Homes in ZIP Code 05343

/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
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/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

/40
$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
/58
$975,000 Sold Nov 27, 2025

20 Jamie Ln, Winhall, VT 05340
- 5 Beds
- 3.5 Baths
- 3,500 Sq Ft
- Built 1987
Last Sold Summary
- $279/SF
- 38 Days On Market
Last Listing Agent David Powers 42 North LP

20 Jamie Ln, Winhall, VT 05340

/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

/38
$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
/34
$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

/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

/45
$1,195,000
- 4 Beds
- 3.5 Baths
- 4,200 Sq Ft
9 Lower Taylor Hill Rd, Winhall, VT 05340

Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

Timothy Mich Doddridge Stratton Real Estate

9 Lower Taylor Hill Rd, Winhall, VT 05340
/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

/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

/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
/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

/14
Not Listed For Sale
0 S Hill Rd, Jamaica, VT 05343

0 S Hill Rd, 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
/39
$615,000 Sold Mar 12, 2025

81 Pond View Rd Unit 81, Winhall, VT 05340
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
- Built 1998
Last Sold Summary
- 2% Below List Price
- $373/SF
- 32 Days On Market
Current Estimated Value $676,013

Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

81 Pond View Rd Unit 81, Winhall, VT 05340

/11
Est $131,561 Not Listed For Sale
12 Sugar Lot Ln, Jamaica, VT 05343

12 Sugar Lot Ln, 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
/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

/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

/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
/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

/34
Not Listed For Sale
- 6 Beds
- 3 Baths
- 2,400 Sq Ft
291 Pikes Falls Rd, Stratton, VT 05360

291 Pikes Falls Rd, Stratton, VT 05360

/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
/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

/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
$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
/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

/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

/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
/38
$779,000 Sold Oct 31, 2025

44 Hilltop Rd, Winhall, VT 05340
- 4 Beds
- 4 Baths
- 2,997 Sq Ft
- Built 1996
Last Sold Summary
- 1% Below List Price
- $260/SF
- 22 Days On Market
Last Listing Agent Christiane Carroccio TPW Real Estate

44 Hilltop Rd, Winhall, VT 05340

/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

/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
/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

/25
Est $295,322 Not Listed For Sale
- 4 Beds
84 Lower Taylor Hill Rd, Winhall, VT 05340

84 Lower Taylor Hill Rd, Winhall, VT 05340

/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
/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

/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

/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
/36
$725,000 Sold Jan 03, 2025

11 Todd Hill Rd, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 1973
Last Sold Summary
- 3% Below List Price
- $403/SF
- 30 Days On Market
Current Estimated Value $821,409

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

11 Todd Hill Rd, Winhall, VT 05340

Showing Results 41 - 80, Page 2 of 18

Vermont Windham County Jamaica 05343

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