Chester town, VT - homes for sale

42 of 42 results displayed

New
$149,000Active
17.7 Acres
0 Trebo Road, Chester, VT 05143
MLS# 5102503Listed by: ENGEL & VOLKERS OKEMO
New
$359,000Active
2 beds 1 baths900 sq. ft.
302 Davidson Hill Road, Chester, VT 05143
MLS# 5102316Listed by: VERMONT REAL ESTATE COMPANY
New
$250,000Active
3 beds -- baths1,500 sq. ft.
3781 Flamstead Road, Chester, VT 05143
MLS# 5102142Listed by: EXP REALTY
$175,000Pending
3 beds 2 baths1,379 sq. ft.
641 Depot Street, Chester, VT 05143
MLS# 5100719Listed by: BARRETT AND VALLEY ASSOCIATES INC.
New
$100,000Active
0.55 Acres
427 Depot Street, Chester, VT 05143
MLS# 5100755Listed by: KW COASTAL AND LAKES & MOUNTAINS REALTY/HANOVER
$79,900Pending
3.85 Acres
734 Gould Road, Chester, VT 05143
MLS# 5100498Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$925,000Active
5 beds 3 baths2,850 sq. ft.
1470 Popple Dungeon Road, Chester, VT 05143
MLS# 5099745Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$229,000Active
27.8 Acres
00 Quarry Road, Chester, VT 01543
MLS# 5098347Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$199,000Active
2 beds 1 baths732 sq. ft.
1372 Potash Brook Road, Chester, VT 05143
MLS# 5098053Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$750,000Active
3 beds 2 baths1,695 sq. ft.
955 Smokeshire Road, Chester, VT 05143
MLS# 5097722Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$649,000Active
3 beds 2 baths2,204 sq. ft.
168 Chandler Road, Chester, VT 05143
MLS# 5097737Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$249,500Active
4 beds 3 baths1,922 sq. ft.
3668 VT Route 103 North, Chester, VT 05143
MLS# 5097620Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$789,000Active
5 beds 3 baths4,388 sq. ft.
223 Coach Road, Chester, VT 05143
MLS# 5097600Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$880,000Active
3 beds 3 baths3,000 sq. ft.
330 Spruce Drive, Andover, VT 05143
MLS# 5096214Listed by: MARY MITCHELL MILLER REAL ESTATE
$450,000Active
5 beds 4 baths3,865 sq. ft.
81 Main Street, Chester, VT 05143
MLS# 5095551Listed by: REAL BROKER LLC
$489,000Active
3 beds 2 baths1,626 sq. ft.
3208 Green Mountain Turnpike, Chester, VT 05143
MLS# 5095486Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$495,000Active
3 beds 2 baths1,800 sq. ft.
3078 VT Route 10, Chester, VT 05143
MLS# 5095371Listed by: KELLEY REAL ESTATE, INC.
$87,500Active
10.4 Acres
00 Snell Road, Chester, VT 05143
MLS# 5094246Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$85,000Active
5 Acres
0 Linden Way, Chester, VT 05143
MLS# 5093908Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$75,000Active
2 beds 1 baths620 sq. ft.
1144 Potash Brook Road, Chester, VT 05143
MLS# 5093286Listed by: BUFFUM REALTY
$138,000Active
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
$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
$469,000Active
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
$119,000Active
7.95 Acres
0 Green Mountain Turnpike #5, Chester, VT 05143
MLS# 5081034Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$99,999Active
3.24 Acres
508 Mattson Road, Chester, VT 05143
MLS# 5082636Listed by: CUMMINGS & CO
$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
$299,000Active
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
$159,000Active
5 Acres
00 Contro Road, Chester, VT 05143
MLS# 5069927Listed by: BRATTLEBORO AREA REALTY
$289,000Pending
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
$290,000Active
75 Acres
1175 Quarry Road, Chester, VT 05143
MLS# 5058824Listed by: BHG MASIELLO KEENE
$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.

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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 July 31, 2026 NH_NNEREN Member Broker: Stephen DeStefano

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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.