View 1673 Dean Brook Road Chester, VT MLS# 5108359
  • Recently Listed
Save 1673 Dean Brook Road Chester, VT MLS# 5108359
1 of 13
$29,900
Studio

Beds

0.0

Baths

1673 Dean Brook Road

Chester, VT

NNEREN
Courtesy of SOUTHERN VERMONT REALTY GROUP
View 1260 Grafton Road Chester, VT MLS# 5107796
  • Recently Listed
Save 1260 Grafton Road Chester, VT MLS# 5107796
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

NNEREN
Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 145 South Main Street Chester, VT MLS# 5107814
  • Recently Listed
Save 145 South Main Street Chester, VT MLS# 5107814
1 of 10
$340,000
3

Beds

2.0

Baths

3,608

Sq.Ft.

145 South Main Street

Chester, VT

NNEREN
Courtesy of NANCY JENKINS REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 548 Crow Hill Road Chester, VT MLS# 5106579
  • Recently Listed
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

NNEREN
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

NNEREN
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
OPEN HOUSE: Saturday 9/5 11:00 AM - 1:00 PM
$255,000
3

Beds

1.1

Baths

1,683

Sq.Ft.

159 Lower Bartonsville Road

Chester, VT

NNEREN
Courtesy of CENTURY 21 HIGHVIEW REALTY
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

NNEREN
Courtesy of BHG MASIELLO KEENE
View 0 Trebo Road Chester, VT MLS# 5102503
Save 0 Trebo Road Chester, VT MLS# 5102503
1 of 12
$149,000
Studio

Beds

0.0

Baths

0 Trebo Road

Chester, VT

NNEREN
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 40
$354,000
2

Beds

1.0

Baths

900

Sq.Ft.

302 Davidson Hill Road

Chester, VT

NNEREN
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
$250,000
3

Beds

2.0

Baths

1,500

Sq.Ft.

3781 Flamstead Road

Chester, VT

NNEREN
Courtesy of EXP REALTY
View 3781 Flamstead Road Chester, VT MLS# 5102143
Save 3781 Flamstead Road Chester, VT MLS# 5102143
1 of 59
$250,000
Studio

Beds

0.0

Baths

3781 Flamstead Road

Chester, VT

NNEREN
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
Studio

Beds

0.0

Baths

427 Depot Street

Chester, VT

NNEREN
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

NNEREN
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
Studio

Beds

0.0

Baths

00 Quarry Road

Chester, VT

NNEREN
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

NNEREN
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

NNEREN
Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 168 Chandler Road Chester, VT MLS# 5097737
  • Virtual Tour
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

NNEREN
Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
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

NNEREN
Courtesy of NANCY JENKINS REAL ESTATE
View 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
  • Virtual Tour
Save 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
1 of 33
$479,000
3

Beds

2.0

Baths

1,626

Sq.Ft.

3208 Green Mountain Turnpike

Chester, VT

NNEREN
Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 81 Main Street Chester, VT MLS# 5095551
  • Virtual Tour
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

NNEREN
Courtesy of REAL BROKER LLC

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)

Find Properties in Chester, VT

Chester, VT Information

Find Properties by Zip

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 9/5/2026”

Trends Information provided by ATTOM Data Solutions.