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

68 homes

Sort:

Recommended

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 enthusiast. 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

$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:
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

$219,000

2 beds1 bath1,872 sq ft

17 Henry Hl, Stamford, VT 05352

1.72 acre lot • Garage • Built 1920

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries, medical services, and more. Inside, the home features 3 spacious bedrooms and 4 bathrooms, including a first-floor primary suite for easy, single-level living. The layout is warm and inviting, highlighted by a lovely three-season room perfect for morning coffee, reading, or enjoying the changin

$725,000

3 beds3 baths2,274 sq ft

490 Barnumville Rd, Manchester Center, VT 05255

Three season room • Expansive level lot • Flat usable acres

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement under the older portion, with a crawlspace under the addition. This main house needs some TLC including interior paint and could use new carpet and vinyl flooring. The smaller second house is located a few hundred feet from the main house and has its own separate driveway and a separte septic system (t

$320,000

3 beds1 bath1,392 sq ft

196 Granger Hollow Rd, North Bennington, VT 05257

Large primary • Large eat-in kitchen • Large living room

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 211 Grandview St, North Bennington, VT 05257, 3 beds, 2 baths

$294,900

3 beds2 baths1,848 sq ft

211 Grandview St, North Bennington, VT 05257

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 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 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 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 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 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 536 Mill Rd, Stamford, VT 05352

$60,000

0 beds— baths— sq ft

536 Mill Rd, Stamford, VT 05352

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

$875,000

6 beds5 baths5,689 sq ft

2677 Rte 30 Rd, Dorset, VT 05251

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 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 266 Robillard Rd, Stamford, VT 05352, 4 beds, 1.5 baths

$179,900

4 beds1.5 baths2,082 sq ft

266 Robillard Rd, Stamford, VT 05352

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

$294,500

3 beds1.5 baths1,934 sq ft

508 Barney Rd, 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 Maple St, Bennington, VT 05201, 4 beds, 2 baths

$194,900

4 beds2 baths1,278 sq ft

215 Maple St, Bennington, VT 05201

Property at 139 Prospect St, Manchester, VT 05254, 3 beds, 2.5 baths

$1,849,000

3 beds2.5 baths3,450 sq ft

139 Prospect St, Manchester, VT 05254

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 120 Village St, East Dorset, VT 05253, 4 beds, 3.5 baths

$439,500

4 beds3.5 baths3,861 sq ft

120 Village St, East Dorset, VT 05253

Property at 1555 E Arlington Rd, Arlington, VT 05250, 5 beds, 3 baths

$465,000

5 beds3 baths2,622 sq ft

1555 E Arlington Rd, Arlington, VT 05250

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 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 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 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 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 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 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 1016 West Rd, Manchester, VT 05254, 4 beds, 5 baths

$1,245,000

4 beds5 baths4,272 sq ft

1016 West Rd, Manchester, VT 05254

Property at 130 Ipan Rd, Shaftsbury, VT 05257, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths2,696 sq ft

130 Ipan Rd, Shaftsbury, VT 05257

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 636 Tunnel St, Readsboro, VT 05350, 4 beds, 3 baths

$499,999

4 beds3 baths3,504 sq ft

636 Tunnel St, Readsboro, VT 05350

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

$224,500

5 beds2 baths2,212 sq ft

1138 Main Rd, Stamford, VT 05352

Viewing page 1 of 2

Vintage Homes for Sale in Bennington County

There are currently 68 vintage homes for sale in Bennington County at a median listing price of $550K. 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 86 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 38 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 30 condos, 1 townhouse, and 11 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.

More real estate resources for Bennington County, VT

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Bennington County, VT

How to buy a house in Bennington County, VT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Vermont

Burlington homes for sale
$547,000
Stowe homes for sale
$1,150,000
Woodstock homes for sale
$995,000
Montpelier homes for sale
$350,000
Brattleboro homes for sale
$370,000
South Burlington homes for sale
$712,450
Shelburne homes for sale
$524,450
Waterbury homes for sale
$450,000
Rutland homes for sale
$270,000
Manchester homes for sale
$1,284,500
Ludlow homes for sale
$585,000
Middlebury homes for sale
$482,500
Barre homes for sale
$279,000
Bennington homes for sale
$272,000
Norwich homes for sale
$0

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 Fri Dec 12 2025 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.