Jamaica, VT Homes

• 

  

  

  /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

  Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

  3458 Vt Route 30, Jamaica, VT 05343
• 

  

  

  /40

  Est $533,267 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
• 

  

  

  /60

  $4,495,500

  • 4 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning 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 surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
• 

  

  

  /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 $507,048

  Last Listing Agent Carrie Mathews Winhall Real Estate

  176 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  

  /31

  Est $641,443 Not Listed For Sale

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

  81 Edie Ln, Jamaica, VT 05343

  81 Edie Ln, Jamaica, VT 05343
• 

  

  /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
• 

  

  /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
• 

  

  /25

  Est $805,240 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
• 

  

  /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
• 

  

  /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 $355,729

  Last Listing Agent Helen Nault

  9 Mountain Acres Rd, Jamaica, VT 05343
• 

  

  /39

  Est $631,924 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
• 

  

  /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
• 

  

  /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 $612,600

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

  418 Diers, Jamaica, VT 05343
• 

  

  /14

  Not Listed For Sale

  0 S Hill Rd, Jamaica, VT 05343

  0 S Hill Rd, Jamaica, VT 05343
• 

  

  /44

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
• 

  

  /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
• 

  

  /11

  Est $131,561 Not Listed For Sale

  12 Sugar Lot Ln, Jamaica, VT 05343

  12 Sugar Lot Ln, Jamaica, VT 05343
• 

  

  /36

  $98,000

  • Land
  • 10 Acres
  • $9,800 per Acre

  1105 S Hill Rd, Jamaica, VT 05343

  Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

  Curtis Trousdale

  1105 S Hill Rd, Jamaica, VT 05343
• 

  

  /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
• 

  

  /21

  Est $221,000 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
• 

  

  /38

  $860,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
• 

  

  /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
• 

  

  /26

  Est $461,715 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
• 

  

  /36

  $210,000

  • Land
  • 30.1 Acres
  • $6,977 per Acre

  184 Schoolhouse Rd, Jamaica, VT 05343

  Jamaica, Vermont's hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

  Curtis Trousdale

  184 Schoolhouse Rd, Jamaica, VT 05343
• 

  

  /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 $462,714

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

  2194 Mowrey Rd, Jamaica, VT 05343
• 

  

  /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
• 

  

  /36

  $575,000

  • 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
• 

  

  /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 $535,498

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

  69 Chapin Ln, Jamaica, VT 05343
• 

  

  /26

  Not Listed For Sale

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

  42 Pine Ln, Jamaica, VT 05359

  42 Pine Ln, Jamaica, VT 05359
• 

  

  /19

  $65,000

  • 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
• 

  

  /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 $726,587

  Last Listing Agent Rachel Febbie EXP Realty

  544 Dalewood Rd, Jamaica, VT 05343
• 

  

  /40

  Est $1,508,282 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
• 

  

  /6

  $54,500 Under Contract

  • Land
  • 2.4 Acres
  • $22,708 per Acre

  0 Route 30 Unit 5048856, Jamaica, VT 05343

  Tucked along a quiet, town-maintained road in Jamaica, Vermont, this beautifully wooded parcel places you right in the heart of southern Vermont’s legendary ski country. Stratton, Magic, and Bromley Mountains are each only minutes away, giving you three distinct downhill experiences—plus miles of lift-served mountain-bike trails—at your fingertips. Yet winter fun is just the beginning: the West

  Joe Castaluccio Winhall Real Estate

  0 Route 30 Unit 5048856, Jamaica, VT 05343
• 

  

  /21

  $327,000 Sold Jan 22, 2025

  63 Reynolds Ln, Jamaica, VT 05343

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $297/SF
  • 35 Days On Market

  Current Estimated Value $348,017

  Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  63 Reynolds Ln, Jamaica, VT 05343
• 

  

  /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
• 

  

  /39

  $890,000

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

  4880 Pikes Falls Rd, Jamaica, VT 05343

  This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4880 Pikes Falls 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

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

  1247 Cole Pond Rd, 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
• 

  

  /56

  $899,000

  • 9 Beds
  • 9 Baths
  • 5,480 Sq Ft

  3732 Vermont 30, Jamaica, VT 05343

  Welcome to the quaint Vermont village of Jamaica! Get ready to let your imagination take over.This historic property boasts two dwellings and a guest cottage. Looking for a family compound to get away from it all?This is your haven! Plenty of room to have friends and family come and stay! So many options.The Main House features 4 ensuite bedrooms! The living room is a late 1700"s delight, with an

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  3732 Vermont 30, Jamaica, VT 05343
• 

  

  /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

Showing Results 41 - 80, Page 2 of 18