11,915

Cheshire, CT Homes

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  • 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
  • 100 Lynwood Drive Extension, Cheshire, CT 06410

    $590,000

    Sold Feb 13, 2026

    100 Lynwood Drive Extension, Cheshire, CT 06410

    • 3 Beds
    • 1.5 Baths
    • 1,360 Sq Ft
    • Built 1955

    Last Sold Summary

    • 10% Above List Price
    • $434/SF
    • 4 Days On Market

    Current Estimated Value $565,248

    Last Listing Agent Julie Corrado Coldwell Banker Realty

    100 Lynwood Drive Extension, Cheshire, CT 06410
  • 5 Waterside Way, Cheshire, CT 06410
    5 Waterside Way, Cheshire, CT 06410
    5 Waterside Way, Cheshire, CT 06410
    /8

    $299,900

    • Land
    • 1.3 Acres
    • $230,692 per Acre

    5 Waterside Way, Cheshire, CT 06410

    Unique opportunity to own Waterfrontage in Cheshire. This one of a kind planned unit development, sitting on the pristine Lake Percival with an exquisite waterfall is offering a 1.32 acre lot available to build your dream home. Boasting vast views of the pond from the building area, with no flood insurance required, bring your contractor to lay out your vision today, or contractor consultations

    Anthony LaCava Berkshire Hathaway NE Prop.

    5 Waterside Way, Cheshire, CT 06410
  • 16 Soderman Way Unit 16, Cheshire, CT 06410

    $570,000

    Sold Nov 07, 2025

    16 Soderman Way Unit 16, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 2,090 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $273/SF
    • 27 Days On Market

    Last Listing Agent Stephanie Plaza Lamacchia Realty

    16 Soderman Way Unit 16, Cheshire, CT 06410
  • 10 Whispering Hollow Ct, Cheshire, CT 06410
    10 Whispering Hollow Ct, Cheshire, CT 06410
    10 Whispering Hollow Ct, Cheshire, CT 06410
    /40

    $1,090,888

    $210K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,163 Sq Ft

    10 Whispering Hollow Ct, Cheshire, CT 06410

    A rare opportunity to own a home in one of Cheshire's premier subdivisions. This custom-built brick residence showcases exceptional craftsmanship, featuring 9-foot ceilings and beautiful hardwood floors throughout. The gourmet kitchen blends function and style, complete with granite countertops, a Viking gas range with professional-grade exhaust hood, Viking refrigerator, built-in wall oven, and

    Mark Gracia William Raveis Real Estate

    10 Whispering Hollow Ct, Cheshire, CT 06410
  • 3 Mountaincrest Dr, Cheshire, CT 06410

    $1,275,000

    Sold Jul 18, 2025

    3 Mountaincrest Dr, Cheshire, CT 06410

    • 4 Beds
    • 5 Baths
    • 4,121 Sq Ft
    • Built 1992

    Last Sold Summary

    • 2% Above List Price
    • $309/SF
    • 30 Days On Market

    Current Estimated Value $1,289,049

    Last Listing Agent Sarah Hull Coldwell Banker Realty

    3 Mountaincrest Dr, Cheshire, CT 06410
  • 88 Shea Cir Unit 88, Cheshire, CT 06410
    88 Shea Cir Unit 88, Cheshire, CT 06410
    88 Shea Cir Unit 88, Cheshire, CT 06410
    /13

    $674,900

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    88 Shea Cir Unit 88, Cheshire, CT 06410

    Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy, offer

    Michael Helmuth EG Group Realty LLC

    88 Shea Cir Unit 88, Cheshire, CT 06410
  • 31 Roslyn Dr, Cheshire, CT 06410

    $500,000

    Sold Aug 29, 2025

    31 Roslyn Dr, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft
    • Built 1955

    Last Sold Summary

    • $321/SF
    • 39 Days On Market

    Current Estimated Value $499,980

    Last Listing Agent Paulo Salgado RE/MAX RISE

    31 Roslyn Dr, Cheshire, CT 06410
  • 1006 King Rd, Cheshire, CT 06410
    1006 King Rd, Cheshire, CT 06410
    1006 King Rd, Cheshire, CT 06410
    /40

    $499,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,577 Sq Ft

    1006 King Rd, Cheshire, CT 06410

    Charm meets modern updates in this lovely, move-in ready home! Enjoy the bright, airy atmosphere with oversized windows and hardwood floors throughout. On the main level, the beautifully renovated kitchen boasts an open layout and high end touches. The living room includes a gas fireplace for cozy nights in. And the flexible floor plan includes a room perfect for a 3rd bedroom, office or den. The

    Jen Pomichter William Pitt Sotheby's Int'l

    1006 King Rd, Cheshire, CT 06410
  • 265 Lancaster Way, Cheshire, CT 06410

    $515,000

    Sold Feb 24, 2026

    265 Lancaster Way, Cheshire, CT 06410

    • 5 Beds
    • 3.5 Baths
    • 2,212 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $233/SF
    • 67 Days On Market

    Current Estimated Value $520,683

    Last Listing Agent Betsy Purtell Purtell Realty LLC

    265 Lancaster Way, Cheshire, CT 06410
    • 1081 King Rd, Cheshire, CT 06410

      Est $478,809

      Not Listed For Sale

      1081 King Rd, Cheshire, CT 06410

      • 3 Beds
      • 1.5 Baths
      • 1,532 Sq Ft
      • Built 1986
      1081 King Rd, Cheshire, CT 06410

      Last Sold Summary

      • 45 Days On Market

  • 1412 Marion Ave, Cheshire, CT 06410
    1412 Marion Ave, Cheshire, CT 06410
    1412 Marion Ave, Cheshire, CT 06410
    /24

    $849,900

    New Construction Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,815 Sq Ft

    1412 Marion Ave, Cheshire, CT 06410

    This house is 45 days from completion! Framed, siding, windows, Heating/AC, Hardwood, baths, kitchen are all in process or done! GREAT NEW CONSTRUCTION READY FOR QUICK DELIVERY FOR NEW OWNERS!! Pictures at end of what same house looked like. GREAT OPPORTUNITY for new homeowners for a new house without any waiting or hassles! Amazing open layout on this modern colonial. This home is perfect for

    Roy Evjen Evjen Agency

    1412 Marion Ave, Cheshire, CT 06410
  • 851 Ward Ln, Cheshire, CT 06410

    $485,000

    Sold Apr 14, 2026

    851 Ward Ln, Cheshire, CT 06410

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1955

    Last Sold Summary

    • 31% Above List Price
    • $367/SF
    • 3 Days On Market

    Current Estimated Value $457,168

    Last Listing Agent Carly Kirsch Lamacchia Realty

    851 Ward Ln, Cheshire, CT 06410
  • 30 Wadsworth Ln Unit 30, Wallingford, CT 06492
    30 Wadsworth Ln Unit 30, Wallingford, CT 06492
    30 Wadsworth Ln Unit 30, Wallingford, CT 06492
    /38

    $650,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,591 Sq Ft

    30 Wadsworth Ln Unit 30, Wallingford, CT 06492

    Tucked away in a serene, wooded setting within the coveted Cheshire Crossing II neighborhood, open to all ages, this exquisite single-family detached home harmonizes sophistication and comfort. Step into a grand foyer, where gleaming hardwood floors lead you to a conveniently situated home office. The open-concept design seamlessly transitions to a formal living and dining area, adorned with

    Norinne Byrne Calcagni Real Estate

    30 Wadsworth Ln Unit 30, Wallingford, CT 06492
  • 1296 Deer Run Cir, Cheshire, CT 06410

    $616,000

    Sold Feb 24, 2026

    1296 Deer Run Cir, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Above List Price
    • $318/SF
    • 5 Days On Market

    Current Estimated Value $606,828

    Last Listing Agent Catherine Leake Coldwell Banker Realty

    1296 Deer Run Cir, Cheshire, CT 06410
  • 1481 Marion Rd, Cheshire, CT 06410
    1481 Marion Rd, Cheshire, CT 06410
    1481 Marion Rd, Cheshire, CT 06410
    /30

    $1,299,000

    New Construction Pending
    • 4 Beds
    • 2.5 Baths
    • 3,775 Sq Ft

    1481 Marion Rd, Cheshire, CT 06410

    Welcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot presents a rare opportunity to build your dream home with a respected local builder known for quality craftsmanship, meticulous attention to detail, and energy-efficient design. The Magnolia model showcases 9' ceilings, hardwood flooring in the main living areas, and a custom-designed kitchen that seamlessly

    Abby Breau New England Prestige Realty

    1481 Marion Rd, Cheshire, CT 06410
  • 67 Southwick Ct Unit 67, Cheshire, CT 06410

    $357,000

    Sold Sep 16, 2025

    67 Southwick Ct Unit 67, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 1,450 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Above List Price
    • $246/SF
    • 37 Days On Market

    Current Estimated Value $360,599

    Last Listing Agent Mela Veltri Case KW Legacy Partners

    67 Southwick Ct Unit 67, Cheshire, CT 06410
  • 39 Winslow Rd, Cheshire, CT 06410
    39 Winslow Rd, Cheshire, CT 06410
    39 Winslow Rd, Cheshire, CT 06410
    /39

    $449,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,758 Sq Ft

    39 Winslow Rd, Cheshire, CT 06410

    Welcome to 39 Winslow Rd in Cheshire-a beautifully updated Cape set in one of the town's most desirable locations. This 3-bedroom, 2 full bath home blends charm, functionality, and modern updates in all the right ways. Step inside to a spacious foyer that doubles as a cozy sitting area, complete with a built-in coffee bar-perfect for starting or ending your day. The fully renovated kitchen

    Joseph Snell Luxe Realty LLC

    39 Winslow Rd, Cheshire, CT 06410
  • 1324 Notch Rd, Cheshire, CT 06410

    $530,000

    Sold Mar 30, 2026

    1324 Notch Rd, Cheshire, CT 06410

    • 4 Beds
    • 2 Baths
    • 1,776 Sq Ft
    • Built 1960

    Last Sold Summary

    • 1% Above List Price
    • $298/SF
    • 73 Days On Market

    Current Estimated Value $521,729

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

    1324 Notch Rd, Cheshire, CT 06410
  • 55 Bellamy Rd, Cheshire, CT 06410
    55 Bellamy Rd, Cheshire, CT 06410
    55 Bellamy Rd, Cheshire, CT 06410
    /24

    $629,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    55 Bellamy Rd, Cheshire, CT 06410

    Welcome to 55 Bellamy Road in the highly desirable neighborhood of Cheshire. This charming home offers 4 bedrooms, one being a primary suite with 1 additional bath upstairs and a half bath downstairs. The Family Room has a beautiful fireplace, ready to be used and leads you to the deck and patio. 2 car garage that has plenty of space. The house has hardwood floors flowing throughout and ready for

    Walter Montero Keller Williams Realty

    55 Bellamy Rd, Cheshire, CT 06410
  • 70 Royalwood Ct, Cheshire, CT 06410

    $531,150

    Sold Aug 22, 2025

    70 Royalwood Ct, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,284 Sq Ft
    • Built 1975

    Last Sold Summary

    • 8% Above List Price
    • $233/SF
    • 24 Days On Market

    Current Estimated Value $536,687

    Last Listing Agent Brette Stern Calcagni Real Estate

    70 Royalwood Ct, Cheshire, CT 06410
  • 1062 Amherst Place, Cheshire, CT 06410
    1062 Amherst Place, Cheshire, CT 06410
    1062 Amherst Place, Cheshire, CT 06410
    /38

    $625,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,270 Sq Ft

    1062 Amherst Place, Cheshire, CT 06410

    This expanded Ranch in Cheshire brings together easy one-level living, inviting indoor spaces, and a backyard built for warm-weather enjoyment. Set at 1062 Amherst Place, the home offers 1,958 sq ft on the main level plus an additional 312 sq ft in the partially finished lower level, along with a 2-car under garage. Hardwood floors run through the living room, dining room, hallway, and bedrooms,

    Katie Smith Berkshire Hathaway NE Prop.

    1062 Amherst Place, Cheshire, CT 06410
  • 320 Highland Ave, Cheshire, CT 06410

    $320,000

    Sold Jun 23, 2025

    320 Highland Ave, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,217 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Above List Price
    • $263/SF
    • 25 Days On Market

    Current Estimated Value $346,320

    Last Listing Agent Sandra Wagner Calcagni Real Estate

    320 Highland Ave, Cheshire, CT 06410
  • 109 Greens Loop, Cheshire, CT 06410
    109 Greens Loop, Cheshire, CT 06410
    109 Greens Loop, Cheshire, CT 06410
    /29

    $329,888

    • 2 Beds
    • 1.5 Baths
    • 1,052 Sq Ft

    109 Greens Loop, Cheshire, CT 06410

    Enjoy peaceful country living in this charming upscale European contemporary townhouse. This well-maintained home features two spacious bedrooms, one full bath, and one half bath, offering comfort and convenience in an attractive setting. The thoughtfully designed floor plan includes a separate laundry and utility area, while the bright eat-in kitchen is equipped with newer stainless-steel

    Mark Gracia William Raveis Real Estate

    109 Greens Loop, Cheshire, CT 06410
  • 253 Elmwood Cir, Cheshire, CT 06410

    $365,000

    Sold Feb 02, 2026

    253 Elmwood Cir, Cheshire, CT 06410

    • 3 Beds
    • 1 Bath
    • 1,242 Sq Ft
    • Built 1954

    Last Sold Summary

    • 11% Above List Price
    • $294/SF
    • 10 Days On Market

    Current Estimated Value $356,524

    Last Listing Agent Nicholas Greene eXp Realty

    253 Elmwood Cir, Cheshire, CT 06410
  • 0 Main St S Unit 24155068, Cheshire, CT 06410
    0 Main St S Unit 24155068, Cheshire, CT 06410
    0 Main St S Unit 24155068, Cheshire, CT 06410
    /19

    $74,995

    • Land
    • 27,007 Sq Ft
    • $120,960 per Acre

    0 Main St S Unit 24155068, Cheshire, CT 06410

    Prime corner lot opportunity in desirable South Cheshire! This 0.62-acre parcel boasts approximately 243 feet of frontage on South Main Street (Route 10) and 138 feet on Fenn Road, offering excellent visibility and dual-road access in a serene residential area. Zoned for single-family residential use with great build potential-imagine your dream home nestled near open space, and convenient

    Josh Arkenbout Coldwell Banker Realty

    0 Main St S Unit 24155068, Cheshire, CT 06410
  • 104 Laurel Terrace, Cheshire, CT 06410

    $535,000

    Sold May 15, 2026

    104 Laurel Terrace, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,846 Sq Ft
    • Built 1956

    Last Sold Summary

    • 10% Above List Price
    • $290/SF
    • 2 Days On Market

    Current Estimated Value $479,268

    Last Listing Agent Matthew Egan Regency Real Estate, LLC

    104 Laurel Terrace, Cheshire, CT 06410

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