,000

  Sold Jan 30, 2026

  585 Pleasant Valley Rd, Jamaica, VT 05343

  • Land
  • 108 Acres
  • $9,259 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 293 Days On Market

  Current Estimated Value $1,003,443

  Last Listing Agent Britt Wohler

  585 Pleasant Valley Rd, Jamaica, VT 05343
• 

  

  /35

  Est $490,239

  Not Listed For Sale

  3796 Vt Route 30, Jamaica, VT 05343

  • 4 Beds
  • 1.5 Baths
  • 3,169 Sq Ft
  • Built 1860

  3796 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
• 

  

  /57

  $850,000

  • 5 Beds
  • 4 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

  Mike England Michael England Real Estate

  4880 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  /36

  $560,000

  Sold Aug 07, 2026

  9 Beaver Pond Ln, Jamaica, VT 05343

  • 4 Beds
  • 4 Baths
  • 1,211 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $462/SF
  • 5 Days On Market

  Last Listing Agent Helen Nault

  9 Beaver Pond Ln, Jamaica, VT 05343
• 

  

  /39

  Est $498,806

  Not Listed For Sale

  3996 Vt Route 30, Jamaica, VT 05343

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

  3996 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 133 Days On Market

  Last Listing Agent Britt Wohler
• 

  

  /22

  $595,000

  • 4 Beds
  • 2 Baths
  • 1,430 Sq Ft

  9 Mountain Acres Rd, Jamaica, VT 05343

  Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

  Carrie Mathews Winhall Real Estate

  9 Mountain Acres Rd, Jamaica, VT 05343
• 

  

  /43

  $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

  Current Estimated Value $855,556

  Last Listing Agent Helen Nault

  460 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /32

  Est $264,866

  Not Listed For Sale

  3790 S Hill Rd, Jamaica, VT 05343

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft
  • Built 1960

  3790 S Hill Rd, Jamaica, VT 05343

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Mike England Michael England Real Estate
• 

  

  /13

  $120,000

  • Land
  • 4.68 Acres
  • $25,641 per Acre

  8559 Vt Route 30, Jamaica, VT 05343

  Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

  TG Glazer Winhall Real Estate

  8559 Vt Route 30, Jamaica, VT 05343
• 

  

  /27

  $245,000

  Sold Nov 14, 2025

  8365 Vt Route 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

  Current Estimated Value $250,012

  Last Listing Agent TG Glazer Winhall Real Estate

  8365 Vt Route 30, Jamaica, VT 05343
• 

  

  /40

  Est $816,000

  Not Listed For Sale

  1223 Cole Pond Rd, Jamaica, VT 05343

  • 3 Beds
  • 4 Baths
  • 2,197 Sq Ft
  • Built 1970

  1223 Cole Pond Rd, Jamaica, VT 05343

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home
• 

  

  /21

  $290,000

  • Land
  • 289.12 Acres
  • $1,003 per Acre

  0 Black Bear Rd Unit 5101033, Jamaica, VT 05343

  Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on

  Thom Milke Fountains Land Inc.

  0 Black Bear Rd Unit 5101033, Jamaica, VT 05343
• 

  

  /41

  $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

  Current Estimated Value $634,713

  Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  202 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /33

  Est $487,717

  Not Listed For Sale

  1706 Vt Route 30, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 1967

  1706 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Christopher Cummings Cummings & Co
• 

  

  /36

  $1,295,000

  $20K PRICE INCREASE

  • 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
• 

  

  /4

  $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

  Current Estimated Value $224,666

  Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

  440 Edie Ln, Jamaica, VT 05343
• 

  

  /32

  Est $250,090

  Not Listed For Sale

  192 Howe Farm Rd, Jamaica, VT 05343

  • 1 Bed
  • 1 Bath
  • 956 Sq Ft
  • Built 1963

  192 Howe Farm Rd, Jamaica, VT 05343

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Alison Cummings Cummings & Co
• 

  

  /44

  $136,000

  • Land
  • 14 Acres
  • $9,714 per Acre

  182 Partridge Ln, Jamaica, VT 05343

  Escape to your own private Vermont retreat on this beautiful 14-acre wooded parcel, tucked away along the path less traveled. A thoughtfully established clearing is home to a travel trailer sheltered beneath a well-built pavilion, creating a comfortable, all-weather basecamp for weekends and seasonal getaways. The sale includes the camper complete with generators, tools and more making this a

  Jessica Landers Barrett and Valley Associates Inc.

  182 Partridge Ln, Jamaica, VT 05343

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