38 Properties Available In Chester
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$450,000
Single Family Home
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


$469,000
Single Family Home
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


$1,495,000
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


$359,000
Single Family Home
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


$925,000
Single Family Home
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


$199,000
Single Family Home
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.


$789,000
Single Family Home
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.


$649,000
Single Family Home
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


$249,500
Single Family Home
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


$489,000
Single Family Home
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


$75,000
Single Family Home
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


$3,300
Single Family Home
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.


$1,200,000
Single Family Home
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


$1,490,000
Single Family Home
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


$1,400
Condo
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.


$649,000
Single Family Home
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


$299,000
Single Family Home
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.


$399,000
Single Family Home
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


$169,000
Single Family Home
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


$650,000
Multi-Family
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


$250,000
Vacant Land
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


$100,000
Vacant Land
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


$285,000
Commercial
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


$229,000
Vacant Land
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

- 1
- 2

