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Cheshire, CT Homes for Sale | Realty.com

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Homes for Sale in Cheshire, CT

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24 of 34 Listings

Map

24 of 34 Listings

Homes for Sale in Cheshire, CT

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24 of 34 Listings

Map

Homes for Sale in Cheshire, CT

24 of 34 Listings

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

New

Active

$325,000

3 bd · 2 ba · — sqft

95 Farview Drive, Cheshire, CT

Doug Coby · Property Edge

New34Active

$499,900

4 bd · 2 ba · — sqft

393 South Rolling Acres Road, Cheshire, CT

Cheryl Rosadino · Berkshire Hathaway NE Prop.

40Active

$429,900

2 bd · 2 ba · — sqft

105 Deepwood Drive, Cheshire, CT

Philip Giampietro · Coldwell Banker Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

40Active

$699,925

3 bd · 3 ba · — sqft

74 Shea Circle, Cheshire, CT

Maria Pirulli · Five Stars Realty

36Active

$612,000

2 bd · 2 ba · — sqft

25 Bramble Way, Cheshire, CT

Arlene Levine · Coldwell Banker Realty

40Active

$524,900

3 bd · 3 ba · — sqft

1430 South Main Street, Cheshire, CT

Sally Bowman · Berkshire Hathaway NE Prop.

40Active

$949,900

4 bd · 4 ba · — sqft

704 Andrea Court, Cheshire, CT

Sally Bowman · Berkshire Hathaway NE Prop.

22Active

$239,800

2 bd · 2 ba · — sqft

353 East Mitchell Avenue Unit 353, Cheshire, CT

Marty Rauch · Marty Rauch Real Estate

36Active

$525,000

3 bd · 2 ba · — sqft

4 Cherrywood Circle, Cheshire, CT

Brette Stern · Calcagni Real Estate

37Active

$850,000

4 bd · 4 ba · — sqft

6 Mount Sanford Road, Cheshire, CT

Iris Meyer · William Raveis Real Estate

39Active

$595,000

4 bd · 2 ba · — sqft

327 West Main Street, Cheshire, CT

Dave Jones · Dave Jones Realty, LLC

40Active

$889,000

5 bd · 5 ba · — sqft

100 Scenic Court, Cheshire, CT

Jessica Danard · Coldwell Banker Realty

40Active

$579,900

4 bd · 3 ba · — sqft

42 Eastgate Drive, Cheshire, CT

Sally Bowman · Berkshire Hathaway NE Prop.

5Active

$771,900

3 bd · 3 ba · — sqft

27 Soderman Way Unit 27, Cheshire, CT

Shannon Chapman · EG Group Realty LLC

33Active

$389,900

2 bd · 1 ba · — sqft

45 Broadview Road, Cheshire, CT

Sally Bowman · Berkshire Hathaway NE Prop.

38Active

$675,000

4 bd · 3 ba · — sqft

35 Brookside Place, Cheshire, CT

Rachel Wardwell · Calcagni Real Estate

Price Reduced37Active

$574,900

3 bd · 2 ba · — sqft

178 Harrison Road, Cheshire, CT

Andrew Calamita · Coldwell Banker Realty

Price Reduced26Active

$399,000

2 bd · 1 ba · — sqft

1016 Sperry Road, Cheshire, CT

Seth Winkleman · Berkshire Hathaway NE Prop.

40Active

$1,375,000

4 bd · 5 ba · — sqft

1 Mountaincrest Drive, Cheshire, CT

Iris Meyer · William Raveis Real Estate

Price Reduced40Active

$749,900

4 bd · 3 ba · — sqft

662 Coleman Road, Cheshire, CT

Siobhan McLaughlin · William Raveis Real Estate

40Active

$1,630,000

5 bd · 5 ba · 6,361 sqft

644 South Brooksvale Road, Cheshire, CT

Brian Burke · Coldwell Banker Realty

39Active

$1,590,000

5 bd · 5 ba · 5,021 sqft

16 Mountaincrest Drive, Cheshire, CT

E. Tyler Della Valle · Dow Della Valle

Price Reduced26Active

$375,900

3 bd · 1 ba · 1,008 sqft

374 Moss Farms Road, Cheshire, CT

Roberta Whalen · LAER Realty Partners

Price Reduced39Active

$335,000

2 bd · 2 ba · — sqft

83 Quarry Village Road Unit 83, Cheshire, CT

Jen Swerdlick · Jennifer Swerdlick

1 2

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.

Cheshire housing market

October 2026 · This period is still settling

Selling at 104.6% of asking price

Buyers here are paying above asking. MLS · 18 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 16, 2026

Median sale price: $645,000$480,500–$860,000 typical range
Sales: 11
Paid in cash: 18.2%

Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

Median list price: $594,450
Homes for sale: 36
Median days on market: 8 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year: 23.3%

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

Median home size: 1,954 sq. ft.

Cheshire, CT community profile

Area: 33.6 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

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.

Cheshire, CT community profile

Area: 33.6 sq. mi.

Source: HJN community data

Cheshire housing market

October 2026 · This period is still settling

Selling at 104.6% of asking price

Buyers here are paying above asking. MLS · 18 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 16, 2026

Median sale price: $645,000$480,500–$860,000 typical range
Sales: 11
Paid in cash: 18.2%

Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

Median list price: $594,450
Homes for sale: 36
Median days on market: 8 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year: 23.3%

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

Median home size: 1,954 sq. ft.