Jamaica, VT Homes

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  /24

  $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
• 

  

  

  /34

  Est $329,289

  Not Listed For Sale

  6217 Vt Route 30, Jamaica, VT 05343

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

  6217 Vt Route 30, Jamaica, VT 05343

  Last Sold Summary

  • 100 Days On Market

  Last Listing Agent Trent Stephens Wohler Realty Group
• 

  

  

  /19

  $63,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  2022 Route 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 Route 30, Jamaica, VT 05343
• 

  

  

  /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 $417,091

  Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

  3458 Vt Route 30, Jamaica, VT 05343
• 

  

  

  /34

  Not Listed For Sale

  498 Goodaleville Rd, South Londonderry, VT 05155

  • 8 Beds
  • 6 Baths
  • 4,600 Sq Ft
  • Built 1860

  498 Goodaleville Rd, South Londonderry, VT 05155

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Christiane Carroccio TPW Real Estate
• 

  

  /27

  $1,450,000

  • Land
  • 201.4 Acres
  • $7,200 per Acre

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360

  Own this large tract of land, over 200 acres that abuts over 1100 additional acres of Green Mountain National Forest. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Currently only 18 of the 200 acres is gravel pit and being reclaimed and closed out on this property. See the Vermont Land Use Permit 2W1316 online for further

  Chris Lowe Lowe's Real Estate, LLC

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360
• 

  

  /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
• 

  

  /40

  Est $577,618

  Not Listed For Sale

  886 Dalewood Rd, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 768 Sq Ft
  • Built 1965

  886 Dalewood Rd, Jamaica, VT 05343

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home
• 

  

  /60

  $8,200,000

  • 6 Beds
  • 10 Baths
  • 10,763 Sq Ft

  557 Trager Rd, Jamaica, VT 05343

  Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

  Kim Morgan-Wohler Wohler Realty Group

  557 Trager Rd, Jamaica, VT 05343
• 

  

  /29

  $249,000

  Sold Jun 24, 2026

  4106 Vt Route 30, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft
  • Built 1840

  Last Sold Summary

  • 27% Below List Price
  • $107/SF
  • 172 Days On Market

  Current Estimated Value $256,240

  Last Listing Agent Carrie Mathews Winhall Real Estate

  4106 Vt Route 30, Jamaica, VT 05343
• 

  

  /26

  Est $322,878

  Not Listed For Sale

  80 Henderson Rd, Jamaica, VT 05343

  • 2 Beds
  • 1.5 Baths
  • 1,122 Sq Ft
  • Built 1900

  80 Henderson Rd, Jamaica, VT 05343

  Last Sold Summary

  • 165 Days On Market

  Last Listing Agent Rachel Febbie EXP Realty
• 

  

  /53

  $460,000

  $65K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
• 

  

  /43

  $102,750

  Sold Aug 05, 2026

  1940 Vermont 30, Jamaica, VT 05343

  • 2 Beds
  • 1.5 Baths
  • 1,040 Sq Ft
  • Built 1968

  Last Sold Summary

  • 18% Below List Price
  • $99/SF
  • 39 Days On Market

  Last Listing Agent Mike England Michael England Real Estate

  1940 Vermont 30, Jamaica, VT 05343
• 

  

  /39

  Est $411,502

  Not Listed For Sale

  559 Pratt Bridge Rd, Jamaica, VT 05343

  • 4 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1978

  559 Pratt Bridge Rd, Jamaica, VT 05343

  Last Sold Summary

  • 181 Days On Market

  Last Listing Agent Joe Castaluccio Winhall Real Estate
• 

  /2

  $195,000

  Under Contract

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  1036 Dalewood 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 residents 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 town's registered voters, the Select Board cannot just sell the property.

  Carrie Mathews Winhall Real Estate

  1036 Dalewood Rd, Jamaica, VT 05343
• 

  

  /35

  $870,000

  Sold May 13, 2026

  24 Sugarbush Dr, Jamaica, VT 05343

  • 5 Beds
  • 3 Baths
  • 2,897 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $300/SF
  • 8 Days On Market

  Last Listing Agent Carrie Mathews Winhall Real Estate

  24 Sugarbush Dr, Jamaica, VT 05343
• 

  

  /40

  Est $535,162

  Not Listed For Sale

  482 Pratt Bridge Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft
  • Built 1988

  482 Pratt Bridge Rd, Jamaica, VT 05343

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Chad Lackey Deerfield Valley Real Estate
• 

  

  /36

  $650,000

  Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,678 Sq Ft

  177 Alwin Ln, Jamaica, VT 05343

  Nestled in a peaceful and private mountain setting, this beautifully maintained home offers a seamless blend of comfort, functionality, and timeless Vermont charm. Thoughtfully updated and designed for easy living.The main level features a spacious primary suite with custom built-in cabinetry, a convenient mudroom, and an updated kitchen highlighted by Vermont Verde marble countertops and

  Helen Nault

  177 Alwin Ln, Jamaica, VT 05343
• 

  

  /22

  $175,000

  Sold Jun 25, 2026

  116 Buck Hill, Jamaica, VT 05343

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Above List Price
  • $167/SF
  • 3 Days On Market

  Current Estimated Value $168,320

  Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

  116 Buck Hill, Jamaica, VT 05343
• 

  

  /31

  Est $599,420

  Not Listed For Sale

  81 Edie Ln, Jamaica, VT 05343

  • 3 Beds
  • 3 Baths
  • 2,593 Sq Ft
  • Built 1987

  81 Edie Ln, Jamaica, VT 05343

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Trent Stephens Wohler Realty Group
• 

  

  /15

  $475,000

  $55K PRICE DROP

  • Land
  • 30 Acres
  • $15,833 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
• 

  

  /17

  $215,000

  Sold Nov 21, 2025

  5997 Vt Route 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

  Current Estimated Value $302,092

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

  5997 Vt Route 30, Jamaica, VT 05343
• 

  

  /30

  Est $605,690

  Not Listed For Sale

  5600 Pikes Falls Rd, Jamaica, VT 05343

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

  5600 Pikes Falls Rd, Jamaica, VT 05343

  Last Sold Summary

  • 170 Days On Market

  Last Listing Agent Jamie Wylie Stratton Real Estate
• 

  

  /47

  $1,140,000

  $60K PRICE DROP

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

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community .Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation.This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, 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

  Current Estimated Value $408,962

  Last Listing Agent Carrie Mathews Winhall Real Estate

  2779 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  /50

  Est $496,156

  Not Listed For Sale

  2194 Mowrey Rd, Jamaica, VT 05343

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

  2194 Mowrey Rd, Jamaica, VT 05343

  Last Sold Summary

  • 47 Days On Market

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

  

  /21

  $175,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft

  1372 Vtrt 100 S, Jamaica, VT 05343

  This chalet, situated conveniently by the river, is ideally located midway between the renowned Stratton and Mount Snow Resorts, making it a perfect retreat for skiing, hiking, and golfing enthusiasts. Just a brief 20-minute drive from both resorts, this three-bedroom, two-bath property presents an excellent opportunity for those looking to invest in a home that requires some updating and

  Mike England Michael England Real Estate

  1372 Vtrt 100 S, Jamaica, VT 05343
• 

  

  /36

  $555,000

  Sold Feb 26, 2026

  64 Gleason Farm Ln, Jamaica, VT 05343

  • 3 Beds
  • 2.5 Baths
  • 2,033 Sq Ft
  • Built 2005

  Last Sold Summary

  • 12% Below List Price
  • $273/SF
  • 196 Days On Market

  Current Estimated Value $554,896

  Last Listing Agent Carrie Mathews Winhall Real Estate

  64 Gleason Farm Ln, Jamaica, VT 05343
• 

  

  /25

  Est $758,855

  Not Listed For Sale

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  • 5 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Built 1968

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Helen Nault
• 

  

  /22

  $86,000

  • Land
  • 6.2 Acres
  • $13,871 per Acre

  1297 River Rd, Jamaica, VT 05343

  Unique! Do you love to camp? swim? fish?.....this may be it for you....Over2000 feet of West River frontage with electric on site and just offpavement and at the intersection of 2 major access road to skiing andrecreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping

  Christine Lewis Brattleboro Area Realty

  1297 River Rd, Jamaica, VT 05343
• 

  

  /35

  $530,000

  Sold Apr 10, 2026

  4138 W Hill Rd S, Jamaica, VT 05343

  • 3 Beds
  • 3 Baths
  • 2,704 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $196/SF
  • 16 Days On Market

  Current Estimated Value $542,246

  Last Listing Agent Patricia Fitzpatrick Skihome Realty

  4138 W Hill Rd S, Jamaica, VT 05343
• 

  

  /39

  Est $656,333

  Not Listed For Sale

  39 Depot St, Jamaica, VT 05343

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft
  • Built 1860

  39 Depot St, Jamaica, VT 05343

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country
• 

  

  /47

  $1,450,000

  • 5 Beds
  • 4 Baths
  • 2,974 Sq Ft

  494-498 Goodaleville Rd, Jamaica, VT 05343

  10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit

  Cheyanne Pugliese

  494-498 Goodaleville Rd, Jamaica, VT 05343
• 

  

  /33

  $308,500

  Sold Jun 25, 2026

  1829 W Jamaica Rd, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft
  • Built 1890

  Last Sold Summary

  • 3% Below List Price
  • $235/SF
  • 27 Days On Market

  Current Estimated Value $315,056

  Last Listing Agent Alison Cummings Cummings & Co

  1829 W Jamaica Rd, Jamaica, VT 05343
• 

  

  /11

  Est $120,869

  Not Listed For Sale

  12 Sugar Lot Ln, Jamaica, VT 05343

  12 Sugar Lot Ln, Jamaica, VT 05343

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Mike England Michael England Real Estate
• 

  

  /11

  $120,000

  • Land
  • 10.2 Acres
  • $11,765 per Acre

  0 S Hill Rd, Jamaica, VT 05343

  The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home.Parcel I is a 10-acre building site located on

  Thom Milke Fountains Land Inc.

  0 S Hill Rd, Jamaica, VT 05343
• 

  

  /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
• 

  

  /37

  Est $477,557

  Not Listed For Sale

  400 Edie Ln, Jamaica, VT 05343

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1987

  400 Edie Ln, Jamaica, VT 05343

  Last Sold Summary

  • 315 Days On Market

  Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty
• 

  

  /60

  $499,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  1905 Turkey Mountain Rd, Jamaica, VT 05343

  Welcome to Cloister Falls, a truly special offering in the Green Mountains! Tucked among extensive grounds with mature gardens, a pond, and thoughtfully landscaped outdoor spaces, this 3+ bed plus den and office, 3 bath log home offers a setting that feels connected to the surrounding Vermont landscape. The property's signature feature is its swimming hole and waterfall , a natural gathering

  Jacki Murano Southern Vermont Realty Group

  1905 Turkey Mountain Rd, Jamaica, VT 05343
• 

  

  /24

  $178,000

  Sold May 29, 2026

  2053 Pikes Falls Rd, Jamaica, VT 05343

  • 1 Bed
  • 1 Bath
  • 265 Sq Ft
  • Built 2022

  Last Sold Summary

  • 21% Below List Price
  • $672/SF
  • 143 Days On Market

  Current Estimated Value $178,991

  Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  2053 Pikes Falls Rd, Jamaica, VT 05343

Showing Results 41 - 80, Page 2 of 18