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Chester town, VT - homes for sale
31 of 31 results displayed
- New
$205,000Active3 beds 2 baths1,232 sq. ft.1876 Popple Dungeon Road, Chester, VT 05143
MLS# 5075068Listed by: BARRETT AND VALLEY ASSOCIATES INC.
- New
$74,500Active16.24 AcresTBD Farrar Road, Chester, VT 05143
MLS# 5074848Listed by: EXP REALTY - New
$399,000Active2 beds 2 baths2,751 sq. ft.3466 VT Route 103 N, Chester, VT 05143
MLS# 5074728Listed by: REAL BROKER LLC 
$129,000Pending10.88 Acres469 Williams Road, Chester, VT 05143
MLS# 5074309Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$649,000Active3 beds 2 baths2,205 sq. ft.688 Hidden Heights Road, Chester, VT 05143
MLS# 5074094Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$399,000Active3 beds 2 baths1,788 sq. ft.1397 Popple Dungeon Road, Chester, VT 05143
MLS# 5073930Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$280,000Pending3 beds 2 baths1,248 sq. ft.818 Davidson Hill Road, Chester, VT 05143
MLS# 5073287Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$399,000Active4 beds 3 baths2,148 sq. ft.40 Fenton Road, Chester, VT 05143
MLS# 5073147Listed by: TPW REAL ESTATE
$390,000Active3 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.
$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
$290,000Active75 Acres1175 Quarry Road, Chester, VT 05143
MLS# 5058824Listed by: BHG MASIELLO KEENE
$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
$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
$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
$229,000Active27.8 Acres00 Quarry Road, Chester, VT 05143
MLS# 4982433Listed by: ENGEL & VOLKERS OKEMO
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Copyright 2026 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 February 2, 2026
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© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.