South Londonderry, VT Homes

/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
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/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 winter 25-26 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

Christiane Carroccio TPW Real Estate

90 Turkey Run Rd, Winhall, VT 05340
/31
$895,000 Sold Dec 12, 2025

73 Cranberry Hill Rd, Winhall, VT 05340
- 4 Beds
- 4.5 Baths
- 2,658 Sq Ft
- Built 1984
Last Sold Summary
- 8% Below List Price
- $337/SF
- 222 Days On Market
Current Estimated Value $893,456

Last Listing Agent Carrie Mathews Winhall Real Estate

73 Cranberry Hill Rd, Winhall, VT 05340

/4
Est $394,009 Not Listed For Sale

283 Main St, South Londonderry, VT 05155
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
- Built 1825
283 Main St, South Londonderry, VT 05155

Last Sold Summary
- 14% Below List Price
- $177/SF
- 157 Days On Market
Last Sold Price $459,000

Last Listing Agent Daire Gibney Barrett and Valley Associates Inc.

/20
$995,000
- 3 Beds
- 3.5 Baths
- 1,800 Sq Ft
56 Shattarack Rd Unit D6, Stratton, VT 05360

Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

Kim Morgan-Wohler Wohler Realty Group

56 Shattarack Rd Unit D6, Stratton, VT 05360
/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

/38
Est $633,690 Not Listed For Sale

116 Deerwood Hill, South Londonderry, VT 05155
- 3 Beds
- 2.5 Baths
- 1,856 Sq Ft
- Built 1977
116 Deerwood Hill, South Londonderry, VT 05155

Last Sold Summary
- 44% Above List Price
- $237/SF
- 3 Days On Market
Last Sold Price $439,000

Last Listing Agent Jessica Citera Cummings & Co

/59
$1,300,000
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
51 Village Square, Stratton, VT 05360

Experience this Extraordinary Location in the heart of the Stratton Resort Village from this RENOVATED and EXPANDED Village Square 4 bedroom unit where you can walk to everything and be on the lifts in just a few minutes. Nothing compares to trailside living in the VILLAGE where convenience abounds and you won't touch your car until it's time to hit the highway. Ski home for lunch and you'll have

Kim Morgan-Wohler Wohler Realty Group

51 Village Square, Stratton, VT 05360
/15
$370,000 Sold Aug 04, 2025

761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360
- 1 Bed
- 1 Bath
- 580 Sq Ft
- Built 1999
Last Sold Summary
- 13% Below List Price
- $638/SF
- 120 Days On Market
Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

761 Stratton Mountain Access Rd Unit 231, Stratton, VT 05360

/23
Est $256,453 Not Listed For Sale

534 Sherwood Forest, Londonderry, VT 05148
- 2 Beds
- 1.5 Baths
- 960 Sq Ft
- Built 1979
534 Sherwood Forest, Londonderry, VT 05148

Last Sold Summary
- 7% Above List Price
- $250/SF
- 9 Days On Market
Last Sold Price $240,000

Last Listing Agent Jessica Citera Cummings & Co

/54
$2,050,000
- 4 Beds
- 4.5 Baths
- 2,486 Sq Ft
97 N Brookwood Rd, Stratton, VT 05360

Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

97 N Brookwood Rd, Stratton, VT 05360
/53
$1,525,000 Sold Sep 30, 2025

3333 Under the Mountain Rd, Londonderry, VT 05148
- 3 Beds
- 3.5 Baths
- 5,105 Sq Ft
- Built 2003
Last Sold Summary
- $299/SF
- 7 Days On Market
Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

3333 Under the Mountain Rd, Londonderry, VT 05148

/37
Est $491,375 Not Listed For Sale

76 Tallwood Cir, Londonderry, VT 05148
- 3 Beds
- 2 Baths
- 976 Sq Ft
- Built 1972
76 Tallwood Cir, Londonderry, VT 05148

Last Sold Summary
- 11% Below List Price
- $569/SF
- 4 Days On Market
Last Sold Price $555,000

Last Listing Agent Carrie Mathews Winhall Real Estate

/38
$1,095,000
- 4 Beds
- 3 Baths
- 3,252 Sq Ft
E1 Rock Ridge Rd, Winhall, VT 05155

Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

Christine Chovan

E1 Rock Ridge Rd, Winhall, VT 05155
/24
$1,025,000 Sold Oct 10, 2025

10 Middle Ridge Rd, Winhall, VT 05155
- 4 Beds
- 3.5 Baths
- 2,160 Sq Ft
- Built 1988
Last Sold Summary
- 6% Above List Price
- $475/SF
- 5 Days On Market
Last Listing Agent Christiane Carroccio TPW Real Estate

10 Middle Ridge Rd, Winhall, VT 05155

/29
Est $258,080 Not Listed For Sale

398 Tallwood Cir, Londonderry, VT 05148
- 2 Beds
- 1 Bath
- 696 Sq Ft
- Built 1970
398 Tallwood Cir, Londonderry, VT 05148

Last Sold Summary
- 14% Above List Price
- $326/SF
- 47 Days On Market
Last Sold Price $227,000

Last Listing Agent Christopher Cummings Cummings & Co

/30
$1,495,000 Pending
- 5 Beds
- 5 Baths
- 4,000 Sq Ft
147 High Meadow Rd, Winhall, VT 05340

Nestled in the heart of Vermont's Stratton Mountain Resort, this beautifully crafted 5 bedroom, 5 bath single-family home offers the perfect blend of rustic charm and modern comfort. Surrounded by towering pines and mountain views, the property offers 2 private acres and easy access to Stratton's World Class skiing and its championship 27 holes of golf. The open concept main living area features

Timothy Mich Doddridge Stratton Real Estate

147 High Meadow Rd, Winhall, VT 05340
/40
$595,000 Sold Nov 10, 2025

4A Ridge, Winhall, VT 05340
- 3 Beds
- 3 Baths
- 1,886 Sq Ft
- Built 1985
Last Sold Summary
- 3% Below List Price
- $315/SF
- 31 Days On Market
Last Listing Agent Christiane Carroccio TPW Real Estate

4A Ridge, Winhall, VT 05340

/40
Est $918,658 Not Listed For Sale

929 Middletown Rd, South Londonderry, VT 05155
- 5 Beds
- 3.5 Baths
- 3,354 Sq Ft
- Built 1850
929 Middletown Rd, South Londonderry, VT 05155

Last Sold Summary
- 11% Below List Price
- $309/SF
- 6 Days On Market
Last Sold Price $1,035,000

Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

/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
$860,000 Sold Jan 23, 2026

8 E Birch Rd Unit 103, Stratton, VT 05360
- 5 Beds
- 4 Baths
- 2,238 Sq Ft
- Built 1979
Last Sold Summary
- 7% Below List Price
- $384/SF
- 111 Days On Market
Last Listing Agent Cheyanne Pugliese

8 E Birch Rd Unit 103, Stratton, VT 05360

/21
Est $541,000 Not Listed For Sale

3378 Under the Mountain Rd, South Londonderry, VT 05155
- 5 Beds
- 4.5 Baths
- 4,482 Sq Ft
- Built 2007
3378 Under the Mountain Rd, South Londonderry, VT 05155

Last Sold Summary
- 3% Above List Price
- $117/SF
- 47 Days On Market
Last Sold Price $525,000

Last Listing Agent Linda Benoit Highland Realty

/60
$1,000,000 Under Contract
- 3 Beds
- 2 Baths
- 2,700 Sq Ft
580 Cross Rd, South Londonderry, VT 05155

Tucked away in a tranquil setting, this newly constructed 3-bedroom, 2-bath barn-style residence is a masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb the beauty of reclaimed exposed overhead beams, while expansive floor-to ceiling custom-crafted windows capture mountain vistas & bathe interiors in golden natural light. Large sliding doors open to the melody

Loana Sargent Wohler Realty Group

580 Cross Rd, South Londonderry, VT 05155
/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

/29
Est $781,499 Not Listed For Sale

109 Fieldstone Way, South Londonderry, VT 05155
- 4 Beds
- 2.5 Baths
- 2,156 Sq Ft
- Built 2003
109 Fieldstone Way, South Londonderry, VT 05155

Last Sold Summary
- 12% Above List Price
- $325/SF
- 10 Days On Market
Last Sold Price $700,000

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

/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
/16
$600,000 Sold Nov 07, 2025

761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360
- 2 Beds
- 2 Baths
- 916 Sq Ft
- Built 1999
Last Sold Summary
- 6% Below List Price
- $655/SF
- 198 Days On Market
Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360

/13
Est $159,218 Not Listed For Sale

1797 Thompsonburg Rd, South Londonderry, VT 05155
- 2 Beds
- 1 Bath
- 1,146 Sq Ft
- Built 1956
1797 Thompsonburg Rd, South Londonderry, VT 05155

Last Sold Summary
- 38% Above List Price
- $100/SF
- 8 Days On Market
Last Sold Price $115,000

Last Listing Agent Rachel Febbie EXP Realty

/31
$699,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

Timothy Mich Doddridge Stratton Real Estate

778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
/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 $568,428 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
- 11% 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
$1,150,000
- 5 Beds
- 3.5 Baths
- 4,017 Sq Ft
11 Founders Hill Rd, Winhall, VT 05360

Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

11 Founders Hill Rd, Winhall, VT 05360
/60
$2,100,000 Sold May 02, 2025

18 Rocky Dell Rd, Winhall, VT 05340
- 7 Beds
- 5.5 Baths
- 6,195 Sq Ft
- Built 2007
Last Sold Summary
- 14% Below List Price
- $339/SF
- 246 Days On Market
Current Estimated Value $2,686,041

Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

18 Rocky Dell Rd, Winhall, VT 05340

/40
Est $955,104 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
- 1% Above List Price
- $432/SF
- 7 Days On Market
Last Sold Price $950,000

Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

/36
$998,500
- 4 Beds
- 3.5 Baths
- 2,070 Sq Ft
32 Shattarack Rd Unit B5, Stratton, VT 05360

They say beauty is only skin deep, but not in the case of this meticulously renovated Slopeside residence, which offers a rare combination of quality, comfort, and location. With more than $500,000 invested, this home delivers far more than surface-level appeal — the kind of work that is not always seen but is most certainly felt. Every system and surface has been thoughtfully addressed. Unlike

Timothy Apps Four Seasons Sotheby's Int'l Realty

32 Shattarack Rd Unit B5, Stratton, VT 05360
/19
$426,000 Sold Jan 16, 2026

46-48 Lower Taylor Hill Rd, Winhall, VT 05340
- 2 Beds
- 2 Baths
- 1,798 Sq Ft
- Built 1963
Last Sold Summary
- 1% Above List Price
- $237/SF
- 1 Day On Market
Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

46-48 Lower Taylor Hill Rd, Winhall, VT 05340

/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

/41
$950,000
- 4 Beds
- 3.5 Baths
- 3,031 Sq Ft
7 Roundtree Rd, Winhall, VT 05340

Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

7 Roundtree Rd, Winhall, VT 05340
/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

/40
Est $572,473 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
- 20% Below List Price
- $931/SF
- 3 Days On Market
Last Sold Price $715,000

Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

Showing Results 41 - 80, Page 2 of 18

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