11,916

Cheshire, CT Homes

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  • 562 Oak Ave, Cheshire, CT 06410
    562 Oak Ave, Cheshire, CT 06410
    562 Oak Ave, Cheshire, CT 06410
    /19

    $325,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,386 Sq Ft

    562 Oak Ave, Cheshire, CT 06410

    Move right in and enjoy this beautifully remodeled 2 bedroom, 1.5 bath townhome in a desirable Cheshire location. This bright and updated unit offers a fantastic opportunity for first-time buyers, downsizers, or anyone looking for low-maintenance living in a convenient setting. Stylish updates, comfortable living spaces, and a practical layout make this a wonderful starter home. Close to

    Maria Bardelli Douglas Elliman of Connecticut

    562 Oak Ave, Cheshire, CT 06410
  • 55 Pine Brook Ct, Cheshire, CT 06410

    $725,000

    Sold Oct 15, 2025

    55 Pine Brook Ct, Cheshire, CT 06410

    • 3 Beds
    • 3.5 Baths
    • 3,663 Sq Ft
    • Built 1985

    Last Sold Summary

    • 27% Below List Price
    • $198/SF
    • 186 Days On Market

    Current Estimated Value $754,985

    Last Listing Agent Brian Botti Botti Realty

    55 Pine Brook Ct, Cheshire, CT 06410
  • 9 Melrose Dr Unit 6, Cheshire, CT 06410
    9 Melrose Dr Unit 6, Cheshire, CT 06410
    9 Melrose Dr Unit 6, Cheshire, CT 06410
    /26

    $1,600,000

    New Construction $452K PRICE INCREASE Pending
    • 4 Beds
    • 3.5 Baths
    • 5,159 Sq Ft

    9 Melrose Dr Unit 6, Cheshire, CT 06410

    Presenting the Old Lyme model! This 4,015 sq ft TO BE BUILT colonial plan is perfection! This house has so many of today's must haves starting with a 2 story foyer, creating an grand entrance. Should you enter through the garage, you will walk through the mudroom with ship lap walls. The main living space on the first floor is a true open concept layout, from the spacious Eat in Kitchen into the

    Dori Degennaro William Raveis Real Estate

    9 Melrose Dr Unit 6, Cheshire, CT 06410
  • 65 Soderman Way Unit 65, Cheshire, CT 06410

    $790,000

    Sold Aug 11, 2025

    65 Soderman Way Unit 65, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $322/SF
    • 275 Days On Market

    Last Listing Agent Jason Helton EG Group Realty LLC

    65 Soderman Way Unit 65, Cheshire, CT 06410
    • 60 Pace Dr, Cheshire, CT 06410

      Est $533,883

      Not Listed For Sale

      60 Pace Dr, Cheshire, CT 06410

      • 4 Beds
      • 1.5 Baths
      • 2,438 Sq Ft
      • Built 1970
      60 Pace Dr, Cheshire, CT 06410

      Last Sold Summary

      • 36 Days On Market

  • 276 Preston Terrace, Cheshire, CT 06410
    276 Preston Terrace, Cheshire, CT 06410
    276 Preston Terrace, Cheshire, CT 06410
    /40

    $729,000

    Open Sun 12PM - 2PM Coming Soon
    • 4 Beds
    • 3 Baths
    • 2,960 Sq Ft

    276 Preston Terrace, Cheshire, CT 06410

    LOCATION, LOCATION, LOCATION! Rarely does an opportunity like this come along. Welcome to this extraordinary, completely remodeled ranch offering the perfect combination of timeless elegance, exceptional craftsmanship, and the convenience of one-floor living. Thoughtfully redesigned from top to bottom, this stunning residence showcases an outstanding floor plan filled with natural light,

    Agnes Nawrocki William Raveis Real Estate

    276 Preston Terrace, Cheshire, CT 06410
  • 34 Lakeview Ave, Cheshire, CT 06410

    $210,000

    Sold Dec 12, 2025

    34 Lakeview Ave, Cheshire, CT 06410

    • 2 Beds
    • 1 Bath
    • 822 Sq Ft
    • Built 1940

    Last Sold Summary

    • 16% Below List Price
    • $255/SF
    • 7 Days On Market

    Current Estimated Value $310,460

    Last Listing Agent Mary Helen Levine Mary Helen Levine Real Estate LLC

    34 Lakeview Ave, Cheshire, CT 06410
  • 30 Philson Ct, Cheshire, CT 06410
    30 Philson Ct, Cheshire, CT 06410
    30 Philson Ct, Cheshire, CT 06410
    /36

    $659,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    30 Philson Ct, Cheshire, CT 06410

    Set on a quiet cul-de sac on almost 2.5 acres, this spacious 4 bedroom, 2.5 bath colonial with lower level finished area and walk out, offers an exceptional opportunity to create something truly special in a highly desirable location. The setting- adorned with mature trees and flowering plants on a large parcel is just lovely, yet is close to all the everyday conveniences. This home features a

    Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

    30 Philson Ct, Cheshire, CT 06410
  • 346 Village Dr, Cheshire, CT 06410

    $560,000

    Sold May 20, 2026

    346 Village Dr, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 1,696 Sq Ft
    • Built 1965

    Last Sold Summary

    • 6% Above List Price
    • $330/SF
    • 2 Days On Market

    Current Estimated Value $528,790

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

    346 Village Dr, Cheshire, CT 06410
  • 8 Melrose Dr, Cheshire, CT 06410
    8 Melrose Dr, Cheshire, CT 06410
    /2

    $1,455,100

    New Construction Pending
    • 5 Beds
    • 3.5 Baths
    • 4,785 Sq Ft

    8 Melrose Dr, Cheshire, CT 06410

    Presenting.... The Quintessential Modern Farmhouse. This TO BE BUILT custom colonial was thoughtfully designed to be Functional and Comfortable! On the exterior of the home will be white vinyl siding and black windows. The floor plan of this home possesses a timeless quality! It will have 5 generous sized bedrooms, one of which is located on the first floor, giving the option of the Primary suite

    Dori Degennaro William Raveis Real Estate

    8 Melrose Dr, Cheshire, CT 06410
  • 17 Ives Hill Ct, Cheshire, CT 06410

    $345,000

    Sold Nov 05, 2025

    17 Ives Hill Ct, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft
    • Built 1974

    Last Sold Summary

    • 1% Below List Price
    • $232/SF
    • 10 Days On Market

    Current Estimated Value $344,100

    Last Listing Agent Roberta Whalen LAER Realty Partners

    17 Ives Hill Ct, Cheshire, CT 06410
  • 200 Chipman Dr, Cheshire, CT 06410
    200 Chipman Dr, Cheshire, CT 06410
    200 Chipman Dr, Cheshire, CT 06410
    /40

    $495,000

    $100K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,933 Sq Ft

    200 Chipman Dr, Cheshire, CT 06410

    OFFER DEADLINE WEDNESDAY 5/27 12:00 NOON 200 Chipman Drive is the home that Cheshire buyers wait for! A move-in ready gem, it offers the ease of one-floor living without sacrificing space or style. With over 3,100 square feet of usable space, a warrantied basement, solar efficiency, updated windows, and set on a one acre lot nestled at the end of a quiet, sought-after prime cul-de-sac location;

    Kathleen DeRossi William Pitt Sotheby's Int'l

    200 Chipman Dr, Cheshire, CT 06410
  • 15 Contour Dr, Cheshire, CT 06410

    $719,999

    Sold Sep 26, 2025

    15 Contour Dr, Cheshire, CT 06410

    • 4 Beds
    • 3.5 Baths
    • 3,101 Sq Ft
    • Built 2022

    Last Sold Summary

    • 6% Below List Price
    • $232/SF
    • 60 Days On Market

    Current Estimated Value $726,671

    Last Listing Agent Chiranjivi Neupane Onest Real Estate

    15 Contour Dr, Cheshire, CT 06410
  • 6 Soderman Way Unit 6, Cheshire, CT 06410
    6 Soderman Way Unit 6, Cheshire, CT 06410
    6 Soderman Way Unit 6, Cheshire, CT 06410
    /40

    $519,900

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    6 Soderman Way Unit 6, Cheshire, CT 06410

    Welcome to effortless luxury living at The Reserve at Stonebridge Crossing, one of Cheshire's most sought-after communities. This stunning 3-bedroom, 2.1-bath townhome offers the perfect combination of modern design, exceptional quality, and a maintenance-free lifestyle, all complemented by highly desirable natural gas heat. From the moment you enter, you'll be captivated by the sun-drenched open

    Agnes Nawrocki William Raveis Real Estate

    6 Soderman Way Unit 6, Cheshire, CT 06410
  • 480 Radmere Rd Unit A, Cheshire, CT 06410

    $260,000

    Sold Jul 07, 2025

    480 Radmere Rd Unit A, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,202 Sq Ft
    • Built 1968

    Last Sold Summary

    • 9% Above List Price
    • $216/SF
    • 47 Days On Market

    Current Estimated Value $264,766

    Last Listing Agent Courtney Angelicola Coldwell Banker Realty

    480 Radmere Rd Unit A, Cheshire, CT 06410
  • 303 Beacon Hill Dr, Cheshire, CT 06410
    303 Beacon Hill Dr, Cheshire, CT 06410
    303 Beacon Hill Dr, Cheshire, CT 06410
    /39

    $744,900

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 2,884 Sq Ft

    303 Beacon Hill Dr, Cheshire, CT 06410

    Located in desirable Beacon Hill neighborhood, this custom-built oversized Cape Cod offers exceptional craftsmanship + thoughtful updates. Featuring hardwood flooring throughout most of the home, the layout blends classic charm with modern amenities. The beautifully remodeled 2020 kitchen is a standout with soapstone countertops, farmhouse sink, AGA gas stove with copper range hood, Big Chill

    Stacey Deangelis Calcagni Real Estate

    303 Beacon Hill Dr, Cheshire, CT 06410
  • 1848 Waterbury Rd, Cheshire, CT 06410

    $415,000

    Sold Jul 10, 2025

    1848 Waterbury Rd, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,955 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Below List Price
    • $212/SF
    • 62 Days On Market

    Current Estimated Value $436,916

    Last Listing Agent Tamikque Escourse Coldwell Banker Realty

    1848 Waterbury Rd, Cheshire, CT 06410
  • 13 Stonegate Cir, Cheshire, CT 06410
    13 Stonegate Cir, Cheshire, CT 06410
    13 Stonegate Cir, Cheshire, CT 06410
    /40

    $739,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,556 Sq Ft

    13 Stonegate Cir, Cheshire, CT 06410

    Beautifully maintained Baldwin model offering exceptional space, comfort, and upgrades throughout! Welcoming foyer with HW flooring opens to elegant dining room with tray ceiling. Spacious eat-in kitchen features granite countertops, beveled granite center island, tile backsplash, recessed lighting, stainless steel appliances, Butler's pantry, wine rack, and slide-out shelves/ drawers. Bright

    Stacey Deangelis Calcagni Real Estate

    13 Stonegate Cir, 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 $645,770

    Last Listing Agent Alex LaRosa Coldwell Banker Realty

    48 Willow St, Cheshire, CT 06410
  • 735 Cook Hill Rd, Cheshire, CT 06410
    735 Cook Hill Rd, Cheshire, CT 06410
    735 Cook Hill Rd, Cheshire, CT 06410
    /35

    $729,900

    • 4 Beds
    • 2.5 Baths
    • 2,748 Sq Ft

    735 Cook Hill Rd, Cheshire, CT 06410

    LOCATION, LOCATION, LOCATION! This gorgeous home on Cook Hill Road sits set back from the road on a 2+ acer level lot. This open floor plan home is sure to please. Large kitchen featuring double ovens, cook top, plenty of counter space and multiple pantry's is a cook's dream. The kitchen is open to an ample casual dining area that overlooks the private level yard. Beyond the casual dining area

    Betsy Stellato LAER Realty Partners

    735 Cook Hill Rd, 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 $396,411

    Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

    840 Westside Rd, Cheshire, CT 06410
  • 269 Academy Rd, Cheshire, CT 06410
    269 Academy Rd, Cheshire, CT 06410
    269 Academy Rd, Cheshire, CT 06410
    /40

    $699,500

    $90K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 3,070 Sq Ft

    269 Academy Rd, Cheshire, CT 06410

    Discover this beautifully expanded Cape, perched high above the street on a private, nearly one-acre lot - minutes from the heart of Cheshire. Offering 2,755 sq ft, this home boasts hardwood floors throughout and a flexible open floor plan for one-level living while providing three finished levels to suit your lifestyle. The sun-filled living room with a wood-burning fireplace flows into a

    Frank Santino MidState Realty, LLC

    269 Academy Rd, 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 $732,377

    Last Listing Agent Ken Demirs Regency Real Estate, LLC

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

    $850,000

    Pending
    • 5 Beds
    • 5 Baths
    • 3,919 Sq Ft

    85 Inverness Ct, Cheshire, CT 06410

    Welcome to your dream home at 85 Inverness Court, a private oasis nestled in one of Cheshire's most desirable neighborhoods. Just moments from scenic hiking trails, & waterfalls, including Roaring Brook Park This spacious and thoughtfully designed 5-bedroom residence offers the perfect blend of luxury, function, and tranquility. At the heart of the home is a chef's dream kitchen - a true culinary

    Matt Healy Coldwell Banker Realty

    85 Inverness 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 $206,041

    Last Listing Agent Amanda Albert Coldwell Banker Realty

    40 Southwick Ct Unit 106, Cheshire, CT 06410
  • 1241 Rice Ave, Cheshire, CT 06410
    1241 Rice Ave, Cheshire, CT 06410
    1241 Rice Ave, Cheshire, CT 06410
    /40

    $499,900

    Pending
    • 3 Beds
    • 2 Baths
    • 2,146 Sq Ft

    1241 Rice Ave, Cheshire, CT 06410

    Welcome to this beautifully maintained ranch-style home where comfort, space, and timeless charm come together effortlessly. Perfectly set on a generous .92-acre lot, this 3-bedroom, 2-bath residence offers thoughtfully designed living space tailored for today's lifestyle, with the ease of one-level living and room to grow. Step inside to a welcoming foyer with a double closet, setting the tone

    Agnes Nawrocki William Raveis Real Estate

    1241 Rice Ave, 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 $352,599

    Last Listing Agent Thomas Scott Coldwell Banker Realty

    114 Spring St, Cheshire, CT 06410
  • 60 Kensington Ct, Cheshire, CT 06410
    60 Kensington Ct, Cheshire, CT 06410
    60 Kensington Ct, Cheshire, CT 06410
    /40

    $949,900

    Under Contract
    • 4 Beds
    • 4 Baths
    • 4,569 Sq Ft

    60 Kensington Ct, Cheshire, CT 06410

    Impeccably maintained and impossible to overlook, this Cheshire home stands in a class of its own. Set on nearly an acre of land in a desirable cul-de-sac neighborhood and bordering protected land, this original-owner gem is a rare find! From the moment you arrive, the charming front porch invites you to stay awhile. Enter a spacious two-story foyer that sets the tone for the exceptional

    Elizabeth Urbanski Coldwell Banker Realty

    60 Kensington Ct, Cheshire, CT 06410

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