11,849

Cheshire, CT Homes

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  • 74 Shea Cir, Cheshire, CT 06410
    74 Shea Cir, Cheshire, CT 06410
    74 Shea Cir, Cheshire, CT 06410
    /29

    $749,000

    $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    74 Shea Cir, Cheshire, CT 06410

    Seller Relocating-Don't Miss This Opportunity! Welcome to The Reserve at Stonebridge Crossing, where luxury, comfort, and low-maintenance living come together in this exceptional Carriage House model. Barely a year old and meticulously maintained, this stunning home offers approximately 2,450 square feet with extensive builder upgrades throughout. Enjoy the appeal of a like-new home without the

    Lori Sierpinski Essentia Realty

    74 Shea Cir, Cheshire, CT 06410
  • 1715 Musso View Ave, Cheshire, CT 06410

    $445,000

    Sold Nov 25, 2025

    1715 Musso View Ave, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,985 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Below List Price
    • $224/SF
    • 102 Days On Market

    Current Estimated Value $456,774

    Last Listing Agent Zach Nichols West View Properties, LLC

    1715 Musso View Ave, Cheshire, CT 06410
    • 430 Cook Hill Rd, Cheshire, CT 06410

      Est $804,816

      Not Listed For Sale

      430 Cook Hill Rd, Cheshire, CT 06410

      • 3 Beds
      • 3.5 Baths
      • 4,059 Sq Ft
      • Built 1956
      430 Cook Hill Rd, Cheshire, CT 06410

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Kyle Howles Better Living Realty, LLC

  • 16 Mountaincrest Dr, Cheshire, CT 06410
    16 Mountaincrest Dr, Cheshire, CT 06410
    16 Mountaincrest Dr, Cheshire, CT 06410
    /39

    $1,590,000

    • 5 Beds
    • 4.5 Baths
    • 5,021 Sq Ft

    16 Mountaincrest Dr, Cheshire, CT 06410

    Perched high above the landscape of South Cheshire, this extraordinary custom-built Colonial is a residence of uncommon beauty, privacy, and scale. Set against the natural backdrop of Bethany Mountain and surrounded by meticulously maintained, park-like grounds, this exceptional 4/5-bedroom home captures magnificent views, abundant sunshine, and a remarkable sense of tranquility. From the moment

    Tyler Della Valle Dow Della Valle

    16 Mountaincrest Dr, Cheshire, CT 06410
  • 1674 Byam Rd, Cheshire, CT 06410

    $335,000

    Sold Mar 03, 2026

    1674 Byam Rd, Cheshire, CT 06410

    • 2 Beds
    • 1 Bath
    • 2,016 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Above List Price
    • $166/SF
    • 66 Days On Market

    Current Estimated Value $349,566

    Last Listing Agent Jesica Beaulieu Dave Jones Realty, LLC

    1674 Byam Rd, Cheshire, CT 06410
    • 445 Wild Flower Place, Cheshire, CT 06410

      Est $924,663

      Not Listed For Sale

      445 Wild Flower Place, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 3,460 Sq Ft
      • Built 1997
      445 Wild Flower Place, Cheshire, CT 06410

      Last Sold Summary

      • 126 Days On Market

      Last Listing Agent Betsy Purtell Purtell Realty LLC

  • 502 Oak Ave Unit 17, Cheshire, CT 06410
    502 Oak Ave Unit 17, Cheshire, CT 06410
    502 Oak Ave Unit 17, Cheshire, CT 06410
    /26

    $199,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    502 Oak Ave Unit 17, Cheshire, CT 06410

    Stylish, beautifully renovated and filled with natural light, this end-unit condominium is located in the well-maintained Birchwood community, surrounded by expansive green space and ample parking. Beautiful, move in condition! The open floor plan offers two spacious bedrooms, a large living room, and a stylish white kitchen with granite countertops, self-closing cabinets with lighting and

    Dorothy Karska-Piech Calcagni Real Estate

    502 Oak Ave Unit 17, Cheshire, CT 06410
  • 14 Colonial Ct, Cheshire, CT 06410

    $625,000

    Sold Jul 17, 2026

    14 Colonial Ct, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 1,820 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Above List Price
    • $343/SF
    • 15 Days On Market

    Current Estimated Value $623,978

    Last Listing Agent Donna Pellegrino Calcagni Real Estate

    14 Colonial Ct, Cheshire, CT 06410
    • 1161 Sperry Rd, Cheshire, CT 06410

      Est $1,053,342

      Not Listed For Sale

      1161 Sperry Rd, Cheshire, CT 06410

      • 3 Beds
      • 5 Baths
      • 8,558 Sq Ft
      • Built 1953
      1161 Sperry Rd, Cheshire, CT 06410

      Last Sold Summary

      • 133 Days On Market

      Last Listing Agent Derek Greene Derek Greene

  • 662 Coleman Rd, Cheshire, CT 06410
    662 Coleman Rd, Cheshire, CT 06410
    662 Coleman Rd, Cheshire, CT 06410
    /40

    $775,000

    $75K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,143 Sq Ft

    662 Coleman Rd, Cheshire, CT 06410

    Stately home set on just under 2 acres in a beautiful country setting. Built from the foundation up in 2006, this home offers soaring ceilings, flowing rooms and space for everyone! The welcoming foyer leads to the dining room highlighted by a fireplace with pellet stove insert, and the living room beyond - both with hardwood floors. A balcony from the upper level looks down on the kitchen with

    Siobhan McLaughlin William Raveis Real Estate

    662 Coleman Rd, Cheshire, CT 06410
  • 1609 Sturbridge Ct, Cheshire, CT 06410

    $762,000

    Sold Jun 18, 2026

    1609 Sturbridge Ct, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 3,144 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Above List Price
    • $242/SF
    • 5 Days On Market

    Current Estimated Value $750,349

    Last Listing Agent Cheri Paulsen Advise Realty Services

    1609 Sturbridge Ct, Cheshire, CT 06410
    • 1330 Sperry Rd, Cheshire, CT 06410

      Not Listed For Sale

      1330 Sperry Rd, Cheshire, CT 06410

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft
      • Built 1948
      1330 Sperry Rd, Cheshire, CT 06410

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Katie Smith Berkshire Hathaway NE Prop.

  • 644 S Brooksvale Rd, Cheshire, CT 06410
    644 S Brooksvale Rd, Cheshire, CT 06410
    644 S Brooksvale Rd, Cheshire, CT 06410
    /40

    $1,630,000

    • 5 Beds
    • 4.5 Baths
    • 6,361 Sq Ft

    644 S Brooksvale Rd, Cheshire, CT 06410

    Nestled on 2.26 beautifully landscaped acres and set well back from the road, this exceptional contemporary Colonial offers a rare blend of privacy, elegance, craftsmanship, and resort-style living. With more than 6,300 square feet of above-grade living space and views of Cheshire Land Trust property, the home enjoys a peaceful natural setting while delivering an extraordinary collection of

    Brian Burke Coldwell Banker Realty

    644 S Brooksvale Rd, Cheshire, CT 06410
  • 936 S Meriden Rd, Cheshire, CT 06410

    $447,000

    Sold Jul 31, 2026

    936 S Meriden Rd, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft
    • Built 1966

    Last Sold Summary

    • 3% Below List Price
    • $224/SF
    • 55 Days On Market

    Current Estimated Value $469,021

    Last Listing Agent Carly Kirsch Lamacchia Realty

    936 S Meriden Rd, Cheshire, CT 06410
    • 91 Southwick Ct, Cheshire, CT 06410

      Est $354,075

      Not Listed For Sale

      91 Southwick Ct, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,015 Sq Ft
      • Built 2005
      91 Southwick Ct, Cheshire, CT 06410

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Robin Thurston Coldwell Banker Realty

  • 125 Wallingford Rd, Cheshire, CT 06410
    125 Wallingford Rd, Cheshire, CT 06410
    125 Wallingford Rd, Cheshire, CT 06410
    /38

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    125 Wallingford Rd, Cheshire, CT 06410

    Welcome home to 125 Wallingford Road in Cheshire, CT! Loaded with curb appeal from the moment you arrive, this sweet 1900s home welcomes you with a wonderful wrap-around porch and fenced-in back yard. Extensively renovated in 2009, this charming 3-bedroom, 2-bath home beautifully blends modern updates with the character of its era. Inside, natural light fills the open main level, where wide red

    Heather Dacey William Raveis Real Estate

    125 Wallingford Rd, Cheshire, CT 06410
  • 405 Sharon Dr, Cheshire, CT 06410

    $625,000

    Sold Jan 07, 2026

    405 Sharon Dr, Cheshire, CT 06410

    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft
    • Built 1967

    Last Sold Summary

    • 6% Above List Price
    • $202/SF
    • 68 Days On Market

    Current Estimated Value $649,343

    Last Listing Agent Kevin Kennedy Coldwell Banker Realty

    405 Sharon Dr, Cheshire, CT 06410
    • 63 Southwick Ct, Cheshire, CT 06410

      Est $391,019

      Not Listed For Sale

      63 Southwick Ct, Cheshire, CT 06410

      • 2 Beds
      • 2.5 Baths
      • 1,450 Sq Ft
      • Built 1999
      63 Southwick Ct, Cheshire, CT 06410

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Sarah Murphy William Raveis Real Estate

  • 722 Allen Ave, Cheshire, CT 06410
    722 Allen Ave, Cheshire, CT 06410
    722 Allen Ave, Cheshire, CT 06410
    /30

    $599,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft

    722 Allen Ave, Cheshire, CT 06410

    ***PRICE REDUCTION*** Need serious garage space? This property features a brand-new commercial-sized detached garage that's ideal for collectors, mechanics, contractors, landscapers, hobbyists, or anyone looking for exceptional storage or workspace. Welcome to 722 Allen Avenue, Cheshire! This beautifully updated 3-bedroom, 2-bath ranch is set on a level 1-acre lot with public water and public

    Michelle Lorenzetti Premier Re Group LLC

    722 Allen Ave, Cheshire, CT 06410
  • 80 Shea Cir, Cheshire, CT 06410

    $717,575

    Sold Jan 02, 2026

    80 Shea Cir, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2025

    Last Sold Summary

    • 7% Above List Price
    • $293/SF
    • 50 Days On Market

    Last Listing Agent Felicity LeClair EG Group Realty LLC

    80 Shea Cir, Cheshire, CT 06410
    • 70 Southwick Ct Unit 302, Cheshire, CT 06410

      Est $293,327

      Not Listed For Sale

      70 Southwick Ct Unit 302, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,101 Sq Ft
      • Built 1998
      70 Southwick Ct Unit 302, Cheshire, CT 06410

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Phil Giampietro Coldwell Banker Realty

  • 16 Deepwood Dr, Cheshire, CT 06410
    16 Deepwood Dr, Cheshire, CT 06410
    16 Deepwood Dr, Cheshire, CT 06410
    /36

    $475,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft

    16 Deepwood Dr, Cheshire, CT 06410

    A striking transformation awaits with this stunningly remodeled 3 BR, 2 bath Gambrel Cape and its spacious oversized garage. Completely updated from top to bottom, this is a rare move in ready gem where every detail has been done for you. Enjoy an unbeatable location near dining, shops and the 11 mile Farmington Canal Heritage Trail! The exterior makes an unforgettable first impression with its

    Lisa Rollins Team Compass Connecticut, LLC

    16 Deepwood Dr, Cheshire, CT 06410
  • 403 Juniper Ln, Cheshire, CT 06410

    $515,000

    Sold Sep 24, 2025

    403 Juniper Ln, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1955

    Last Sold Summary

    • 10% Above List Price
    • $325/SF
    • 38 Days On Market

    Current Estimated Value $535,520

    Last Listing Agent Kathleen Maloney Coldwell Banker Realty

    403 Juniper Ln, Cheshire, CT 06410
    • 28 Southwick Ct, Cheshire, CT 06410

      Est $364,648

      Not Listed For Sale

      28 Southwick Ct, Cheshire, CT 06410

      • 2 Beds
      • 2.5 Baths
      • 1,379 Sq Ft
      • Built 1998
      28 Southwick Ct, Cheshire, CT 06410

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Norinne Byrne Calcagni Real Estate

  • 2 Saxon Woods Ct, Cheshire, CT 06410
    2 Saxon Woods Ct, Cheshire, CT 06410
    2 Saxon Woods Ct, Cheshire, CT 06410
    /31

    $497,700

    • 3 Beds
    • 2 Baths
    • 2,459 Sq Ft

    2 Saxon Woods Ct, Cheshire, CT 06410

    DESIRABLE COPPER HILL STAND-A-LONE RANCH CONDO in Cheshire on a Cul-de-sac Setting !!! BRING your vision to life at 2 Saxon Woods Court. This home offers great bones and a flexible layout, ready for your personal touch. With some updating, this home presents a wonderful opportunity to create the home of your dreams in a peaceful, private setting. This spacious standalone condo is tucked away on a

    Rose Zolnik Coldwell Banker Realty

    2 Saxon Woods Ct, Cheshire, CT 06410
  • 324 S Meriden Rd, Cheshire, CT 06410

    $875,000

    Sold Mar 13, 2026

    324 S Meriden Rd, Cheshire, CT 06410

    • 4 Beds
    • 4.5 Baths
    • 3,946 Sq Ft
    • Built 1992

    Last Sold Summary

    • 12% Below List Price
    • $222/SF
    • 139 Days On Market

    Current Estimated Value $953,026

    Last Listing Agent Tanya Uhelsky Century 21 AllPoints Realty

    324 S Meriden Rd, Cheshire, CT 06410
    • 40 Southwick Ct Unit 310, Cheshire, CT 06410

      Est $298,511

      Not Listed For Sale

      40 Southwick Ct Unit 310, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,132 Sq Ft
      • Built 2000
      40 Southwick Ct Unit 310, Cheshire, CT 06410

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Mollie Abend Berkshire Hathaway NE Prop.

  • 25 Whispering Hollow Ct, Cheshire, CT 06410
    25 Whispering Hollow Ct, Cheshire, CT 06410
    25 Whispering Hollow Ct, Cheshire, CT 06410
    /40

    $1,748,600

    Pending
    • 6 Beds
    • 7 Baths
    • 10,485 Sq Ft

    25 Whispering Hollow Ct, Cheshire, CT 06410

    Welcome to The Cheshire Estate on Whispering Hollow Court. Set on a private 1.84-acre lot in an intimate enclave of homes on a cul-de-sac, this modern brick Colonial offers over 10,000 sf of living space across three levels - a rare opportunity to live comfortably and entertain often. The two-story great room anchors the main level, with French doors opening to the patio, outdoor kitchen, and

    George Santos William Raveis Real Estate

    25 Whispering Hollow Ct, Cheshire, CT 06410
  • 1800 Blackberry Place, Cheshire, CT 06410

    $830,367

    Sold Sep 03, 2026

    1800 Blackberry Place, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft
    • Built 2025

    Last Sold Summary

    • 7% Above List Price
    • $415/SF
    • 313 Days On Market

    Last Listing Agent Kathleen Maloney Coldwell Banker Realty

    1800 Blackberry Place, Cheshire, CT 06410
    • 80 Southwick Ct Unit 202, Cheshire, CT 06410

      Est $217,213

      Not Listed For Sale

      80 Southwick Ct Unit 202, Cheshire, CT 06410

      • 1 Bed
      • 1 Bath
      • 813 Sq Ft
      • Built 2006
      80 Southwick Ct Unit 202, Cheshire, CT 06410

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Jessica Danard Coldwell Banker Realty

  • 1253 Marion Rd, Cheshire, CT 06410
    1253 Marion Rd, Cheshire, CT 06410
    1253 Marion Rd, Cheshire, CT 06410
    /40

    $590,000

    Pending
    • 5 Beds
    • 5 Baths
    • 3,401 Sq Ft

    1253 Marion Rd, Cheshire, CT 06410

    Welcome to a truly unique opportunity in Cheshire! This legal two-family property offers exceptional versatility, space, and potential, making it ideal for extended family, an in-law arrangement, or generating additional rental income. Set on over 2 acres in a peaceful setting and located within Cheshire's award-winning school district, this property is a rare find. The main residence offers an

    Karen Floriano William Raveis Real Estate

    1253 Marion Rd, Cheshire, CT 06410
  • 625 Tamarack Rd, Cheshire, CT 06410

    $750,000

    Sold Oct 21, 2025

    625 Tamarack Rd, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 2,345 Sq Ft
    • Built 1997

    Last Sold Summary

    • 3% Below List Price
    • $320/SF
    • 6 Days On Market

    Current Estimated Value $797,837

    Last Listing Agent Peter Digangi Dow Della Valle

    625 Tamarack Rd, Cheshire, CT 06410
    • 40 Southwick Ct Unit 111, Cheshire, CT 06410

      Est $307,542

      Not Listed For Sale

      40 Southwick Ct Unit 111, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,151 Sq Ft
      • Built 2000
      40 Southwick Ct Unit 111, Cheshire, CT 06410

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Stacey Deangelis Calcagni Real Estate

  • 25 Stacy Ct, Cheshire, CT 06410
    25 Stacy Ct, Cheshire, CT 06410
    25 Stacy Ct, Cheshire, CT 06410
    /37

    $499,900

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,905 Sq Ft

    25 Stacy Ct, Cheshire, CT 06410

    ***Seller is asking for highest and best Due 12 pm on Tuesday August 18th. *** Welcome to 25 Stacy Court, a well-maintained raised ranch set on 0.92 acres in a desirable Cheshire cul-de-sac. Offered by the original owners after 55 years, this 1,905-square-foot home features three bedrooms, one full and one half baths, hardwood floors throughout the main level and plenty of indoor and outdoor

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    25 Stacy Ct, Cheshire, CT 06410
  • 130 Bates Dr, Cheshire, CT 06410

    $435,000

    Sold Jun 09, 2026

    130 Bates Dr, Cheshire, CT 06410

    • 3 Beds
    • 1 Bath
    • 1,065 Sq Ft
    • Built 1955

    Last Sold Summary

    • 9% Above List Price
    • $408/SF
    • 53 Days On Market

    Current Estimated Value $432,395

    Last Listing Agent Kelly Ryan William Raveis Real Estate

    130 Bates Dr, Cheshire, CT 06410
    • 70 Southwick Ct Unit 211, Cheshire, CT 06410

      Est $304,140

      Not Listed For Sale

      70 Southwick Ct Unit 211, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,151 Sq Ft
      • Built 1998
      70 Southwick Ct Unit 211, Cheshire, CT 06410

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

  • 213 Robin Ln, Cheshire, CT 06410
    213 Robin Ln, Cheshire, CT 06410
    213 Robin Ln, Cheshire, CT 06410
    /34

    $399,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,374 Sq Ft

    213 Robin Ln, Cheshire, CT 06410

    Welcome to this turnkey ranch ready for its new owner. The home has been thoughtfully renovated over the past few years. Enjoy the peace of mind of moving in without needing to do a thing! With a little over 1300 sq ft of living space on the main level, this could be a great spot for new homeowners or downsizers. Walking into the home, you will be greeted by the newly done kitchen and flexible

    Peter Onofrio LAER Realty Partners

    213 Robin Ln, Cheshire, CT 06410
  • 1517 Blackberry Place, Cheshire, CT 06410

    $795,949

    Sold Jul 02, 2026

    1517 Blackberry Place, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $398/SF
    • 419 Days On Market

    Last Listing Agent Kathleen Maloney Coldwell Banker Realty

    1517 Blackberry Place, Cheshire, CT 06410
    • 7 Brubaker Rd, Cheshire, CT 06410

      Est $417,685

      Not Listed For Sale

      7 Brubaker Rd, Cheshire, CT 06410

      • 3 Beds
      • 1 Bath
      • 1,556 Sq Ft
      • Built 1955
      7 Brubaker Rd, Cheshire, CT 06410

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Emma Funaro LPT Realty

  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /25

    $489,900

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,355 Sq Ft

    Unlisted Address

    This is an excellent opportunity! It's in a prime location, and you won't want to miss out on this lovely home. It features an updated custom kitchen, three bedrooms, and a half-bathroom. There's also a partially finished basement and a very large backyard.

    Mitchell Stevenson William Raveis Real Estate

    Unlisted Address

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