View 23 School Street Chester, VT MLS# 5111465
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Save 23 School Street Chester, VT MLS# 5111465
1 of 15
$649,000
0.0

Baths

13,788

Sq.Ft.

23 School Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 3537 Popple Dungeon Road Chester, VT MLS# 5110600
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Save 3537 Popple Dungeon Road Chester, VT MLS# 5110600
1 of 22
$249,900
2

Beds

1.0

Baths

930

Sq.Ft.

3537 Popple Dungeon Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 1673 Dean Brook Road Chester, VT MLS# 5108359
Save 1673 Dean Brook Road Chester, VT MLS# 5108359
1 of 13
$29,900
0.0

Baths

1673 Dean Brook Road

Chester, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 1260 Grafton Road Chester, VT MLS# 5107796
Save 1260 Grafton Road Chester, VT MLS# 5107796
1 of 50
$700,000
2

Beds

3.0

Baths

1,556

Sq.Ft.

1260 Grafton Road

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 548 Crow Hill Road Chester, VT MLS# 5106579
Save 548 Crow Hill Road Chester, VT MLS# 5106579
1 of 47
$599,000
4

Beds

2.0

Baths

1,908

Sq.Ft.

548 Crow Hill Road

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3713 Trebo Road Chester, VT MLS# 5106191
Save 3713 Trebo Road Chester, VT MLS# 5106191
1 of 28
$289,900
3

Beds

2.1

Baths

1,508

Sq.Ft.

3713 Trebo Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 159 Lower Bartonsville Road Chester, VT MLS# 5106226
Save 159 Lower Bartonsville Road Chester, VT MLS# 5106226
1 of 23
$255,000
3

Beds

1.1

Baths

1,683

Sq.Ft.

159 Lower Bartonsville Road

Chester, VT

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Courtesy of CENTURY 21 HIGHVIEW REALTY
View 0 Trebo Road Chester, VT MLS# 5102503
Save 0 Trebo Road Chester, VT MLS# 5102503
1 of 12
$149,000
0.0

Baths

0 Trebo Road

Chester, VT

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Courtesy of ENGEL & VOLKERS OKEMO
View 302 Davidson Hill Road Chester, VT MLS# 5102316
Save 302 Davidson Hill Road Chester, VT MLS# 5102316
1 of 43
$330,000
2

Beds

1.0

Baths

900

Sq.Ft.

302 Davidson Hill Road

Chester, VT

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Courtesy of VERMONT REAL ESTATE COMPANY
View 3781 Flamstead Road Chester, VT MLS# 5102142
Save 3781 Flamstead Road Chester, VT MLS# 5102142
1 of 60
$225,000
3

Beds

2.0

Baths

1,500

Sq.Ft.

3781 Flamstead Road

Chester, VT

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Courtesy of EXP REALTY
View 3781 Flamstead Road Chester, VT MLS# 5102143
Save 3781 Flamstead Road Chester, VT MLS# 5102143
1 of 59
$225,000
0.0

Baths

3781 Flamstead Road

Chester, VT

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Courtesy of EXP REALTY
View 427 Depot Street Chester, VT MLS# 5100755
Save 427 Depot Street Chester, VT MLS# 5100755
1 of 22
$100,000
0.0

Baths

427 Depot Street

Chester, VT

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Courtesy of KW COASTAL AND LAKES & MOUNTAINS REALTY/HANOVER
View 39 S Main Street Chester, VT MLS# 5100522
Save 39 S Main Street Chester, VT MLS# 5100522
1 of 9
$285,000
1,802

Sq.Ft.

39 S Main Street

Chester, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 00 Quarry Road Chester, VT MLS# 5098347
Save 00 Quarry Road Chester, VT MLS# 5098347
1 of 25
$229,000
0.0

Baths

00 Quarry Road

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3668 VT Route 103 North Chester, VT MLS# 5097620
Save 3668 VT Route 103 North Chester, VT MLS# 5097620
1 of 38
$229,500
4

Beds

2.1

Baths

1,922

Sq.Ft.

3668 VT Route 103 North

Chester, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 3668 VT Route 103 North Chester, VT MLS# 5097621
Save 3668 VT Route 103 North Chester, VT MLS# 5097621
1 of 38
$249,500
4

Beds

3.0

Baths

1,922

Sq.Ft.

3668 VT Route 103 North

Chester, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 168 Chandler Road Chester, VT MLS# 5097737
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Save 168 Chandler Road Chester, VT MLS# 5097737
1 of 60
$649,000
3

Beds

2.0

Baths

2,204

Sq.Ft.

168 Chandler Road

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
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Save 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
1 of 33
$449,000
3

Beds

2.0

Baths

1,626

Sq.Ft.

3208 Green Mountain Turnpike

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 81 Main Street Chester, VT MLS# 5095551
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Save 81 Main Street Chester, VT MLS# 5095551
1 of 58
$445,000
5

Beds

4.0

Baths

3,865

Sq.Ft.

81 Main Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 0 Linden Way Chester, VT MLS# 5093908
Save 0 Linden Way Chester, VT MLS# 5093908
1 of 22
$79,000
0.0

Baths

0 Linden Way

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.

About Chester

Listings in Chester, VT

44

Estimated median home price

$262,500
Chester VT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chester, Vermont real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chester, VT.

Homes for Sale by Price in Chester, VT

Price Count
$0 - 100K 8
$100K - 200K 6
$200K - 300K 12
$300K - 400K 3
$400K - 500K 4
$500K - 600K 2
$600K - 700K 5
$700K - 800K 1
$800K - 900K 1
$900K - 1M 0
$1M - Max 2

Homes for Sale by Type in Chester, VT

Property Type Count
Single Family 21
Townhouse 0
Condo 0
Commercial 3
Rental 1
Lots and Land 15
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 2
Farms 0

(Data as of 9/25/2026)

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Information deemed reliable but not guaranteed.

“Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 10/1/2026”

Trends Information provided by ATTOM Data Solutions.