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29 listings

Homes for Sale in Chester, VT

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20 of 29 Listings

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20 of 29 Listings

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

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 Reduced40Active

$354,000

2 bd · 1 ba · 900 sqft

302 Davidson Hill Road, Chester, VT

Tyler Buswell · Vermont Real Estate Company

Price Reduced60Active

$225,000

3 bd · 2 ba · 1,500 sqft

3781 Flamstead Road, Chester, VT

Amy Hill · EXP Realty

Price Reduced38Active

$229,500

4 bd · 3 ba · 1,922 sqft

3668 Vt Route 103 North, Chester, VT

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

60Active

$649,000

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

$449,000

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 Reduced47Active

$549,000

4 bd · 3 ba · 2,464 sqft

3341 Trebo Road, Chester, VT

Daire Gibney · Barrett and Valley Associates Inc.

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.

37Active

$399,000

4 bd · 3 ba · 2,148 sqft

40 Fenton Road, Chester, VT

John M Napier · TPW Real Estate

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.

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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

New construction
With a pool

Nearby areas

ZIP codes

05149 (130)
05356 (97)
05701 (96)
05751 (56)
05156 (51)
05091 (47)
05143 (46)
05155 (45)

Cities

Ludlow (131)
Dover (100)
Rutland City (84)
Killington (55)
Woodstock (53)

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

Your local brokerage

John White

Realty.com

Lic. #81.0094848

Call John

Nearby areas

ZIP codes

05149 (130)
05356 (97)
05701 (96)
05751 (56)
05156 (51)
05091 (47)
05143 (46)
05155 (45)

Cities

Ludlow (131)
Dover (100)
Rutland City (84)
Killington (55)
Woodstock (53)

Springfield (49)

Winhall (39)

Stratton (38)

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 Homes for Sale | Realty.com