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

129 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
Cheap 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
Cheap 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

NEW 30 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
TURN-KEY VERMONT MOUNTAIN RETREAT JUST MINUTES FROM BROMLEY & STRATTON! Beautifully renovated in 2021, this fully furnished 3-bedroom, 2-bath condominium offers the perfect combination of Vermont charm, modern comfort, and year-round recreation. Located just one minute from Bromley Mountain and approximately ten minutes from Stratton, this property is ideally situated for skiing, hiking, mountain biking, golf, shopping, and all that Southern Vermont has to offer. The spacious interior features an updated kitchen with granite countertops and stainless-steel appliances, comfortable living spaces, and a cozy wood stove perfect for relaxing after a day on the slopes. Large windows bring i

$399,000

3 beds2 baths1,225 sq ft

Large windows • Cozy wood stove • Updated kitchen

16B Bromley Knolls Rd Unit B, Winhall, VT 05340

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character. Inside, the versatility of this home truly shines. The main level offers a comfortable living room with striking open wood ceilings that naturally become the focal point of the space, creating a warm setting for relaxing and gathering with family and friends. The kitchen flows easily into the dining area, making everyday meals and entertaining feel effortless. A convenient first floor laundry r

$375,000

3 beds2 baths1,911 sq ft

New deck • Charming dutch door • 1.16 acre lot

21 Russett Dr, Bennington, VT 05201

Property at 390 Smith Dr, Readsboro, VT 05350, 2 beds, 2 baths

$349,000

2 beds2 baths1,808 sq ft

390 Smith Dr, Readsboro, VT 05350

Property at 2 W Road Park, Bennington, VT 05201, 3 beds, 1.5 baths

$49,900

3 beds1.5 baths924 sq ft

2 W Road Park, Bennington, VT 05201

Property at 928 Main Rd, Stamford, VT 05352, 4 beds, 2 baths

$449,000

4 beds2 baths3,096 sq ft

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 112 Aldrich Rd, Peru, VT 05152, 3 beds, 2 baths

$350,000

3 beds2 baths1,056 sq ft

112 Aldrich Rd, Peru, VT 05152

Property at 291 Spring Hill Rd, Bennington, VT 05201, 3 beds, 2 baths

$375,000

3 beds2 baths2,016 sq ft

291 Spring Hill Rd, Bennington, VT 05201

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 87 B Hill Rd, Pownal, VT 05261, 3 beds, 2.5 baths

$425,000

3 beds2.5 baths2,760 sq ft

87 B Hill Rd, Pownal, VT 05261

Property at 903 Gage St, Bennington, VT 05201, 3 beds, 2 baths

$232,500

3 beds2 baths1,582 sq ft

903 Gage St, Bennington, VT 05201

Property at 631 Oberdorf Ave, Readsboro, VT 05350, 3 beds, 2 baths

$169,000

3 beds2 baths1,248 sq ft

631 Oberdorf Ave, Readsboro, VT 05350

Property at 207 Sycamore Rd, Woodford, VT 05201, 4 beds, 1 bath

$150,000

4 beds1 bath1,536 sq ft

207 Sycamore Rd, Woodford, VT 05201

Property at 889 Overlea Rd, Bennington, VT 05201, 3 beds, 2 baths

$169,000

3 beds2 baths924 sq ft

889 Overlea Rd, Bennington, VT 05201

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 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 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 65 E Birch Rd #43, Stratton, VT 05155, 2 beds, 2 baths

$425,000

2 beds2 baths1,110 sq ft

65 E Birch Rd #43, Stratton, VT 05155

Property at 432 South St Unit A11, Bennington, VT 05201, 2 beds, 1.5 baths

$169,900

2 beds1.5 baths819 sq ft

432 South St Unit A11, Bennington, VT 05201

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 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 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 1806 Bosley Hill Rd, Readsboro, VT 05350, 3 beds, 2.5 baths

$279,000

3 beds2.5 baths1,568 sq ft

1806 Bosley Hill Rd, Readsboro, VT 05350

Property at 258 Harvest Hills Dr, North Bennington, VT 05257, 3 beds, 2 baths

$385,000

3 beds2 baths2,067 sq ft

258 Harvest Hills Dr, North Bennington, VT 05257

Property at 527 Jennings Brook Dr, Bennington, VT 05201, 2 beds, 2 baths

$379,000

2 beds2 baths1,190 sq ft

527 Jennings Brook Dr, Bennington, VT 05201

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 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 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 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 14 Bromley Knolls Rd, Winhall, VT 05340, 6 beds, 4 baths

$150,000

6 beds4 baths1,224 sq ft

14 Bromley Knolls Rd, Winhall, VT 05340

Property at 60 Tori Ln, Bennington, VT 05201, 2 beds, 1 bath

$142,900

2 beds1 bath784 sq ft

60 Tori Ln, Bennington, VT 05201

Property at 432 South St Unit C10, Bennington, VT 05201, 2 beds, 1.5 baths

$135,000

2 beds1.5 baths948 sq ft

432 South St Unit C10, Bennington, VT 05201

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Cheap Homes for Sale in Bennington County

There are currently 129 cheap 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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