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

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Registered offenders on the map

Show registered offenders

Registered offenders on the map

Show registered offenders

Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

Luxury Homes in Chester, CT

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

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Rentals
Commercial

Registered offenders on the map

Show registered offenders

2 listings

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

Luxury Homes in Chester, CT

Luxury Homes in Chester, CT

2 Listings

Luxury Homes in Chester, CT

2 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

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

Explore Chester homes

By price

Under $300K
Under $500K
Under $700K
Luxury

By bedrooms

2 beds
3 beds
4 beds
5 beds

By type

Single family
Townhomes
Condos
Manufactured homes
Multi-family homes
Co-ops

By feature

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.

© 2026 Realty.com. All rights reserved.PrivacyTermsCalifornia Privacy RightsAccessibilityLicensing

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.

New construction
With a pool

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925