View 147 Pleasant View Lane Chester, VT MLS# 5084462
$569,000
3

Beds

2.0

Baths

2,966

Sq.Ft.

147 Pleasant View Lane

Chester, VT

NNEREN
Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3341 Trebo Road Chester, VT MLS# 5086105
$549,000
4

Beds

2.1

Baths

2,464

Sq.Ft.

3341 Trebo Road

Chester, VT

NNEREN
Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 64 Maple Street Chester, VT MLS# 5087175
  • Virtual Tour
1 of 60
$479,000
3

Beds

3.0

Baths

2,676

Sq.Ft.

64 Maple Street

Chester, VT

NNEREN
Courtesy of REAL BROKER LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 547 Williams Road Chester, VT MLS# 5085214
$474,900
3

Beds

2.0

Baths

1,320

Sq.Ft.

547 Williams Road

Chester, VT

NNEREN
Courtesy of EDGE REALTY VERMONT
View 40 Fenton Road Chester, VT MLS# 5073147
  • New Construction
1 of 37
$399,000
4

Beds

2.1

Baths

2,148

Sq.Ft.

40 Fenton Road

Chester, VT

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

Beds

2.0

Baths

1,304

Sq.Ft.

663 Depot Street

Chester, VT

NNEREN
Courtesy of REAL BROKER LLC
View 1397 Popple Dungeon Road Chester, VT MLS# 5073930
$349,000
3

Beds

2.0

Baths

1,788

Sq.Ft.

1397 Popple Dungeon Road

Chester, VT

NNEREN
Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 397 River Street Chester, VT MLS# 5087965
$349,000
4

Beds

3.0

Baths

3,332

Sq.Ft.

397 River Street

Chester, VT

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

Beds

1.0

Baths

2,096

Sq.Ft.

335 North Street

Chester, VT

NNEREN
Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 447 Elm Street Chester, VT MLS# 5061241
$299,000
3

Beds

2.0

Baths

1,488

Sq.Ft.

447 Elm Street

Chester, VT

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

Beds

0.0

Baths

2,702

Sq.Ft.

41 VT Route 103 South

Chester, VT

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

Beds

0.0

Baths

1175 Quarry Road

Chester, VT

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

Beds

2.1

Baths

1,475

Sq.Ft.

106 Contro Road

Chester, VT

NNEREN
Courtesy of BRATTLEBORO AREA REALTY
View 45 Dalrymple Street Chester, VT MLS# 5082324
$269,000
3

Beds

1.0

Baths

1,168

Sq.Ft.

45 Dalrymple Street

Chester, VT

NNEREN
Courtesy of BUFFUM REALTY
View 202 Mountain View Chester, VT MLS# 5088678
$250,000
3

Beds

1.1

Baths

1,140

Sq.Ft.

202 Mountain View

Chester, VT

NNEREN
Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 000 Green Mountain Turnpike Chester, VT MLS# 5023272
$249,000
Studio

Beds

0.0

Baths

000 Green Mountain Turnpike

Chester, VT

NNEREN
Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 00 Quarry Road Chester, VT MLS# 4982433
$229,000
Studio

Beds

0.0

Baths

00 Quarry Road

Chester, VT

NNEREN
Courtesy of ENGEL & VOLKERS OKEMO
View 160 Depot Street Chester, VT MLS# 5047277
$225,000
3

Beds

1.0

Baths

1,327

Sq.Ft.

160 Depot Street

Chester, VT

NNEREN
Courtesy of RE/MAX SUMMIT
View 00 Vermont Route 103 Chester, VT MLS# 5053371
$200,000
Studio

Beds

0.0

Baths

00 Vermont Route 103

Chester, VT

NNEREN
Courtesy of LANGE & LANGE
View 377 Coach Road # Lot #15 Chester, VT MLS# 5079082
$175,000
Studio

Beds

0.0

Baths

377 Coach Road # Lot #15

Chester, VT

NNEREN
Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.

About Chester

Listings in Chester, VT

38

Estimated median home price

$279,000
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 11
$200K - 300K 9
$300K - 400K 5
$400K - 500K 2
$500K - 600K 2
$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 19
Townhouse 0
Condo 0
Commercial 3
Rental 3
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 6/8/2026)

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 6/10/2026”

Trends Information provided by ATTOM Data Solutions.