11,916

Cheshire, CT Homes

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  • 335 Redwood Ln, Cheshire, CT 06410
    335 Redwood Ln, Cheshire, CT 06410
    335 Redwood Ln, Cheshire, CT 06410
    /40

    $579,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,758 Sq Ft

    335 Redwood Ln, Cheshire, CT 06410

    Highest &Best Monday 6/1 9PM. Beautifully updated 4-bedroom, 2.5-bath Raised Ranch ideally situated in a sought-after neighborhood setting with underground utilities & sidewalks. Set on a professionally landscaped, level yard designed for relaxation & entertaining, this move-in ready home blends timeless craftsmanship & modern sophistication. The stunning sun-filled kitchen features Omega solid

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 244-9258

    335 Redwood Ln, Cheshire, CT 06410
  • 291 Maple Ave Unit 2, Cheshire, CT 06410
    291 Maple Ave Unit 2, Cheshire, CT 06410
    291 Maple Ave Unit 2, Cheshire, CT 06410
    /14

    $2,350 Per Month

    • 3 Beds
    • 1 Bath
    • 1,190 Sq Ft
    • Apartment for Rent

    291 Maple Ave Unit 2, Cheshire, CT 06410

    Fully updated second-floor 3-bedroom, 1-bath apartment located in the heart of Cheshire. This spacious 1,190 SF unit features a modern kitchen with granite countertops, updated finishes throughout, and a beautifully tiled bathroom. Enjoy the convenience of in-unit washer and dryer, generous living space, and plenty of natural light. Conveniently located near shopping, restaurants, parks, and

    Justin Sudol Alpha Capital Realty, LLC

    291 Maple Ave Unit 2, Cheshire, CT 06410
  • 14 Woodridge Dr Unit 14, Cheshire, CT 06410

    $260,000

    Sold Jan 28, 2026

    14 Woodridge Dr Unit 14, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Above List Price
    • $236/SF
    • 46 Days On Market

    Current Estimated Value $255,276

    Last Listing Agent Kathleen Maloney Coldwell Banker Realty

    14 Woodridge Dr Unit 14, Cheshire, CT 06410
  • 1274 Cheshire St, Cheshire, CT 06410
    1274 Cheshire St, Cheshire, CT 06410
    1274 Cheshire St, Cheshire, CT 06410
    /40

    $699,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,068 Sq Ft

    1274 Cheshire St, Cheshire, CT 06410

    Welcome to this stunning and immaculately maintained 4-bedroom, 2.5-bathroom colonial, perfectly situated on a quiet cul-de-sac. This home boasts an inviting, bright, and open atmosphere, offering plenty of privacy and a peaceful setting. Inside, you'll find an updated kitchen equipped with sleek stainless-steel appliances, seamlessly connected to the spacious living room. Hardwood floors run

    Agent Photo

    Tanya Uhelsky

    RE/MAX RISE

    (475) 265-2053

    1274 Cheshire St, Cheshire, CT 06410
  • 64 E Mitchell Ave Unit 33, Cheshire, CT 06410
    64 E Mitchell Ave Unit 33, Cheshire, CT 06410
    64 E Mitchell Ave Unit 33, Cheshire, CT 06410
    /17

    $2,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    64 E Mitchell Ave Unit 33, Cheshire, CT 06410

    Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful

    Angela DeMonte Calcagni Real Estate

    64 E Mitchell Ave Unit 33, Cheshire, CT 06410
  • 241 Beacon Hill Dr, Cheshire, CT 06410

    $570,000

    Sold Dec 04, 2025

    241 Beacon Hill Dr, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 3,500 Sq Ft
    • Built 1967

    Last Sold Summary

    • 5% Below List Price
    • $163/SF
    • 61 Days On Market

    Current Estimated Value $576,522

    Last Listing Agent Kelly Ryan William Raveis Real Estate

    241 Beacon Hill Dr, Cheshire, CT 06410
  • 870 Jarvis St, Cheshire, CT 06410
    870 Jarvis St, Cheshire, CT 06410
    870 Jarvis St, Cheshire, CT 06410
    /38

    $699,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,541 Sq Ft

    870 Jarvis St, Cheshire, CT 06410

    Wonderfully spacious, bright, and modern 4-bedroom, 2.5-bath Colonial set on a professionally landscaped lot with a large, level, fully fenced backyard. Featuring an open floor plan with 9-foot ceilings on the main level, this home is ideal for both everyday living and entertaining. The beautiful kitchen offers a granite island, ample cabinetry, and opens seamlessly to a gracious formal dining

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 439-5985

    870 Jarvis St, Cheshire, CT 06410
  • 85 Brentwood Dr, Cheshire, CT 06410
    85 Brentwood Dr, Cheshire, CT 06410
    85 Brentwood Dr, Cheshire, CT 06410
    /37

    $4,200 Per Month

    • 4 Beds
    • 3 Baths
    • 2,095 Sq Ft
    • House for Rent

    85 Brentwood Dr, Cheshire, CT 06410

    Beautiful 4 Bedroom House *w/ an In-Law* in Cheshire! Garage Parking, Central Air, & a Beautiful Backyard Main House Features: - 3 bedrooms - 2 bathrooms - Bright, open floor plan kitchen/living room with dining nook - Big kitchen with tons of prep space & newer appliances, perfect for any occasion! - Primary bedroom w/ an en-suite bathroom - Finished basement with 4th bedroom, bonus room, and

    Olivia Turek Farnam Realty Group

    85 Brentwood Dr, Cheshire, CT 06410
  • 168 Pleasant Dr, Cheshire, CT 06410

    $550,000

    Sold Sep 30, 2025

    168 Pleasant Dr, Cheshire, CT 06410

    • 4 Beds
    • 3 Baths
    • 2,212 Sq Ft
    • Built 1963

    Last Sold Summary

    • $249/SF
    • 36 Days On Market

    Current Estimated Value $559,125

    Last Listing Agent Phil Giampietro Coldwell Banker Realty

    168 Pleasant Dr, Cheshire, CT 06410
    • 752 Ives Row, Cheshire, CT 06410

      Est $779,869

      Not Listed For Sale

      752 Ives Row, Cheshire, CT 06410

      • 5 Beds
      • 3.5 Baths
      • 3,265 Sq Ft
      • Built 2009
      752 Ives Row, Cheshire, CT 06410

      Last Sold Summary

      • 48 Days On Market

  • 20 Stacy Ct, Cheshire, CT 06410
    20 Stacy Ct, Cheshire, CT 06410
    20 Stacy Ct, Cheshire, CT 06410
    /40

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,140 Sq Ft

    20 Stacy Ct, Cheshire, CT 06410

    This cul-de-sac gem has to be the 2026 Curb Appeal Winner! Beautifully maintained gardens bursting w/ seasonal color, a lush green lawn, & attractive landscaping create a welcoming first impression. A stone paver driveway & gorgeous pathway lead to the inviting entrance. Soaring cathedral ceilings & gleaming hardwood floors create a wonderful first impression. The living room w/ fireplace flows

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 937-2923

    20 Stacy Ct, Cheshire, CT 06410
  • 64 E Mitchell Ave Unit 51, Cheshire, CT 06410
    64 E Mitchell Ave Unit 51, Cheshire, CT 06410
    64 E Mitchell Ave Unit 51, Cheshire, CT 06410
    /17

    $2,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    64 E Mitchell Ave Unit 51, Cheshire, CT 06410

    Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful

    Nancy Lydell Calcagni Real Estate

    64 E Mitchell Ave Unit 51, Cheshire, CT 06410
  • 621 Wiese Rd, Cheshire, CT 06410

    $470,000

    Sold Feb 27, 2026

    621 Wiese Rd, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft
    • Built 1959

    Last Sold Summary

    • 12% Below List Price
    • $276/SF
    • 68 Days On Market

    Current Estimated Value $480,220

    Last Listing Agent Nikki Trocchio Calcagni Real Estate

    621 Wiese Rd, Cheshire, CT 06410
    • 18 Alyssa Dr, Cheshire, CT 06410

      Est $799,009

      Not Listed For Sale

      18 Alyssa Dr, Cheshire, CT 06410

      • 3 Beds
      • 2.5 Baths
      • 2,677 Sq Ft
      • Built 2008
      18 Alyssa Dr, Cheshire, CT 06410

      Last Sold Summary

      • 38 Days On Market

  • 568 Wiese Rd, Cheshire, CT 06410
    568 Wiese Rd, Cheshire, CT 06410
    568 Wiese Rd, Cheshire, CT 06410
    /40

    $540,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,633 Sq Ft

    568 Wiese Rd, Cheshire, CT 06410

    Welcome to 568 Wiese Rd in the heart of Cheshire, a beautifully maintained home set in one of the town's most desirable areas. From the moment you arrive, you'll notice the thoughtfully designed landscaping that creates incredible curb appeal and a true sense of privacy. Step into the backyard and discover your own private sanctuary. Lush greenery, mature plantings, and carefully curated outdoor

    Agent Photo

    Rudy Pierre

    YellowBrick Real Estate LLC

    (475) 242-6022

    568 Wiese Rd, Cheshire, CT 06410
  • 1123 Waterbury Rd Unit 2A, Cheshire, CT 06410
    1123 Waterbury Rd Unit 2A, Cheshire, CT 06410
    /2

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Apartment for Rent

    1123 Waterbury Rd Unit 2A, Cheshire, CT 06410

    Available July 2026, this desirable end unit in the private Bayberry Knoll. Heat included in rent price. Kitchen has been updated with granite, stainless steel appliances including a dishwasher, and fashionable tile flooring. 2 spacious bedrooms with generous closet space. Newer bathroom. Complex is conveniently located off Waterbury Road, near i-84 and downtown Cheshire.

    Alex LaRosa Coldwell Banker Realty

    1123 Waterbury Rd Unit 2A, Cheshire, CT 06410
  • 46 Soderman Way Unit 46, Cheshire, CT 06410

    $730,000

    Sold Apr 30, 2026

    46 Soderman Way Unit 46, Cheshire, CT 06410

    • 3 Beds
    • 3.5 Baths
    • 2,975 Sq Ft
    • Built 2024

    Last Sold Summary

    • 6% Below List Price
    • $245/SF
    • 19 Days On Market

    Last Listing Agent Stanley Martone Lamacchia Realty

    46 Soderman Way Unit 46, Cheshire, CT 06410
  • 27 S Pond Cir, Cheshire, CT 06410
    27 S Pond Cir, Cheshire, CT 06410
    27 S Pond Cir, Cheshire, CT 06410
    /40

    $675,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    27 S Pond Cir, Cheshire, CT 06410

    HIGHEST AND BEST BY 5/12/2026 NOON. Welcome to this classic Colonial located in the highly desirable South Pond subdivision, offering sidewalks, underground utilities, and a scenic neighborhood pond with benches. This spacious vinyl-sided home features beautiful hardwood floors, a flexible floor plan, and an ideal location close to schools, shopping, major highways, and the bus line. The

    Agent Photo

    Marc Seigel & Lauren Seigel-Gross

    RE/MAX RISE

    (475) 265-3051

    27 S Pond Cir, Cheshire, CT 06410
  • 500 Oak Ave Unit 21, Cheshire, CT 06410
    500 Oak Ave Unit 21, Cheshire, CT 06410
    500 Oak Ave Unit 21, Cheshire, CT 06410
    /21

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    500 Oak Ave Unit 21, Cheshire, CT 06410

    Welcome to Birchwood Condominiums! This beautifully updated first-floor, two-bedroom condo is available for immediate occupancy. Recently refreshed throughout, the unit features fresh paint, refinished hardwood floors, and a brand-new bathtub and shower. Spacious bedrooms and a full bath provide comfortable living in a well-maintained community. Rent includes heat, hot water, water, and sewer,

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    500 Oak Ave Unit 21, Cheshire, CT 06410
  • 319 Beacon Hill Dr, Cheshire, CT 06410

    $830,000

    Sold Jun 12, 2025

    319 Beacon Hill Dr, Cheshire, CT 06410

    • 4 Beds
    • 4 Baths
    • 3,994 Sq Ft
    • Built 1964

    Last Sold Summary

    • 12% Above List Price
    • $208/SF
    • 2 Days On Market

    Current Estimated Value $839,058

    Last Listing Agent Sarah Andrea Coldwell Banker Realty

    319 Beacon Hill Dr, Cheshire, CT 06410
  • 1811 Blackberry Place, Cheshire, CT 06410
    1811 Blackberry Place, Cheshire, CT 06410
    /2

    $1,109,410

    New Construction Pending
    • 4 Beds
    • 2.5 Baths
    • 3,036 Sq Ft

    1811 Blackberry Place, Cheshire, CT 06410

    New construction in a neighborhood setting. Cheshire's newest development. Blackberry Woods, has a wonderful range of lot types including those with beautiful views of Meriden Mountain, those with plenty of privacy, and those with wonderful backyard options. The Montgomery Model features 9' ceilings and hardwood flooring on the main floor, a custom-designed kitchen opening to family room with gas

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 463-4250

    1811 Blackberry Place, Cheshire, CT 06410
  • 64 E Mitchell Ave Unit 1, Cheshire, CT 06410
    64 E Mitchell Ave Unit 1, Cheshire, CT 06410
    64 E Mitchell Ave Unit 1, Cheshire, CT 06410
    /17

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    64 E Mitchell Ave Unit 1, Cheshire, CT 06410

    Welcome to Maplecroft Village! Nestled in the heart of Cheshire, our ranch-style apartment complex, built in 2024, boasts contemporary design while being conveniently located to shopping, schools, and major highways. These thoughtfully designed 2-bedroom apartments offer 1350 square feet of luxurious living space and are equipped with all the latest modern amenities. Each unit offers beautiful

    Nikki Trocchio Calcagni Real Estate

    64 E Mitchell Ave Unit 1, Cheshire, CT 06410
  • 4 Soderman Way Unit 4, Cheshire, CT 06410

    $500,000

    Sold Dec 09, 2025

    4 Soderman Way Unit 4, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2023

    Last Sold Summary

    • 9% Below List Price
    • $270/SF
    • 79 Days On Market

    Last Listing Agent Khaliq Brown CLMA Realty

    4 Soderman Way Unit 4, Cheshire, CT 06410
  • 1840 Blackberry Place, Cheshire, CT 06410
    1840 Blackberry Place, Cheshire, CT 06410
    1840 Blackberry Place, Cheshire, CT 06410
    /3

    $890,000

    New Construction Pending
    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1840 Blackberry Place, Cheshire, CT 06410

    Build the custom home of your dreams on ~ 1 acre of land in Blackberry Woods. Consider the Spruce model which offers 2,600 sqft of living space w/ 4 Bedrooms and 2 1/2 Baths. It includes a spacious foyer with double coat closets, mudroom, half bath & laundry off garage entry, an open floor plan between the family room, dinette & kitchen, gas log fireplace, and kitchen pantry. The formal dining

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 447-1624

    1840 Blackberry Place, Cheshire, CT 06410
  • 106 Far Horizon Dr, Cheshire, CT 06410

    $659,900

    Sold May 06, 2026

    106 Far Horizon Dr, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 1,872 Sq Ft
    • Built 1963

    Last Sold Summary

    • 15% Above List Price
    • $353/SF
    • 6 Days On Market

    Current Estimated Value $593,406

    Last Listing Agent Brette Stern Calcagni Real Estate

    106 Far Horizon Dr, Cheshire, CT 06410
    • 7 Ben Ct, Wallingford, CT 06492

      Est $713,612

      Not Listed For Sale

      7 Ben Ct, Wallingford, CT 06492

      • 3 Beds
      • 2 Baths
      • 2,524 Sq Ft
      • Built 1992
      7 Ben Ct, Wallingford, CT 06492

      Last Sold Summary

      • 47 Days On Market

  • 1600 S Main St, Cheshire, CT 06410
    1600 S Main St, Cheshire, CT 06410
    1600 S Main St, Cheshire, CT 06410
    /21

    $799,000

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    1600 S Main St, Cheshire, CT 06410

    Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal. One level living at its finest, with 9ft ceilings throughout, custom kitchen w/granite countertops and center island, hardwood flooring in the main living areas, gas fireplace in the family room and a mudroom with half bath and laundry. Large Primary bedroom with bathroom en-suite, and walk-in closet. 2 guest

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 251-8839

    1600 S Main St, Cheshire, CT 06410
  • 112 Laurel Terrace, Cheshire, CT 06410

    $426,500

    Sold Jan 13, 2026

    112 Laurel Terrace, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1957

    Last Sold Summary

    • 2% Above List Price
    • $304/SF
    • 14 Days On Market

    Current Estimated Value $425,574

    Last Listing Agent Douglas Ledewitz Pulse Realty LLC

    112 Laurel Terrace, Cheshire, CT 06410
  • 1830 Blackberry Place, Cheshire, CT 06410
    1830 Blackberry Place, Cheshire, CT 06410
    /2

    $1,182,050

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,531 Sq Ft

    1830 Blackberry Place, Cheshire, CT 06410

    Exciting opportunity to build your very own 2531 sqft ranch with wonderful curb appeal. One level living at its finest, with 9ft ceilings throughout, custom kitchen w/granite countertops and center island, hardwood flooring in the main living areas, gas fireplace in the family room and a mudroom with half bath and laundry. Large Primary bedroom with bathroom en-suite, and walk-in closet. 2 guest

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 635-4188

    1830 Blackberry Place, Cheshire, CT 06410
  • 20 Bramble Way, Cheshire, CT 06410

    $670,000

    Sold Dec 29, 2025

    20 Bramble Way, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 3,591 Sq Ft
    • Built 2006

    Last Sold Summary

    • $187/SF
    • 6 Days On Market

    Current Estimated Value $674,872

    Last Listing Agent Karen Brimberg William Raveis Real Estate

    20 Bramble Way, Cheshire, CT 06410
  • 1841 Blackberry Place, Cheshire, CT 06410
    1841 Blackberry Place, Cheshire, CT 06410
    /2

    $929,000

    New Construction Pending
    • 4 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    1841 Blackberry Place, Cheshire, CT 06410

    Stunning 4 bedroom, 2.5 bathroom Colonial, The Birch offers gracious living and a wonderful floor plan. Culinary enthusiasts will love the large walk in pantry, granite-topped cabinetry with center island that opens to a spacious family room with vaulted ceiling. The wonderful layout for entertaining is completed by a formal dining room. Easily work from home with the main floor study. The

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 472-8934

    1841 Blackberry Place, Cheshire, CT 06410
  • 18 Hawthorne Dr, Cheshire, CT 06410

    $490,000

    Sold Jul 07, 2025

    18 Hawthorne Dr, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft
    • Built 1955

    Last Sold Summary

    • 17% Above List Price
    • $269/SF
    • 39 Days On Market

    Current Estimated Value $482,624

    Last Listing Agent Sarah Kolman The Heritage Group, LLC

    18 Hawthorne Dr, Cheshire, CT 06410

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