View 1260 Grafton Road Chester, VT MLS# 5107796
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1 of 48
OPEN HOUSE: Saturday 9/5 12:00 PM - 2:00 PM
$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 3630 Vt Route 103 N Chester, VT MLS# 5044879
Save 3630 Vt Route 103 N Chester, VT MLS# 5044879
1 of 30
$650,000
3

Beds

3.0

Baths

4,324

Sq.Ft.

3630 Vt Route 103 N

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3630 Vt Rt 103 N Chester, VT MLS# 5044894
Save 3630 Vt Rt 103 N Chester, VT MLS# 5044894
1 of 30
$650,000
4,324

Sq.Ft.

3630 Vt Rt 103 N

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 548 Crow Hill Road Chester, VT MLS# 5106579
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Save 548 Crow Hill Road Chester, VT MLS# 5106579
1 of 47
OPEN HOUSE: Saturday 9/5 9:00 AM - 11:00 AM
$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 3341 Trebo Road Chester, VT MLS# 5086105
Save 3341 Trebo Road Chester, VT MLS# 5086105
1 of 47
$549,000
4

Beds

2.1

Baths

2,464

Sq.Ft.

3341 Trebo Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
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1 of 33
$479,000
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 64 Maple Street Chester, VT MLS# 5087175
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1 of 60
$469,000
3

Beds

3.0

Baths

2,676

Sq.Ft.

64 Maple Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 81 Main Street Chester, VT MLS# 5095551
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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 176 Meadow Road Chester, VT MLS# 5082995
Save 176 Meadow Road Chester, VT MLS# 5082995
1 of 43
$419,900
5

Beds

2.0

Baths

1,982

Sq.Ft.

176 Meadow Road

Chester, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 40 Fenton Road Chester, VT MLS# 5073147
Save 40 Fenton Road Chester, VT MLS# 5073147
1 of 37
$399,000
4

Beds

2.1

Baths

2,148

Sq.Ft.

40 Fenton Road

Chester, VT

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Courtesy of TPW REAL ESTATE
View 663 Depot Street Chester, VT MLS# 5086202
Save 663 Depot Street Chester, VT MLS# 5086202
1 of 51
$390,000
3

Beds

2.0

Baths

1,304

Sq.Ft.

663 Depot Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 302 Davidson Hill Road Chester, VT MLS# 5102316
Save 302 Davidson Hill Road Chester, VT MLS# 5102316
1 of 40
$354,000
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 145 South Main Street Chester, VT MLS# 5097411
Save 145 South Main Street Chester, VT MLS# 5097411
1 of 10
$340,000
3,608

Sq.Ft.

145 South Main Street

Chester, VT

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Courtesy of NANCY JENKINS REAL ESTATE
View 145 South Main Street Chester, VT MLS# 5107814
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$340,000
3

Beds

2.0

Baths

3,608

Sq.Ft.

145 South Main Street

Chester, VT

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Courtesy of NANCY JENKINS REAL ESTATE
View 1397 Popple Dungeon Road Chester, VT MLS# 5073930
Save 1397 Popple Dungeon Road Chester, VT MLS# 5073930
1 of 31
$299,000
3

Beds

2.0

Baths

1,788

Sq.Ft.

1397 Popple Dungeon Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
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 447 Elm Street Chester, VT MLS# 5104543
Save 447 Elm Street Chester, VT MLS# 5104543
1 of 25
$289,000
3

Beds

2.0

Baths

1,488

Sq.Ft.

447 Elm Street

Chester, VT

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Courtesy of BHG MASIELLO KEENE
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 1175 Quarry Road Chester, VT MLS# 5058824
Save 1175 Quarry Road Chester, VT MLS# 5058824
1 of 25
$270,000
Studio

Beds

0.0

Baths

1175 Quarry Road

Chester, VT

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Courtesy of BHG MASIELLO KEENE

About Chester

Listings in Chester, VT

46

Estimated median home price

$287,000
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 5
$400K - 500K 4
$500K - 600K 2
$600K - 700K 4
$700K - 800K 1
$800K - 900K 1
$900K - 1M 0
$1M - Max 3

Homes for Sale by Type in Chester, VT

Property Type Count
Single Family 22
Townhouse 0
Condo 0
Commercial 5
Rental 2
Lots and Land 15
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 1
Farms 0

(Data as of 9/5/2026)

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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 9/6/2026”

Trends Information provided by ATTOM Data Solutions.