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Cheshire, CT Homes for Sale | Realty.com
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32 listings
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Homes for Sale in Cheshire, CT

Homes for Sale in Cheshire, CT

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24 of 32 Listings
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Homes for Sale in Cheshire, CT

24 of 32 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 6 Mount Sanford Road — photoNew36Active

    $850,000

    4 bd · 4 ba · — sqft

    6 Mount Sanford Road, Cheshire, CT

    Iris Meyer · William Raveis Real Estate

  2. 327 West Main Street — photo39Active

    $595,000

    4 bd · 2 ba · — sqft

    327 West Main Street, Cheshire, CT

    Dave Jones · Dave Jones Realty, LLC

  3. 135 Wallingford Road — photo39Active

    $315,000

    3 bd · 1 ba · — sqft

    135 Wallingford Road, Cheshire, CT

    Devon Taylor Assael · Dave Jones Realty, LLC

  4. 100 Scenic Court — photo40Active

    $889,000

    5 bd · 5 ba · — sqft

    100 Scenic Court, Cheshire, CT

    Jessica Danard · Coldwell Banker Realty

  5. 42 Eastgate Drive — photo40Active

    $579,900

    4 bd · 3 ba · — sqft

    42 Eastgate Drive, Cheshire, CT

    Sally Bowman · Berkshire Hathaway NE Prop.

  6. 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

  7. 45 Broadview Road — photo33Active

    $389,900

    2 bd · 1 ba · — sqft

    45 Broadview Road, Cheshire, CT

    Sally Bowman · Berkshire Hathaway NE Prop.

  8. 35 Brookside Place — photo38Active

    $675,000

    4 bd · 3 ba · — sqft

    35 Brookside Place, Cheshire, CT

    Rachel Wardwell · Calcagni Real Estate

  9. 7 Edith Place — photo31Active

    $479,900

    4 bd · 5 ba · — sqft

    7 Edith Place, Cheshire, CT

    Robert Roya Jr. · Aspen Realty Group

  10. 72 Quarry Village Road Unit 72 — photo36Active

    $425,000

    2 bd · 3 ba · — sqft

    72 Quarry Village Road Unit 72, Cheshire, CT

    David Aurigemma · Regency Real Estate, LLC

  11. 420 Robin Court Unit 420 — photo35Active

    $230,000

    2 bd · 3 ba · — sqft

    420 Robin Court Unit 420, Cheshire, CT

    Dawn D'Auria · Coldwell Banker Realty

  12. 178 Harrison Road — photo37Active

    $589,900

    3 bd · 2 ba · — sqft

    178 Harrison Road, Cheshire, CT

    Andrew Calamita · Coldwell Banker Realty

  13. 1016 Sperry Road — photo26Active

    $415,000

    2 bd · 1 ba · — sqft

    1016 Sperry Road, Cheshire, CT

    Seth Winkleman · Berkshire Hathaway NE Prop.

  14. 1 Mountaincrest Drive — photo40Active

    $1,375,000

    4 bd · 5 ba · — sqft

    1 Mountaincrest Drive, Cheshire, CT

    Iris Meyer · William Raveis Real Estate

  15. 50 Saint Joseph Street — photo35Active

    $349,999

    3 bd · 2 ba · — sqft

    50 Saint Joseph Street, Cheshire, CT

    Angelo Graziano · Social & Co Realty

  16. 662 Coleman Road — photo40Active

    $775,000

    4 bd · 3 ba · — sqft

    662 Coleman Road, Cheshire, CT

    Siobhan McLaughlin · William Raveis Real Estate

  17. 368 Charles Drive — photoPrice Reduced38Active

    $749,000

    4 bd · 3 ba · — sqft

    368 Charles Drive, Cheshire, CT

    Kristy Agli · Kelsey & Co. Real Estate

  18. 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

  19. 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

  20. 374 Moss Farms Road — photoPrice Reduced26Active

    $379,900

    3 bd · 1 ba · 1,008 sqft

    374 Moss Farms Road, Cheshire, CT

    Roberta Whalen · LAER Realty Partners

  21. 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

  22. 1827 Marion Road — photo23Active

    $1,999,000

    4 bd · 2 ba · 2,160 sqft

    1827 Marion Road, Cheshire, CT

    Louis Roy Evjen · Evjen Agency

  23. 885 South Brooksvale Road — photoPrice Reduced40Active

    $1,279,000

    5 bd · 5 ba · 3,948 sqft

    885 South Brooksvale Road, Cheshire, CT

    Nancy Lydell · Calcagni Real Estate

  24. 443 East Mitchell Avenue Unit 443 — photo30Active

    $199,900

    1 bd · 1 ba · 853 sqft

    443 East Mitchell Avenue Unit 443, Cheshire, CT

    Elizabeth Sabo · Coldwell Banker Realty

12
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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, CT community profile

Area
33.6 sq. mi.

Source: HJN community data

Cheshire housing market

September 2026

Cheshire 12-month median sale price trend

Selling at 102.2% of asking price

Buyers here are paying above asking. MLS · 32 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price
$575,000$385,000–$672,450 typical range
Price per sq. ft.
$309
Sales
39
Paid in cash
30.8%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price
$549,900
Homes for sale
37
Median days on market
7 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year
18.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 1, 2026

Median home size
1,954 sq. ft.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas