Bennington County, VT homes for sale & real estate

215 homes

Sort:

Recommended

VIDEO TOUR

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Nestled in one of Vermonts most sought-after locations, this exceptional Colonial home boasts sweeping panoramic views of the Green Mountain National Forest and the picturesque Northshire Valley, offering a peaceful and private retreat just minutes from the vibrant town of Manchester. Perfectly oriented to capture stunning morning sunrises, this 2.8-acre property provides the ideal balance of seclusion and convenience, with easy access to award-winning restaurants, boutique shops, golf courses, and premier ski resorts like Stratton and Bromley, making it a perfect choice for year-round living or a seasonal escape. The home features a large screened-in porch that opens into a charming countr

$850,000

4 beds3 baths3,659 sq ft

445 Canterbury Rd, Manchester Center, VT 05255

Country kitchen • Panoramic views • Northshire valley

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Charming North Bennington Home in a Desirable Neighborhood. Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the home. The dining room features a sliding glass door that opens to a spacious back deck, perfect for outdoor dining and relaxing. A covered front porch adds classic New England charm and a welcoming touch. With a large attached garage

$340,000

4 beds1 bath1,680 sq ft

19 Royal St, North Bennington, VT 05257

Spacious back deck • Covered front porch • Renovated bathroom

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

$249,000

5 beds3 baths2,184 sq ft

137-139 Park St, Bennington, VT 05201

5,227 sq ft lot • Garage • Built 1900

VIDEO TOUR

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons for reading, and late winter for tapping maples, reconnecting with the rhythms of nature. A wide porch gazes across to rounded hills. The screened porch, with its pass-through to the kitchen, is perfect for summer suppers. Under the dappled shade of trees, a walled stone terrace we

$1,995,000

5 beds3 baths6,323 sq ft

2589 W Sandgate Rd, Arlington, VT 05250

Two clear brooks • Wide porch • Ancient maple trees

VIDEO TOUR

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape. Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for chilly evenings. Cathedral ceilings soar, enhancing the spacious feel. The primary suite is a true sanctuary, boasting a spa-like bathroom with double sinks, a jetted tub, a separate shower, and an expansive walk-in closet. Enjoy private balconies directly from your bedroom, offering stunning vistas and a t

$860,000

4 beds3.5 baths4,104 sq ft

25 Benson Fuller Rd, Winhall, VT 05340

Private acre • Primary ensuite • Spa-like bathroom

Property at 15 Wind Hill Rd, Manchester Center, VT 05255, 5 beds, 2 baths

$4,000,000

5 beds2 baths3,347 sq ft

15 Wind Hill Rd, Manchester Center, VT 05255

Property at 417 Maple Hill Rd, Arlington, VT 05250, 1 bed, 1 bath

$500,000

1 bed1 bath300 sq ft

417 Maple Hill Rd, Arlington, VT 05250

Property at 3888-3904 VT Route 7A, Arlington, VT 05250, 17 beds, 19 baths

$1,745,000

17 beds19 baths14,861 sq ft

3888-3904 VT Route 7A, Arlington, VT 05250

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 68 Owls Nest Cir Unit B-7, Manchester, VT 05254, 3 beds, 2 baths

$625,000

3 beds2 baths2,070 sq ft

68 Owls Nest Cir Unit B-7, Manchester, VT 05254

Property at 233 Squires Rd, Manchester Center, VT 05255, 2 beds, 1 bath

$1,200,000

2 beds1 bath1,056 sq ft

233 Squires Rd, Manchester Center, VT 05255

Property at 2001 Depot St, Manchester, VT 05255, 6 beds, 7 baths

$1,190,000

6 beds7 baths5,400 sq ft

2001 Depot St, Manchester, VT 05255

Property at 927 Water St, North Bennington, VT 05257, 5 beds, 4 baths

$374,900

5 beds4 baths3,400 sq ft

927 Water St, North Bennington, VT 05257

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 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

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 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 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 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 759 Stratton Mountain Access Rd #339, Stratton, VT 05155, 3 beds, 3 baths

$995,000

3 beds3 baths1,501 sq ft

759 Stratton Mountain Access Rd #339, Stratton, VT 05155

Property at 1677 Barnumville Rd, Manchester Center, VT 05255, 4 beds, 2.5 baths

$1,350,000

4 beds2.5 baths4,634 sq ft

1677 Barnumville Rd, Manchester Center, VT 05255

Property at 40 Jameson Flts Unit D, Manchestr Ctr, VT 05255, 3 beds, 2.5 baths

$849,000

3 beds2.5 baths1,980 sq ft

40 Jameson Flts Unit D, Manchestr Ctr, VT 05255

Property at 11 Pond View Rd, Winhall, VT 05340, 3 beds, 3 baths

$617,000

3 beds3 baths1,650 sq ft

11 Pond View Rd, Winhall, VT 05340

Property at 38 Jamesons Flts, Manchester, VT 05255, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths1,760 sq ft

38 Jamesons Flts, Manchester, VT 05255

Property at 162 Highland Ave, Manchester Center, VT 05255, 5 beds, 3 baths

$599,000

5 beds3 baths3,836 sq ft

162 Highland Ave, Manchester Center, VT 05255

Property at 25 Mountain Haunts Rd, Bondville, VT 05340, 6 beds, 6.5 baths

$2,999,000

6 beds6.5 baths6,650 sq ft

25 Mountain Haunts Rd, Bondville, VT 05340

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

$399,900

4 beds2 baths2,368 sq ft

263 Elm St, Shaftsbury, VT 05262

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 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 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 3622 Dorset West Rd, Dorset, VT 05251, 3 beds, 2 baths

$750,000

3 beds2 baths2,610 sq ft

3622 Dorset West Rd, Dorset, VT 05251

Property at 33 Forest Haunts Rd, Bondville, VT 05340, 4 beds, 4 baths

$1,350,000

4 beds4 baths4,640 sq ft

33 Forest Haunts Rd, Bondville, VT 05340

Property at 527 Benson Rd, Manchester Center, VT 05255, 5 beds, 4 baths

$4,975,000

5 beds4 baths6,998 sq ft

527 Benson Rd, Manchester Center, VT 05255

Property at 1228 Skiparee Rd, North Pownal, VT 05260, 4 beds, 3 baths

$2,100,000

4 beds3 baths3,780 sq ft

1228 Skiparee Rd, North Pownal, VT 05260

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 14 Old Ridge Rd, Bondville, VT 05340, 4 beds, 4 baths

$1,975,000

4 beds4 baths4,270 sq ft

14 Old Ridge Rd, Bondville, VT 05340

Property at 20 Bishop Rd, Searsburg, VT 05363, 5 beds, 2 baths

$775,000

5 beds2 baths3,500 sq ft

20 Bishop Rd, Searsburg, VT 05363

Property at 515 W Fields Rd, Manchester, VT 05254, 5 beds, 5.5 baths

$6,900,000

5 beds5.5 baths6,500 sq ft

515 W Fields Rd, Manchester, VT 05254

Property at 41 Moose Hollow Rd, Winhall, VT 05340

$95,000

— beds— baths— sq ft

41 Moose Hollow Rd, Winhall, VT 05340

Property at 1337 Chunks Brook Rd, Arlington, VT 05250

$84,900

— beds— baths— sq ft

1337 Chunks Brook Rd, Arlington, VT 05250

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

$125,000

— beds— baths— sq ft

311 Beechwood Ln #19, Peru, VT 05152

Viewing page 4 of 6

Average home prices near Bennington County, VT

Cities

Jamaica homes for sale
$637,000
Wilmington homes for sale
$737,000
Manchester homes for sale
$1,269,000
Stratton Mountain homes for sale
$1,012,000
Arlington homes for sale
$368,000
Bennington homes for sale
$272,000
Manchester Center homes for sale
$687,000
Chimney Hill homes for sale
$499,000
Dorset homes for sale
$875,000
North Bennington homes for sale
$340,000

Counties

Bennington County, VT real estate trends

All Home Types trends in Bennington County, VT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$405,500

-28.6% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Bennington County, VT

$405,500

-28.6%

See more Bennington County, VT market insights

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
$549,450
Stowe homes for sale
$1,150,000
Woodstock homes for sale
$1,095,000
Montpelier homes for sale
$350,000
Brattleboro homes for sale
$360,000
South Burlington homes for sale
$666,130
Shelburne homes for sale
$549,900
Waterbury homes for sale
$424,500
Rutland homes for sale
$269,000
Manchester homes for sale
$1,269,000
Ludlow homes for sale
$585,000
Barre homes for sale
$279,000
Middlebury homes for sale
$482,500
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 Wed Dec 10 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.