Homes in ZIP Code 05343

/54
$639,900 Under Contract
- 3 Beds
- 3 Baths
- 2,700 Sq Ft
98 Gleason Farm Ln, Jamaica, VT 05343

Nestled within a peaceful pine grove on 11.5 private acres between Stratton Mountain Resort and Mount Snow, this renovated 3-bedroom, 3-bathroom residence offers the perfect blend of secluded Vermont beauty and modern design. The heart of the home is a dramatic great room featuring 20+ foot soaring ceilings, skylights, and expansive windows that flood the space with natural light. On chilly

Lauren Behm

Berkshire Hathaway HomeServices Stratton Home

(802) 988-7628

98 Gleason Farm Ln, Jamaica, VT 05343
/36
$28,000 per month
- 5 Beds
- 3 Baths
- 2,912 Sq Ft
- House for Rent
1138 River Rd, Jamaica, VT 05343

WINTER 2026-2027 SEASONAL RENTAL AVAILABLE - $28,000 Plus prepaid utilities - 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

Jennifer Hovey-Densmore Deerfield Valley Real Estate

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

/13
Not Listed For Sale

0 Pikes Falls Rd Unit 4993566, Stratton, VT 05360
0 Pikes Falls Rd Unit 4993566, Stratton, VT 05360

Last Sold Summary
- 111 Days On Market
Last Sold Price $150,000

Last Listing Agent Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

/60
$849,000
- 5 Beds
- 4.5 Baths
- 3,840 Sq Ft
42 Blackberry Ln, Jamaica, VT 05343

Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

MaryKate Grey Stratton Real Estate

42 Blackberry Ln, Jamaica, VT 05343
/14
$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
/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 $225,463

Last Listing Agent Mike England Michael England Real Estate

533 Pratt Bridge Rd, Jamaica, VT 05343

/32
Est $471,323 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
- 5% Above List Price
- $249/SF
- 40 Days On Market
Last Sold Price $449,000

Last Listing Agent Carrie Mathews Winhall Real Estate

/8
$275,000 Under Contract
- 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
/29
$30,000 per month
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
- Townhouse for Rent
90 Turkey Run Rd, Winhall, VT 05340

Intervale Rental. Available for the 26-27 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom serves the

Christiane Carroccio TPW Real Estate

90 Turkey Run Rd, Winhall, VT 05340
/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 $317,161

Last Listing Agent Jacki Murano Southern Vermont Realty Group

756 Turkey Mountain Rd, Jamaica, VT 05343

/48
Est $638,068 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
- 1% Below List Price
- $246/SF
- 4 Days On Market
Last Sold Price $645,000

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

/11
$495,000 Under Contract
- 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
/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

/35
Est $484,425 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
- 31% Above List Price
- $117/SF
- 7 Days On Market
Last Sold Price $371,195

Last Listing Agent Jacki Murano Southern Vermont Realty Group

/7
$195,000 Under Contract
- 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
/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 $442,848

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

132 Pratt Bridge Rd, Jamaica, VT 05343

/39
Est $495,267 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
- 32% Above List Price
- $122/SF
- 133 Days On Market
Last Sold Price $375,000

Last Listing Agent Britt Wohler

/15
$650,000 Under Contract
- 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
/27
$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

/32
Est $303,288 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
- 7% Below List Price
- $564/SF
- 80 Days On Market
Last Sold Price $325,000

Last Listing Agent Mike England Michael England Real Estate

/33
$1,399,999
- 6 Beds
- 4 Baths
- 3,800 Sq Ft
121 High Meadow Rd, Winhall, VT 05340

Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

Ralph Harvey Listwithfreedom.com

121 High Meadow Rd, Winhall, VT 05340
/4
$225,000 Sold Dec 19, 2025

00 Margeaux Ln, Stratton, VT 05155
- Land
- 1.99 Acres
- $113,065 per Acre
Last Sold Summary
- 189 Days On Market
Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

00 Margeaux Ln, Stratton, VT 05155

/18
Est $541,865 Not Listed For Sale

155 Pratt Bridge Rd, Jamaica, VT 05343
- 4 Beds
- 2.5 Baths
- 2,050 Sq Ft
- Built 1971
155 Pratt Bridge Rd, Jamaica, VT 05343

Last Sold Summary
- 6% Above List Price
- $249/SF
- 3 Days On Market
Last Sold Price $510,000

Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

/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
/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 $1,013,968

Last Listing Agent Britt Wohler

585 Pleasant Valley Rd, Jamaica, VT 05343

/40
Est $880,460 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% Below List Price
- $432/SF
- 7 Days On Market
Last Sold Price $950,000

Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

/38
$1,450,000
- 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
/2
$210,000 Sold Aug 29, 2025

0 Gold Medal Cir Unit 5027515, Stratton, VT 05155
- Land
- 2.1 Acres
- $100,000 per Acre
Last Sold Summary
- 16% Below List Price
- 190 Days On Market
Last Listing Agent Ross Powers TPW Real Estate

0 Gold Medal Cir Unit 5027515, Stratton, VT 05155

/33
Est $456,789 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
- 9% Below List Price
- $591/SF
- 6 Days On Market
Last Sold Price $501,000

Last Listing Agent Christopher Cummings Cummings & Co

/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
/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 $868,204

Last Listing Agent Helen Nault

460 Stratton Gate Rd, Jamaica, VT 05343

/32
Est $262,443 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
- 5% Below List Price
- $288/SF
- 3 Days On Market
Last Sold Price $275,000

Last Listing Agent Alison Cummings Cummings & Co

/35
$849,000 Under Contract
- 5 Beds
- 3 Baths
- 2,897 Sq Ft
24 Sugarbush Dr, Jamaica, VT 05343

Nestled in the highly sought-after Forest Farms neighborhood on Stratton Mountain, this beautifully updated 5-bedroom, 3-bath mountain retreat on Sugarbush Drive offers the perfect blend of comfort, style, and breathtaking natural beauty. The home features an open-concept living space designed to showcase the stunning surroundings, highlighted by a dramatic wall of glass that frames gorgeous

Carrie Mathews Winhall Real Estate

24 Sugarbush Dr, 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 $241,876

Last Listing Agent TG Glazer Winhall Real Estate

8365 Vt Route 30, Jamaica, VT 05343

/21
Est $389,287 Not Listed For Sale

60 River Rd, Jamaica, VT 05343
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
- Built 1977
60 River Rd, Jamaica, VT 05343

Last Sold Summary
- 66% Above List Price
- $111/SF
- 171 Days On Market
Last Sold Price $234,000

Last Listing Agent Jacki Murano Southern Vermont Realty Group

/44
$1,140,000
- 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 room for

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

70 Hunter Ln, Jamaica, VT 05343
/30
$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 $663,071

Last Listing Agent Jamie Wylie Stratton Real Estate

5600 Pikes Falls Rd, 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
- $239/SF
- 22 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Christiane Carroccio TPW Real Estate

/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 chilly

Robin Apps Four Seasons Sotheby's Int'l Realty

25 Benson Fuller Dr, Jamaica, VT 05343

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Vermont Windham County Jamaica 05343

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