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
View 688 Hidden Heights Road Chester, VT MLS# 5074094
Save 688 Hidden Heights Road Chester, VT MLS# 5074094
1 of 60
$649,000
3

Beds

2.0

Baths

2,205

Sq.Ft.

688 Hidden Heights Road

Chester, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 147 Pleasant View Lane Chester, VT MLS# 5084462
Save 147 Pleasant View Lane Chester, VT MLS# 5084462
1 of 53
$569,000
3

Beds

2.0

Baths

2,966

Sq.Ft.

147 Pleasant View Lane

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3341 Trebo Road Chester, VT MLS# 5086105
  • Recently Listed
Save 3341 Trebo Road Chester, VT MLS# 5086105
1 of 47
$569,000
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 514 First Avenue Chester, VT MLS# 5068855
Save 514 First Avenue Chester, VT MLS# 5068855
1 of 37
$529,000
5

Beds

5.0

Baths

3,880

Sq.Ft.

514 First Avenue

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 547 Williams Road Chester, VT MLS# 5085214
Save 547 Williams Road Chester, VT MLS# 5085214
1 of 60
$479,000
3

Beds

2.0

Baths

1,320

Sq.Ft.

547 Williams Road

Chester, VT

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Courtesy of EDGE REALTY VERMONT
View 64 Maple Street Chester, VT MLS# 5087175
  • Recently Listed with Virtual Tour
Save 64 Maple Street Chester, VT MLS# 5087175
1 of 60
$479,000
4

Beds

3.0

Baths

2,676

Sq.Ft.

64 Maple Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 183 Vt Rt 103 Chester, VT MLS# 5084571
Save 183 Vt Rt 103 Chester, VT MLS# 5084571
1 of 3
$475,000
4,938

Sq.Ft.

183 Vt Rt 103

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 176 Meadow Road Chester, VT MLS# 5082995
Save 176 Meadow Road Chester, VT MLS# 5082995
1 of 43
$425,000
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
  • New Construction
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
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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 1397 Popple Dungeon Road Chester, VT MLS# 5073930
Save 1397 Popple Dungeon Road Chester, VT MLS# 5073930
1 of 31
$349,000
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 397 River Street Chester, VT MLS# 5087965
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Save 397 River Street Chester, VT MLS# 5087965
1 of 39
OPEN HOUSE: Saturday 5/16 11:00 AM - 1:00 PM
$349,000
4

Beds

3.0

Baths

3,332

Sq.Ft.

397 River Street

Chester, VT

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Courtesy of CUMMINGS & CO
View 335 North Street Chester, VT MLS# 5080199
Save 335 North Street Chester, VT MLS# 5080199
1 of 55
$340,000
3

Beds

1.0

Baths

2,096

Sq.Ft.

335 North Street

Chester, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 447 Elm Street Chester, VT MLS# 5061241
Save 447 Elm Street Chester, VT MLS# 5061241
1 of 29
$329,000
3

Beds

2.0

Baths

1,488

Sq.Ft.

447 Elm Street

Chester, VT

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Courtesy of CUMMINGS & CO
View 41 VT Route 103 South Chester, VT MLS# 5070146
  • Virtual Tour
Save 41 VT Route 103 South Chester, VT MLS# 5070146
1 of 33
$295,000
Studio

Beds

0.0

Baths

2,702

Sq.Ft.

41 VT Route 103 South

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 1175 Quarry Road Chester, VT MLS# 5058824
Save 1175 Quarry Road Chester, VT MLS# 5058824
1 of 20
$290,000
Studio

Beds

0.0

Baths

1175 Quarry Road

Chester, VT

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Courtesy of BHG MASIELLO KEENE
View 106 Contro Road Chester, VT MLS# 5069928
Save 106 Contro Road Chester, VT MLS# 5069928
1 of 14
$289,000
2

Beds

2.1

Baths

1,475

Sq.Ft.

106 Contro Road

Chester, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 15 Breezy Lane Chester, VT MLS# 5086079
  • Virtual Tour
Save 15 Breezy Lane Chester, VT MLS# 5086079
1 of 37
$270,000
2

Beds

1.0

Baths

1,026

Sq.Ft.

15 Breezy Lane

Chester, VT

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Courtesy of BUFFUM REALTY

About Chester

Listings in Chester, VT

41

Estimated median home price

$290,000
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 3
$100K - 200K 10
$200K - 300K 9
$300K - 400K 6
$400K - 500K 4
$500K - 600K 3
$600K - 700K 3
$700K - 800K 0
$800K - 900K 0
$900K - 1M 0
$1M - Max 3

Homes for Sale by Type in Chester, VT

Property Type Count
Single Family 21
Townhouse 0
Condo 0
Commercial 4
Rental 4
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 5/16/2026)

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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 5/16/2026”

Trends Information provided by ATTOM Data Solutions.