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35 Properties
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35 Properties Available In Chester

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VT >Chester >
Market Insights
40 The Common, Chester, VT 05143
Active

$1,495,000

40 The Common, Chester, VT 05143

Listed by Patrick Kelley of Real Broker LLC

PrimeMLS
1302 Popple Dungeon RD, Chester, VT 05143
Price Dropped by $200K

$1,490,000

1302 Popple Dungeon RD, Chester, VT 05143

5 Beds5 Baths5,400 SqFt

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
76 Goldthwaite RD, Chester, VT 05143
Active

$1,200,000

76 Goldthwaite RD, Chester, VT 05143

4 Beds3 Baths3,308 SqFt

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
3630 VT RT 103 N, Chester, VT 05143
Active

$650,000

3630 VT RT 103 N, Chester, VT 05143

2 Acres Lot

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
3630 Vt Route 103 N, Chester, VT 05143
Active

$650,000

3630 Vt Route 103 N, Chester, VT 05143

3 Beds3 Baths4,324 SqFt

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
688 Hidden Heights RD, Chester, VT 05143
Active

$649,000

688 Hidden Heights RD, Chester, VT 05143

3 Beds2 Baths2,205 SqFt

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties Off: 802-228-8877

PrimeMLS
64 Maple ST, Chester, VT 05143
3D
Active

$479,000

64 Maple ST, Chester, VT 05143

3 Beds3 Baths2,676 SqFt

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
40 Fenton RD, Chester, VT 05143
Active

$399,000

40 Fenton RD, Chester, VT 05143

4 Beds3 Baths2,148 SqFt

Listed by John M Napier of TPW Real Estate

PrimeMLS
663 Depot ST, Chester, VT 05143
Active

$390,000

663 Depot ST, Chester, VT 05143

3 Beds2 Baths1,304 SqFt

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
1397 Popple Dungeon RD, Chester, VT 05143
Price Dropped by $50K

$349,000

1397 Popple Dungeon RD, Chester, VT 05143

3 Beds2 Baths1,788 SqFt

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
397 River ST, Chester, VT 05143
Price Dropped by $24K

$325,000

397 River ST, Chester, VT 05143

4 Beds3 Baths3,332 SqFt

Listed by Lisa Kelley of Cummings & Co

PrimeMLS
447 Elm ST, Chester, VT 05143
Price Dropped by $30K

$299,000

447 Elm ST, Chester, VT 05143

3 Beds2 Baths1,488 SqFt

Listed by Lisa Kelley of Cummings & Co

PrimeMLS
41 VT Route 103 South, Chester, VT 05143
3D
Price Dropped by $4K

$295,000

41 VT Route 103 South, Chester, VT 05143

2,702 SqFt

Listed by Glenn Olney of Barrett and Valley Associates Inc.

PrimeMLS
1175 Quarry RD, Chester, VT 05143
Active

$290,000

1175 Quarry RD, Chester, VT 05143

75 Acres

Listed by Jessica Samples of BHG Masiello Keene

PrimeMLS
106 Contro RD, Chester, VT 05143
Active

$289,000

106 Contro RD, Chester, VT 05143

2 Beds3 Baths1,475 SqFt

Listed by Christine M Lewis of Brattleboro Area Realty

PrimeMLS
000 Green Mountain TPKE, Chester, VT 05143
Price Dropped by $26K

$249,000

000 Green Mountain TPKE, Chester, VT 05143

84 Acres

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
00 Quarry RD, Chester, VT 05143
Active

$229,000

00 Quarry RD, Chester, VT 05143

27.8 Acres

Listed by Gail Beardmore of Engel & Volkers Okemo Cell: 802-236-5431

PrimeMLS
160 Depot ST, Chester, VT 05143
Active

$225,000

160 Depot ST, Chester, VT 05143

3 Beds1 Bath1,327 SqFt

Listed by Joshua Lemieux of Remax Summit

PrimeMLS
00 Vermont Route 103, Chester, VT 05143
Active

$200,000

00 Vermont Route 103, Chester, VT 05143

6.63 Acres

Listed by Rachael Rogala of Rachael Rogala Inc.

PrimeMLS
377 Coach RD #Lot #15, Chester, VT 05143
Active

$175,000

377 Coach RD #Lot #15, Chester, VT 05143

12.51 Acres

Listed by Elissa Scully of Mary W. Davis Realtor & Assoc., Inc. Off: 802-228-8811

PrimeMLS
3019 Popple Dungeon RD, Chester, VT 05143
Active

$169,000

3019 Popple Dungeon RD, Chester, VT 05143

1 Bed1 Bath200 SqFt

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
3553 VT Route 103 N, Chester, VT 05143
Active

$164,000

3553 VT Route 103 N, Chester, VT 05143

0.75 Acres Lot

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
00 Contro RD, Chester, VT 05143
Active

$159,000

00 Contro RD, Chester, VT 05143

5 Acres

Listed by Christine M Lewis of Brattleboro Area Realty

PrimeMLS
250 Fenton RD, Chester, VT 05148
Active

$153,000

250 Fenton RD, Chester, VT 05148

4.7 Acres

Listed by Rachel Febbie of EXP Realty Cell: 802-375-5502

PrimeMLS
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Gibson Sotheby's International Realty

Mike Quail License ID: 9539367

+1(978) 406-9294 mike@thequailgroup.com

21 Central St Manchester MA 01944

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      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. Mortgage Calculator
      5. Affordability Calculator
      6. Recent Listings
      Sell
      1. Home Valuation
      2. Sell My Home
      Services
      About
      1. About Me
      2. My Resume
      3. Contact Us
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      5. Client Survey
      Market Snapshot
      Partner Lender
Gibson Sotheby's International Realty

Mike Quail License ID: 9539367

+1(978) 406-9294 mike@thequailgroup.com

21 Central St Manchester MA 01944

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.