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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

11 listings

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Save search

Homes for Sale in Chester, CT

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11 listings

Homes for Sale in Chester, CT

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11 Listings

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Homes for Sale in Chester, CT

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

40Active

$749,900

4 bd · 3 ba · — sqft

13 High Field Lane, Chester, CT

Susan Malan · William Pitt Sotheby's Int'l

40Active

$450,000

3 bd · 1 ba · — sqft

6 School Lane, Chester, CT

Hilary Reid · Coldwell Banker Realty

39Active

$775,000

3 bd · 3 ba · — sqft

7 Hickory Hill Drive, Chester, CT

Rachel Welch · William Raveis Real Estate

25Active

$289,000

2 bd · 1 ba · — sqft

173 West Main Street, Chester, CT

Erica Stone · iHeart Homes Real Estate LLC

39Active

$715,000

4 bd · 4 ba · — sqft

275 West Main Street, Chester, CT

Nancy Bullis · Coldwell Banker Realty

25Active

$379,900

3 bd · 2 ba · — sqft

40 Castle View Drive, Chester, CT

Craig Milton · Re/Max Valley Shore

40Active

$699,000

3 bd · 3 ba · — sqft

42 Straits Road, Chester, CT

Donna Genovese · Great Estates, CT

40Active

$1,900,000

4 bd · 4 ba · 3,957 sqft

47 East Kings Highway, Chester, CT

Al Chiarito · Chiarito Real Estate LLC

38Active

$2,995,000

4 bd · 6 ba · 4,926 sqft

288 Middlesex Avenue, Chester, CT

Nancy Mesham · Coldwell Banker Realty

Price Reduced24Active

$237,500

1 bd · 1 ba · 1,034 sqft

90 Water Street, Chester, CT

Ryan O'Keeffe · Salzillo Realty Company

Price Reduced30Active

$252,500

3 bd · 1 ba · 1,217 sqft

92 Water Street, Chester, CT

Ryan O'Keeffe · Salzillo Realty Company

Listing data & MLS disclosures

SmartMLS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

Chester housing market

October 2026 · This period is still settling

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $699,000
Homes for sale: 11

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,802 sq. ft.

Chester, CT community profile

Area: 16.5 sq. mi.

Source: HJN community data

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

Listing data & MLS disclosures

SmartMLS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

Chester, CT Homes for Sale | Realty.com

Chester, CT community profile

Area: 16.5 sq. mi.

Source: HJN community data

Chester housing market

October 2026 · This period is still settling

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $699,000
Homes for sale: 11

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,802 sq. ft.