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Chester, VT
Map
48 Properties Available

48 Properties Available

The average price in the selected areas has remained stable. Learn more
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40 The Common, Chester, VT 05143
1/60
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
1/53
Price Dropped by $200K

$1,490,000

5 Beds5 Baths5,400 SqFt

1302 Popple Dungeon RD, Chester, VT 05143

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

PrimeMLS
76 Goldthwaite RD, Chester, VT 05143
1/39
Active

$1,200,000

4 Beds3 Baths3,308 SqFt

76 Goldthwaite RD, Chester, VT 05143

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

PrimeMLS
1470 Popple Dungeon RD, Chester, VT 05143
1/58
Active

$925,000

5 Beds3 Baths2,850 SqFt

1470 Popple Dungeon RD, Chester, VT 05143

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

PrimeMLS
223 Coach RD, Chester, VT 05143
1/44
Price Dropped by $60K

$789,000

5 Beds3 Baths4,388 SqFt

223 Coach RD, Chester, VT 05143

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
955 Smokeshire RD, Chester, VT 05143
1/59
Under Contract

$750,000

3 Beds2 Baths1,695 SqFt

955 Smokeshire RD, Chester, VT 05143

Listed by Katherine K Burns of William Raveis Real Estate Vermont Properties Off: 802-228-8877

PrimeMLS
3630 VT RT 103 N, Chester, VT 05143
1/30
Active

$650,000

2 Acres Lot

3630 VT RT 103 N, Chester, VT 05143

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
1/30
Active

$650,000

3 Beds3 Baths4,324 SqFt

3630 Vt Route 103 N, Chester, VT 05143

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

PrimeMLS
168 Chandler RD, Chester, VT 05143
1/60
Active

$649,000

3 Beds2 Baths2,204 SqFt

168 Chandler RD, Chester, VT 05143

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

PrimeMLS
688 Hidden Heights RD, Chester, VT 05143
1/60
Active

$649,000

3 Beds2 Baths2,205 SqFt

688 Hidden Heights RD, Chester, VT 05143

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

PrimeMLS
3341 Trebo RD, Chester, VT 05143
1/47
Under Contract

$549,000

4 Beds3 Baths2,464 SqFt

3341 Trebo RD, Chester, VT 05143

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
3078 VT Route 10, Chester, VT 05143
1/60
Under Contract

$495,000

3 Beds2 Baths1,800 SqFt

3078 VT Route 10, Chester, VT 05143

Listed by Tyleen Murray of Kelley Real Estate, Inc.

PrimeMLS
3208 Green Mountain TPKE, Chester, VT 05143
1/34
Active

$489,000

3 Beds2 Baths1,626 SqFt

3208 Green Mountain TPKE, Chester, VT 05143

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

PrimeMLS
64 Maple ST, Chester, VT 05143
1/60
Price Dropped by $10K
3D

$469,000

3 Beds3 Baths2,676 SqFt

64 Maple ST, Chester, VT 05143

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
81 Main ST, Chester, VT 05143
1/58
Price Dropped by $10K
3D

$450,000

5 Beds4 Baths3,865 SqFt

81 Main ST, Chester, VT 05143

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
176 Meadow RD, Chester, VT 05143
1/43
Price Dropped by $5K

$419,900

5 Beds2 Baths1,982 SqFt

176 Meadow RD, Chester, VT 05143

Listed by Lauren Behm of Berkshire Hathaway HomeServices Stratton Home

PrimeMLS
40 Fenton RD, Chester, VT 05143
1/37
Active

$399,000

4 Beds3 Baths2,148 SqFt

40 Fenton RD, Chester, VT 05143

Listed by John M Napier of TPW Real Estate

PrimeMLS
663 Depot ST, Chester, VT 05143
1/51
Under Contract

$390,000

3 Beds2 Baths1,304 SqFt

663 Depot ST, Chester, VT 05143

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
145 South Main ST, Chester, VT 05143
1/10
Active

$385,000

0.8 Acres Lot

145 South Main ST, Chester, VT 05143

Listed by The Nancy Jenkins Team of Nancy Jenkins Real Estate

PrimeMLS
302 Davidson Hill RD, Chester, VT 05143
1/27
Open Sun 1PM-3PM

$359,000

2 Beds1 Bath900 SqFt

302 Davidson Hill RD, Chester, VT 05143

Listed by Tyler Buswell of Vermont Real Estate Company

PrimeMLS
397 River ST, Chester, VT 05143
1/41
Under Contract

$325,000

4 Beds3 Baths3,332 SqFt

397 River ST, Chester, VT 05143

Listed by Lisa Kelley of Cummings & Co

PrimeMLS
1397 Popple Dungeon RD, Chester, VT 05143
1/31
Price Dropped by $50K

$299,000

3 Beds2 Baths1,788 SqFt

1397 Popple Dungeon RD, Chester, VT 05143

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
1175 Quarry RD, Chester, VT 05143
1/20
Active

$290,000

75 Acres

1175 Quarry RD, Chester, VT 05143

Listed by Jessica Samples of BHG Masiello Keene

PrimeMLS
106 Contro RD, Chester, VT 05143
1/14
Under Contract

$289,000

2 Beds3 Baths1,475 SqFt

106 Contro RD, Chester, VT 05143

Listed by Christine M Lewis of Brattleboro Area Realty

PrimeMLS
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EV_Villa_RGB_TM
Engel & Völkers
Caleb DeVries
36 Maplewood Ave, Portsmouth, NH, 03801, USA

+1(603) 937-7784

caleb.devries@engelvoelkers.com

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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.

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EV_Villa_RGB_TM
Engel & Völkers
Caleb DeVries
36 Maplewood Ave, Portsmouth, NH, 03801, USA

+1(603) 937-7784

caleb.devries@engelvoelkers.com

Get My App

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.

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

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