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Connecticut · Real Estate

Homes for Sale in
Cheshire, CT

As of November 10, 2026, per SmartMLS, there are 38 homes for sale in Cheshire, Connecticut with an average list price of $686,972.

Cheshire is a well-regarded New Haven County town of about 29,000 with excellent schools, established neighborhoods, and a strong sense of community that consistently earns it placement among Connecticut's best places to raise a family. Located between Waterbury and Meriden with direct I-691 access, it offers genuine suburban quality at prices noticeably below coastal New Haven County. The Farmington Canal Heritage Trail runs through the center of town.

For Sale

38

active listings

Median Sale Price

$550K

$96K–$1.7M

Avg. Size Sold

2,185 sf

last 12 mo

vs. Ask Price

+2.9%

avg. paid vs. ask

Stats based on 338 closings in the last 12 months · SmartMLS, as of Nov 10, 2026

Showing 12 of 38 listings in Cheshire

105 Deepwood Drive, Cheshire, CT
Coming Soon OH 11/14 · 12pm–2pm
$429,900
2 bd · 2 ba · 1,104 sqft
105 Deepwood Drive
Cheshire, CT 06410
Coldwell Banker Realty SmartMLS
74 Shea Circle, Cheshire, CT
Active
$699,925
3 bd · 3 ba · 2,450 sqft  ·  Condominium
74 Shea Circle
Cheshire, CT 06410
Five Stars Realty SmartMLS
25 Bramble Way, Cheshire, CT
Coming Soon
$612,000
2 bd · 2 ba · 2,083 sqft  ·  Condominium
25 Bramble Way
Cheshire, CT 06410
Coldwell Banker Realty SmartMLS
1430 South Main Street, Cheshire, CT
Active
$524,900
3 bd · 3 ba · 1,932 sqft
1430 South Main Street
Cheshire, CT 06410
Berkshire Hathaway NE Prop. SmartMLS
353 East Mitchell Avenue #353, Cheshire, CT
Active
$239,800
2 bd · 2 ba · 1,200 sqft  ·  Condominium
353 East Mitchell Avenue #353
Cheshire, CT 06410
Marty Rauch Real Estate SmartMLS
704 Andrea Court, Cheshire, CT
Active
$949,900
4 bd · 4 ba · 3,845 sqft
704 Andrea Court
Cheshire, CT 06410
Berkshire Hathaway NE Prop. SmartMLS
70 Southwick Court #212, Cheshire, CT
Active
$215,000
1 bd · 1 ba · 755 sqft  ·  Condominium
70 Southwick Court #212
Cheshire, CT 06410
William Raveis Real Estate SmartMLS
4 Cherrywood Circle, Cheshire, CT
Coming Soon
$525,000
3 bd · 2 ba · 2,043 sqft
4 Cherrywood Circle
Cheshire, CT 06410
Calcagni Real Estate SmartMLS
6 Mount Sanford Road, Cheshire, CT
Active
$850,000
4 bd · 4 ba · 2,536 sqft
6 Mount Sanford Road
Cheshire, CT 06410
William Raveis Real Estate SmartMLS
327 West Main Street, Cheshire, CT
Active
$595,000
4 bd · 2 ba · 2,123 sqft
327 West Main Street
Cheshire, CT 06410
Dave Jones Realty, LLC SmartMLS
42 Eastgate Drive, Cheshire, CT
Active
$579,900
4 bd · 3 ba · 2,042 sqft
42 Eastgate Drive
Cheshire, CT 06410
Berkshire Hathaway NE Prop. SmartMLS
747 West Main Street #H, Cheshire, CT
Active
$349,900
2 bd · 2 ba · 1,908 sqft  ·  Condominium
747 West Main Street #H
Cheshire, CT 06410
Alpha Capital Realty, LLC SmartMLS
Read our Living in Cheshire, CT guide
Cheshire real estate agents: market numbers and who to call
See All 38 Homes in Cheshire

Buying a Home in Cheshire, CT

Current Market Snapshot

Entry Price
$50K
lowest listed
Avg. Price
$687K
list price
Top of Market
$1.6M
highest listed
Listings by Bedroom Count
1 bed
1
2 beds
9
3 beds
11
4 beds
9
5 beds
4
Property Types Available
Single Family · 22 Condo / Co-Op · 12 Land · 4

As of November 10, 2026, the Cheshire real estate market has 38 active listings with an average list price of $686,972 and a price range from $49,995 to $1,630,000. Single Family homes make up the largest share of available inventory. Most listings are 3-bedroom homes. The average home size is 2,148 sq ft. All listings are sourced directly from SmartMLS and updated every 15 minutes.

Frequently Asked Questions

How many homes are for sale in Cheshire, CT right now?
As of November 10, 2026, per SmartMLS, there are 38 active listings in Cheshire, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Cheshire, CT?
As of November 10, 2026, per SmartMLS, the average list price in Cheshire is $686,972. Homes currently range from $49,995 to $1,630,000.
What size homes are most common in Cheshire, CT?
The most common listing in Cheshire is a 3-bedroom home (11 listings). Other common sizes include 2-bedroom (9) and 4-bedroom (9). The average home size is 2,148 sq ft.
What types of homes are available in Cheshire, CT?
Current listings in Cheshire include: Single Family (22), Condo / Co-Op (12), Land (4).
Is Cheshire, CT a good place to buy a home?
Cheshire is a well-regarded New Haven County town of about 29,000 with excellent schools, established neighborhoods, and a strong sense of community that consistently earns it placement among Connecticut's best places to raise a family. Located between Waterbury and Meriden with direct I-691 access, it offers genuine suburban quality at prices noticeably below coastal New Haven County. The Farmington Canal Heritage Trail runs through the center of town.
Does RYZE Realty Group serve Cheshire, CT?
Yes — RYZE Realty Group is a Connecticut real estate team serving buyers and sellers across New Haven County and the greater Connecticut market, including Cheshire. Contact us for a free consultation.