Realty.com
Buy

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
Sell

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
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

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
Cheshire, CT Homes for Sale | Realty.com
Realty.com
Buy

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 searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

36 listings
Sell

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
Home Loans
Find an Agent
Save search

Homes for Sale in Cheshire, CT

Homes for Sale in Cheshire, CT

Hide Map
24 of 36 Listings
Map

Homes for Sale in Cheshire, CT

24 of 36 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 256 Nob Hill Road — photoNew39Active

    $599,900

    3 bd · 3 ba · — sqft

    256 Nob Hill Road, Cheshire, CT

    Stacey Deangelis · Calcagni Real Estate

  2. listing photo40Active

    $549,000

    3 bd · 2 ba · — sqft

    Address withheld · Cheshire, CT

    Michelle Lorenzetti · Premier Re Group LLC

  3. 1016 Sperry Road — photo26Active

    $415,000

    2 bd · 1 ba · — sqft

    1016 Sperry Road, Cheshire, CT

    Seth Winkleman · Berkshire Hathaway NE Prop.

  4. 385 Sir Walter Drive — photo40Active

    $649,900

    3 bd · 3 ba · — sqft

    385 Sir Walter Drive, Cheshire, CT

    Daniela Volo · Calcagni Real Estate

  5. 50 Saint Joseph Street — photo35Active

    $349,999

    3 bd · 2 ba · — sqft

    50 Saint Joseph Street, Cheshire, CT

    Angelo Graziano · Social & Co Realty

  6. 1 Mountaincrest Drive — photo40Active

    $1,375,000

    4 bd · 5 ba · — sqft

    1 Mountaincrest Drive, Cheshire, CT

    Iris Meyer · William Raveis Real Estate

  7. 273 Winthrop Drive — photo35Active

    $454,900

    3 bd · 2 ba · — sqft

    273 Winthrop Drive, Cheshire, CT

    Tanya Uhelsky · Century 21 AllPoints Realty

  8. 662 Coleman Road — photo40Active

    $775,000

    4 bd · 3 ba · — sqft

    662 Coleman Road, Cheshire, CT

    Siobhan McLaughlin · William Raveis Real Estate

  9. 388 Sharon Drive — photoPrice Reduced39Active

    $409,900

    3 bd · 2 ba · — sqft

    388 Sharon Drive, Cheshire, CT

    Dana Longley · Coldwell Banker Realty

  10. 190 Remus Road — photoPrice Reduced35Active

    $499,900

    4 bd · 2 ba · — sqft

    190 Remus Road, Cheshire, CT

    Philip Giampietro · Coldwell Banker Realty

  11. 368 Charles Drive — photo38Active

    $769,000

    4 bd · 3 ba · — sqft

    368 Charles Drive, Cheshire, CT

    Kristy Agli · Kelsey & Co. Real Estate

  12. 531 Blacks Road — photoPrice Reduced40Active

    $599,000

    3 bd · 4 ba · — sqft

    531 Blacks Road, Cheshire, CT

    Cindy Cox · William Raveis Real Estate

  13. 1100 Coleman Road — photo38Active

    $695,000

    4 bd · 3 ba · 2,280 sqft

    1100 Coleman Road, Cheshire, CT

    Bev Mosch · William Pitt Sotheby's Int'l

  14. 233 Forest Lane — photo27Active

    $319,900

    3 bd · 2 ba · — sqft

    233 Forest Lane, Cheshire, CT

    Wesley Krombel · Real Broker CT, LLC

  15. 122 Green Hill Lane — photo40Active

    $439,900

    3 bd · 2 ba · 1,572 sqft

    122 Green Hill Lane, Cheshire, CT

    Robert Murphy · Station Cities

  16. 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

  17. 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

  18. 374 Moss Farms Road — photo26Active

    $384,900

    3 bd · 1 ba · 1,008 sqft

    374 Moss Farms Road, Cheshire, CT

    Roberta Whalen · LAER Realty Partners

  19. 110 Green Hill Lane — photo26Active

    $429,900

    5 bd · 2 ba · 1,584 sqft

    110 Green Hill Lane, Cheshire, CT

    Cynthia Ruiz · Anchor Real Estate LLC

  20. 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

  21. 125 Wallingford Road — photoPrice Reduced38Active

    $425,000

    3 bd · 2 ba · 1,568 sqft

    125 Wallingford Road, Cheshire, CT

    Heather Dacey · William Raveis Real Estate

  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 443 — photo30Active

    $199,900

    1 bd · 1 ba · 853 sqft

    443 East Mitchell Avenue 443, Cheshire, CT

    Elizabeth Sabo · Coldwell Banker Realty

12
Realty.com

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

Equal Housing OpportunityEqual Housing Lender

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.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

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.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas

    Cheshire, CT community profile

    Area
    33.6 sq. mi.

    Source: HJN community data

    Cheshire housing market

    September 2026 · This period is still settling

    Cheshire 12-month median sale price trend

    Selling at 102.2% of asking price

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

    Homes that sold · County records, as of Sep 11, 2026

    Median sale price
    $605,500$435,000–$704,148 typical range
    Sales
    12
    Paid in cash
    41.7%

    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
    24.7%

    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.