Luxury homes for sale & real estate in Bennington County, VT

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ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
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 inside to find a spacious, light filled interior with clean contemporary lines, warm natural materials, and an inviting open layout ideal for gathering with family and friends. Large windows bring the outdoors in, while generous living spaces provide plenty of room to relax after a day on the moun

$870,000

4 beds3.5 baths3,031 sq ft

7 Roundtree Rd, Winhall, VT 05340

Private acres • Inviting open layout • 1.37 acre lot

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
A picturesque, tree-lined driveway leads to this beautifully renovated Contemporary Farmhouse, set on 17+/- acres of open meadows with spectacular, sweeping mountain views. Blending classic Vermont charm with modern comfort, this exceptional property offers a peaceful country retreat just 30 minutes from Manchester. At the heart of the home is a brand-new cook’s kitchen with generous workspace and a welcoming center island, perfect for gathering with family and friends. The bright dining room flows into an intimate sitting area warmed by a wood stove. The spacious living room features soaring ceilings, exposed wood beams, and custom built-ins, creating a warm and inviting atmosphere.

$1,450,000

5 beds5 baths6,129 sq ft

1035 Holy Smoke Rd, Shaftsbury, VT 05262

Wood stove • Tree lined driveway • Stone fireplace

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Beautifully Renovated Dorset Home on 3.02 Acres Discover the perfect blend of traditional Vermont charm and modern style in this beautiful 4-bedroom, 4-bath home, set on 3.02 picturesque acres in desirable Dorset, Vermont. Thoughtfully renovated, this quality-built home offers a wonderful balance of spacious gathering areas and inviting spaces to relax and unwind. The heart of the home features an expansive, open living and dining area with soaring ceilings, flowing seamlessly into the kitchen to create an ideal setting for entertaining and everyday living. Upon entering the home one is greeted by a welcoming entry hall. A charming den tucked just off the main living space offers a cozy re

$2,250,000

4 beds3.5 baths4,831 sq ft

122 Blue Heron Ln, Dorset, VT 05251

Mudroom laundry area • 3.02 acres • Sunroom

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
This is your opportunity to own a beautifully renovated home in the heart of historic Manchester Village. Just a short walk to shops, restaurants, Burr and Burton Academy, the Southern Vermont Arts Center, and the Equinox Preserve, this home offers the perfect combination of village living, thoughtful design, and modern comfort. Inside, French oak floors, custom white oak built-ins, handcrafted railings, and a cozy Jøtul gas fireplace create a warm and inviting atmosphere. The kitchen features soapstone countertops, a Wolf range, and a Sub-Zero refrigerator. The sun-filled primary suite offers a walk-in closet with custom built-ins and a beautifully finished private bathroom with a d

$1,350,000

3 beds3.5 baths2,170 sq ft

326 West Rd, Manchester Center, VT 05254

Wolf range • French oak floors • Jøtul gas fireplace

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Set on 2.9 beautiful acres in the heart of Manchester Village, this well-maintained Cape-style home offers a wonderful blend of classic Vermont charm, comfortable living, and breathtaking mountain scenery. With five bedrooms, four baths, a heated in-ground pool, and magnificent views of Equinox Mountain, this special property is an inviting retreat in one of Southern Vermont’s most desirable locations. From nearly every room, take in the ever-changing beauty of majestic Equinox Mountain. Watch the seasons unfold, from lush summer greens and brilliant autumn foliage to snow-covered winter landscapes and the fresh promise of spring. Designed with convenient main-level living, the home f

$1,200,000

5 beds4 baths4,450 sq ft

310 Longview Dr, Manchester, VT 05254

In-ground pool • Spacious patio • 2.9 acre lot

Property at 2313 Barnumville Rd, Manchester Center, VT 05255, 5 beds, 5 baths

$1,200,000

5 beds5 baths5,092 sq ft

2313 Barnumville Rd, Manchester Center, VT 05255

Property at 60 W Ridge Rd, Winhall, VT 05340, 4 beds, 4 baths

$2,950,000

4 beds4 baths3,621 sq ft

60 W Ridge Rd, Winhall, VT 05340

Property at 284 Elm St Unit A&B, Manchester Center, VT 05255, 6 beds, 7 baths

$895,000

6 beds7 baths4,608 sq ft

284 Elm St Unit A&B, Manchester Center, VT 05255

Property at 165 High Meadow Rd, Winhall, VT 05340, 4 beds, 4.5 baths

$2,250,000

4 beds4.5 baths3,034 sq ft

165 High Meadow Rd, Winhall, VT 05340

Property at 2100 Monument Ave, Bennington, VT 05201, 4 beds, 3 baths

$975,000

4 beds3 baths3,326 sq ft

2100 Monument Ave, Bennington, VT 05201

Property at 300 Nims Rd, Dorset, VT 05251, 6 beds, 7.5 baths

$6,250,000

6 beds7.5 baths10,739 sq ft

300 Nims Rd, Dorset, VT 05251

Property at 1958 Mt. Anthony Rd, North Pownal, VT 05260, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,117 sq ft

1958 Mt. Anthony Rd, North Pownal, VT 05260

Property at 363 Alden Rd #9, Sunderland, VT 05250, 3 beds, 2.5 baths

$1,075,000

3 beds2.5 baths1,536 sq ft

363 Alden Rd #9, Sunderland, VT 05250

Property at 400 Spring Brook Rd, Arlington, VT 05250, 4 beds, 3.5 baths

$1,375,000

4 beds3.5 baths3,828 sq ft

400 Spring Brook Rd, Arlington, VT 05250

Property at 180 High Meadow Rd, Winhall, VT 05340, 5 beds, 4 baths

$1,500,000

5 beds4 baths4,173 sq ft

180 High Meadow Rd, Winhall, VT 05340

Property at 259 Beechnut Dr, Peru, VT 05152, 4 beds, 3 baths

$975,000

4 beds3 baths3,548 sq ft

259 Beechnut Dr, Peru, VT 05152

Property at 866 E Manchester Rd, Manchester Center, VT 05255, 5 beds, 4 baths

$1,375,000

5 beds4 baths4,491 sq ft

866 E Manchester Rd, Manchester Center, VT 05255

Property at 209 Jack Cross Rd, Shaftsbury, VT 05262, 4 beds, 3.5 baths

$1,990,000

4 beds3.5 baths3,844 sq ft

209 Jack Cross Rd, Shaftsbury, VT 05262

Property at 844 E Manchester Rd, Manchester Center, VT 05255, 4 beds, 4 baths

$1,075,000

4 beds4 baths3,982 sq ft

844 E Manchester Rd, Manchester Center, VT 05255

Property at 20 W Branch Rd, Winhall, VT 05340, 4 beds, 4 baths

$1,050,000

4 beds4 baths2,380 sq ft

20 W Branch Rd, Winhall, VT 05340

Property at 78 Bonnet St, Manchester Center, VT 05255, 4 beds, 4 baths

$975,000

4 beds4 baths5,164 sq ft

78 Bonnet St, Manchester Center, VT 05255

Property at 3269 Route 30, Dorset, VT 05251, 4 beds, 3 baths

$995,000

4 beds3 baths2,614 sq ft

3269 Route 30, Dorset, VT 05251

Property at 1474 Dorset West Rd, Dorset, VT 05251, 3 beds, 3 baths

$1,295,000

3 beds3 baths2,457 sq ft

1474 Dorset West Rd, Dorset, VT 05251

Property at 1996 N Pownal Rd, Pownal, VT 05260, 3 beds, 2.5 baths

$1,100,000

3 beds2.5 baths2,911 sq ft

1996 N Pownal Rd, Pownal, VT 05260

Property at 93 Elizabeth Ct, Sunderland, VT 05250, 5 beds, 4.5 baths

$1,815,000

5 beds4.5 baths5,588 sq ft

93 Elizabeth Ct, Sunderland, VT 05250

Property at 601 Riverbend Dr, Manchester Center, VT 05254, 4 beds, 3.5 baths

$1,450,000

4 beds3.5 baths3,551 sq ft

601 Riverbend Dr, Manchester Center, VT 05254

Property at 84 Frost Pond Rd, Dorset, VT 05251, 5 beds, 3 baths

$1,595,000

5 beds3 baths5,287 sq ft

84 Frost Pond Rd, Dorset, VT 05251

Property at 40 Kelleher Rd, Dorset, VT 05251, 3 beds, 3 baths

$949,000

3 beds3 baths1,823 sq ft

40 Kelleher Rd, Dorset, VT 05251

Property at 440 Marcia Ln, Dorset, VT 05251, 5 beds, 6.5 baths

$4,995,000

5 beds6.5 baths7,455 sq ft

440 Marcia Ln, Dorset, VT 05251

Property at 36 Beaver St, Winhall, VT 05340, 3 beds, 4 baths

$1,650,000

3 beds4 baths5,072 sq ft

36 Beaver St, Winhall, VT 05340

Property at 159 Winhall Hollow Rd, Winhall, VT 05340, 7 beds, 9.5 baths

$5,575,000

7 beds9.5 baths9,915 sq ft

159 Winhall Hollow Rd, Winhall, VT 05340

Property at 39 Eagle Rdg, Dorset, VT 05251, 5 beds, 4.5 baths

$1,375,000

5 beds4.5 baths4,376 sq ft

39 Eagle Rdg, Dorset, VT 05251

Property at 238 Seminary Ave, Manchester, VT 05254, 5 beds, 4 baths

$995,000

5 beds4 baths4,126 sq ft

238 Seminary Ave, Manchester, VT 05254

Property at 27 Mountain View Rd, Winhall, VT 05340, 6 beds, 6.5 baths

$1,895,000

6 beds6.5 baths5,896 sq ft

27 Mountain View Rd, Winhall, VT 05340

Property at 3542 North Rd, Sunderland, VT 05250, 3 beds, 2 baths

$989,000

3 beds2 baths1,680 sq ft

3542 North Rd, Sunderland, VT 05250

Property at 2529 Main St, Manchester Center, VT 05254, 5 beds, 2 baths

$925,000

5 beds2 baths3,522 sq ft

2529 Main St, Manchester Center, VT 05254

Property at 11 Founders Hill Rd, Winhall, VT 05340, 6 beds, 3.5 baths

$1,200,000

6 beds3.5 baths4,017 sq ft

11 Founders Hill Rd, Winhall, VT 05340

Property at 66 Somerset Rd, Searsburg, VT 05363, 4 beds, 3 baths

$989,900

4 beds3 baths5,697 sq ft

66 Somerset Rd, Searsburg, VT 05363

Property at 2236 River Rd, Manchester, VT 05255, 5 beds, 7 baths

$3,900,000

5 beds7 baths11,736 sq ft

2236 River Rd, Manchester, VT 05255

Property at 2334 Morse Hill Rd, Dorset, VT 05251, 2 beds, 3.5 baths

$2,850,000

2 beds3.5 baths5,731 sq ft

2334 Morse Hill Rd, Dorset, VT 05251

Property at 1944 Monument Ave, Bennington, VT 05201, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths4,120 sq ft

1944 Monument Ave, Bennington, VT 05201

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Luxury Homes for Sale in Bennington County

There are currently 85 luxury homes for sale in Bennington County at a median listing price of $544K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Bennington County stay on the market for 83 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 48 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 38 condos, 0 townhouses, and 12 multi-family units for sale in Bennington County last month. Find your dream home in Bennington County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Bennington County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Bennington County. If you're looking to sell your home in the Bennington County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Bennington County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Mon Oct 26 2026 on the search page

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