4 bedroom homes for sale in Bennington County, VT

view of snowy exterior featuring stucco siding

snow covered property featuring a chimney and a sunroom

1 day on Rocket

$10,000 Closing Credit¹

$975,000

4 beds • 4.5 baths • 2,658 sqft

73 Cranberry Hill Rd, Winhall VT 05340

#5031975, Carrie Mathews, Listing Office: Winhall Real Estate

living area with a stone fireplace, lofted ceiling, a ceiling fan, and wood walls

living area with wooden walls, wood finished floors, vaulted ceiling, and ceiling fan with notable chandelier

living area featuring light wood finished floors, a notable chandelier, wood walls, and high vaulted ceiling

1 day on Rocket

$5,213 Closing Credit¹

$439,000

4 beds • 1.5 baths • 1,344 sqft

2 Lower Stratton Valley Rd, Winhall VT 05340

#5031973, Mike Masters, Listing Office: Four Seasons Sotheby's Int'l Realty

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ranch-style home with roof with shingles, driveway, a chimney, a front lawn, and a garage

ranch-style home featuring a garage, a front yard, a chimney, and driveway

3 days on Rocket

$3,561 Closing Credit¹

$299,900

4 beds • 2.5 baths • 2,272 sqft

17 Tel Rd, Bennington VT 05201

#5031604, Kelley McCarthy, Listing Office: Mahar McCarthy Real Estate

$8,906 Closing Credit¹

$750,000

4 beds • 3.5 baths • 6,650 sqft

338 Main St, Bennington VT 05201

#5031039, Max Squiers, Listing Office: KW Vermont - Brenda Jones Real Estate Group

chalet / cabin featuring a garage and a deck

$10,000 Closing Credit¹

$1,150,000

4 beds • 3.5 baths • 4,478 sqft

41/43 Cranberry Hill Rd, Winhall VT 05340

#5030678, Alison Cummings, Listing Office: Cummings & Co

Video tour

$9,488 Closing Credit¹

$799,000

4 beds • 3.5 baths • 3,347 sqft

12 Jamie Ln, Winhall VT 05340

#5029870, Kevin Moran, Listing Office: Four Seasons Sotheby's Int'l Realty

snow covered property featuring a wooden deck

exterior space featuring a wooden deck and a chimney

$10,000 Closing Credit¹

$1,025,000

4 beds • 3.5 baths • 2,672 sqft

13 Windtree Rd, Winhall VT 05340

#5029619, Kim Morgan-Wohler, Listing Office: Wohler Realty Group

Room to negotiate?

Median Sold Price

$327.5K

Based on our February 2025 Market Report.

view of front of property featuring a porch and a garage

view of front of home featuring a porch and a garage

Video tour

$10,000 Closing Credit¹

$1,029,000

4 beds • 3.5 baths • 2,280 sqft

17 Roundtree Rd, Winhall VT 05340

#5026451, Sarah Nichols, Listing Office: Winhall Real Estate

view of front facade with a garage, covered porch, and a front yard

new england style home featuring a front lawn and a porch

$10,000 Closing Credit¹

$875,000

4 beds • 3.5 baths • 5,700 sqft

56 Mending Walls Rd, Manchester VT 05255

#5024531, Derek Greene, Listing Office: Derek Greene

$5,688 Closing Credit¹

$479,000

4 beds • 3.5 baths • 3,861 sqft

120 Village St, Dorset VT 05253

#5023329, Jill Simon, Listing Office: Josiah Allen Real Estate, Manchester Branch Office

view of front facade featuring a wooden deck, a sunroom, a front yard, and central AC

view of front of house featuring a sunroom, a front yard, and a deck

$2,007 Closing Credit¹

$169,000

4 beds • 1 bath • 952 sqft

250 Magee Rd, Stamford VT 05352

#244749, Susan Colvin, Listing Office: MONARCH REALTY, INC.

view of front of house with a front yard and covered porch

view of front of property with a porch and a front yard

$3,824 Closing Credit¹

$322,000

4 beds • 3 baths • 2,308 sqft

106 Putnam St, Bennington VT 05201

#5016954, Kristin Comeau, Listing Office: TPW Real Estate

$10,000 Closing Credit¹

$1,250,000

4 beds • 2.5 baths • 2,400 sqft

77 Fuller Rd W, Bennington VT 05201

#5014607, Jason Saphire, Listing Office: www.HomeZu.com

view of front of property with driveway, a shingled roof, and a front yard

view of front of home featuring gravel driveway and stucco siding

cape cod house with stucco siding, roof with shingles, french doors, and a front yard

$10,000 Closing Credit¹

$1,950,000

4 beds • 4.5 baths • 4,891 sqft

430 Riverbend Dr, Manchester VT 05254

#5008910, Laura Beckwith, Listing Office: Josiah Allen Real Estate, Inc.

view of front facade featuring a chimney, metal roof, a standing seam roof, and a front yard

view of home's exterior with stone siding, faux log siding, driveway, and a garage

$7,113 Closing Credit¹

$599,000

4 beds • 2.5 baths • 3,100 sqft

357 Kansas Rd, Sunderland VT 05252

#5007071, Andrea Kaplan, Listing Office: Four Seasons Sotheby's Int'l Realty

view of front of home featuring a front yard

$2,363 Closing Credit¹

$199,000

4 beds • 4 baths • 3,576 sqft

883 Vt Route 7a, Shaftsbury VT 05262

#5005228, Monique Geannelis, Listing Office: Mahar McCarthy Real Estate

greek revival house featuring a garage and a front yard

view of front of home featuring a garage

$10,000 Closing Credit¹

$1,700,000

4 beds • 4.5 baths • 4,272 sqft

1016 W Rd, Manchester VT 05254

#5004187, Laura Beckwith, Listing Office: Josiah Allen Real Estate, Inc.

view of mountain feature with a rural view

$10,000 Closing Credit¹

$1,275,000

4 beds • 4 baths • 4,598 sqft

3402 Vt Route 313w, Arlington VT 05250

#4994079, Margretta Fischer, Listing Office: Wohler Realty Group

Bennington County, VT Real Estate Market Overview

Browse 18 4 bedroom homes for sale in Bennington County, VT. View properties, photos, nearby real estate with school and housing market information. In February 2025 in Bennington County, VT there were 0% more homes for sale than in January 2025. In February 2025, listings were on the market for 0 days. During the same period, the median list price in this real estate market was $327,500. Over 4 listings were sold over their listed price in February 2025 in Bennington County, VT. In the same period over 14 listings were sold below the listed price and 2 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

Schools near Bennington County, VT

Elementary Schools

Sunderland Elementary School
98 Bear Ridge Rd
Public District PK-6
Pownal Elementary School
94 Schoolhouse Rd
Public District PK-6
Fisher Elementary School
504 E Arlington Rd
Public District PK-5

Middle Schools

Flood Brook School
91 VT Route 11
Public District PK-8
Manchester Elementary/Middle School
80 Memorial Ave
Public District PK-8
Dorset Elementary School
130 School Dr
Public District PK-8

High Schools

Arlington Memorial School
529 E Arlington Rd
Public District 6-12
Twin Valley Middle High School
4299 VT Route 100
Public District 6-12
Mt. Anthony Senior Uhsd #14
301 Park Street Ext
Public District 9-12

Data provided by Great Schools

4 bedroom homes for sale in Bennington County, VT

Bennington County, VT Real Estate Market Overview

What is it like to live in Bennington County, VT

Overview

Schools near Bennington County, VT

Housing market reports in Bennington County

Homes for sale near Bennington County, VT

Top real estate cities in Vermont