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

107 homes

Sort:

Recommended

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
Well-maintained 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, an eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice backyard, 2 covered parking spaces under a large carport, and an additional 2-car garage/barn with workshop space, shed access, and a large open upper level for storage or potential additional use. Ideal for multi-generational living or income-producing investment. Move-in ready!

$245,000

4 beds2 baths1,652 sq ft

209 Grove St, Bennington, VT 05201

Covered parking • Laundry room • Eat in kitchen

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
Charming Downtown Victorian - Income Opportunity Meets Timeless Style Tucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each unit-one upstairs, one downstairs-offers over 1,140 square feet of well-maintained and tastefully furnished living space. All utilities are separate for each unit. Currently operating as a successful Airbnb with consistent 5-star reviews, this property is truly turnkey, ready to welcome guests or new own

$279,900

5 beds2 baths2,294 sq ft

218 Union St, Bennington, VT 05201

Separate utilities • Short term rentals • Turnkey property

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
Classic late 1800's Colonial home located in the center of the Village of Pawlet. This home offers four bedrooms, one bath in 1500 square feet. All on a 0.16 lot with a detached one car garage. Lot is level and open. Although she'll need some love -- she'll shine again!!

$69,900

4 beds1 bath1,500 sq ft

2984 VT Route 153, Pawlet, VT 05761

6,969 sq ft lot • Garage • Built 1890

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean aesthetic. Retreat to the spacious primary bedroom, complete with a generous walk-in closet to keep everything organized and clutter-free. Whether you're looking for a full-time residence or a charming second home, this condo fits the bill. Enjoy being just minutes from downtown shops and restaurants,

$145,000

2 beds1.5 baths852 sq ft

432 South St Unit C6, Bennington, VT 05201

Large windows • Open floor plan • Walk-in closet

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Cheap Home for sale in Bennington County, VT:
New Price! Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light graces this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining area just off the eat-in kitchen. The first floor laundry room, full bathroom, and a second bedroom round out the first floor. The second level features two additional bedrooms, a second bath and an office/ bonus space. Easy first-floor living and comfortable family flow. The full poured concrete base

$389,000

4 beds2 baths2,368 sq ft

263 Elm St, Shaftsbury, VT 05262

Large level backyard • New buderus boiler • Mountain view

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

$368,000

3 beds2 baths1,337 sq ft

78 Carbonti Cir, Arlington, VT 05250

Property at 516 Oberdorf Rd, Readsboro, VT 05350, 2 beds, 2 baths

$299,000

2 beds2 baths1,624 sq ft

516 Oberdorf Rd, Readsboro, VT 05350

Property at 32 Cassie Ln, Bennington, VT 05201, 2 beds, 2 baths

$96,406

2 beds2 baths777 sq ft

32 Cassie Ln, Bennington, VT 05201

Property at 32-34 Sage St, North Bennington, VT 05257, 5 beds, 2 baths

$190,000

5 beds2 baths1,478 sq ft

32-34 Sage St, North Bennington, VT 05257

Property at 41 Audrey Ln, Bennington, VT 05201, 2 beds, 2 baths

$96,906

2 beds2 baths777 sq ft

41 Audrey Ln, Bennington, VT 05201

Property at 10 Cassie Ln, Bennington, VT 05201-0000, 2 beds, 2 baths

$96,906

2 beds2 baths777 sq ft

10 Cassie Ln, Bennington, VT 05201-0000

Property at 1337 Chunks Brook Rd, Arlington, VT 05250

$84,900

— beds— baths— sq ft

1337 Chunks Brook Rd, Arlington, VT 05250

Property at 41 Moose Hollow Rd, Winhall, VT 05340

$95,000

— beds— baths— sq ft

41 Moose Hollow Rd, Winhall, VT 05340

Property at 942 Rt 315, Pawlet, VT 05768

$350,000

— beds— baths— sq ft

942 Rt 315, Pawlet, VT 05768

Property at 311 Beechwood Ln #19, Peru, VT 05152

$125,000

— beds— baths— sq ft

311 Beechwood Ln #19, Peru, VT 05152

Property at 1347 Morse Hill Rd Lot 12-A, East Dorset, VT 05253

$329,000

— beds— baths— sq ft

1347 Morse Hill Rd Lot 12-A, East Dorset, VT 05253

Property at 21 Sunderland Hill Rd Lot 21, Sunderland, VT 05250

$160,000

— beds— baths— sq ft

21 Sunderland Hill Rd Lot 21, Sunderland, VT 05250

Property at 00 Heartwellville View Rd #32, Readsboro, VT 05350

$14,000

— beds— baths— sq ft

00 Heartwellville View Rd #32, Readsboro, VT 05350

Property at 236-240 Grandview St, Bennington, VT 05201

$99,000

— beds— baths— sq ft

236-240 Grandview St, Bennington, VT 05201

Property at 1319 Vail Rd, Bennington, VT 05201

$120,000

— beds— baths— sq ft

1319 Vail Rd, Bennington, VT 05201

Property at 00 Ross Rd, Winhall, VT 05340

$385,000

— beds— baths— sq ft

00 Ross Rd, Winhall, VT 05340

Property at 777 Butternut Gutter, Arlington, VT 05250

$165,000

— beds— baths— sq ft

777 Butternut Gutter, Arlington, VT 05250

Property at 0 Sunset Hill Rd Unit B, Pownal, VT 05261

$65,000

— beds— baths— sq ft

0 Sunset Hill Rd Unit B, Pownal, VT 05261

Property at 00 Bill T Dr, Readsboro, VT 05350

$109,000

— beds— baths— sq ft

00 Bill T Dr, Readsboro, VT 05350

Property at Oberhugel Rd, Stamford, VT 05350

$14,999

— beds— baths— sq ft

Oberhugel Rd, Stamford, VT 05350

Property at 00 Heartwellville View Rd Unit 34/35, Readsboro, VT 05350

$27,999

— beds— baths— sq ft

00 Heartwellville View Rd Unit 34/35, Readsboro, VT 05350

Property at 1 & 2 Joy Ln, Arlington, VT 05250

$85,000

— beds— baths— sq ft

1 & 2 Joy Ln, Arlington, VT 05250

Property at Alpendorf Ave, Readsboro, VT 05350

$9,999

— beds— baths— sq ft

Alpendorf Ave, Readsboro, VT 05350

Property at 00 Heartwellville View Rd Unit 38/39, Readsboro, VT 05350

$28,000

— beds— baths— sq ft

00 Heartwellville View Rd Unit 38/39, Readsboro, VT 05350

Property at 248 French Hollow Rd #1, Winhall, VT 05340

$400,000

— beds— baths— sq ft

248 French Hollow Rd #1, Winhall, VT 05340

Property at Lebensdorf Ln, Readsboro, VT 05350

$19,999

— beds— baths— sq ft

Lebensdorf Ln, Readsboro, VT 05350

Property at 0 Hidden Valley Rd, Shaftsbury, VT 05262

$65,000

— beds— baths— sq ft

0 Hidden Valley Rd, Shaftsbury, VT 05262

Property at 88 Cedar Ln #5, Peru, VT 05152

$249,000

— beds— baths— sq ft

88 Cedar Ln #5, Peru, VT 05152

Property at 0 US Route 7, Pownal, VT 05261

$20,000

— beds— baths— sq ft

0 US Route 7, Pownal, VT 05261

Viewing page 2 of 3

Cheap Homes for Sale in Bennington County

There are currently 107 cheap 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

Cities

Nearby Counties

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
$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.