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38 Properties

38 Properties Available In Chester

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VT >Chester >
Market Insights
81 Main ST, Chester, VT 05143
3D

$450,000

Price Dropped by $10K

Single Family Home

5 Beds 4 Baths 3,865 SqFt

81 Main ST, Chester, VT 05143

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living spac...

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
64 Maple ST, Chester, VT 05143
3D

$469,000

Price Dropped by $10K

Single Family Home

3 Beds 3 Baths 2,676 SqFt

64 Maple ST, Chester, VT 05143

Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an ...

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
40 The Common, Chester, VT 05143
1/60 60

$1,495,000

Active

Commercial

40 The Common, Chester, VT 05143

A rare opportunity to own one of southern Vermont's most beloved hospitality landmarks. Located directly on the pictures...

Listed by Patrick Kelley of Real Broker LLC

PrimeMLS
302 Davidson Hill RD, Chester, VT 05143
1/27 27

$359,000

Open 8/9 1PM-3PM

Single Family Home

2 Beds 1 Bath 900 SqFt

302 Davidson Hill RD, Chester, VT 05143

This well built log home packs quite the punch. The open concept first floor spills out onto the generous front deck, es...

Listed by Tyler Buswell of Vermont Real Estate Company

PrimeMLS
1470 Popple Dungeon RD, Chester, VT 05143
1/58 58

$925,000

Active

Single Family Home

5 Beds 3 Baths 2,850 SqFt

1470 Popple Dungeon RD, Chester, VT 05143

Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a...

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties Off: 802-228-8877

PrimeMLS
1372 Potash Brook RD, Chester, VT 05143
1/22 22

$199,000

Price Dropped by $1K

Single Family Home

2 Beds 1 Bath 732 SqFt

1372 Potash Brook RD, Chester, VT 05143

Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inv...

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
223 Coach RD, Chester, VT 05143
1/44 44

$789,000

Price Dropped by $60K

Single Family Home

5 Beds 3 Baths 4,388 SqFt

223 Coach RD, Chester, VT 05143

Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on ...

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
168 Chandler RD, Chester, VT 05143
1/60 60

$649,000

Active

Single Family Home

3 Beds 2 Baths 2,204 SqFt

168 Chandler RD, Chester, VT 05143

Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacen...

Listed by Diane Rousseau of Four Seasons Sotheby's Int'l Realty Diane.Rousseau@FourSeasonsSIR.com

PrimeMLS
3668 VT Route 103 North, Chester, VT 05143
1/38 38

$249,500

Active

Single Family Home

4 Beds 3 Baths 1,922 SqFt

3668 VT Route 103 North, Chester, VT 05143

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based bu...

Listed by Dan Vigeant of Mary W. Davis Realtor & Assoc., Inc. Off: 802-228-8811

PrimeMLS
3208 Green Mountain TPKE, Chester, VT 05143
1/34 34

$489,000

Active

Single Family Home

3 Beds 2 Baths 1,626 SqFt

3208 Green Mountain TPKE, Chester, VT 05143

Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines mo...

Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty geralyn.donohue@fourseasonssir.com

PrimeMLS
1144 Potash Brook RD, Chester, VT 05143
1/17 17

$75,000

Active

Single Family Home

2 Beds 1 Bath 620 SqFt

1144 Potash Brook RD, Chester, VT 05143

Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced...

Listed by Julie Buffum of Buffum Realty

PrimeMLS
735 Main ST, Chester, VT 05143
1/11 11

$3,300

Active

Single Family Home

4 Beds 3 Baths 2,200 SqFt

735 Main ST, Chester, VT 05143

SUMMER SEASON RENTAL!! ...Lovely antique home within walking distance of Chester Village. Fully furnished, clean & comfo...

Listed by Team BVA Rentals of Barrett and Valley Associates Inc.

PrimeMLS
76 Goldthwaite RD, Chester, VT 05143
1/39 39

$1,200,000

Active

Single Family Home

4 Beds 3 Baths 3,308 SqFt

76 Goldthwaite RD, Chester, VT 05143

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acr...

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
1302 Popple Dungeon RD, Chester, VT 05143
1/53 53

$1,490,000

Price Dropped by $200K

Single Family Home

5 Beds 5 Baths 5,400 SqFt

1302 Popple Dungeon RD, Chester, VT 05143

Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. O...

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
32 S. Main ST ##7, Chester, VT 05143
1/8 8

$1,400

Active

Condo

2 Beds 1 Bath 750 SqFt

32 S. Main ST ##7, Chester, VT 05143

Traditional two bedroom apartment on Main Street in Chester. Walking distance to amenities. Coin-op laundry on site. $1...

Listed by Team BVA Rentals of Barrett and Valley Associates Inc.

PrimeMLS
688 Hidden Heights RD, Chester, VT 05143
1/60 60

$649,000

Active

Single Family Home

3 Beds 2 Baths 2,205 SqFt

688 Hidden Heights RD, Chester, VT 05143

Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views an...

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties Off: 802-228-8877

PrimeMLS
1397 Popple Dungeon RD, Chester, VT 05143
1/31 31

$299,000

Price Dropped by $50K

Single Family Home

3 Beds 2 Baths 1,788 SqFt

1397 Popple Dungeon RD, Chester, VT 05143

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here f...

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
40 Fenton RD, Chester, VT 05143
1/37 37

$399,000

Active

Single Family Home

4 Beds 3 Baths 2,148 SqFt

40 Fenton RD, Chester, VT 05143

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own san...

Listed by John M Napier of TPW Real Estate

PrimeMLS
3019 Popple Dungeon RD, Chester, VT 05143
1/20 20

$169,000

Active

Single Family Home

1 Bed 1 Bath 200 SqFt

3019 Popple Dungeon RD, Chester, VT 05143

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Br...

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
3630 Vt Route 103 N, Chester, VT 05143
1/30 30

$650,000

Active

Multi-Family

3 Beds 3 Baths 4,324 SqFt

3630 Vt Route 103 N, Chester, VT 05143

Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifull...

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty gary.coger@fourseasonssir.com

PrimeMLS
3781 Flamstead RD, Chester, VT 05143
1/59 59

$250,000

New

Vacant Land

10.02 Acres

3781 Flamstead RD, Chester, VT 05143

Ten beautiful acres on Flamstead Road in Chester, Vermont! Currently there is a 2 bedroom, 2 bathroom 1972 mobile home t...

Listed by Amy Hill of EXP Realty Cell: 802-299-7791

PrimeMLS
427 Depot ST, Chester, VT 05143
1/22 22

$100,000

New

Vacant Land

0.55 Acres

427 Depot ST, Chester, VT 05143

Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Stre...

Listed by Taylor Medeiros-Batey of KW Coastal and Lakes & Mountains Realty/Hanover

PrimeMLS
39 S Main ST, Chester, VT 05143
1/9 9

$285,000

Active

Commercial

1,802 SqFt

39 S Main ST, Chester, VT 05143

Do you hear the calling... This prime commercial building, located just south of Chester's famous town green, sits on a ...

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties Off: 802-228-8877

PrimeMLS
00 Quarry RD, Chester, VT 01543
1/19 19

$229,000

Active

Vacant Land

27.8 Acres

00 Quarry RD, Chester, VT 01543

27.8 +/- acre wooded parcel close to Chester Village with potential long range views. Driveway has been cut and a cleari...

Listed by Geralyn Donohue of Four Seasons Sotheby's Int'l Realty geralyn.donohue@fourseasonssir.com

PrimeMLS
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IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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Real Broker LLC

Mandolyn McIntyre Crow License ID: 082.0134671

+1(802) 683-1617 mandolynvt@gmail.com

39 Central St, Woodstock, VT, 05091, USA

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IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

SITE MAP

      Sellers
      Buyers
      Client Testimonials
      Join Us At Real
defaultdefault

Real Broker LLC

Mandolyn McIntyre Crow License ID: 082.0134671

+1(802) 683-1617 mandolynvt@gmail.com

39 Central St, Woodstock, VT, 05091, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility