Chester town, VT - homes for sale

37 of 37 results displayed

New
$87,500Active
10.4 Acres
00 Snell Road, Chester, VT 05143
MLS# 5094246Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
New
$85,000Active
5 Acres
0 Linden Way, Chester, VT 05143
MLS# 5093908Listed by: BARRETT AND VALLEY ASSOCIATES INC.
New
$75,000Active
2 beds 1 baths620 sq. ft.
1144 Potash Brook Road, Chester, VT 05143
MLS# 5093286Listed by: BUFFUM REALTY
$153,000Active
4.7 Acres
250 Fenton Road, Chester, VT 05148
MLS# 5090458Listed by: EXP REALTY
$5,150,000Active
8 beds 8 baths10,062 sq. ft.
3800 Weston Andover Road, Andover, VT 05143
MLS# 5089880Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$200,000Pending
-- beds -- baths384 sq. ft.
91 VT Route 35, Athens, VT 05143
MLS# 5089534Listed by: BERKLEY & VELLER GREENWOOD COUNTRY
$250,000Active
3 beds 2 baths1,140 sq. ft.
202 Mountain View, Chester, VT 05143
MLS# 5088678Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$1,200,000Active
4 beds 3 baths3,308 sq. ft.
76 Goldthwaite Road, Chester, VT 05143
MLS# 5088175Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$325,000Active
4 beds 3 baths3,332 sq. ft.
397 River Street, Chester, VT 05143
MLS# 5087965Listed by: CUMMINGS & CO
$1,490,000Active
5 beds 5 baths5,400 sq. ft.
1302 Popple Dungeon Road, Chester, VT 05143
MLS# 5087874Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$479,000Active
3 beds 3 baths2,676 sq. ft.
64 Maple Street, Chester, VT 05143
MLS# 5087175Listed by: REAL BROKER LLC
$549,000Active
4 beds 3 baths2,464 sq. ft.
3341 Trebo Road, Chester, VT 05143
MLS# 5086105Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$390,000Active
3 beds 2 baths1,304 sq. ft.
663 Depot Street, Chester, VT 05143
MLS# 5086202Listed by: REAL BROKER LLC
$474,900Active
3 beds 2 baths1,320 sq. ft.
547 Williams Road, Chester, VT 05143
MLS# 5085214Listed by: EDGE REALTY VERMONT
$569,000Pending
3 beds 2 baths2,966 sq. ft.
147 Pleasant View Lane, Chester, VT 05143
MLS# 5084462Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$129,000Active
7.95 Acres
0 Green Mountain Turnpike #5, Chester, VT 05143
MLS# 5081034Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$120,000Active
3.24 Acres
508 Mattson Road, Chester, VT 05143
MLS# 5082636Listed by: CUMMINGS & CO
$340,000Active
3 beds 1 baths2,096 sq. ft.
335 North Street, Chester, VT 05143
MLS# 5080199Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$175,000Active
12.51 Acres
377 Coach Road #Lot 15, Chester, VT 05143
MLS# 5079082Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$74,500Active
16.24 Acres
TBD Farrar Road, Chester, VT 05143
MLS# 5074848Listed by: EXP REALTY
$649,000Active
3 beds 2 baths2,205 sq. ft.
688 Hidden Heights Road, Chester, VT 05143
MLS# 5074094Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$349,000Active
3 beds 2 baths1,788 sq. ft.
1397 Popple Dungeon Road, Chester, VT 05143
MLS# 5073930Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$399,000Active
4 beds 3 baths2,148 sq. ft.
40 Fenton Road, Chester, VT 05143
MLS# 5073147Listed by: TPW REAL ESTATE
$295,000Active
-- beds -- baths2,702 sq. ft.
41 VT Route 103 South, Chester, VT 05143
MLS# 5070146Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$159,000Active
5 Acres
00 Contro Road, Chester, VT 05143
MLS# 5069927Listed by: BRATTLEBORO AREA REALTY
$289,000Active
2 beds 3 baths1,475 sq. ft.
106 Contro Road, Chester, VT 05143
MLS# 5069928Listed by: BRATTLEBORO AREA REALTY
$169,000Active
1 beds 1 baths200 sq. ft.
3019 Popple Dungeon Road, Chester, VT 05143
MLS# 5067929Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$74,000Active
15.5 Acres
00 Remington Road, Chester, VT 05143
MLS# 5061671Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$299,000Active
3 beds 2 baths1,488 sq. ft.
447 Elm Street, Chester, VT 05143
MLS# 5061241Listed by: CUMMINGS & CO
$290,000Active
75 Acres
1175 Quarry Road, Chester, VT 05143
MLS# 5058824Listed by: BHG MASIELLO KEENE
$200,000Active
6.63 Acres
00 Vermont Route 103, Chester, VT 05143
MLS# 5053371Listed by: LANGE & LANGE
$115,000Active
3.35 Acres
00 VT Route 103 N #Lot 4, Chester, VT 05143
MLS# 5052955Listed by: LANGE & LANGE
$115,000Active
3.28 Acres
00 VT Route 103 N #Lot 3, Chester, VT 05143
MLS# 5052948Listed by: LANGE & LANGE
$225,000Active
3 beds 1 baths1,327 sq. ft.
160 Depot Street, Chester, VT 05143
MLS# 5047277Listed by: RE/MAX SUMMIT
$650,000Active
3 beds 3 baths4,324 sq. ft.
3630 Vt Route 103 N, Chester, VT 05143
MLS# 5044879Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$249,000Active
84 Acres
000 Green Mountain Turnpike, Chester, VT 05143
MLS# 5023272Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$229,000Active
27.8 Acres
00 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 June 17, 2026 NH_NNEREN Member Broker: Jim D’Amico

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.