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Connecticut · Real Estate

Homes for Sale in
Chester, CT

As of November 10, 2026, per SmartMLS, there are 10 homes for sale in Chester, Connecticut with an average list price of $880,360.

Chester is a small Connecticut River Valley town of about 3,900 that punches well above its weight in culture and character. Part of the loosely defined "Connecticut River Valley arts corridor," it's home to upscale galleries, destination restaurants, and a walkable village center. The Goodspeed Opera House is a short ferry ride across the river in East Haddam. Small, charming, and genuinely distinctive.

For Sale

10

active listings

Median Sale Price

$549K

$140K–$1.3M

Avg. Size Sold

2,101 sf

last 12 mo

vs. Ask Price

-0.9%

avg. paid vs. ask

Stats based on 45 closings in the last 12 months · SmartMLS, as of Nov 10, 2026

Showing 10 of 10 listings in Chester

13 High Field Lane, Chester, CT
Active
$749,900
4 bd · 3 ba · 2,662 sqft
13 High Field Lane
Chester, CT 06412
William Pitt Sotheby's Int'l SmartMLS
7 Hickory Hill Drive, Chester, CT
Active
$775,000
3 bd · 3 ba · 3,002 sqft
7 Hickory Hill Drive
Chester, CT 06412
William Raveis Real Estate SmartMLS
173 West Main Street, Chester, CT
Active
$289,000
2 bd · 1 ba · 1,392 sqft
173 West Main Street
Chester, CT 06412
iHeart Homes Real Estate LLC SmartMLS
40 Castle View Drive, Chester, CT
Active
$349,900
3 bd · 2 ba · 1,142 sqft
40 Castle View Drive
Chester, CT 06412
Re/Max Valley Shore SmartMLS
42 Straits Road, Chester, CT
Active
$674,900
3 bd · 3 ba · 2,882 sqft
42 Straits Road
Chester, CT 06412
Great Estates, CT SmartMLS
84-86 Spring Street, Chester, CT
Active
$579,900
4 bd · 3 ba · 3,506 sqft  ·  2 Family
84-86 Spring Street
Chester, CT 06412
Carbutti & Co., Realtors SmartMLS
47 East Kings Highway, Chester, CT
Active
$1,900,000
4 bd · 4 ba · 3,957 sqft
47 East Kings Highway
Chester, CT 06412
Chiarito Real Estate LLC SmartMLS
288 Middlesex Avenue, Chester, CT
Active
$2,995,000
4 bd · 6 ba · 4,926 sqft
288 Middlesex Avenue
Chester, CT 06412
Coldwell Banker Realty SmartMLS
90 Water Street, Chester, CT
Active
$237,500
1 bd · 1 ba · 1,034 sqft
90 Water Street
Chester, CT 06412
Salzillo Realty Company SmartMLS
92 Water Street, Chester, CT
Active
$252,500
3 bd · 1 ba · 1,217 sqft
92 Water Street
Chester, CT 06412
Salzillo Realty Company SmartMLS
Read our Living in Chester, CT guide

Buying a Home in Chester, CT

Current Market Snapshot

Entry Price
$238K
lowest listed
Avg. Price
$880K
list price
Top of Market
$3M
highest listed
Listings by Bedroom Count
1 bed
1
2 beds
1
3 beds
4
4 beds
4
Property Types Available
Single Family · 9 Multi-Family For Sale · 1

As of November 10, 2026, the Chester real estate market has 10 active listings with an average list price of $880,360 and a price range from $237,500 to $2,995,000. Single Family homes make up the largest share of available inventory. Most listings are 3-bedroom homes. The average home size is 2,572 sq ft. All listings are sourced directly from SmartMLS and updated every 15 minutes.

Frequently Asked Questions

How many homes are for sale in Chester, CT right now?
As of November 10, 2026, per SmartMLS, there are 10 active listings in Chester, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Chester, CT?
As of November 10, 2026, per SmartMLS, the average list price in Chester is $880,360. Homes currently range from $237,500 to $2,995,000.
What size homes are most common in Chester, CT?
The most common listing in Chester is a 3-bedroom home (4 listings). Other common sizes include 4-bedroom (4) and 1-bedroom (1). The average home size is 2,572 sq ft.
What types of homes are available in Chester, CT?
Current listings in Chester include: Single Family (9), Multi-Family For Sale (1).
Is Chester, CT a good place to buy a home?
Chester is a small Connecticut River Valley town of about 3,900 that punches well above its weight in culture and character. Part of the loosely defined "Connecticut River Valley arts corridor," it's home to upscale galleries, destination restaurants, and a walkable village center. The Goodspeed Opera House is a short ferry ride across the river in East Haddam. Small, charming, and genuinely distinctive.
Does RYZE Realty Group serve Chester, CT?
Yes — RYZE Realty Group is a Connecticut real estate team serving buyers and sellers across Middlesex County and the greater Connecticut market, including Chester. Contact us for a free consultation.