$695,000
4
3Bds
3Ba
2,232sqft
Single family home for sale
Winhall Real Estate
$695,000
4
3Bds
3Ba
2,232sqft
Single family home for sale
Winhall Real Estate
$650,000
1
--Bds
--Ba
4,324sqft
Multi family home for sale
Four Seasons Sotheby'S Int'L Realty
$650,000
5
--Bds
--Ba
10.03acres lot
Land for sale
Four Seasons Sotheby'S Int'L Realty
$649,000
2
3Bds
2Ba
2,204sqft
Single family home for sale
Four Seasons Sotheby'S Int'L Realty
$599,000
3
4Bds
2Ba
1,908sqft
Single family home for sale
Four Seasons Sotheby'S Int'L Realty
$595,000
15
--Bds
--Ba
220.11acres lot
Land for sale
William Raveis Real Estate Vermont Properties
$550,000
3
3Bds
2Ba
1,946sqft
Single family home for sale
Barrett And Valley Associates Inc.
$549,000
3
2Bds
2Ba
850sqft
Single family home for sale
Southern Vermont Realty Group
$549,000
4
4Bds
3Ba
2,464sqft
Single family home for sale
Barrett And Valley Associates Inc.
$525,000
3
4Bds
4Ba
2,656sqft
Single family home for sale
William Raveis Real Estate Vermont Properties
$449,000
5
3Bds
2Ba
1,626sqft
Single family home for sale
Four Seasons Sotheby'S Int'L Realty
$372,500
5
--Bds
--Ba
24.5acres lot
Land for sale
Mary Mitchell Miller Real Estate
$359,000
1
2Bds
1Ba
900sqft
Single family home for sale
Vermont Real Estate Company
$340,000
4
--Bds
--Ba
3,608sqft
Multi family home for sale
Nancy Jenkins Real Estate
$299,000
6
3Bds
2Ba
1,788sqft
Single family home for sale
Barrett And Valley Associates Inc.
$279,000
3
5Bds
3Ba
1,812sqft
Single family home for sale
Town And Country Realty
$249,900
1
2Bds
1Ba
930sqft
Manufactured home for sale
Barrett And Valley Associates Inc.
$249,000
4
--Bds
--Ba
84acres lot
Land for sale
Barrett And Valley Associates Inc.
$229,500
1
4Bds
3Ba
1,922sqft
Single family home for sale
Mary W. Davis Realtor & Assoc., Inc.
$229,000
5
--Bds
--Ba
27.8acres lot
Land for sale
Four Seasons Sotheby'S Int'L Realty
$175,000
2
3Bds
2Ba
1,379sqft
Sale Pending
Barrett And Valley Associates Inc.
$169,000
8
1Bd
1Ba
200sqft
Single family home for sale
Four Seasons Sotheby'S Int'L Realty
$119,000
6
--Bds
--Ba
7.95acres lot
Land for sale
Barrett And Valley Associates Inc.
$100,000
1
--Bds
--Ba
23,958sqft lot
Land for sale
Kw Coastal And Lakes & Mountains Realty/Hanover
$87,500
3
--Bds
--Ba
10.4acres lot
Land for sale
Four Seasons Sotheby'S Int'L Realty
$85,000
--Bds
--Ba
3.99acres lot
Land for sale
Four Seasons Sotheby'S Int'L Realty
$75,000
4
2Bds
1Ba
620sqft
Single family home for sale
Buffum Realty
$74,000
5
--Bds
--Ba
15.5acres lot
Land for sale
Berkshire Hathaway Homeservices Stratton Home
$29,900
3
--Bds
--Ba
3.2acres lot
Sale Pending
Southern Vermont Realty Group
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Chester is a balanced market, giving buyers and sellers room to negotiate. With 4 months of supply and homes averaging 86 days on the market, you can make decisions without the pressure of a highly competitive market.
Balanced Market
86
39
In Nov 2025 · YoY
Current rate · YoY
30-Year Fixed
30-yr fixed rate 6.23% · Data as of Nov 2025 · Source: Houzeo Research.
View Full Chester Market Report39
Homes Available
$ 385,000
Median List Price
86 Days
Avg on Market
Do Real Estate on the Go!