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

85 homes

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ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous 2-story Deck with outdoor shower. This property is the ultimate vacation or year-round residence with no detail overlooked. A Fabulous, grand Main Living area with high ceilings features a wood-burning Fireplace in the Living room which is open to the large Dining room w/ sitting area, wet bar and slid

$1,495,000

5 beds5 baths5,029 sq ft

20 Blackberry Ln, Peru, VT 05152

Multi level property • Village clubhouse • Outdoor shower

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Located in the beautiful countryside of Manchester, Vermont, 1613 West Road offers a peaceful setting with the kind of charm and character that makes this property truly one of a kind. Surrounded by scenic mountain views, open land, and natural surroundings, the property strikes a perfect balance of privacy and convenience. Just a short drive from the heart of Manchester, you enjoy easy access to local dining, shops, and everyday amenities while still coming home to a quiet, private country setting. The home is spacious, warm, and welcoming. Filled with natural light, with large windows that highlight the surrounding landscape, as well as a wood-burning fireplace in the home. The layout is

$3,250,000

5 beds5.5 baths8,156 sq ft

1613 West Rd, Manchester Center, VT 05255

Large windows • Countryside setting • Natural surroundings

FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on both sides, bringing the outdoors in from nearly every room. The comfortable five-bedroom home features a main-level primary suite with a spacious walk-in closet, an inviting eat-in kitchen, a separate dining room, and a welcoming living room anchored by a fireplace. Mini-split systems provide effici

$2,300,000

5 beds3.5 baths3,332 sq ft

241 High Hill Rd, Manchester Center, VT 05255

Expansive windows • Walk-in closet • Mountain views

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
11 Round Tree Road, Winhall, VT 05340 A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and kitchenette. Wonderful staircase leading to the second floor. Great open living space and bedrooms throughout including a useful loft with bathroom. Quality metal roof sheds snow easily. A must-see property at Stratton.

$1,325,000

4 beds3.5 baths3,400 sq ft

11 Round Tree Rd, Winhall, VT 05340

Kitchenette • Stone façade • U-shaped driveway

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain v

$875,000

3 beds2 baths1,600 sq ft

447 Rock Bottom Ln, Peru, VT 05255

Private acres • National forest • Perennial gardens

Property at 777 McCooey Dr, Manchester, VT 05255, 3 beds, 2.5 baths

$1,390,000

3 beds2.5 baths3,264 sq ft

777 McCooey Dr, Manchester, VT 05255

Property at 123 Nichols Rd, Peru, VT 05152, 6 beds, 5.5 baths

$3,500,000

6 beds5.5 baths4,690 sq ft

123 Nichols Rd, Peru, VT 05152

Property at 1949 South Rd, Peru, VT 05152, 4 beds, 4 baths

$1,699,000

4 beds4 baths2,951 sq ft

1949 South Rd, Peru, VT 05152

Property at 3191 Route 30, Dorset, VT 05251, 5 beds, 5 baths

$1,039,000

5 beds5 baths3,031 sq ft

3191 Route 30, Dorset, VT 05251

Property at 2436 Mad Tom Rd, East Dorset, VT 05253, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths2,746 sq ft

2436 Mad Tom Rd, East Dorset, VT 05253

Property at 153 High Meadow Rd, Winhall, VT 05340, 4 beds, 3 baths

$1,130,000

4 beds3 baths3,357 sq ft

153 High Meadow Rd, Winhall, VT 05340

Property at 3039 Route 30, Dorset, VT 05251, 4 beds, 5.5 baths

$2,495,000

4 beds5.5 baths4,506 sq ft

3039 Route 30, Dorset, VT 05251

Property at 109 Winhall Hollow Rd, Winhall, VT 05340, 1 bath

$1,200,000

Studio1 bath950 sq ft

109 Winhall Hollow Rd, Winhall, VT 05340

Property at 134 Grapevine Ln, Pownal, VT 05261, 4 beds, 3.5 baths

$999,000

4 beds3.5 baths7,102 sq ft

134 Grapevine Ln, Pownal, VT 05261

Property at 551 W Fields Rd, Manchester, VT 05254, 6 beds, 8 baths

$5,995,000

6 beds8 baths10,993 sq ft

551 W Fields Rd, Manchester, VT 05254

Property at 276 Wilcox Hollow Rd, Sandgate, VT 05250, 3 beds, 2.5 baths

$1,575,000

3 beds2.5 baths3,368 sq ft

276 Wilcox Hollow Rd, Sandgate, VT 05250

Property at 543 Lower Hollow Rd, Dorset, VT 05251, 5 beds, 4.5 baths

$2,285,000

5 beds4.5 baths4,647 sq ft

543 Lower Hollow Rd, Dorset, VT 05251

Property at 1677 Barnumville Rd, Manchester Center, VT 05255, 4 beds, 2.5 baths

$1,275,000

4 beds2.5 baths4,084 sq ft

1677 Barnumville Rd, Manchester Center, VT 05255

Property at 527 Sleighbell Ln, Manchester Center, VT 05255, 4 beds, 5.5 baths

$1,450,000

4 beds5.5 baths4,530 sq ft

527 Sleighbell Ln, Manchester Center, VT 05255

Property at 59 Garden Loop Rd, Winhall, VT 05340, 4 beds, 4.5 baths

$2,500,000

4 beds4.5 baths3,762 sq ft

59 Garden Loop Rd, Winhall, VT 05340

Property at 1310 Dorset Hill Rd, East Dorset, VT 05253, 4 beds, 3 baths

$1,795,000

4 beds3 baths3,370 sq ft

1310 Dorset Hill Rd, East Dorset, VT 05253

Property at 609-617 Depot St, Manchester Center, VT 05255, 6 beds

$850,000

6 beds— baths2,060 sq ft

609-617 Depot St, Manchester Center, VT 05255

Property at 33 Stone Lodge Rd, Winhall, VT 05340, 4 beds, 3.5 baths

$2,399,000

4 beds3.5 baths4,536 sq ft

33 Stone Lodge Rd, Winhall, VT 05340

Property at 932 McNamara Rd, Dorset, VT 05251, 4 beds, 3 baths

$1,425,000

4 beds3 baths3,931 sq ft

932 McNamara Rd, Dorset, VT 05251

Property at 2167 Myers Rd, Shaftsbury, VT 05262, 3 beds, 3 baths

$1,795,000

3 beds3 baths5,228 sq ft

2167 Myers Rd, Shaftsbury, VT 05262

Property at 155 Brookman Rd, Pownal, VT 05261, 3 beds, 2 baths

$875,000

3 beds2 baths2,000 sq ft

155 Brookman Rd, Pownal, VT 05261

Property at 68 Green Peak Orch S, East Dorset, VT 05253, 5 beds, 5 baths

$2,950,000

5 beds5 baths6,900 sq ft

68 Green Peak Orch S, East Dorset, VT 05253

Property at 397 Fern Hl, Dorset, VT 05251, 5 beds, 4.5 baths

$1,600,000

5 beds4.5 baths4,243 sq ft

397 Fern Hl, Dorset, VT 05251

Property at 1182 1184 East Manchester Rd, Manchester Center, VT 05255, 9 beds, 8.5 baths

$4,995,000

9 beds8.5 baths7,900 sq ft

1182 1184 East Manchester Rd, Manchester Center, VT 05255

Property at 3888-3904 VT Route 7A, Arlington, VT 05250, 17 beds, 19 baths

$1,495,000

17 beds19 baths14,861 sq ft

3888-3904 VT Route 7A, Arlington, VT 05250

Property at 924 Henderson Rd, Williamstown, MA 01267, 4 beds, 2 baths

$850,000

4 beds2 baths3,507 sq ft

924 Henderson Rd, Williamstown, MA 01267

Property at 233 Squires Rd, Manchester Center, VT 05255, 2 beds, 1 bath

$1,200,000

2 beds1 bath1,056 sq ft

233 Squires Rd, Manchester Center, VT 05255

Property at 24 VT Route 11, Landgrove, VT 05148, 6 beds, 7 baths

$850,000

6 beds7 baths5,764 sq ft

24 VT Route 11, Landgrove, VT 05148

Property at 1594 VT Route 7A, Shaftsbury, VT 05262, 5 baths

$995,000

— beds5 baths4,724 sq ft

1594 VT Route 7A, Shaftsbury, VT 05262

Property at 288 Cedar Ln, Peru, VT 05152, 9 beds, 7 baths

$2,275,000

9 beds7 baths5,512 sq ft

288 Cedar Ln, Peru, VT 05152

Property at 525 Andrea Dr, Stamford, VT 05352, 5 beds, 3.5 baths

$1,599,000

5 beds3.5 baths5,403 sq ft

525 Andrea Dr, Stamford, VT 05352

Property at 437 Pratt Rd, Pownal, VT 05261, 4 beds, 1 bath

$975,000

Land69.30 acres (lot)

437 Pratt Rd, Pownal, VT 05261

Property at 00 Pine Tree Ln, Manchester Center, VT 05255

$865,000

Land18.30 acres (lot)

00 Pine Tree Ln, Manchester Center, VT 05255

Property at B Prospect St, Manchester Center, VT 05254

$1,425,000

Land38.00 acres (lot)

B Prospect St, Manchester Center, VT 05254

Property at 00 Montgomery Rd, Pownal, VT 05261

$1,295,000

Land52.61 acres (lot)

00 Montgomery Rd, Pownal, VT 05261

Property at 00 VT Route 11, Peru, VT 05152

$1,900,000

Land199.00 acres (lot)

00 VT Route 11, Peru, VT 05152

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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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