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Chester town, VT - homes for sale
42 of 42 results displayed
- New
$169,000Active1 beds 1 baths200 sq. ft.3019 Popple Dungeon Road, Chester, VT 05143
MLS# 5067929Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
- New
$149,900Active2 beds 1 baths1,120 sq. ft.4351 Vermont RT 11 West, Chester, VT 05143
MLS# 5067061Listed by: BRATTLEBORO AREA REALTY 
$448,888Active4 beds 2 baths1,728 sq. ft.4877 VT Route 103, Chester, VT 05143
MLS# 5064343Listed by: EXP 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
$895,000Active4 beds 4 baths2,775 sq. ft.725 Flamstead Road, Chester, VT 05143
MLS# 5063387Listed 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
$549,000Active3 beds 4 baths2,256 sq. ft.246 Putnam Hill Road, Chester, VT 05143
MLS# 5062155Listed by: ENGEL & VOLKERS OKEMO
$74,000Active15.5 Acres00 Remington Road, Chester, VT 05143
MLS# 5061671Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$349,000Active2 beds 1 baths803 sq. ft.1470 Flamstead Road, Chester, VT 05143
MLS# 5061244Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$389,000Active3 beds 2 baths1,488 sq. ft.447 Elm Street, Chester, VT 05143
MLS# 5061241Listed by: CUMMINGS & CO
$189,900Pending3 beds 2 baths960 sq. ft.284 Flamstead Road, Chester, VT 05143
MLS# 5061165Listed by: HIGHLAND REALTY
Listed by BHGRE$599,900Active4 beds 3 baths2,689 sq. ft.1573 Flamstead Road, Chester, VT 05143
MLS# 5060829Listed by: BHG MASIELLO KEENE
$229,000Active1 beds 1 baths528 sq. ft.106 Hall Road, Chester, VT 05143
MLS# 5059814Listed by: REAL BROKER LLC
$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
$425,000Active4 beds 2 baths2,562 sq. ft.26 Main Street, Chester, VT 05143
MLS# 5058562Listed by: ENGEL & VOLKERS OKEMO
$249,500Active1 beds 1 baths1,424 sq. ft.2739 Route 11, Chester, VT 05143
MLS# 5058302Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$879,000Active2 beds 2 baths1,576 sq. ft.1342 Old Stage Road, Chester, VT 05143
MLS# 5056637Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$685,000Active3 beds 2 baths2,205 sq. ft.688 Hidden Heights Road, Chester, VT 05143
MLS# 5055278Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES- Open Sat, 10:30am to 1pm
$649,900Active4 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
$225,000Active3 beds 1 baths1,024 sq. ft.442 103 S, Chester, VT 05143
MLS# 5052054Listed by: LANGE & LANGE
$339,900Active2 beds 1 baths900 sq. ft.302 Davidson Hill Road, Chester, VT 05143
MLS# 5051283Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$85,000Active1.82 Acres0 Remington Road #7, Chester, VT 05143
MLS# 5049898Listed by: DIAMOND REALTY
$55,000Active1.52 Acres0 Remington Road #11, Chester, VT 05143
MLS# 5049900Listed by: DIAMOND REALTY
$1,125,000Active4 beds 3 baths2,772 sq. ft.157 Thompson Road, Chester, VT 05143
MLS# 5048851Listed by: WINHALL REAL ESTATE
$239,000Active3 beds 1 baths1,440 sq. ft.419 Coach Road, Chester, VT 05143
MLS# 5048752Listed by: LOWE'S REAL ESTATE, LLC
$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
$395,000Active6 beds 1 baths2,308 sq. ft.525 Route 103 N, Chester, VT 05143
MLS# 5047187Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$594,000Active5 beds 4 baths3,470 sq. ft.1057 Quarry Road, Chester, VT 05143
MLS# 5047173Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$95,000Pending3.24 AcresLot 3 Mattson Road, Chester, VT 05143
MLS# 5045357Listed by: CUMMINGS & CO
$998,000Active4 beds 4 baths3,920 sq. ft.1847 Trebo Road, Chester, VT 05143
MLS# 5048707Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$625,000Active3 beds 3 baths4,324 sq. ft.3630 Vt Route 103 N, Chester, VT 05143
MLS# 5044879Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$399,000Active4 beds 4 baths2,710 sq. ft.491 Farrar Road, Chester, VT 05143
MLS# 5044528Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$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.
$169,000Pending-- beds 4 baths3,024 sq. ft.515 Main Street, Chester, VT 05143
MLS# 5007795Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$95,000Active10.4 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 October 31, 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.