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

60 homes

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NEW 3 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
This 4 unit multi family property located in Manchester's Depot district has been owned and managed by the same partnership group for over 30 years. The property is fully occupied with good tenants and is in excellent condition. There are two apartments on the first floor and two apartments on the second floor. There is ample of off street parking behind the building. There is coin operated laundry in the basement for additional revenue. There is a central heating system but each unit has its own electric meter, so heat is included in the rent but tenants pay their own electric. The in town location provides tenants with easy access to all the amenities that Manchester has to offer. The lis

$640,000

5 beds4 baths3,732 sq ft

105 Elm St, Manchester Center, VT 05255

Off street parking • Fully occupied • Excellent condition

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
Nestled on more than two acres of beautifully maintained countryside and mature forest, this renovated 1892 farmhouse blends New England charm with peaceful seclusion and easy access to local attractions. Just 15 minutes from Mass MoCA, 25 minutes from Mount Snow, and close to hiking and ATV trails, it’s perfect for outdoor enthusiasts. Inside, you’ll find a warm and thoughtfully updated home with three bedrooms and two full bathrooms. The eat-in kitchen combines rustic character and modern convenience, while the living spaces feature two original brick chimney stacks, one with a wood stove that can heat the first floor, and the other venting a cozy fireplace. A detached two-car

$415,000

3 beds2 baths1,816 sq ft

281 Old County Ln, Readsboro, VT 05350

Renovated farmhouse • Wood stove • Eat-in kitchen

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday conveniences. Set amid natural beauty, the home welcomes cozy living spaces, and a warm, comfortable atmosphere that makes it easy to feel at home. The proximity to Bennington College adds to the area’s vibrant, creative energy and makes this an ideal location for year-round living, a weekend

$245,000

2 beds2 baths911 sq ft

726 Rice Ln, Bennington, VT 05201

Cape-style home • Natural beauty • 1.1 acre lot

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly larger, brighter, and more versatile. Fresh paint, flooring, LED lighting, and a convenient half bath make it easy to imagine anything from a charming shop to a café, office suite, or creative workspace. The basement offers abundant storage with built-in shelving. Second floor features a beautifull

$295,000

1 bed1.5 baths1,680 sq ft

318 North St, Bennington, VT 05201

Fresh paint • Led lighting • Mixed-use property

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main building is configured with multiple residential-style suites, many with fireplaces, plus generous common areas suited for multifamily conversion, extended-stay residential use, or other permitted residential layouts. A separate on-site restaurant space is currently leased, providing additional income tie

$975,000

— beds— baths8,888 sq ft

124 Elm St, Bennington, VT 05201

Income production • Zoning approvals • Well maintained

Property at 17 Henry Hl, Stamford, VT 05352, 2 beds, 1 bath

$219,000

2 beds1 bath1,872 sq ft

17 Henry Hl, Stamford, VT 05352

Property at 2677 Rte 30 Rd, Dorset, VT 05251, 6 beds, 5 baths

$825,000

6 beds5 baths5,689 sq ft

2677 Rte 30 Rd, Dorset, VT 05251

Property at 196 Granger Hollow Rd, North Bennington, VT 05257, 3 beds, 1 bath

$310,000

3 beds1 bath1,392 sq ft

196 Granger Hollow Rd, North Bennington, VT 05257

Property at 4697 Main Rd, Stamford, VT 05352, 4 beds, 2 baths

$148,900

4 beds2 baths1,596 sq ft

4697 Main Rd, Stamford, VT 05352

Property at 126 Simeon Dean Rd, Shaftsbury, VT 05262, 4 beds, 3 baths

$579,900

4 beds3 baths2,529 sq ft

126 Simeon Dean Rd, Shaftsbury, VT 05262

Property at 940 Gage St, Bennington, VT 05201, 3 beds, 1.5 baths

$300,000

3 beds1.5 baths1,570 sq ft

940 Gage St, Bennington, VT 05201

Property at 490 Barnumville Rd, Manchester Center, VT 05255, 3 beds, 3 baths

$725,000

3 beds3 baths2,274 sq ft

490 Barnumville Rd, Manchester Center, VT 05255

Property at 207 Silver St, Bennington, VT 05201, 4 beds, 2 baths

$299,000

4 beds2 baths2,000 sq ft

207 Silver St, Bennington, VT 05201

Property at 21 County Rd, Pownal, VT 05261, 4 beds, 2 baths

$450,000

4 beds2 baths2,884 sq ft

21 County Rd, Pownal, VT 05261

Property at 58 Mount Anthony Rd, Bennington, VT 05201, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths2,715 sq ft

58 Mount Anthony Rd, Bennington, VT 05201

Property at 107 Coolidge Ave, Bennington, VT 05201, 4 beds, 2 baths

$249,900

4 beds2 baths1,702 sq ft

107 Coolidge Ave, Bennington, VT 05201

Property at 144 Taconic Ave, Manchester, VT 05254, 6 beds, 5.5 baths

$1,895,000

6 beds5.5 baths5,178 sq ft

144 Taconic Ave, Manchester, VT 05254

Property at 5406 5408 Main St, Manchester Center, VT 05255, 5 beds, 3.5 baths

$629,000

5 beds3.5 baths3,271 sq ft

5406 5408 Main St, Manchester Center, VT 05255

Property at 103 Norton St, Bennington, VT 05201, 4 beds, 2 baths

$339,000

4 beds2 baths1,728 sq ft

103 Norton St, Bennington, VT 05201

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

$189,900

4 beds2 baths1,278 sq ft

215 Maple St, Bennington, VT 05201

Property at 126 Washington Ave, Bennington, VT 05201, 6 beds, 3 baths

$415,000

6 beds3 baths5,208 sq ft

126 Washington Ave, Bennington, VT 05201

Property at 1594 Vermont Route 7A, Shaftsbury, VT 05262, 5 baths

$995,000

— beds5 baths4,724 sq ft

1594 Vermont Route 7A, Shaftsbury, VT 05262

Property at 536 Mill Rd, Stamford, VT 05352

$60,000

0 beds— baths— sq ft

536 Mill Rd, Stamford, VT 05352

Property at 1439 Main St, Manchester Center, VT 05255, 2 beds, 2 baths

$550,000

2 beds2 baths2,218 sq ft

1439 Main St, Manchester Center, VT 05255

Property at 1182 1184 East Manchester Rd, Manchester Center, VT 05255, 9 beds, 8.5 baths

$5,250,000

9 beds8.5 baths7,900 sq ft

1182 1184 East Manchester Rd, Manchester Center, VT 05255

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 113 Main St, Bennington, VT 05201, 3 beds, 1 bath

$230,000

3 beds1 bath1,092 sq ft

113 Main St, Bennington, VT 05201

Property at 215 & 221 VT Route 30, Dorset, VT 05251, 6 beds, 3 baths

$2,300,000

6 beds3 baths3,340 sq ft

215 & 221 VT Route 30, Dorset, VT 05251

Property at 3530 VT Route 346, Pownal, VT 05261, 3 beds, 2.5 baths

$249,900

3 beds2.5 baths1,810 sq ft

3530 VT Route 346, Pownal, VT 05261

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 5515 Main St, Manchester, VT 05255, 2 beds, 2 baths

$549,000

2 beds2 baths4,044 sq ft

5515 Main St, Manchester, VT 05255

Property at 263 Elm St, Shaftsbury, VT 05262, 4 beds, 2 baths

$389,000

4 beds2 baths2,368 sq ft

263 Elm St, Shaftsbury, VT 05262

Property at 48 Canal Dr, Readsboro, VT 05350, 3 beds, 1 bath

$245,000

3 beds1 bath1,064 sq ft

48 Canal Dr, Readsboro, VT 05350

Property at 557 Beech St, Manchester Center, VT 05255, 3 beds, 1 bath

$319,000

3 beds1 bath836 sq ft

557 Beech St, Manchester Center, VT 05255

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 1138 Main Rd, Stamford, VT 05352, 5 beds, 2 baths

$224,500

5 beds2 baths2,212 sq ft

1138 Main Rd, Stamford, VT 05352

Property at 3264 Route 153, West Rupert, VT 05776, 2 beds, 1 bath

$259,000

2 beds1 bath1,400 sq ft

3264 Route 153, West Rupert, VT 05776

Property at 142 Mt Aeolus Rd, Manchester Center, VT 05255, 2 beds, 2 baths

$549,000

2 beds2 baths3,478 sq ft

142 Mt Aeolus Rd, Manchester Center, VT 05255

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 3309 3321 Main St, Manchester, VT 05254, 11 beds, 7.5 baths

$1,300,000

11 beds7.5 baths9,560 sq ft

3309 3321 Main St, Manchester, VT 05254

Property at 24 VT Route 11, Londonderry, VT 05148, 6 beds, 7 baths

$895,000

6 beds7 baths5,764 sq ft

24 VT Route 11, Londonderry, VT 05148

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Vintage Homes for Sale in Bennington County

There are currently 60 vintage homes for sale in Bennington County at a median listing price of $535K. 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 103 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 43 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 29 condos, 1 townhouse, and 12 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 Jan 06 2026 on the search page

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