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

83 homes

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NEW 10 HRS AGO

$159,900

3 beds1 bath1,534 sq ft

1.1 acre lot • Built 1895

493 Main Rd, Stamford, VT 05352

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
200 feet of Walloomsac River front . There is a second kitchen for a possible in-law or AB & B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

$179,000

3 beds2 baths1,600 sq ft

Rv parking • Second kitchen • Replacement windows

130 Morgan St, Bennington, VT 05201

NEW 35 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous space for rocking chairs or outdoor seating, it's the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in the peaceful surroundings. Step inside and you'll immediately notice the beautiful hardwood floors and natural wood trim that carry throughout the main living s

$325,000

3 beds1 bath1,248 sq ft

Covered front porch • Enclosed back porch • Natural wood trim

51 Pageant St, Bennington, VT 05201

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom guest cottage. The stunning chef's kitchen is truly the centerpiece of the home, featuring high-end appliances, a dramatic quartz waterfall countertop, and a generous 10-foot island designed for both everyday living and entertaining. Just off the kitchen is a gorgeous screened-in porch, creating a wo

$1,695,000

3 beds2.5 baths4,120 sq ft

5.63 acres • 10-foot island • Historic home

1944 Monument Ave, Bennington, VT 05201

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
Welcome to the heart of Stamford, Vermont, where small-town charm meets endless opportunity. Set on 3.99 level acres with beautiful mountain views, this former historic general store has been transformed into a spacious 3,096 sq. ft. residence designed for today's flexible lifestyle. The main home offers 3 bedrooms, open living spaces, and room for everyone, while the separate second-floor apartment is perfect for extended family, Airbnb guests, a home business, or rental income. Spend summer days by the 28-foot inground pool, entertain under the picnic pavilion, relax on the deck, and enjoy parking for up to 8 vehicles. Just minutes from the Massachusetts border and downtown North Adams, y

$449,000

4 beds2 baths3,096 sq ft

Picnic pavilion • Inground pool • Mountain views

928 Main Rd, Stamford, VT 05352

Property at 1955 VT Route 100, Readsboro, VT 05350, 4 beds, 1.5 baths

$239,900

4 beds1.5 baths2,104 sq ft

1955 VT Route 100, Readsboro, VT 05350

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 1131 Route 30, Dorset, VT 05251, 4 beds, 2.5 baths

$595,000

4 beds2.5 baths2,399 sq ft

1131 Route 30, Dorset, VT 05251

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 1625 Barnumville Rd, Manchester Center, VT 05255, 3 beds, 2 baths

$550,000

3 beds2 baths2,009 sq ft

1625 Barnumville 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 232 Depot St, Bennington, VT 05201, 3 beds, 1 bath

$189,900

3 beds1 bath1,206 sq ft

232 Depot St, Bennington, VT 05201

Property at 6365 Vermont Rte 7a, Arlington, VT 05250, 4 beds, 3 baths

$598,000

4 beds3 baths— sq ft

6365 Vermont Rte 7a, Arlington, VT 05250

Property at 7066 Main St, Readsboro, VT 05350, 3 beds, 2 baths

$209,000

3 beds2 baths1,718 sq ft

7066 Main St, Readsboro, VT 05350

Property at 710 Main St, Bennington, VT 05201, 8 beds, 4 baths

$349,000

8 beds4 baths3,637 sq ft

710 Main St, Bennington, VT 05201

Property at 1649 E Manchester Rd, Manchester Center, VT 05255, 5 beds, 2 baths

$579,900

5 beds2 baths2,050 sq ft

1649 E Manchester Rd, Manchester Center, VT 05255

Property at 118 Foster Dr, Bennington, VT 05201, 5 beds, 2 baths

$210,000

5 beds2 baths2,200 sq ft

118 Foster Dr, Bennington, VT 05201

Property at 81 Fern Hl, Dorset, VT 05251, 2 beds, 2.5 baths

$1,200,000

2 beds2.5 baths1,950 sq ft

81 Fern Hl, Dorset, VT 05251

Property at 110 Short St, Bennington, VT 05201, 8 beds, 4 baths

$350,000

8 beds4 baths2,586 sq ft

110 Short St, Bennington, VT 05201

Property at 107 Jefferson Ave, Bennington, VT 05201, 3 beds, 2 baths

$209,900

3 beds2 baths1,608 sq ft

107 Jefferson Ave, Bennington, VT 05201

Property at 253 Perkins Rd, Rupert, VT 05776, 4 beds, 2 baths

$430,000

4 beds2 baths2,768 sq ft

253 Perkins Rd, Rupert, VT 05776

Property at 712 VT Route 30, Dorset, VT 05251, 2 beds, 1 bath

$359,000

2 beds1 bath1,686 sq ft

712 VT Route 30, 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 262 Union St, Bennington, VT 05201, 3 beds, 1.5 baths

$299,000

3 beds1.5 baths1,411 sq ft

262 Union St, Bennington, VT 05201

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 302 US RTE 7, Pownal, VT 05261, 2 beds, 1 bath

$169,900

2 beds1 bath848 sq ft

302 US RTE 7, Pownal, VT 05261

Property at 569 Buck Hill Rd, Arlington, VT 05250, 5 beds, 2 baths

$250,000

5 beds2 baths2,952 sq ft

569 Buck Hill Rd, Arlington, VT 05250

Property at 96 Twitchell Hill Rd, Shaftsbury, VT 05262, 4 beds, 2.5 baths

$439,000

4 beds2.5 baths1,868 sq ft

96 Twitchell Hill Rd, Shaftsbury, VT 05262

Property at 109 County St, Bennington, VT 05201, 4 beds, 2 baths

$264,900

4 beds2 baths1,146 sq ft

109 County St, Bennington, VT 05201

Property at 924 VT Route 7A, Shaftsbury, VT 05262, 2 beds, 1 bath

$199,000

2 beds1 bath924 sq ft

924 VT Route 7A, Shaftsbury, VT 05262

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 348 Center St, Pownal, VT 05261, 2 beds, 1 bath

$198,900

2 beds1 bath1,332 sq ft

348 Center St, Pownal, VT 05261

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 305 Weeks St, Bennington, VT 05201, 3 beds, 1.5 baths

$205,000

3 beds1.5 baths1,632 sq ft

305 Weeks St, Bennington, VT 05201

Property at 298 Mad Tom Rd, East Dorset, VT 05251, 3 beds, 2 baths

$449,000

3 beds2 baths1,382 sq ft

298 Mad Tom Rd, East Dorset, VT 05251

Property at 127 Dewey St, Bennington, VT 05201, 5 beds, 2 baths

$150,000

5 beds2 baths1,575 sq ft

127 Dewey St, Bennington, VT 05201

Property at 107 Lyons St, Bennington, VT 05201, 4 beds, 2 baths

$80,000

4 beds2 baths1,465 sq ft

107 Lyons St, Bennington, VT 05201

Property at 432 South St Unit D2, Bennington, VT 05201, 3 beds, 2.5 baths

$179,000

3 beds2.5 baths1,485 sq ft

432 South St Unit D2, Bennington, VT 05201

Property at 1000 Investors Ln, Manchester, VT 05255

$4,177,625

— beds— baths33,801 sq ft

1000 Investors Ln, Manchester, VT 05255

Property at 938 VT Route 7A, Shaftsbury, VT 05262, 8 beds, 4 baths

$457,000

8 beds4 baths3,648 sq ft

938 VT Route 7A, Shaftsbury, VT 05262

Property at 8 West St, North Bennington, VT 05257, 3 beds, 1.5 baths

$265,000

3 beds1.5 baths1,408 sq ft

8 West St, North Bennington, VT 05257

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Vintage Homes for Sale in Bennington County

There are currently 83 vintage homes for sale in Bennington County at a median listing price of $527K. 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 Aug 19 2026 on the search page

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