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Chester town, VT - homes for sale
40 of 40 results displayed
- New
$649,000Active-- beds -- baths13,788 sq. ft.23 School Street, Chester, VT 05143
MLS# 5111465Listed by: REAL BROKER LLC
- New
$249,900Active2 beds 1 baths930 sq. ft.3537 Popple Dungeon Road, Chester, VT 05143
MLS# 5110600Listed by: BARRETT AND VALLEY ASSOCIATES INC. 
$29,900Pending3.2 Acres1673 Dean Brook Road, Chester, VT 05143
MLS# 5108359Listed by: SOUTHERN VERMONT REALTY GROUP
$975,000Active235.3 Acres00 Pratt Bridge Road, Jamaica, VT 05143
MLS# 5107954Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$700,000Active2 beds 3 baths1,556 sq. ft.1260 Grafton Road, Chester, VT 05143
MLS# 5107796Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$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
$289,900Active3 beds 3 baths1,508 sq. ft.3713 Trebo Road, Chester, VT 05143
MLS# 5106191Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$149,000Active17.7 Acres0 Trebo Road, Chester, VT 05143
MLS# 5102503Listed by: ENGEL & VOLKERS OKEMO
$354,000Active2 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
$879,900Active5 beds 3 baths2,800 sq. ft.1470 Popple Dungeon Road, Chester, VT 05143
MLS# 5099745Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$229,000Active27.8 Acres00 Quarry Road, Chester, VT 01543
MLS# 5098347Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$649,000Active3 beds 2 baths2,204 sq. ft.168 Chandler Road, Chester, VT 05143
MLS# 5097737Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$229,500Active4 beds 3 baths1,922 sq. ft.3668 VT Route 103 North, Chester, VT 05143
MLS# 5097620Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$789,000Active5 beds 3 baths4,388 sq. ft.223 Coach Road, Chester, VT 05143
MLS# 5097600Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$445,000Active5 beds 4 baths3,865 sq. ft.81 Main Street, Chester, VT 05143
MLS# 5095551Listed by: REAL BROKER LLC
$449,000Active3 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
$125,000Active4.7 Acres250 Fenton Road, Chester, VT 05148
MLS# 5090458Listed by: EXP REALTY
$5,150,000Active8 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
$469,000Active3 beds 3 baths2,676 sq. ft.64 Maple Street, Chester, VT 05143
MLS# 5087175Listed by: REAL BROKER LLC
$549,000Active4 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
$419,900Active5 beds 2 baths1,982 sq. ft.176 Meadow Road, Chester, VT 05143
MLS# 5082995Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$119,000Active7.95 Acres0 Green Mountain Turnpike #5, Chester, VT 05143
MLS# 5081034Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$99,999Active3.24 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
$299,000Active3 beds 2 baths1,788 sq. ft.1397 Popple Dungeon Road, Chester, VT 05143
MLS# 5073930Listed 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
$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
Listed by BHGRE$270,000Active75 Acres1175 Quarry Road, Chester, VT 05143
MLS# 5058824Listed by: BHG MASIELLO KEENE
$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.
Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
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 September 28, 2026
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© 2026 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.
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.
© 2026 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.