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Chester, VT Homes for Sale | Realty.com

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Homes for Sale in Chester, VT

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22 of 30 Listings

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22 of 30 Listings

41Active

Homes for Sale in Chester, VT

Hide Map

22 of 30 Listings

Map

Homes for Sale in Chester, VT

22 of 30 Listings

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

41Active

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

$495,000

3 bd · 3 ba · 2,464 sqft

3341 Trebo Road, Chester, VT

Dan Vigeant · Mary W. Davis Realtor & Assoc., Inc.

28Active

$240,000

2 bd · 1 ba · 912 sqft

148 Kevadus Circle, Chester, VT

Paul Rodenhauser · BHG Masiello Keene

Price Reduced21Active

$259,000

4 bd · 1 ba · 1,324 sqft

426 Vermont Route 103, Chester, VT

Thaddeus Abare · Barrett and Valley Associates Inc.

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

38Active

$549,000

4 bd · 2 ba · 2,190 sqft

204 Fletcher Road, Chester, VT

Julie Buffum · Buffum Realty

25Active

$129,900

2 bd · 1 ba · 756 sqft

473 Elm Street, Chester, VT

Erin Kendall · EXP Realty

Price Reduced9Active

$109,900

3 bd · 2 ba · 980 sqft

4351 Vermont Route 11 W, Chester, VT

Derek Greene · Derek Greene

22Active

$249,900

2 bd · 1 ba · 930 sqft

3537 Popple Dungeon Road, Chester, VT

Thaddeus J Abare · Barrett and Valley Associates Inc.

Price Reduced47Active

$599,000

4 bd · 2 ba · 1,908 sqft

548 Crow Hill Road, Chester, VT

Jay Farrar · Four Seasons Sotheby's Int'l Realty

Price Reduced60Active

$225,000

3 bd · 2 ba · 1,500 sqft

3781 Flamstead Road, Chester, VT

Amy Hill · EXP Realty

Price Reduced60Active

$627,000

3 bd · 2 ba · 2,204 sqft

168 Chandler Road, Chester, VT

Diane Rousseau · Four Seasons Sotheby's Int'l Realty

Price Reduced58Active

$445,000

5 bd · 4 ba · 3,865 sqft

81 Main Street, Chester, VT

Betsy Adamovich · Real Broker LLC

Price Reduced33Active

$425,000

3 bd · 2 ba · 1,626 sqft

3208 Green Mountain Turnpike, Chester, VT

Geralyn Donohue · Four Seasons Sotheby's Int'l Realty

17Active

$75,000

2 bd · 1 ba · 620 sqft

1144 Potash Brook Road, Chester, VT

Julie Buffum · Buffum Realty

39Active

$1,200,000

4 bd · 3 ba · 3,308 sqft

76 Goldthwaite Road, Chester, VT

Gary Coger · Four Seasons Sotheby's Int'l Realty

Price Reduced53Active

$1,349,000

5 bd · 5 ba · 5,400 sqft

1302 Popple Dungeon Road, Chester, VT

Gary Coger · Four Seasons Sotheby's Int'l Realty

39Active

$349,000

4 bd · 3 ba · 3,332 sqft

397 River Street, Chester, VT

Lisa Kelley · Cummings & Co

60Active

$479,000

4 bd · 3 ba · 2,676 sqft

64 Maple Street, Chester, VT

Betsy Adamovich · Real Broker LLC

51Active

$390,000

3 bd · 2 ba · 1,304 sqft

663 Depot Street, Chester, VT

Betsy Adamovich · Real Broker LLC

Price Reduced60Active

$474,900

3 bd · 2 ba · 1,320 sqft

547 Williams Road, Chester, VT

Terri Edgerley · Edge Realty Vermont

43Active

$425,000

5 bd · 2 ba · 1,982 sqft

176 Meadow Road, Chester, VT

Lauren Behm · Berkshire Hathaway HomeServices Stratton Home

60Active

$649,000

3 bd · 2 ba · 2,205 sqft

688 Hidden Heights Road, Chester, VT

Joseph Karl · William Raveis Real Estate Vermont Properties

Price Reduced31Active

$349,000

3 bd · 2 ba · 1,788 sqft

1397 Popple Dungeon Road, Chester, VT

Daire Gibney · Barrett and Valley Associates Inc.

1 2

Listing data & MLS disclosures

NEREN: Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this web site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
PrimeMLS: Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this web site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Chester housing market

October 2026 · This period is still settling

Homes on the market · MLS, as of Oct 18, 2026

Median list price: $461,950
Homes for sale: 40

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,556 sq. ft.

Chester, VT community profile

Area: 108.2 sq. mi.

Source: HJN community data

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

Listing data & MLS disclosures

NEREN: Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this web site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
PrimeMLS: Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this web site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Chester, VT community profile

Area: 108.2 sq. mi.

Source: HJN community data

Chester housing market

October 2026 · This period is still settling

Homes on the market · MLS, as of Oct 18, 2026

Median list price: $461,950
Homes for sale: 40

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,556 sq. ft.