Chester town, VT Properties for Sale with Local Expertise | ERA

42 of 42 results displayed

New
$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
New
$149,900Active
2 beds 1 baths1,120 sq. ft.
4351 Vermont RT 11 West, Chester, VT 05143
MLS# 5067061Listed by: BRATTLEBORO AREA REALTY
$448,888Active
4 beds 2 baths1,728 sq. ft.
4877 VT Route 103, Chester, VT 05143
MLS# 5064343Listed by: EXP REALTY
$199,000Active
2 beds 3 baths1,640 sq. ft.
1833 Mattson Road, Chester, VT 05143
MLS# 5063899Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$895,000Active
4 beds 4 baths2,775 sq. ft.
725 Flamstead Road, Chester, VT 05143
MLS# 5063387Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$329,000Active
3 beds 2 baths1,525 sq. ft.
870 Cummings Road, Chester, VT 05143
MLS# 5063236Listed by: BUFFUM REALTY
$549,000Active
3 beds 4 baths2,256 sq. ft.
246 Putnam Hill Road, Chester, VT 05143
MLS# 5062155Listed by: ENGEL & VOLKERS OKEMO
$74,000Active
15.5 Acres
00 Remington Road, Chester, VT 05143
MLS# 5061671Listed by: BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
$349,000Active
2 beds 1 baths803 sq. ft.
1470 Flamstead Road, Chester, VT 05143
MLS# 5061244Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$389,000Active
3 beds 2 baths1,488 sq. ft.
447 Elm Street, Chester, VT 05143
MLS# 5061241Listed by: CUMMINGS & CO
$189,900Pending
3 beds 2 baths960 sq. ft.
284 Flamstead Road, Chester, VT 05143
MLS# 5061165Listed by: HIGHLAND REALTY
$599,900Active
4 beds 3 baths2,689 sq. ft.
1573 Flamstead Road, Chester, VT 05143
MLS# 5060829Listed by: BHG MASIELLO KEENE
$229,000Active
1 beds 1 baths528 sq. ft.
106 Hall Road, Chester, VT 05143
MLS# 5059814Listed by: REAL BROKER LLC
$145,000Active
22.23 Acres
918 Lovers Lane Road, Chester, VT 05143
MLS# 5058859Listed by: NORTHLAND REAL ESTATE
$300,000Active
75 Acres
1175 Quarry Road, Chester, VT 05143
MLS# 5058824Listed by: BHG MASIELLO KEENE
$425,000Active
4 beds 2 baths2,562 sq. ft.
26 Main Street, Chester, VT 05143
MLS# 5058562Listed by: ENGEL & VOLKERS OKEMO
$249,500Active
1 beds 1 baths1,424 sq. ft.
2739 Route 11, Chester, VT 05143
MLS# 5058302Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$879,000Active
2 beds 2 baths1,576 sq. ft.
1342 Old Stage Road, Chester, VT 05143
MLS# 5056637Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$685,000Active
3 beds 2 baths2,205 sq. ft.
688 Hidden Heights Road, Chester, VT 05143
MLS# 5055278Listed by: WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
$625,000Active
4 beds 3 baths2,794 sq. ft.
95 Church Street, Chester, VT 05143
MLS# 5054818Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$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 baths1,024 sq. ft.
442 103 S, Chester, VT 05143
MLS# 5052054Listed by: LANGE & LANGE
$339,900Active
2 beds 1 baths900 sq. ft.
302 Davidson Hill Road, Chester, VT 05143
MLS# 5051283Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$85,000Active
1.82 Acres
0 Remington Road #7, Chester, VT 05143
MLS# 5049898Listed by: DIAMOND REALTY
$55,000Active
1.52 Acres
0 Remington Road #11, Chester, VT 05143
MLS# 5049900Listed by: DIAMOND REALTY
$1,125,000Active
4 beds 3 baths2,772 sq. ft.
157 Thompson Road, Chester, VT 05143
MLS# 5048851Listed by: WINHALL REAL ESTATE
$239,000Active
3 beds 1 baths1,440 sq. ft.
419 Coach Road, Chester, VT 05143
MLS# 5048752Listed by: LOWE'S REAL ESTATE, LLC
$599,000Active
7 beds 4 baths3,850 sq. ft.
534 Elm Street, Chester, VT 05143
MLS# 5047552Listed by: KELLEY REAL ESTATE, INC.
$225,000Active
3 beds 1 baths1,327 sq. ft.
160 Depot Street, Chester, VT 05143
MLS# 5047277Listed by: REMAX SUMMIT
$395,000Active
6 beds 1 baths2,308 sq. ft.
525 Route 103 N, Chester, VT 05143
MLS# 5047187Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$594,000Active
5 beds 4 baths3,470 sq. ft.
1057 Quarry Road, Chester, VT 05143
MLS# 5047173Listed by: MARY W. DAVIS REALTOR & ASSOC., INC.
$95,000Pending
3.24 Acres
Lot 3 Mattson Road, Chester, VT 05143
MLS# 5045357Listed by: CUMMINGS & CO
$998,000Active
4 beds 4 baths3,920 sq. ft.
1847 Trebo Road, Chester, VT 05143
MLS# 5048707Listed by: FOUR SEASONS SOTHEBY'S INT'L REALTY
$625,000Active
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
$399,000Active
4 beds 4 baths2,710 sq. ft.
491 Farrar Road, Chester, VT 05143
MLS# 5044528Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$495,000Active
6 beds 5 baths3,217 sq. ft.
423 Main Street, Chester, VT 05142
MLS# 5034061Listed by: DIAMOND REALTY
$275,000Active
91 Acres
000 Green Mountain Turnpike, Chester, VT 05143
MLS# 5023272Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$169,000Pending
-- beds 4 baths3,024 sq. ft.
515 Main Street, Chester, VT 05143
MLS# 5007795Listed by: BARRETT AND VALLEY ASSOCIATES INC.
$95,000Active
10.4 Acres
0 Snell Road, Chester, VT 05143
MLS# 4999159Listed by: ENGEL & VOLKERS OKEMO
$219,000Active
27.8 Acres
00 Quarry Road, Chester, VT 05143
MLS# 4982433Listed by: ENGEL & VOLKERS OKEMO

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Copyright 2025 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 3, 2025

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About ERA real estate blog Franchise ERA global Contact us

Buy and sell

Sell information ERA Distinctive Properties All homes for sale All real estate agents All real estate offices

Resources

Find an agent Join ERA Offices

Terms of use Accessibility statement DMCA notice Fraud alert Privacy notice Fair housing Do not sell or share my personal information Submit agent or broker complaint

Protect your home and budget with an American Home Shield© home warranty. Learn more

© 2023 - 2025 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.