Single family homes for sale in Chester, VT

4 days on Rocket

$5,807 Closing Credit¹

$489,000

3 beds • 2 baths • 1,304 sqft

663 Depot St, Chester, VT 05143

#5038088, Betsy Adamovich, Listing Office: Real Broker LLC

$5,344 Closing Credit¹

$450,000

4 beds • 2.5 baths • 2,868 sqft

332 Hidden Heights Rd, Chester, VT 05143

#5037126, John Tolosky, Listing Office: Barrett and Valley Associates Inc.

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$2,255 Closing Credit¹

$189,900

3 beds • 2 baths • 1,876 sqft

2350 Vt Route 10, Chester, VT 05143

#5034997, Derek Greene, Listing Office: Derek Greene

Tour

$10,000 Closing Credit¹

$1,200,000

3 beds • 4 baths • 3,739 sqft

1502 Popple Dungeon Rd, Chester, VT 05143

#5034215, Betty McEnaney, Listing Office: Diamond Realty

$4,263 Closing Credit¹

$359,000

4 beds • 2 baths • 1,248 sqft

26 Dorman Rd, Andover, VT 05143

#5029533, Daire Gibney, Listing Office: Barrett and Valley Associates Inc.

$8,906 Closing Credit¹

$750,000

3 beds • 2.5 baths • 2,605 sqft

31 Palmer Rd, Chester, VT 05143

#5029353, Leila Tarantelli, Listing Office: KW Coastal and Lakes & Mountains Realty/Hanover

Tour

$8,300,000

8 beds • 7.5 baths • 10,062 sqft

3800 Weston Andover Rd, Andover, VT 05143

#5015743, Steve Stettler, Listing Office: Four Seasons Sotheby's Int'l Realty

Room to negotiate?

Median Sold Price

$362.5K

Based on our March 2025 Market Report.

$3,266 Closing Credit¹

$275,000

3 beds • 2 baths • 1,232 sqft

81 Trombley Rd, Andover, VT 05143

#5001000, Erin Kendall, Listing Office: EXP Realty

$6,994 Closing Credit¹

$589,000

4 beds • 3.5 baths • 2,356 sqft

559 Davidson Hill Rd, Chester, VT 05143

#4996384, Julie Buffum, Listing Office: Buffum Realty

$3,561 Closing Credit¹

$299,900

2 beds • 1 bath • 1,134 sqft

87 Trombley Rd, Andover, VT 05143

#4987366, Erin Kendall, Listing Office: EXP Realty

$5,938 Closing Credit¹

$500,000

4 beds • 2 baths • 1,728 sqft

4877 Vt Route 103, Chester, VT 05143

#4986618, Erin Kendall, Listing Office: EXP Realty

Chester, VT Real Estate Market Overview

Browse 11 homes for sale in Chester, VT. View properties, photos, nearby real estate with school and housing market information. Between February 2025 and March 2025, Chester, VT real estate market has seen decrease in the number of listings by 5.3%. The median list price of listings available in March 2025 was $362,500, while the average time on the real estate market was 0 days. Over 0 listings were sold over their listed price in March 2025 in Chester, VT. In the same period over 1 listings were sold below the listed price and 1 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Chester, VT

Overview

Chester is located in Windsor County, Vermont. There are roughly 3,162 residents, living in 1,403 households. The average temperature for Chester this time of the year is low of 40F and high of 67F. On average, Chester gets about 4.08 inches of precipitation in May. Most residents are home owners (74%), have a high school diploma (48%) and are single, no kids (43%).

Data provided by Home Junction

Single family homes for sale in Chester, VT

Chester, VT Real Estate Market Overview

What is it like to live in Chester, VT

Overview

Housing market reports in Windsor County

Homes for sale near Chester, VT

Top real estate cities in Vermont