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36 Properties
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36 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
Active

$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
1470 Popple Dungeon RD, Chester, VT 05143
Open Sun 10AM-12PM

$900,000

1470 Popple Dungeon RD, Chester, VT 05143

5 Beds3 Baths2,800 SqFt

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

PrimeMLS
223 Coach RD, Chester, VT 05143
Price Dropped by $60K

$789,000

223 Coach RD, Chester, VT 05143

5 Beds3 Baths4,388 SqFt

Listed by Daire Gibney of Barrett and Valley Associates Inc.

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
168 Chandler RD, Chester, VT 05143
Active

$649,000

168 Chandler RD, Chester, VT 05143

3 Beds2 Baths2,204 SqFt

Listed by Diane Rousseau of Four Seasons Sotheby's Int'l Realty Diane.Rousseau@FourSeasonsSIR.com

PrimeMLS
3208 Green Mountain TPKE, Chester, VT 05143
Price Dropped by $10K

$479,000

3208 Green Mountain TPKE, Chester, VT 05143

3 Beds2 Baths1,626 SqFt

Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty geralyn.donohue@fourseasonssir.com

PrimeMLS
81 Main ST, Chester, VT 05143
3D
Price Dropped by $10K

$450,000

81 Main ST, Chester, VT 05143

5 Beds4 Baths3,865 SqFt

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
176 Meadow RD, Chester, VT 05143
Price Dropped by $5K

$419,900

176 Meadow RD, Chester, VT 05143

5 Beds2 Baths1,982 SqFt

Listed by Lauren Behm of Berkshire Hathaway HomeServices Stratton Home

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
145 South Main ST, Chester, VT 05143
Active

$385,000

145 South Main ST, Chester, VT 05143

0.8 Acres Lot

Listed by The Nancy Jenkins Team of Nancy Jenkins Real Estate

PrimeMLS
302 Davidson Hill RD, Chester, VT 05143
Price Dropped by $5K

$354,000

302 Davidson Hill RD, Chester, VT 05143

2 Beds1 Bath900 SqFt

Listed by Tyler Buswell of Vermont Real Estate Company

PrimeMLS
3713 Trebo RD, Chester, VT 05143
New

$289,900

3713 Trebo RD, Chester, VT 05143

3 Beds3 Baths1,508 SqFt

Listed by Thaddeus J Abare of Barrett and Valley Associates Inc.

PrimeMLS
39 S Main ST, Chester, VT 05143
Active

$285,000

39 S Main ST, Chester, VT 05143

1,802 SqFt

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

PrimeMLS
1175 Quarry RD, Chester, VT 05143
Price Dropped by $20K

$270,000

1175 Quarry RD, Chester, VT 05143

75 Acres

Listed by Jessica Samples of BHG Masiello Keene

PrimeMLS
159 Lower Bartonsville RD, Chester, VT 05143
Open Sat 11AM-1PM

$255,000

159 Lower Bartonsville RD, Chester, VT 05143

3 Beds2 Baths1,683 SqFt

Listed by Abby Gerbick of Century 21 Highview Realty Off: 603-542-7766

PrimeMLS
3781 Flamstead RD, Chester, VT 05143
Active

$250,000

3781 Flamstead RD, Chester, VT 05143

10.02 Acres

Listed by Amy Hill of EXP Realty Cell: 802-299-7791

PrimeMLS
3668 VT Route 103 North, Chester, VT 05143
Active

$249,500

3668 VT Route 103 North, Chester, VT 05143

4 Beds3 Baths1,922 SqFt

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

PrimeMLS
000 Green Mountain TPKE, Chester, VT 05143
Active

$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 01543
Active

$229,000

00 Quarry RD, Chester, VT 01543

27.8 Acres

Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty geralyn.donohue@fourseasonssir.com

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
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
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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.