Homes with Basements for Sale in Bennington, VT

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ABOUT THIS HOME
Home with Basement for sale in Bennington, VT:
Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c. 1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized ki

$695,000

3 beds2.5 baths2,715 sq ft

58 Mount Anthony Rd, Bennington, VT 05201

Sprawling views • Formal dining room • Exposed beams

ABOUT THIS HOME
Home with Basement for sale in Bennington, VT:
Lovely ranch home with 2 bedrooms on a great level lot. Come see all the improvements including but not limited to, new flooring, new kitchen counter, new stove, new dishwasher, fresh paint throughout, new boiler, new oil tank, and new light fixtures. Come see what else this home has to offer.

$185,000

2 beds1 bath880 sq ft

2591 Chapel Rd, Bennington, VT 05201

New stove • New boiler • Fresh paint

ABOUT THIS HOME
Home with Basement for sale in Bennington, VT:
Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball courts), and the local bus station, this home combines in-town convenience with tranquil riverside living. Originally designed as a two-family house, it has been thoughtfully converted into a spacious single-family residence. The main level features a kitchen with built-ins and new flooring,

$249,900

4 beds2 baths1,702 sq ft

107 Coolidge Ave, Bennington, VT 05201

Rec center • New flooring • River frontage

ABOUT THIS HOME
Home with Basement for sale in Bennington, VT:
Tucked away from the road and surrounded by nature, this inviting duplex in Bennington offers the perfect blend of privacy, charm, and convenience. Whether you're looking for a smart investment or a place to call home while earning rental income, this property is a must-see! Each spacious unit features 3 comfortable bedrooms, an updated full bath, bright living and dining rooms, and a classic kitchen complete with a nostalgic walk-in pantry, electric range, and refrigerator. Laundry hookups are available for both units — one conveniently located in the pantry upstairs, and the other in the basement, which also provides generous storage space. Enjoy peace of mind with separate utilitie

$239,900

6 beds2 baths2,400 sq ft

110 S Branch St, Bennington, VT 05201

Separate utilities • Updated full bath • Classic kitchen

ABOUT THIS HOME
Home with Basement for sale in Bennington, VT:
Built in 1965, this one level home offers approximately 1302 finished square feet, two bedrooms and one full bath, fireplace, unfinished basement and deck. This home sits on an approximate 44867 sqft lot. This property is in uninhabitable condition and boarded up. UNSAFE TO ENTER, foundation cracked, fallen and caved in.

$37,100

2 beds1 bath1,302 sq ft

933 E Rd, Bennington, VT 05201

1.03 acre lot • Built 1965 • Listed 26 days

Property at 134 Monument Ave, Bennington, VT 05201, 3 beds, 2.5 baths

$695,000

3 beds2.5 baths2,868 sq ft

134 Monument Ave, Bennington, VT 05201

Property at 508 Barney Rd, Bennington, VT 05201, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths1,934 sq ft

508 Barney Rd, Bennington, VT 05201

Property at 848 Coleville Rd, Bennington, VT 05201, 4 beds, 3 baths

$450,000

4 beds3 baths2,030 sq ft

848 Coleville Rd, Bennington, VT 05201

Property at 89 Merson St, Bennington, VT 05201, 3 beds, 1.5 baths

$339,000

3 beds1.5 baths1,829 sq ft

89 Merson St, Bennington, VT 05201

Property at 317 Pleasant St, Bennington, VT 05201, 5 beds, 2 baths

$215,000

5 beds2 baths2,201 sq ft

317 Pleasant St, Bennington, VT 05201

Property at 115 Grandview St, Bennington, VT 05201, 5 beds, 2.5 baths

$475,000

5 beds2.5 baths2,104 sq ft

115 Grandview St, Bennington, VT 05201

Property at 989 Carpenter Hill Rd, Pownal, VT 05261, 3 beds, 1 bath

$365,000

3 beds1 bath1,660 sq ft

989 Carpenter Hill Rd, Pownal, VT 05261

Property at 215 Maple St, Bennington, VT 05201, 4 beds, 2 baths

$199,900

4 beds2 baths1,278 sq ft

215 Maple St, Bennington, VT 05201

Property at 624 Main St, Bennington, VT 05201, 2 beds, 1 bath

$269,000

2 beds1 bath2,500 sq ft

624 Main St, Bennington, VT 05201

Property at 704 Fox Hill Rd, Bennington, VT 05201, 3 beds, 2 baths

$575,000

3 beds2 baths1,535 sq ft

704 Fox Hill Rd, Bennington, VT 05201

Property at 109 Evergreen Dr, Bennington, VT 05201, 3 beds, 1 bath

$135,000

3 beds1 bath1,508 sq ft

109 Evergreen Dr, Bennington, VT 05201

Property at 682 Fox Hill Rd, Bennington, VT 05201, 3 beds, 2 baths

$625,000

3 beds2 baths1,416 sq ft

682 Fox Hill Rd, Bennington, VT 05201

Property at 755 Main St, Bennington, VT 05201, 3 beds, 1.5 baths

$145,000

3 beds1.5 baths1,485 sq ft

755 Main St, Bennington, VT 05201

Property at 209 Grove St, Bennington, VT 05201, 4 beds, 2 baths

$245,000

4 beds2 baths1,652 sq ft

209 Grove St, Bennington, VT 05201

Property at 1086 West Rd, Bennington, VT 05201, 9 beds, 6 baths

$1,950,000

9 beds6 baths6,956 sq ft

1086 West Rd, Bennington, VT 05201

Property at 226 North St, Bennington, VT 05201, 5 beds, 2 baths

$295,000

5 beds2 baths2,418 sq ft

226 North St, Bennington, VT 05201

Property at 130 Morgan St, Bennington, VT 05201, 3 beds, 2 baths

$199,000

3 beds2 baths1,600 sq ft

130 Morgan St, Bennington, VT 05201

Property at 203-205 Northside Dr, Bennington, VT 05201, 3 beds, 2.5 baths

$600,000

3 beds2.5 baths1,248 sq ft

203-205 Northside Dr, Bennington, VT 05201

Property at 137-139 Park St, Bennington, VT 05201, 5 beds, 3 baths

$249,000

5 beds3 baths2,184 sq ft

137-139 Park St, Bennington, VT 05201

Property at 218 Union St, Bennington, VT 05201, 5 beds, 2 baths

$297,500

5 beds2 baths2,294 sq ft

218 Union St, Bennington, VT 05201

Property at 14 Robinson Ave, Bennington, VT 05201, 3 beds, 1 bath

$219,500

3 beds1 bath1,254 sq ft

14 Robinson Ave, Bennington, VT 05201

Property at 303-305 Gage St, Bennington, VT 05201, 6 beds, 2 baths

$225,000

6 beds2 baths2,112 sq ft

303-305 Gage St, Bennington, VT 05201

Property at 245 Southshire Dr, Bennington, VT 05201, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths2,116 sq ft

245 Southshire Dr, Bennington, VT 05201

Property at 905 County St, Bennington, VT 05201, 4 beds, 2 baths

$169,900

4 beds2 baths2,643 sq ft

905 County St, Bennington, VT 05201

Property at 423-425 Main St, Bennington, VT 05201, 6 beds, 4 baths

$499,000

6 beds4 baths15,179 sq ft

423-425 Main St, Bennington, VT 05201

Property at 254 Union St, Bennington, VT 05201, 4 beds, 2 baths

$295,000

4 beds2 baths1,792 sq ft

254 Union St, Bennington, VT 05201

Property at 34 Southshire Dr, Bennington, VT 05201, 4 beds, 3.5 baths

$599,900

4 beds3.5 baths3,742 sq ft

34 Southshire Dr, Bennington, VT 05201

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Homes with Basements for Sale in Bennington

There are currently 32 homes with basements for sale in Bennington at a median listing price of $250K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Bennington stay on the market for 94 days. This map is refreshed with the newest listings in Bennington every 15 minutes.

In the past month, 16 homes have been sold in Bennington. In addition to houses in Bennington, there was also 1 condo, 1 townhouse, and 10 multi-family units for sale in Bennington last month. Find your dream home in Bennington 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 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Bennington. Our Bennington real estate stats and trends will give you more information about home buying and selling trends in Bennington. If you're looking to sell your home in the Bennington area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Bennington 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 2025 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 Oct 29 2025 on the search page

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