11,849

Cheshire, CT Homes

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  • /40

    $449,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,446 Sq Ft

    460 Oak Ave, Cheshire, CT 06410

    Highest and Best due by 5 pm Sunday 7/26. Welcome home to this well-maintained home offering comfort, convenience, and thoughtful updates throughout. The inviting family room features a cozy Vermont Castings wood stove, while mini-split systems provide efficient air conditioning on the first floor. Enjoy summer days in the 24' round above-ground pool (54" deep) with an deck that's just 5 years

    Agent Photo

    Cindy Forlenzo

    Coldwell Banker Realty

    460 Oak Ave, Cheshire, CT 06410
  • /4

    Starting at $2,595

    Total Monthly Price

    • 2 Beds

    1728 Highland Ave, Cheshire, CT 06410

    Highland Farms combines a comfortable suburban location with access to nearby restaurants and services. Located less than a mile from The Shops at Stone Bridge, a brand new shopping center offering grocery, retail, and more. Please contact the Leasing Office for availability.

    Highland Farms

    1728 Highland Ave, Cheshire, CT 06410
  • 95 Orleton Ct, Cheshire, CT 06410

    $655,000

    Sold Feb 27, 2026

    95 Orleton Ct, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft
    • Built 1998

    Last Sold Summary

    • $227/SF
    • 124 Days On Market

    Current Estimated Value $684,601

    Last Listing Agent Jason Saphire www.HomeZu.com

    95 Orleton Ct, Cheshire, CT 06410
    • 80 Jill Ln, Cheshire, CT 06410

      Est $606,867

      Not Listed For Sale

      80 Jill Ln, Cheshire, CT 06410

      • 3 Beds
      • 1.5 Baths
      • 1,826 Sq Ft
      • Built 1982
      80 Jill Ln, Cheshire, CT 06410

      Last Sold Summary

      • 99 Days On Market

      Last Listing Agent Dawn D'Auria Coldwell Banker Realty

  • /29

    $455,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1 Bath
    • 1,764 Sq Ft

    445 Lincoln Dr, Cheshire, CT 06410

    Welcome to 445 Lincoln Drive in Cheshire! This beautifully remodeled home offers the perfect blend of modern updates and comfortable living. Step inside to discover a bright, inviting interior featuring a renovated kitchen with stylish finishes, an updated bathroom, and thoughtful improvements throughout. The finished lower level provides valuable additional living space-perfect for a family

    Agent Photo

    Lucy Cordero

    KW Legacy Partners

    445 Lincoln Dr, Cheshire, CT 06410
  • /34

    Starting at $2,589

    Total Monthly Price

    • Studio - 3 Beds

    106 Stonebridge Ct, Cheshire, CT 06410

    Riverpointe Cheshire encompasses 300 apartment homes within 10 buildings spread amongst beautifully manicured landscape. This stunning community features studios, one-bedroom (with option for a den), two-bedroom, and three-bedroom residences. The community will be completed with sophisticated unit and common area finishes as well as a robust amenity program for all residents to enjoy.Riverpointe

    Riverpointe Cheshire

    106 Stonebridge Ct, Cheshire, CT 06410
  • 1364 Avon Blvd, Cheshire, CT 06410

    $410,000

    Sold Nov 03, 2025

    1364 Avon Blvd, Cheshire, CT 06410

    • 3 Beds
    • 1.5 Baths
    • 1,142 Sq Ft
    • Built 1953

    Last Sold Summary

    • 8% Above List Price
    • $359/SF
    • 7 Days On Market

    Current Estimated Value $421,451

    Last Listing Agent Melanie Ricci Coldwell Banker Realty

    1364 Avon Blvd, Cheshire, CT 06410
    • 136 Crescent Cir, Cheshire, CT 06410

      Est $495,126

      Not Listed For Sale

      136 Crescent Cir, Cheshire, CT 06410

      • 3 Beds
      • 1.5 Baths
      • 1,706 Sq Ft
      • Built 1956
      136 Crescent Cir, Cheshire, CT 06410

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Mela Veltri Case KW Legacy Partners

  • /37

    $199,000

    Pending
    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    480 Oak Ave Unit 64, Cheshire, CT 06410

    Why Rent When You Can Own this pristine condo located in the well maintained Birchwood community? This sundrenched unit boasts kitchen appointed with newer stainless appliances and beautiful white cabinetry, spacious living room with dining area offering hardwood flooring, two spacious bedrooms both offering hardwood flooring and updated full bath. Additional amenities include private storage

    Agent Photo

    Linda Mayfield

    RE/MAX RISE

    480 Oak Ave Unit 64, Cheshire, CT 06410
  • /35

    Starting at $1,831

    Total Monthly Price

    • Studio - 2 Beds

    50 Hazel Dr, Cheshire, CT 06410

    Lakeside of Cheshire

    50 Hazel Dr, Cheshire, CT 06410
  • 144 Fairway Dr Unit 144, Cheshire, CT 06410

    $330,000

    Sold Sep 01, 2026

    144 Fairway Dr Unit 144, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,052 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $314/SF
    • 5 Days On Market

    Current Estimated Value $318,579

    Last Listing Agent Kris Lippi Get Listed Realty

    144 Fairway Dr Unit 144, Cheshire, CT 06410
    • 12 N Pond Rd, Cheshire, CT 06410

      Est $757,674

      Not Listed For Sale

      12 N Pond Rd, Cheshire, CT 06410

      • 4 Beds
      • 3.5 Baths
      • 3,020 Sq Ft
      • Built 1989
      12 N Pond Rd, Cheshire, CT 06410

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Heidi Weed Lamacchia Realty

  • /25

    $355,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,015 Sq Ft

    97 Southwick Ct Unit 97, Cheshire, CT 06410

    ***Highest and Best Deadline Sunday 9/13 at 12:00 pm. ***. Just what you've been waiting for! Rarely available and highly sought-after, this ranch-style unit at Southwick offers the ease of one-level living, an attached garage and a wonderful low-maintenance lifestyle. Step inside to a spacious, welcoming living and dining area with plenty of room for everyday living and entertaining. The

    Agent Photo

    Sarah Andrea

    Coldwell Banker Realty

    97 Southwick Ct Unit 97, Cheshire, CT 06410
  • /32

    $3,850 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,214 Sq Ft
    • House for Rent

    480 Higgins Rd, Cheshire, CT 06410

    Welcome to 480 Higgins Road! This spacious 4-bedroom, 2.5-bath Cape Cod-style home offers a flexible floor plan and plenty of room to spread out. The main level features a living room, large eat-in kitchen open to the family room, and sliders leading to a sunroom overlooking the private backyard. A primary bedroom with full bath, an additional bedroom, and a convenient half bath with laundry

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    480 Higgins Rd, Cheshire, CT 06410
  • 458 Castle Glenn, Cheshire, CT 06410

    $865,000

    Sold Nov 07, 2025

    458 Castle Glenn, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 3,646 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Above List Price
    • $237/SF
    • 1 Day On Market

    Current Estimated Value $815,883

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

    458 Castle Glenn, Cheshire, CT 06410
    • 1200 Peck Ln, Cheshire, CT 06410

      Est $412,382

      Not Listed For Sale

      1200 Peck Ln, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,469 Sq Ft
      • Built 1991
      1200 Peck Ln, Cheshire, CT 06410

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Roberta Havlick William Raveis Real Estate

  • /30

    $459,900

    Pending
    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    979 Farmington Dr, Cheshire, CT 06410

    Fantastic location for this expansive ranch. Offering sunroom, hardwood flooring throughout the home, Fireplaced living room, open layout Flat yard unfinished lower level for even more expansion Updated heating, central air-conditioning. oversized 2/3 car garage. this home is in one of the most desirable locations in Cheshire Must see

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    979 Farmington Dr, Cheshire, CT 06410
  • /7

    $1,775 Per Month

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

    356 Highland Ave, Cheshire, CT 06410

    Amazing property and a great place to make a home-- We have a 1 Bedroom now ($1595) and we will have a 2 Bedroom for MID September ($1775). Don't wait to get in touch with us about these Great units in a fantastic location- No smoking, No pets-- Good credit and Good income needed to qualify. Heat and Hot water, cold water, sewer, trash included in the rent. Super onsite, ample parking.

    356 Highland Ave, Cheshire, CT 06410
  • 488 Radmere Rd Unit B, Cheshire, CT 06410

    $240,000

    Sold Nov 06, 2025

    488 Radmere Rd Unit B, Cheshire, CT 06410

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

    Last Sold Summary

    • $200/SF
    • 49 Days On Market

    Current Estimated Value $254,108

    Last Listing Agent Katie Smith Berkshire Hathaway NE Prop.

    488 Radmere Rd Unit B, Cheshire, CT 06410
    • 67 Southwick Ct Unit 67, Cheshire, CT 06410

      Est $369,429

      Not Listed For Sale

      67 Southwick Ct Unit 67, Cheshire, CT 06410

      • 2 Beds
      • 2.5 Baths
      • 1,450 Sq Ft
      • Built 1998
      67 Southwick Ct Unit 67, Cheshire, CT 06410

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Mela Veltri Case KW Legacy Partners

  • /35

    $799,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,798 Sq Ft

    352 Patton Dr, Cheshire, CT 06410

    All the benefits of new construction but none of the wait! This very lightly lived-in 2020 Colonial has all the bells & whistles. Soaring ceilings, open modern floor plan, finished basement, fully fenced back yard, in ground heated pool (2025) & pool house all set in a loop street neighborhood close to so many amenities. Enjoy Bartlem Park, the Linear Trail, coffee shops, events on the Green, the

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    352 Patton Dr, Cheshire, CT 06410
  • /10

    $2,600 Per Month

    • 1 Bed
    • 1 Bath
    • 461 Sq Ft
    • House for Rent

    281 Spring St, Cheshire, CT 06410

    Discover comfort and convenience in this beautifully renovated rental located in the desirable town of Cheshire. This brand new one bedroom, one bathroom residence features a modern galley kitchen equipped with sleek stainless steel appliances, offering both style and functionality. Enjoy a private entrance for added peace and privacy, and step outside to a spacious backyard perfect for

    Matthew Olander KW Legacy Partners

    281 Spring St, Cheshire, CT 06410
  • 204 Greens Loop Unit 204, Cheshire, CT 06410

    $317,000

    Sold Oct 10, 2025

    204 Greens Loop Unit 204, Cheshire, CT 06410

    • 2 Beds
    • 1.5 Baths
    • 1,578 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Above List Price
    • $201/SF
    • 24 Days On Market

    Current Estimated Value $324,929

    Last Listing Agent Evan Johnson Coldwell Banker Realty

    204 Greens Loop Unit 204, Cheshire, CT 06410
    • 37 Warren St, Cheshire, CT 06410

      Est $806,655

      Not Listed For Sale

      37 Warren St, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 2016
      37 Warren St, Cheshire, CT 06410

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Alex LaRosa Coldwell Banker Realty

  • /33

    $435,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,323 Sq Ft

    448 Mixville Rd, Cheshire, CT 06410

    Welcome to your dream home, nestled in a serene wooded lot and perfectly located near the picturesque Mixville Park. This stunning residence features three spacious bedrooms and two and a half baths, offering ample space for relaxation and entertainment. As you step inside, you'll be greeted by hardwood floors that flow seamlessly throughout the main level, creating a warm and inviting

    Agent Photo

    Nick Prevost

    William Raveis Real Estate

    448 Mixville Rd, Cheshire, CT 06410
  • /11

    $850 Per Month

    • 1 Bath
    • 184 Sq Ft
    • House for Rent

    19 Stony Hill Rd Unit 12, Cheshire, CT 06410

    Studio apartment ready for occupancy!! Heat and Hot Water included. Convenient location. 2 month's security plus 1st month's rent required to move in. Application, credit check, background and eviction check required. No Pets!! No smoking or any kind!! No laundry in unit or on site!! Excellent credit required.

    Ann Micacci Berkshire Hathaway NE Prop.

    19 Stony Hill Rd Unit 12, Cheshire, CT 06410
  • 83 Shea Cir Unit 83, Cheshire, CT 06410

    $765,735

    Sold Feb 24, 2026

    83 Shea Cir Unit 83, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2026

    Last Sold Summary

    • 14% Above List Price
    • $313/SF
    • 55 Days On Market

    Last Listing Agent Jason Helton EG Group Realty LLC

    83 Shea Cir Unit 83, Cheshire, CT 06410
    • 5 Bethany Mountain Rd, Cheshire, CT 06410

      Not Listed For Sale

      5 Bethany Mountain Rd, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 3,280 Sq Ft
      • Built 2025
      5 Bethany Mountain Rd, Cheshire, CT 06410

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Roy Evjen Evjen Agency

  • /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

    1840 Blackberry Place, Cheshire, CT 06410
  • /21

    $2,400 Per Month

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

    1335 Wolf Hill Rd, Cheshire, CT 06410

    Renovated rental available in desirable Cheshire!

    George Daniolos eRealty Advisors, Inc.

    1335 Wolf Hill Rd, Cheshire, CT 06410
  • 239 Bates Dr, Cheshire, CT 06410

    $370,000

    Sold Oct 09, 2025

    239 Bates Dr, Cheshire, CT 06410

    • 3 Beds
    • 2.5 Baths
    • 1,646 Sq Ft
    • Built 1956

    Last Sold Summary

    • 6% Above List Price
    • $225/SF
    • 70 Days On Market

    Current Estimated Value $423,669

    Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

    239 Bates Dr, Cheshire, CT 06410
    • 857 Ward Ln, Cheshire, CT 06410

      Not Listed For Sale

      857 Ward Ln, Cheshire, CT 06410

      • 5 Beds
      • 3 Baths
      • 3,425 Sq Ft
      • Built 2023
      857 Ward Ln, Cheshire, CT 06410

      Last Sold Summary

      • 188 Days On Market

      Last Listing Agent Roy Evjen Evjen Agency

  • /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

    1600 S Main St, Cheshire, CT 06410
  • /35

    $3,800 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,670 Sq Ft
    • House for Rent

    387 Mixville Rd, Cheshire, CT 06410

    Freshly painted and offering generous space, this well-maintained apartment occupies the first and second floors of a two-family Colonial. With four bedrooms, 2.5 bathrooms and a flexible layout, there is plenty of room to spread out. The first floor features freshly refinished hardwood floors and a remodeled kitchen with new appliances, including a dishwasher, range, microwave and refrigerator.

    The Sally Bowman Team Berkshire Hathaway NE Prop.

    387 Mixville Rd, Cheshire, CT 06410
  • 20 Watch Hill Rd, Cheshire, CT 06410

    $466,000

    Sold Jul 17, 2026

    20 Watch Hill Rd, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,086 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Above List Price
    • $223/SF
    • 50 Days On Market

    Current Estimated Value $480,372

    Last Listing Agent Karen Brimberg William Raveis Real Estate

    20 Watch Hill Rd, Cheshire, CT 06410
    • 263 S Brooksvale Rd, Cheshire, CT 06410

      Not Listed For Sale

      263 S Brooksvale Rd, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 2,578 Sq Ft
      • Built 2023
      263 S Brooksvale Rd, Cheshire, CT 06410

      Last Sold Summary

      • 378 Days On Market

      Last Listing Agent Donna Pellegrino Calcagni Real Estate

  • /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

    1830 Blackberry Place, Cheshire, CT 06410
  • 106 Woodland Dr, Cheshire, CT 06410

    $605,000

    Sold Apr 01, 2026

    106 Woodland Dr, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 2,247 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Above List Price
    • $269/SF
    • 11 Days On Market

    Current Estimated Value $581,704

    Last Listing Agent Felipe Segura Coldwell Banker Realty

    106 Woodland Dr, Cheshire, CT 06410
    • 715 Whispering Oaks Ct, Cheshire, CT 06410

      Not Listed For Sale

      715 Whispering Oaks Ct, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 3,388 Sq Ft
      • Built 2024
      715 Whispering Oaks Ct, Cheshire, CT 06410

      Last Sold Summary

      • 199 Days On Market

      Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  • /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

    1841 Blackberry Place, Cheshire, CT 06410

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$536,275
Median Single Family Sale Price
$560,000
Median Townhouse Sale Price
$532,327
Median 2 Bedroom Sale Price
$341,450
Median 1 Bedroom Sale Price
$183,450
Average Price Per Sq Ft
$297
Number of Homes for Sale
11,849
Last 12 months Home Sales
338
Months of Supply
1.20
Median List Price
$529,900
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
2%
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