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Chester town, VT - homes for sale
37 of 37 results displayed
- New
$55,000Active1.52 Acres0 Remington Road, Chester, VT 05143
MLS# 5116457Listed by: DIAMOND REALTY
- New
$269,000Active4 beds 1 baths1,324 sq. ft.426 Vermont Route 103, Chester, VT 05143
MLS# 5115637Listed by: BARRETT AND VALLEY ASSOCIATES INC. 
$549,000Active4 beds 2 baths2,190 sq. ft.204 Fletcher Road, Chester, VT 05143
MLS# 5115206Listed by: BUFFUM REALTY
$129,900Active2 beds 1 baths756 sq. ft.473 Elm Street, Chester, VT 05143
MLS# 5114929Listed by: EXP REALTY
$105,000Active3.28 AcresLot 3 VT Route 103, Chester, VT 05143
MLS# 5114885Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$105,000Active3.35 AcresLot 4 VT Route 103, Chester, VT 05143
MLS# 5114886Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$114,900Active3 beds 2 baths980 sq. ft.4351 Vermont Route 11 W, Chester, VT 05143
MLS# 5114547Listed by: DEREK GREENE
$168,000Active12.51 Acres377 Coach Road, Chester, VT 05143
MLS# 5113361Listed by: EXP REALTY
$229,000Active2 beds 1 baths1,008 sq. ft.547 Andover Road, Chester, VT 05143
MLS# 5112828Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$649,000Active-- beds -- baths13,788 sq. ft.23 School Street, Chester, VT 05143
MLS# 5111465Listed by: REAL BROKER LLC
$249,900Active2 beds 1 baths930 sq. ft.3537 Popple Dungeon Road, Chester, VT 05143
MLS# 5110600Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$975,000Active235.3 Acres00 Pratt Bridge Road, Jamaica, VT 05143
MLS# 5107954Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$599,000Active4 beds 2 baths1,908 sq. ft.548 Crow Hill Road, Chester, VT 05143
MLS# 5106579Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$330,000Pending2 beds 1 baths900 sq. ft.302 Davidson Hill Road, Chester, VT 05143
MLS# 5102316Listed by: VERMONT REAL ESTATE COMPANY
$225,000Active3 beds 2 baths1,500 sq. ft.3781 Flamstead Road, Chester, VT 05143
MLS# 5102142Listed by: EXP REALTY
$100,000Active0.55 Acres427 Depot Street, Chester, VT 05143
MLS# 5100755Listed by: KW COASTAL AND LAKES & MOUNTAINS REALTY/HANOVER
$229,000Active27.8 Acres00 Quarry Road, Chester, VT 01543
MLS# 5098347Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$627,000Active3 beds 2 baths2,204 sq. ft.168 Chandler Road, Chester, VT 05143
MLS# 5097737Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$209,500Active4 beds 3 baths1,922 sq. ft.3668 VT Route 103 North, Chester, VT 05143
MLS# 5097621Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$445,000Active5 beds 4 baths3,865 sq. ft.81 Main Street, Chester, VT 05143
MLS# 5095551Listed by: REAL BROKER LLC
$425,000Active3 beds 2 baths1,626 sq. ft.3208 Green Mountain Turnpike, Chester, VT 05143
MLS# 5095486Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$87,500Active10.4 Acres00 Snell Road, Chester, VT 05143
MLS# 5094246Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$79,000Active5 Acres0 Linden Way, Chester, VT 05143
MLS# 5093908Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$75,000Active2 beds 1 baths620 sq. ft.1144 Potash Brook Road, Chester, VT 05143
MLS# 5093286Listed by: BUFFUM REALTY
$4,150,000Active8 beds 8 baths10,062 sq. ft.3800 Weston Andover Road, Andover, VT 05143
MLS# 5089880Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$1,200,000Active4 beds 3 baths3,308 sq. ft.76 Goldthwaite Road, Chester, VT 05143
MLS# 5088175Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$1,349,000Active5 beds 5 baths5,400 sq. ft.1302 Popple Dungeon Road, Chester, VT 05143
MLS# 5087874Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$535,000Active4 beds 3 baths2,464 sq. ft.3341 Trebo Road, Chester, VT 05143
MLS# 5086105Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$390,000Active3 beds 2 baths1,304 sq. ft.663 Depot Street, Chester, VT 05143
MLS# 5086202Listed by: REAL BROKER LLC
$99,999Pending3.24 Acres508 Mattson Road, Chester, VT 05143
MLS# 5082636Listed by: CUMMINGS & CO
$74,500Active16.24 AcresTBD Farrar Road, Chester, VT 05143
MLS# 5074848Listed by: EXP REALTY
$399,000Active4 beds 3 baths2,148 sq. ft.40 Fenton Road, Chester, VT 05143
MLS# 5073147Listed by: TPW REAL ESTATE
$159,000Active5 Acres00 Contro Road, Chester, VT 05143
MLS# 5069927Listed by: BRATTLEBORO AREA REALTY
$169,000Active1 beds 1 baths200 sq. ft.3019 Popple Dungeon Road, Chester, VT 05143
MLS# 5067929Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$74,000Active15.5 Acres00 Remington Road, Chester, VT 05143
MLS# 5061671Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$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
$249,000Active84 Acres000 Green Mountain Turnpike, Chester, VT 05143
MLS# 5023272Listed by: BARRETT AND VALLEY ASSOCIATES INC.
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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 November 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.