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Cheshire, CT Homes for Sale | Realty.com
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34 listings

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Homes for Sale in Cheshire, CT

Homes for Sale in Cheshire, CT

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24 of 34 Listings
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Homes for Sale in Cheshire, CT

24 of 34 Listings

  1. 95 Farview Drive — photoNew22Active

    $325,000

    3 bd · 2 ba · — sqft

    95 Farview Drive, Cheshire, CT

    Doug Coby · Property Edge

  2. 393 South Rolling Acres Road — photoNew34Active

    $499,900

    4 bd · 2 ba · — sqft

    393 South Rolling Acres Road, Cheshire, CT

    Cheryl Rosadino · Berkshire Hathaway NE Prop.

  3. 105 Deepwood Drive — photo40Active

    $429,900

    2 bd · 2 ba · — sqft

    105 Deepwood Drive, Cheshire, CT

    Philip Giampietro · Coldwell Banker Realty

  4. 74 Shea Circle — photo40Active

    $699,925

    3 bd · 3 ba · — sqft

    74 Shea Circle, Cheshire, CT

    Maria Pirulli · Five Stars Realty

  5. 25 Bramble Way — photo36Active

    $612,000

    2 bd · 2 ba · — sqft

    25 Bramble Way, Cheshire, CT

    Arlene Levine · Coldwell Banker Realty

  6. 1430 South Main Street — photo40Active

    $524,900

    3 bd · 3 ba · — sqft

    1430 South Main Street, Cheshire, CT

    Sally Bowman · Berkshire Hathaway NE Prop.

  7. 704 Andrea Court — photo40Active

    $949,900

    4 bd · 4 ba · — sqft

    704 Andrea Court, Cheshire, CT

    Sally Bowman · Berkshire Hathaway NE Prop.

  8. 353 East Mitchell Avenue Unit 353 — photo22Active

    $239,800

    2 bd · 2 ba · — sqft

    353 East Mitchell Avenue Unit 353, Cheshire, CT

    Marty Rauch · Marty Rauch Real Estate

  9. 4 Cherrywood Circle — photo36Active

    $525,000

    3 bd · 2 ba · — sqft

    4 Cherrywood Circle, Cheshire, CT

    Brette Stern · Calcagni Real Estate

  10. 6 Mount Sanford Road — photo37Active

    $850,000

    4 bd · 4 ba · — sqft

    6 Mount Sanford Road, Cheshire, CT

    Iris Meyer · William Raveis Real Estate

  11. 327 West Main Street — photo39Active

    $595,000

    4 bd · 2 ba · — sqft

    327 West Main Street, Cheshire, CT

    Dave Jones · Dave Jones Realty, LLC

  12. 100 Scenic Court — photo40Active

    $889,000

    5 bd · 5 ba · — sqft

    100 Scenic Court, Cheshire, CT

    Jessica Danard · Coldwell Banker Realty

  13. 42 Eastgate Drive — photo40Active

    $579,900

    4 bd · 3 ba · — sqft

    42 Eastgate Drive, Cheshire, CT

    Sally Bowman · Berkshire Hathaway NE Prop.

  14. 27 Soderman Way Unit 27 — photo5Active

    $771,900

    3 bd · 3 ba · — sqft

    27 Soderman Way Unit 27, Cheshire, CT

    Shannon Chapman · EG Group Realty LLC

  15. 45 Broadview Road — photo33Active

    $389,900

    2 bd · 1 ba · — sqft

    45 Broadview Road, Cheshire, CT

    Sally Bowman · Berkshire Hathaway NE Prop.

  16. 35 Brookside Place — photo38Active

    $675,000

    4 bd · 3 ba · — sqft

    35 Brookside Place, Cheshire, CT

    Rachel Wardwell · Calcagni Real Estate

  17. 178 Harrison Road — photoPrice Reduced37Active

    $574,900

    3 bd · 2 ba · — sqft

    178 Harrison Road, Cheshire, CT

    Andrew Calamita · Coldwell Banker Realty

  18. 1016 Sperry Road — photoPrice Reduced26Active

    $399,000

    2 bd · 1 ba · — sqft

    1016 Sperry Road, Cheshire, CT

    Seth Winkleman · Berkshire Hathaway NE Prop.

  19. 1 Mountaincrest Drive — photo40Active

    $1,375,000

    4 bd · 5 ba · — sqft

    1 Mountaincrest Drive, Cheshire, CT

    Iris Meyer · William Raveis Real Estate

  20. 662 Coleman Road — photoPrice Reduced40Active

    $749,900

    4 bd · 3 ba · — sqft

    662 Coleman Road, Cheshire, CT

    Siobhan McLaughlin · William Raveis Real Estate

  21. 644 South Brooksvale Road — photo40Active

    $1,630,000

    5 bd · 5 ba · 6,361 sqft

    644 South Brooksvale Road, Cheshire, CT

    Brian Burke · Coldwell Banker Realty

  22. 16 Mountaincrest Drive — photo39Active

    $1,590,000

    5 bd · 5 ba · 5,021 sqft

    16 Mountaincrest Drive, Cheshire, CT

    E. Tyler Della Valle · Dow Della Valle

  23. 374 Moss Farms Road — photoPrice Reduced26Active

    $375,900

    3 bd · 1 ba · 1,008 sqft

    374 Moss Farms Road, Cheshire, CT

    Roberta Whalen · LAER Realty Partners

  24. 83 Quarry Village Road Unit 83 — photoPrice Reduced39Active

    $335,000

    2 bd · 2 ba · — sqft

    83 Quarry Village Road Unit 83, Cheshire, CT

    Jen Swerdlick · Jennifer Swerdlick

12
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Listing data & MLS disclosures

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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

Cheshire 12-month median sale price trend

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