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Chester town, VT - homes for sale
32 of 32 results displayed
$239,000Active2 beds 1 baths1,222 sq. ft.1374 VT Route 103 N, Chester, VT 05143
MLS# 5070689Listed by: CUMMINGS & CO
$425,000Active3 beds 1 baths1,608 sq. ft.531 Main Street, Chester, VT 05143
MLS# 5070720Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$299,000Active-- beds -- baths2,702 sq. ft.41 VT Route 103 South, Chester, VT 05143
MLS# 5070146Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$815,000Active3 beds 3 baths2,466 sq. ft.810 Quarry Road, Chester, VT 05143
MLS# 5070079Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$159,000Active5 Acres00 Contro Road, Chester, VT 05143
MLS# 5069927Listed by: BRATTLEBORO AREA REALTY
$289,000Active2 beds 3 baths1,475 sq. ft.106 Contro Road, Chester, VT 05143
MLS# 5069928Listed by: BRATTLEBORO AREA REALTY
$529,000Active5 beds 5 baths3,880 sq. ft.514 First Avenue, Chester, VT 05143
MLS# 5068855Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$169,000Active1 beds 1 baths200 sq. ft.3019 Popple Dungeon Road, Chester, VT 05143
MLS# 5067929Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$149,900Active2 beds 1 baths1,120 sq. ft.4351 Vermont RT 11 West, Chester, VT 05143
MLS# 5067061Listed by: BRATTLEBORO AREA REALTY
$199,000Active2 beds 3 baths1,640 sq. ft.1833 Mattson Road, Chester, VT 05143
MLS# 5063899Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$329,000Active3 beds 2 baths1,525 sq. ft.870 Cummings Road, Chester, VT 05143
MLS# 5063236Listed by: BUFFUM REALTY
$74,000Active15.5 Acres00 Remington Road, Chester, VT 05143
MLS# 5061671Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$369,000Active3 beds 2 baths1,488 sq. ft.447 Elm Street, Chester, VT 05143
MLS# 5061241Listed by: CUMMINGS & CO
$145,000Active22.23 Acres918 Lovers Lane Road, Chester, VT 05143
MLS# 5058859Listed by: NORTHLAND REAL ESTATE
Listed by BHGRE$300,000Active75 Acres1175 Quarry Road, Chester, VT 05143
MLS# 5058824Listed by: BHG MASIELLO KEENE
$879,000Active2 beds 2 baths1,576 sq. ft.1342 Old Stage Road, Chester, VT 05143
MLS# 5056637Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$625,000Active4 beds 3 baths2,794 sq. ft.95 Church Street, Chester, VT 05143
MLS# 5054818Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$200,000Active6.63 Acres00 Vermont Route 103, Chester, VT 05143
MLS# 5053371Listed by: LANGE & LANGE
$115,000Active3.35 Acres00 VT Route 103 N #Lot 4, Chester, VT 05143
MLS# 5052955Listed by: LANGE & LANGE
$115,000Active3.28 Acres00 VT Route 103 N #Lot 3, Chester, VT 05143
MLS# 5052948Listed by: LANGE & LANGE
$55,000Active1.52 Acres0 Remington Road #11, Chester, VT 05143
MLS# 5049900Listed by: DIAMOND REALTY
$995,000Active4 beds 3 baths2,772 sq. ft.157 Thompson Road, Chester, VT 05143
MLS# 5048851Listed by: WINHALL REAL ESTATE
$229,000Active3 beds 1 baths1,440 sq. ft.419 Coach Road, Chester, VT 05143
MLS# 5048752Listed by: LOWE'S REAL ESTATE, LLC
$599,000Active-- beds -- baths3,850 sq. ft.534 Elm Street, Chester, VT 05143
MLS# 5047931Listed by: KELLEY REAL ESTATE, INC.
$599,000Active7 beds 4 baths3,850 sq. ft.534 Elm Street, Chester, VT 05143
MLS# 5047552Listed by: KELLEY REAL ESTATE, INC.
$225,000Active3 beds 1 baths1,327 sq. ft.160 Depot Street, Chester, VT 05143
MLS# 5047277Listed by: REMAX SUMMIT
$594,000Active5 beds 4 baths3,470 sq. ft.1057 Quarry Road, Chester, VT 05143
MLS# 5047173Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$650,000Active3 beds 3 baths4,324 sq. ft.3630 Vt Route 103 N, Chester, VT 05143
MLS# 5044879Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$495,000Active6 beds 5 baths3,217 sq. ft.423 Main Street, Chester, VT 05142
MLS# 5034061Listed by: DIAMOND REALTY
$275,000Active91 Acres000 Green Mountain Turnpike, Chester, VT 05143
MLS# 5023272Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$89,000Active10.4 Acres0 Snell Road, Chester, VT 05143
MLS# 4999159Listed by: ENGEL & VOLKERS OKEMO
$219,000Active27.8 Acres00 Quarry Road, Chester, VT 05143
MLS# 4982433Listed by: ENGEL & VOLKERS OKEMO
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Copyright 2025 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated December 18, 2025
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Protect your home and budget with an American Home Shield© home warranty. Learn more© 2025 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.