Homes with Basements for Sale in Bennington County, VT

178 homes

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FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Bennington County, VT:
Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities. The main residence features three bedrooms and one bathroom, with a practical layout flowing from the kitchen into the dining area and living room. A rear deck overlooks the wooded landscape, providing a peaceful spot to enjoy the surrounding natural setting. The detached guest house offers two bedrooms, one bathroom, and a kitchen

$190,000

5 beds2 baths2,200 sq ft

118 Foster Dr, Bennington, VT 05201

Over 5.5 acres • Expansive acreage • Rear deck

ABOUT THIS HOME
Home with Basement for sale in Bennington County, VT:
Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and varied unit sizes, this property is well-suited for continued use as an investment property or for an owner-occupant seeking the ability to adjust housing needs over time. No showing until the open house on Sunday 8/9 Noon - 2 pm

$349,000

8 beds4 baths3,637 sq ft

710 Main St, Bennington, VT 05201

Off street parking • Downtown bennington • Four unit property

ABOUT THIS HOME
Home with Basement for sale in Bennington County, VT:
This Contemporary Chalet sit on a quiet rural town maintained road. The property is a tasteful blend of woodland and grassy yard with gardens. You can enter from the garage , above ground , and walk up an interior staircase to the the next level. There is also a half bath and laundry room and plenty of room for side-by-sides, snowmobiles and seasonal gear! On the second level there is a very large living room with dining area that has access to the large front deck which is perfect for entertaining! There is also a kitchen, bedroom and full bath on this level as well as a door to the back brick garden area. The third level has two nice size bedrooms and a full bath!

$269,000

3 beds2.5 baths1,568 sq ft

1806 Bosley Hill Rd, Readsboro, VT 05350

Large front deck • 10 acre lot • Garage

FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Bennington County, VT:
Uncommonly Superb View -- A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the l

$1,200,000

3 beds2.5 baths2,911 sq ft

1996 N Pownal Rd, Pownal, VT 05260

Dramatic living room • 40 acre setting • Screened porch

FLOOR PLAN

$395,000

4 beds2 baths1,593 sq ft

1111 Old Depot Rd, Shaftsbury, VT 05262

4 acre lot • Garage • Built 1960

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 252 Tudor Rd, Sandgate, VT 05250, 2 beds, 1 bath

$250,000

2 beds1 bath1,504 sq ft

252 Tudor Rd, Sandgate, 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 40 Jameson Flts, Manchester Center, VT 05255, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths1,760 sq ft

40 Jameson Flts, Manchester Center, VT 05255

Property at 105 Hicks Ave, Bennington, VT 05201, 3 beds, 2 baths

$180,000

3 beds2 baths1,640 sq ft

105 Hicks Ave, Bennington, VT 05201

Property at 2734 Mad Tom Rd, East Dorset, VT 05253, 2 beds, 2 baths

$799,000

2 beds2 baths1,420 sq ft

2734 Mad Tom Rd, East Dorset, VT 05253

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 498 Town Line Rd, Bennington, VT 05201, 4 beds, 2.5 baths

$460,000

4 beds2.5 baths3,312 sq ft

498 Town Line Rd, Bennington, VT 05201

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 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 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 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 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 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 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 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 655 Squirrel Hollow Rd, East Dorset, VT 05253, 4 beds, 2.5 baths

$1,997,000

4 beds2.5 baths4,125 sq ft

655 Squirrel Hollow Rd, East Dorset, VT 05253

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 87 Grinka Farm Dr, Readsboro, VT 05350, 4 beds, 2.5 baths

$524,900

4 beds2.5 baths2,120 sq ft

87 Grinka Farm Dr, Readsboro, VT 05350

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 1253 Old West Rd, Arlington, VT 05250, 2 beds, 2 baths

$399,000

2 beds2 baths1,648 sq ft

1253 Old West Rd, Arlington, VT 05250

Property at 509 Thompson Pond Rd, Pownal, VT 05261, 2 beds, 2 baths

$299,000

2 beds2 baths1,542 sq ft

509 Thompson Pond Rd, Pownal, VT 05261

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 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 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 2572 Morse Hill Rd, Dorset, VT 05251, 4 beds, 3 baths

$825,000

4 beds3 baths4,112 sq ft

2572 Morse Hill Rd, Dorset, VT 05251

Property at 1278 Harrington Rd, North Bennington, VT 05201, 3 beds, 2 baths

$595,000

3 beds2 baths2,379 sq ft

1278 Harrington Rd, North Bennington, VT 05201

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 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 392 Powderhorn Rd, Manchester Center, VT 05255, 4 beds, 2.5 baths

$745,000

4 beds2.5 baths2,220 sq ft

392 Powderhorn Rd, Manchester Center, VT 05255

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 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 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 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 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 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

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Homes with Basements for Sale in Bennington County

There are currently 178 homes with basements for sale in Bennington County at a median listing price of $525K. 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 Tue Aug 25 2026 on the search page

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