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34 Properties

34 Properties Available In Chester

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VT >Chester >
Market Insights
64 Maple ST, Chester, VT 05143
3D

$479,000

New

Single Family Home

4 Beds 3 Baths 2,676 SqFt

64 Maple ST, Chester, VT 05143

Located in the village of Chester, this 4-bedroom, 3-bath property offers a rare amount of space and flexibility for an ...

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
663 Depot ST, Chester, VT 05143
1/51 51

$390,000

Active

Single Family Home

3 Beds 2 Baths 1,304 SqFt

663 Depot ST, Chester, VT 05143

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that's hard to find in an old...

Listed by Betsy Adamovich of Real Broker LLC

PrimeMLS
40 The Common, Chester, VT 05143
1/39 39

$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
397 River ST, Chester, VT 05143
1/39 39

$349,000

Open Sat 11AM-1PM

Single Family Home

4 Beds 3 Baths 3,332 SqFt

397 River ST, Chester, VT 05143

Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting ...

Listed by Lisa Kelley of Cummings & Co

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

$1,690,000

New

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
3341 Trebo RD, Chester, VT 05143
1/47 47

$569,000

Active

Single Family Home

4 Beds 3 Baths 2,464 SqFt

3341 Trebo RD, Chester, VT 05143

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and V...

Listed by Daire Gibney of Barrett and Valley Associates Inc.

PrimeMLS
547 Williams RD, Chester, VT 05143
1/60 60

$499,000

Active

Single Family Home

3 Beds 2 Baths 1,320 SqFt

547 Williams RD, Chester, VT 05143

Welcome to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, yet close to skiing, ...

Listed by Terri Edgerley of Edge Realty Vermont

PrimeMLS
147 Pleasant View LN, Chester, VT 05143
1/53 53

$595,000

Active

Single Family Home

3 Beds 2 Baths 2,966 SqFt

147 Pleasant View LN, Chester, VT 05143

Tucked away at the end of a quiet lane on three scenic acres, this well-maintained home offers a rare blend of privacy, ...

Listed by Jay Farrar of Four Seasons Sotheby's Int'l Realty

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
32 S. Main ST ##4, Chester, VT 05143
1/6 6

$1,100

Active

Condo

1 Bed 1 Bath 600 SqFt

32 S. Main ST ##4, Chester, VT 05143

Traditional one 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

$349,000

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
106 Contro RD, Chester, VT 05143
1/14 14

$289,000

Active

Single Family Home

2 Beds 3 Baths 1,475 SqFt

106 Contro RD, Chester, VT 05143

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and el...

Listed by Christine M Lewis of Brattleboro Area Realty

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
447 Elm ST, Chester, VT 05143
1/29 29

$329,000

Price Dropped by $20K

Single Family Home

3 Beds 2 Baths 1,488 SqFt

447 Elm ST, Chester, VT 05143

Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and...

Listed by Lisa Kelley of Cummings & Co

PrimeMLS
160 Depot ST, Chester, VT 05143
1/26 26

$225,000

Active

Single Family Home

3 Beds 1 Bath 1,327 SqFt

160 Depot ST, Chester, VT 05143

Don't miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of char...

Listed by Joshua Lemieux of Remax Summit

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
508 Mattson RD, Chester, VT 05143
1/12 12

$120,000

Active

Vacant Land

3.24 Acres

508 Mattson RD, Chester, VT 05143

This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this...

Listed by Jessica Citera of Cummings & Co

PrimeMLS
0 Green Mountain TPKE #5, Chester, VT 05143
1/9 9

$129,000

Active

Vacant Land

7.95 Acres

0 Green Mountain TPKE #5, Chester, VT 05143

Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, be...

Listed by Thaddeus J Abare of Barrett and Valley Associates Inc.

PrimeMLS
377 Coach RD #Lot #15, Chester, VT 05143
1/3 3

$175,000

Active

Vacant Land

12.51 Acres

377 Coach RD #Lot #15, Chester, VT 05143

Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and V...

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

PrimeMLS
TBD Farrar RD, Chester, VT 05143
1/18 18

$74,500

Active

Vacant Land

16.24 Acres

TBD Farrar RD, Chester, VT 05143

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This...

Listed by Erin Kendall of EXP Realty Phone: 802-579-5658

PrimeMLS
41 VT Route 103 South, Chester, VT 05143
3D

$299,000

Active

Multi-Family

2,702 SqFt

41 VT Route 103 South, Chester, VT 05143

Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the...

Listed by Glenn Olney of Barrett and Valley Associates Inc.

PrimeMLS
00 Contro RD, Chester, VT 05143
1/3 3

$159,000

Active

Vacant Land

5 Acres

00 Contro RD, Chester, VT 05143

There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for ...

Listed by Christine M Lewis of Brattleboro Area Realty

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

Get My App

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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