11,925

Cheshire, CT Homes

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  • 424 Cedar Ln, Cheshire, CT 06410
    424 Cedar Ln, Cheshire, CT 06410
    424 Cedar Ln, Cheshire, CT 06410
    /40

    $505,000

    $20K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,266 Sq Ft

    424 Cedar Ln, Cheshire, CT 06410

    Present owner has done many updates during the time they lived here. New roof (2025), New furnace(2026), New AC Compressor(2023), New Flooring (2021), New Propane tanks(2023), Upgraded baths(2021), New granite in kitchen(2022). Still time for new buyer to make it your own with cosmetics to your liking! Step outside into your own private resort, designed entirely around warm-weather enjoyment. The

    Kevin Kennedy Coldwell Banker Realty

    424 Cedar Ln, Cheshire, CT 06410
  • 48 Willow St, Cheshire, CT 06410

    $647,250

    Sold Dec 30, 2025

    48 Willow St, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,494 Sq Ft
    • Built 2017

    Last Sold Summary

    • 3% Above List Price
    • $260/SF
    • 5 Days On Market

    Current Estimated Value $672,874

    Last Listing Agent Alex LaRosa Coldwell Banker Realty

    48 Willow St, Cheshire, CT 06410
  • 44 Williamsburg Dr, Cheshire, CT 06410
    44 Williamsburg Dr, Cheshire, CT 06410
    44 Williamsburg Dr, Cheshire, CT 06410
    /25

    $499,900

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,554 Sq Ft

    44 Williamsburg Dr, Cheshire, CT 06410

    Welcome home to this beautifully updated ranch in a highly desirable neighborhood, just minutes from shopping, restaurants, and everyday conveniences. This move-in ready home features hardwood floors throughout and a spacious living room with a classic brick fireplace and Vermont Castings wood-burning insert, creating a warm and inviting gathering space. The dining room flows seamlessly into the

    Stacey Deangelis Calcagni Real Estate

    44 Williamsburg Dr, Cheshire, CT 06410
  • 840 Westside Rd, Cheshire, CT 06410

    $475,000

    Sold May 08, 2026

    840 Westside Rd, Cheshire, CT 06410

    • 3 Beds
    • 1 Bath
    • 1,491 Sq Ft
    • Built 1978

    Last Sold Summary

    • 20% Above List Price
    • $319/SF
    • 1 Day On Market

    Current Estimated Value $439,844

    Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

    840 Westside Rd, Cheshire, CT 06410
  • 34 Pehr Ln, Cheshire, CT 06410
    34 Pehr Ln, Cheshire, CT 06410
    34 Pehr Ln, Cheshire, CT 06410
    /38

    $439,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,431 Sq Ft

    34 Pehr Ln, Cheshire, CT 06410

    Move-in ready ranch set on a private .80-acre cul-de-sac lot in Cheshire. This 3-bedroom, 2-bath home offers hardwood floors, central air, city water and sewer, and mature, low-maintenance landscaping - all for effortless everyday living. With nearly 1,500 square feet of finished interior space, another 500 of outdoor patio and deck, and thoughtful storage and built-ins throughout, this home

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    34 Pehr Ln, Cheshire, CT 06410
  • 10 W Ridge Ct, Cheshire, CT 06410

    $725,000

    Sold Dec 02, 2025

    10 W Ridge Ct, Cheshire, CT 06410

    • 4 Beds
    • 3.5 Baths
    • 2,709 Sq Ft
    • Built 2017

    Last Sold Summary

    • 14% Below List Price
    • $268/SF
    • 75 Days On Market

    Current Estimated Value $749,986

    Last Listing Agent Ken Demirs Regency Real Estate, LLC

    10 W Ridge Ct, Cheshire, CT 06410
  • 85 Scenic Ct, Cheshire, CT 06410
    85 Scenic Ct, Cheshire, CT 06410
    85 Scenic Ct, Cheshire, CT 06410
    /40

    $899,000

    $50K PRICE DROP Under Contract
    • 5 Beds
    • 3.5 Baths
    • 5,187 Sq Ft

    85 Scenic Ct, Cheshire, CT 06410

    A private hilltop retreat with over 5,000 square feet of finished living space, an in-ground pool, walk-out lower level, and secluded resort-style setting- Welcome to 85 Scenic Court. This custom-built 5 bedroom, 3.5 bath colonial is set back on a private, beautifully landscaped lot and offers an exceptional blend of space, comfort, privacy, and luxury. The main level features a private office

    Jeffrey Puciato Puciato Altieri Realty Group

    85 Scenic Ct, Cheshire, CT 06410
  • 40 Southwick Ct Unit 106, Cheshire, CT 06410

    $210,000

    Sold Dec 18, 2025

    40 Southwick Ct Unit 106, Cheshire, CT 06410

    • Studio
    • 1 Bath
    • 600 Sq Ft
    • Built 2004

    Last Sold Summary

    • $350/SF
    • 64 Days On Market

    Current Estimated Value $207,798

    Last Listing Agent Amanda Albert Coldwell Banker Realty

    40 Southwick Ct Unit 106, Cheshire, CT 06410
  • 1116 Wallingford Rd, Cheshire, CT 06410
    1116 Wallingford Rd, Cheshire, CT 06410
    /2

    $229,000

    • Land
    • 1.84 Acres
    • $124,457 per Acre

    1116 Wallingford Rd, Cheshire, CT 06410

    Your blank canvas - with a head start A rare opportunity to build the home you've been picturing on a 1.84-acre lot in Cheshire. The existing structure will be removed prior to closing - or within 60 days of closing at the latest - leaving you a cleared, ready-to-build site with the foundation remaining in place. That foundation is the difference-maker. Pouring a new foundation is one of the most

    George Daniolos eRealty Advisors, Inc.

    1116 Wallingford Rd, Cheshire, CT 06410
  • 114 Spring St, Cheshire, CT 06410

    $340,000

    Sold Aug 08, 2025

    114 Spring St, Cheshire, CT 06410

    • 3 Beds
    • 1 Bath
    • 1,406 Sq Ft
    • Built 1850

    Last Sold Summary

    • 7% Above List Price
    • $242/SF
    • 43 Days On Market

    Current Estimated Value $356,523

    Last Listing Agent Thomas Scott Coldwell Banker Realty

    114 Spring St, Cheshire, CT 06410
    • 65 Abrams Rd, Cheshire, CT 06410

      Est $1,416,217

      Not Listed For Sale

      65 Abrams Rd, Cheshire, CT 06410

      • 6 Beds
      • 9 Baths
      • 8,099 Sq Ft
      • Built 1988
      65 Abrams Rd, Cheshire, CT 06410

      Last Sold Summary

      • 163 Days On Market

  • 29 Nathan Hale Ct, Cheshire, CT 06410
    29 Nathan Hale Ct, Cheshire, CT 06410
    29 Nathan Hale Ct, Cheshire, CT 06410
    /40

    $650,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,301 Sq Ft

    29 Nathan Hale Ct, Cheshire, CT 06410

    Privacy & seclusion meet convenience in the heart of Cheshire at 29 Nathan Hale Court. Offered for the first time by its original owner, this well maintained, newer-built home delivers the modern features today's buyers are searching for-without the premium price tag of new construction. Step inside to a two-story foyer that welcomes you into a bright, open floor plan. The stunning, fully

    Lauren Freedman Coldwell Banker Realty

    29 Nathan Hale Ct, Cheshire, CT 06410
  • 4 Brookfield Ct, Cheshire, CT 06410

    $670,000

    Sold Dec 15, 2025

    4 Brookfield Ct, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $291/SF
    • 39 Days On Market

    Current Estimated Value $679,621

    Last Listing Agent Brette Stern Calcagni Real Estate

    4 Brookfield Ct, Cheshire, CT 06410
  • 80 Southwick Ct Unit 201, Cheshire, CT 06410
    80 Southwick Ct Unit 201, Cheshire, CT 06410
    80 Southwick Ct Unit 201, Cheshire, CT 06410
    /22

    $209,000

    Pending
    • 1 Bed
    • 1 Bath
    • 807 Sq Ft

    80 Southwick Ct Unit 201, Cheshire, CT 06410

    A rare opportunity to own this beautifully maintained condo just one month after its previous sale. The new owner had planned to relocate and make this their full-time residence, but a change in personal circumstances has created an unexpected opportunity for a new owner. Freshly painted and move-in ready! If you've been looking for low-maintenance living in Cheshire, now is your chance to jump

    Rebecca Bower Forever Homes Real Estate LLC

    80 Southwick Ct Unit 201, Cheshire, CT 06410
  • 975 Wolf Hill Rd, Cheshire, CT 06410

    $565,000

    Sold Feb 19, 2026

    975 Wolf Hill Rd, Cheshire, CT 06410

    • 3 Beds
    • 3 Baths
    • 1,882 Sq Ft
    • Built 1947

    Last Sold Summary

    • 2% Below List Price
    • $300/SF
    • 10 Days On Market

    Current Estimated Value $568,547

    Last Listing Agent Rachel Wardwell Calcagni Real Estate

    975 Wolf Hill Rd, Cheshire, CT 06410
  • 54 Hemlock Ridge, Cheshire, CT 06410
    54 Hemlock Ridge, Cheshire, CT 06410
    54 Hemlock Ridge, Cheshire, CT 06410
    /34

    $375,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,673 Sq Ft

    54 Hemlock Ridge, Cheshire, CT 06410

    Great opportunity to experience the Cheshire lifestyle! I am an older three bedroom home with 1.5 baths and a two car garage on quiet cul-de-sac minutes from town center, schools, shopping, cultural events, restaurants, walking trails and more. I was built in 1955 and comfortably housed the same family since my initial construction. I am now waiting for new owners with a vision and creative mine

    Frank Balisciano Coldwell Banker Realty

    54 Hemlock Ridge, Cheshire, CT 06410
  • 135 Shea Cir Unit 135, Cheshire, CT 06410

    $547,560

    Sold Apr 21, 2026

    135 Shea Cir Unit 135, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Above List Price
    • $296/SF
    • 32 Days On Market

    Last Listing Agent Michael Helmuth EG Group Realty LLC

    135 Shea Cir Unit 135, Cheshire, CT 06410
  • 39 Green Hill Ln, Cheshire, CT 06410
    39 Green Hill Ln, Cheshire, CT 06410
    39 Green Hill Ln, Cheshire, CT 06410
    /36

    $449,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,656 Sq Ft

    39 Green Hill Ln, Cheshire, CT 06410

    Welcome home to this beautifully updated 3-bedroom ranch in the highly desirable town of Cheshire. This move-in ready property combines modern comfort with classic charm in a peaceful neighborhood setting. Step inside to find a bright, open layout featuring gleaming hardwood floors, an updated eat-in kitchen with sleek countertops and stainless-steel appliances, and a spacious living room perfect

    janet colello Century 21 AllPoints Realty

    39 Green Hill Ln, Cheshire, CT 06410
  • 107 Country Club Rd, Cheshire, CT 06410

    $552,500

    Sold May 06, 2026

    107 Country Club Rd, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,088 Sq Ft
    • Built 1975

    Last Sold Summary

    • 9% Above List Price
    • $265/SF
    • 36 Days On Market

    Current Estimated Value $543,188

    Last Listing Agent Frank Lazowski Laz Real Estate, LLC

    107 Country Club Rd, Cheshire, CT 06410
  • 59 Williams Rd, Cheshire, CT 06410
    59 Williams Rd, Cheshire, CT 06410
    59 Williams Rd, Cheshire, CT 06410
    /37

    $659,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,124 Sq Ft

    59 Williams Rd, Cheshire, CT 06410

    Some homes check the boxes. This one checks them all and then pulls you in with something harder to quantify: the feeling that you've found exactly where you're supposed to be. Tucked away on a private rear acre in one of Cheshire's most coveted in-town locations, this beautifully maintained 3-4 bedroom, 2.5-bath colonial offers the rare combination of peaceful seclusion and unbeatable

    Leanne Delrosso Lamacchia Realty

    59 Williams Rd, Cheshire, CT 06410
  • 66 Old Towne Rd, Cheshire, CT 06410

    $350,000

    Sold Apr 28, 2026

    66 Old Towne Rd, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 1,536 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $228/SF
    • 96 Days On Market

    Current Estimated Value $367,822

    Last Listing Agent The Sally Bowman Team Berkshire Hathaway NE Prop.

    66 Old Towne Rd, Cheshire, CT 06410
  • 21 Melrose Dr Unit Lot 2, Cheshire, CT 06410
    21 Melrose Dr Unit Lot 2, Cheshire, CT 06410
    /2

    $1,815,000

    New Construction Pending
    • 6 Beds
    • 8 Baths
    • 6,008 Sq Ft

    21 Melrose Dr Unit Lot 2, Cheshire, CT 06410

    A truly SPECTACULAR house plan on a truly PICTURESQUE lot! This to be built home will be simply breathtaking at just over 6,000 sq ft.

    Dori Degennaro William Raveis Real Estate

    21 Melrose Dr Unit Lot 2, Cheshire, CT 06410
  • 25 Goldenrod Ct, Cheshire, CT 06410

    $646,500

    Sold Mar 13, 2026

    25 Goldenrod Ct, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,311 Sq Ft
    • Built 1972

    Last Sold Summary

    • 8% Below List Price
    • $280/SF
    • 171 Days On Market

    Current Estimated Value $676,131

    Last Listing Agent Mark Gracia William Raveis Real Estate

    25 Goldenrod Ct, Cheshire, CT 06410
  • 25 Charter Oak Dr, Cheshire, CT 06410
    25 Charter Oak Dr, Cheshire, CT 06410
    25 Charter Oak Dr, Cheshire, CT 06410
    /39

    $749,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,440 Sq Ft

    25 Charter Oak Dr, Cheshire, CT 06410

    Tucked away in a quiet neighborhood, this 4-bedroom Colonial showcases exceptional pride of ownership inside and out. Set on beautifully manicured, park-like grounds, the backyard is a destination all its own, designed for entertaining, recreation, and relaxation. Enjoy a half-court basketball court that also accommodates pickleball, a putting green, a spacious patio, a covered pavilion with TV

    Heidi Weed Lamacchia Realty

    25 Charter Oak Dr, Cheshire, CT 06410
  • 1325 Avon Blvd, Cheshire, CT 06410

    $400,000

    Sold Dec 04, 2025

    1325 Avon Blvd, Cheshire, CT 06410

    • 3 Beds
    • 1 Bath
    • 1,316 Sq Ft
    • Built 1953

    Last Sold Summary

    • $304/SF
    • 69 Days On Market

    Current Estimated Value $404,060

    Last Listing Agent Cindy Forlenzo Coldwell Banker Realty

    1325 Avon Blvd, Cheshire, CT 06410
  • 17 Melrose Dr Unit Lot 3, Cheshire, CT 06410
    17 Melrose Dr Unit Lot 3, Cheshire, CT 06410
    17 Melrose Dr Unit Lot 3, Cheshire, CT 06410
    /3

    $1,299,000

    New Construction Pending
    • 4 Beds
    • 5 Baths
    • 4,011 Sq Ft

    17 Melrose Dr Unit Lot 3, Cheshire, CT 06410

    A beautiful new construction home!! Only 2 lots remain in the desirable Orchard View subdivision. Introducing the expanded Essex plan at 4,011 square feet. A very spacious home with 9 ft ceilings on the main level, a generous sized kitchen, and a beautiful cathedral ceiling in the Family Room that perfectly highlights the propane fireplace. A very functional mudroom area right off the 3 car

    Dori Degennaro William Raveis Real Estate

    17 Melrose Dr Unit Lot 3, Cheshire, CT 06410
  • 440 Mount Sanford Rd, Cheshire, CT 06410

    $710,000

    Sold Jan 08, 2026

    440 Mount Sanford Rd, Cheshire, CT 06410

    • 4 Beds
    • 4 Baths
    • 3,816 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $186/SF
    • 16 Days On Market

    Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

    440 Mount Sanford Rd, Cheshire, CT 06410

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