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

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NEW 12 HRS AGOVIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Escape to the mountains and enjoy everything Stratton, Vermont has to offer in this fabulous 4 bedroom, 4 bath contemporary home, ideally located on a private cul-de-sac in the heart of Stratton Resort. Designed for gathering with family and friends, the home features a spacious open floor plan with a cathedral-ceiling living room, wood-burning fireplace, open kitchen and dining area, and plenty of room to spread out. The main level features a primary en-suite bedroom. Upstairs, you’ll find a second en-suite bedroom, an additional bedroom with a nearby full bathroom, and a private loft perfect for reading, relaxing, or watching TV. The lower level offers a bunk room, full bathroom, an

$1,050,000

4 beds4 baths2,380 sq ft

20 W Branch Rd, Winhall, VT 05340

Open floor plan • Private cul-de-sac • 1.37 acre lot

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

OPEN SAT, 10AM TO 12PM

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Where Vermont Living Feels Effortless Dorset Home, Guest Cottage, Pond & Mountain Views Settle into the beauty of Dorset with a property that feels like a true Vermont retreat. This lovingly maintained offering pairs a welcoming main residence with a separate one-bedroom cottage, 4.5 acres of open land, a private pond, and beautiful views creating a rare opportunity to enjoy space, privacy, and flexibility in one memorable setting. The main home welcomes you with a light-filled sunroom, a wonderful place to relax and enjoy the surrounding scenery. The renovated eat in kitchen with a fireplace features beautiful, leathered granite countertops, stainless steel appliances while the spa

$949,000

3 beds3 baths1,823 sq ft

40 Kelleher Rd, Dorset, VT 05251

Light filled sunroom • Guest cottage • Private pond

OPEN THU, 12PM TO 2PMVIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Follow the historic "Wilbur" Half-Mile Stone Wall along River Road in Manchester, and just beyond the Wilburton Inn, you’ll discover the private entrance to Riverbend Drive. Tucked into one of Southern Vermont’s most beautiful settings, Riverbend is an exclusive community of exceptional homes on beautifully maintained 2 to 4 acre lots. 601 Riverbend Drive is a stunning 4BR/3.5BA Colonial on a private 3.05-acre lot with sweeping mountain views and a welcoming circular driveway. Designed by Ramsey Gourd and built by Keelan and Company, the home showcases exceptional craftsmanship, custom millwork, native maple floors, 9-foot ceilings and thoughtful details throughout. At

$1,450,000

4 beds3.5 baths3,551 sq ft

601 Riverbend Dr, Manchester Center, VT 05254

Exclusive community • Private entrance • Circular driveway

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Nestled in a peaceful five acre setting just minutes from the shopping, dining, and everyday conveniences of both Bennington and Manchester, this beautifully maintained home offers privacy, comfort, and accessibility. Thoughtfully updated, this home offers a timeless, inviting style designed to feel welcoming for years to come. The newly renovated high end kitchen is both beautiful and functional, while two spacious primary en-suites provide exceptional flexibility and privacy. The first floor primary suite wing is a true retreat, featuring a luxurious bathroom with marble tile, frameless glass shower, double vanity and walk in closet. Upstairs, the brand new second primary ensuite offers a

$940,000

4 beds4 baths3,974 sq ft

145 White Farm Ln, Shaftsbury, VT 05262

Five acre setting • Heat pump systems • 5 acre lot

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

$1,375,000

3 beds3 baths2,457 sq ft

1474 Dorset West Rd, Dorset, VT 05251

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

$995,000

5 beds2 baths3,522 sq ft

2529 Main St, Manchester, VT 05254

Property at 212 Taconic Rd, Manchester, VT 05254, 5 beds, 4 baths

$1,600,000

5 beds4 baths4,700 sq ft

212 Taconic Rd, Manchester, VT 05254

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 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 11 Founders Hill Rd, Winhall, VT 05155, 6 beds, 3.5 baths

$1,200,000

6 beds3.5 baths4,017 sq ft

11 Founders Hill Rd, Winhall, VT 05155

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 84 Overlook Rd, East Dorset, VT 05253, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths2,035 sq ft

84 Overlook Rd, East Dorset, VT 05253

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

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 181 Route 11, Bondville, VT 05340, 2 beds, 3.5 baths

$1,195,000

2 beds3.5 baths3,873 sq ft

181 Route 11, Bondville, VT 05340

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

$3,500,000

6 beds5.5 baths3,690 sq ft

123 Nichols Rd, Peru, VT 05152

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

$1,100,000

4 beds4 baths5,164 sq ft

78 Bonnet St, Manchester Center, VT 05255

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

$1,750,000

4 beds3.5 baths3,828 sq ft

400 Spring Brook Rd, Arlington, VT 05250

Property at 312 Beartown Rd, Manchester Center, VT 05255, 4 beds, 3.5 baths

$1,775,000

4 beds3.5 baths3,000 sq ft

312 Beartown Rd, Manchester Center, VT 05255

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

$1,125,000

4 beds3 baths2,614 sq ft

3269 Route 30, Dorset, VT 05251

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

$1,575,000

3 beds2.5 baths3,264 sq ft

777 McCooey Dr, Manchester, VT 05255

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 50 Grouse Ln, Dorset, VT 05251, 4 beds, 4.5 baths

$1,250,000

4 beds4.5 baths5,170 sq ft

50 Grouse Ln, Dorset, VT 05251

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

$1,200,000

3 beds2.5 baths2,911 sq ft

1996 N Pownal Rd, Pownal, VT 05260

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

$1,795,000

5 beds3 baths5,287 sq ft

84 Frost Pond Rd, Dorset, VT 05251

Property at 20 Blackberry Ln, Peru, VT 05152, 5 beds, 5 baths

$1,495,000

5 beds5 baths5,029 sq ft

20 Blackberry Ln, Peru, VT 05152

Property at 241 High Hill Rd, Manchester Center, VT 05255, 5 beds, 3.5 baths

$2,300,000

5 beds3.5 baths3,332 sq ft

241 High Hill Rd, Manchester Center, VT 05255

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

$1,475,000

5 beds4 baths4,491 sq ft

866 E Manchester Rd, Manchester Center, VT 05255

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 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 525 Andrea Dr, Stamford, VT 05352, 4 beds, 2.5 baths

$1,599,000

4 beds2.5 baths5,403 sq ft

525 Andrea Dr, Stamford, VT 05352

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 1613 West Rd, Manchester Center, VT 05255, 5 beds, 4.5 baths

$3,250,000

5 beds4.5 baths8,156 sq ft

1613 West Rd, 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 3373 Main St, Manchester, VT 05254, 4 beds, 5.5 baths

$895,000

4 beds5.5 baths4,502 sq ft

3373 Main St, Manchester, VT 05254

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 447 Rock Bottom Ln, Peru, VT 05255, 3 beds, 2 baths

$875,000

3 beds2 baths1,600 sq ft

447 Rock Bottom Ln, Peru, VT 05255

Property at 1268 Myers Rd, Shaftsbury, VT 05262, 4 beds, 3.5 baths

$1,495,000

4 beds3.5 baths4,023 sq ft

1268 Myers Rd, Shaftsbury, VT 05262

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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 $529K. 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 74 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 47 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 39 condos, 0 townhouses, and 17 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 Wed Sep 02 2026 on the search page

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