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

96 homes

Sort:

Recommended

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
Affordable housing on your holiday wish list? Look no further. This charming home—originally built as a single-family residence—offers generous space, character, and flexibility to meet a variety of needs. The current layout reflects a long-ago duplex conversion, but by reopening a now-closed interior door, it can easily function again as a cohesive single-family home. The main level offers two bedrooms, a full bath with classic wainscoting and pedestal sink, kitchen with breakfast bar, dining room with hardwood floors, and a spacious living room with a gas stove and peaceful views of the South Stream. Upstairs is another large bedroom with generous closet space, full bath with

$209,000

3 beds2 baths1,680 sq ft

116 Morgan St, Bennington, VT 05201

Duplex conversion • 8,712 sq ft lot • 2 garage spots

ABOUT THIS HOME
Cheap 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
Cheap Home for sale in Bennington County, VT:
Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a Livingroom or studio space with plenty of natural light. The detached garage rounds out the move in ready Village Home. A short walk to all downtown amenities, coffee shops, restaurants and shopping The Boiler is 5 years old and the kitchen appliances were also recently replaced. 1 hour to Albany Internati

$299,000

4 beds2 baths2,000 sq ft

207 Silver St, Bennington, VT 05201

Private entrance • In home office • 3 season sunroom

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
Remarkable 3BR Birch Hill Value! Exceptional three-bedroom, two-bath end unit at Birch Hill! This well-thought-out floor plan is a true standout, providing two distinct living areas ideal for entertaining guests or relaxing after a day on the slopes. Features include an updated kitchen and dining space, two modernized baths, and a practical, renovated mudroom—essential for storing all your outdoor gear. Enjoy winter views of Stratton Mountain from in front of the fireplace, warm summer evenings and vibrant fall colors on your enlarged private deck, and appreciate the convenience of in-unit laundry. As an end unit, you benefit from extra privacy and an abundance of natural light throug

$430,000

3 beds2 baths1,215 sq ft

8 Silver Birch Rd #8, Winhall, VT 05340

Private deck • Outdoor pool • Winter views

$219,000

2 beds1 bath1,872 sq ft

17 Henry Hl, Stamford, VT 05352

1.72 acre lot • Garage • Built 1920

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

$320,000

3 beds1 bath1,392 sq ft

196 Granger Hollow Rd, North Bennington, VT 05257

Property at 933 East Rd, Bennington, VT 05201, 2 beds, 1 bath

$35,300

2 beds1 bath1,302 sq ft

933 East Rd, Bennington, VT 05201

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 108 Baker Dr, Bennington, VT 01237, 2 beds, 2 baths

$82,900

2 beds2 baths980 sq ft

108 Baker Dr, Bennington, VT 01237

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

$349,000

2 beds2 baths1,542 sq ft

509 Thompson Pond Rd, Pownal, VT 05261

Property at 2842 Vermont Route 7A, Shaftsbury, VT 05262, 3 beds, 2 baths

$375,000

3 beds2 baths2,661 sq ft

2842 Vermont Route 7A, Shaftsbury, VT 05262

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 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 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 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 3 Kimball Hill Rd #1, Winhall, VT 05340, 3 beds, 2 baths

$375,000

3 beds2 baths1,344 sq ft

3 Kimball Hill Rd #1, Winhall, VT 05340

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 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 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 114 Colebrook Rd, East Arlington, VT 05252, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths2,800 sq ft

114 Colebrook Rd, East Arlington, VT 05252

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

$269,000

2 beds1 bath1,400 sq ft

3264 Route 153, West Rupert, VT 05776

Property at 51 Russell St Unit D, Arlington, VT 05250, 2 beds, 1.5 baths

$289,000

2 beds1.5 baths1,417 sq ft

51 Russell St Unit D, Arlington, VT 05250

Property at 100 Walsh Rd, Sandgate, VT 05250, 3 beds, 2 baths

$375,000

3 beds2 baths2,400 sq ft

100 Walsh Rd, Sandgate, VT 05250

Property at 6982 Main St, Readsboro, VT 05350, 9 beds

$250,000

9 beds— baths3,810 sq ft

6982 Main St, Readsboro, VT 05350

Property at 432 South St Unit C6, Bennington, VT 05201, 2 beds, 1.5 baths

$145,000

2 beds1.5 baths852 sq ft

432 South St Unit C6, 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 2984 VT Route 153, Pawlet, VT 05761, 4 beds, 1 bath

$69,900

4 beds1 bath1,500 sq ft

2984 VT Route 153, Pawlet, VT 05761

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

$279,900

5 beds2 baths2,294 sq ft

218 Union St, Bennington, VT 05201

Property at 22 Carlen St, Manchester Center, VT 05255, 3 beds, 2 baths

$360,000

3 beds2 baths1,590 sq ft

22 Carlen St, Manchester Center, VT 05255

Property at 139 Bergwelt Ln, Readsboro, VT 05350, 3 beds, 2 baths

$424,900

3 beds2 baths1,560 sq ft

139 Bergwelt Ln, Readsboro, VT 05350

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 78 Carbonti Cir, Arlington, VT 05250, 3 beds, 2 baths

$368,000

3 beds2 baths1,337 sq ft

78 Carbonti Cir, Arlington, VT 05250

Viewing page 1 of 3

Cheap Homes for Sale in Bennington County

There are currently 96 cheap homes for sale in Bennington County at a median listing price of $549K. 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 Cheap Homes

Nearby Cities with Cheap 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
$557,000
Stowe homes for sale
$1,124,500
Woodstock homes for sale
$1,095,000
Montpelier homes for sale
$350,000
Brattleboro homes for sale
$375,000
South Burlington homes for sale
$683,260
Shelburne homes for sale
$524,450
Waterbury homes for sale
$450,000
Rutland homes for sale
$269,000
Ludlow homes for sale
$595,000
Manchester homes for sale
$1,300,000
Barre homes for sale
$275,000
Middlebury homes for sale
$482,500
Bennington homes for sale
$259,450
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 Sun Dec 21 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.