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

NNEREN
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 168 Chandler Road Chester, VT MLS# 5097737
  • Recently Listed with 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

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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 3078 VT Route 10 Chester, VT MLS# 5095371
Save 3078 VT Route 10 Chester, VT MLS# 5095371
1 of 60
$495,000
3

Beds

2.0

Baths

1,800

Sq.Ft.

3078 VT Route 10

Chester, VT

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Courtesy of KELLEY REAL ESTATE, INC.
View 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
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Save 3208 Green Mountain Turnpike Chester, VT MLS# 5095486
1 of 34
$489,000
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
$475,000
5

Beds

4.0

Baths

3,865

Sq.Ft.

81 Main Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 64 Maple Street Chester, VT MLS# 5087175
  • Virtual Tour
Save 64 Maple Street Chester, VT MLS# 5087175
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 34 School Street Chester, VT MLS# 5097413
  • Recently Listed
Save 34 School Street Chester, VT MLS# 5097413
1 of 7
$465,000
3,940

Sq.Ft.

34 School Street

Chester, VT

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Courtesy of NANCY JENKINS REAL ESTATE
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 145 South Main Street Chester, VT MLS# 5097411
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Save 145 South Main Street Chester, VT MLS# 5097411
1 of 10
$385,000
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
$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
Save 397 River Street Chester, VT MLS# 5087965
1 of 41
$325,000
4

Beds

3.0

Baths

3,332

Sq.Ft.

397 River Street

Chester, VT

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Courtesy of CUMMINGS & CO
View 447 Elm Street Chester, VT MLS# 5061241
Save 447 Elm Street Chester, VT MLS# 5061241
1 of 30
$299,000
3

Beds

2.0

Baths

1,488

Sq.Ft.

447 Elm Street

Chester, VT

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Courtesy of CUMMINGS & CO
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 3668 VT Route 103 North Chester, VT MLS# 5097620
  • Recently Listed
Save 3668 VT Route 103 North Chester, VT MLS# 5097620
1 of 38
$249,500
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
  • Recently Listed
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 000 Green Mountain Turnpike Chester, VT MLS# 5023272
Save 000 Green Mountain Turnpike Chester, VT MLS# 5023272
1 of 22
$249,000
Studio

Beds

0.0

Baths

000 Green Mountain Turnpike

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.

About Chester

Listings in Chester, VT

42

Estimated median home price

$289,500
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 5
$100K - 200K 11
$200K - 300K 7
$300K - 400K 4
$400K - 500K 5
$500K - 600K 1
$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 20
Townhouse 0
Condo 0
Commercial 5
Rental 3
Lots and Land 15
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 7/11/2026)

Find Properties in Chester, VT

Chester, VT Information

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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 7/12/2026”

Trends Information provided by ATTOM Data Solutions.