11,915

Cheshire, CT Homes

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  • 1244 Long Hill Rd, Cheshire, CT 06410
    1244 Long Hill Rd, Cheshire, CT 06410
    1244 Long Hill Rd, Cheshire, CT 06410
    /38

    $449,900 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    1244 Long Hill Rd, Cheshire, CT 06410

    Welcome to 1244 Long Hill Road, where comfort, style, and functionality come together seamlessly. This charming 3-bedroom residence offers an inviting, floor plan complemented by thoughtful updates throughout. Step inside to a spacious living and dining area, perfect for both entertaining and everyday living. The kitchen features updated appliances and sleek granite countertops, providing a

    Michael Barbaro Huntsman,Meade & Partners Comp

    1244 Long Hill Rd, 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 $1,290,740

    Last Listing Agent Sarah Hull Coldwell Banker Realty

    3 Mountaincrest Dr, Cheshire, CT 06410
    • 2 S Brooksvale Rd, Cheshire, CT 06410

      Not Listed For Sale

      2 S Brooksvale Rd, Cheshire, CT 06410

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

      Last Sold Summary

      • $299/SF
      • 378 Days On Market

      Last Sold Price $769,825

      Last Listing Agent Donna Pellegrino Calcagni Real Estate

  • 344 Towpath Ln, Cheshire, CT 06410
    344 Towpath Ln, Cheshire, CT 06410
    344 Towpath Ln, Cheshire, CT 06410
    /32

    $659,000

    • 3 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    344 Towpath Ln, Cheshire, CT 06410

    Discover the beauty of suburban living at 344 Towpath Lane, in the heart of Cheshire! This inviting home offers the perfect blend of comfort, light, and connection to nature. A generous family room anchors the main living space, filled with energizing natural sunlight from the skylights and soaring cathedral ceiling. It flows effortlessly into the open kitchen with granite and stainless

    Laura Squillante Berkshire Hathaway NE Prop.

    344 Towpath Ln, 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 $501,200

    Last Listing Agent Paulo Salgado RE/MAX RISE

    31 Roslyn Dr, Cheshire, CT 06410
    • 265 S Brooksvale Rd, Cheshire, CT 06410

      Est $738,949 Not Listed For Sale

      265 S Brooksvale Rd, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 2,340 Sq Ft
      • Built 2023
      265 S Brooksvale Rd, Cheshire, CT 06410

      Last Sold Summary

      • 4% Above List Price
      • $305/SF
      • 390 Days On Market

      Last Sold Price $713,257

      Last Listing Agent Donna Pellegrino Calcagni Real Estate

  • 0 Waterbury Rd Unit 24047391, Cheshire, CT 06410
    0 Waterbury Rd Unit 24047391, Cheshire, CT 06410
    0 Waterbury Rd Unit 24047391, Cheshire, CT 06410
    /3

    $260,000

    • Land
    • 4.61 Acres
    • $56,399 per Acre

    0 Waterbury Rd Unit 24047391, Cheshire, CT 06410

    4.61-Acre Lot on Waterbury Road, Cheshire. Discover the perfect blend of privacy and convenience with this stunning 4.61-acre lot located on Waterbury Road. This treed and rolling lot features a small stream in one corner, offering a serene and picturesque setting. Currently a single lot, it may be subdividable, providing potential for future development. Ideal for those seeking privacy and a

    Mark Foreman Press/Cuozzo Realtors

    0 Waterbury Rd Unit 24047391, 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 $515,454

    Last Listing Agent Betsy Purtell Purtell Realty LLC

    265 Lancaster Way, Cheshire, CT 06410
    • 1243 Avon Blvd, Cheshire, CT 06410

      Est $425,749 Not Listed For Sale

      1243 Avon Blvd, Cheshire, CT 06410

      • 3 Beds
      • 1 Bath
      • 1,508 Sq Ft
      • Built 1954
      1243 Avon Blvd, Cheshire, CT 06410

      Last Sold Summary

      • $282/SF
      • 7 Days On Market

      Last Sold Price $426,000

      Last Listing Agent Pat DelVento III Coldwell Banker Realty

  • 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
    • 0.62 Acre
    • $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
  • 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 $375,888

    Last Listing Agent Carly Kirsch Lamacchia Realty

    851 Ward Ln, Cheshire, CT 06410
    • 200 Bates Dr, Cheshire, CT 06410

      Est $377,478 Not Listed For Sale

      200 Bates Dr, Cheshire, CT 06410

      • 2 Beds
      • 1 Bath
      • 1,096 Sq Ft
      • Built 1954
      200 Bates Dr, Cheshire, CT 06410

      Last Sold Summary

      • 15% Above List Price
      • $299/SF
      • 4 Days On Market

      Last Sold Price $327,500

      Last Listing Agent Brandon D'Angelo Calcagni Real Estate

  • 124 Southwick Ct, Cheshire, CT 06410
    124 Southwick Ct, Cheshire, CT 06410
    124 Southwick Ct, Cheshire, CT 06410
    /27

    $339,900 Pending

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

    124 Southwick Ct, Cheshire, CT 06410

    Enjoy one level living in this 2 Bedroom, 2 Bath Southwick Adult (55+) community. The Living Area is light and bright with high ceilings, Dining area and a slider that leads to a private patio. A well equipped Kitchen with tile flooring, tile backsplash and pantry, is open to the Dining area. The Primary Bedroom features a walk-in closet, attached full bath and slider to the yard area and

    Phil Giampietro Coldwell Banker Realty

    124 Southwick Ct, Cheshire, CT 06410
  • 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 $604,496

    Last Listing Agent Catherine Leake Coldwell Banker Realty

    1296 Deer Run Cir, Cheshire, CT 06410
    • 215 Bates Dr, Cheshire, CT 06410

      Est $572,134 Not Listed For Sale

      215 Bates Dr, Cheshire, CT 06410

      • 4 Beds
      • 3 Baths
      • 2,418 Sq Ft
      • Built 1953
      215 Bates Dr, Cheshire, CT 06410

      Last Sold Summary

      • 23% Above List Price
      • $192/SF
      • 6 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Brette Stern Calcagni Real Estate

  • 80 Orleton Ct, Cheshire, CT 06410
    80 Orleton Ct, Cheshire, CT 06410
    80 Orleton Ct, Cheshire, CT 06410
    /39

    $639,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,351 Sq Ft

    80 Orleton Ct, Cheshire, CT 06410

    Beautifully maintained and truly move-in ready, this 4-bedroom Colonial is tucked away on a quiet cul-de-sac in a desirable, family-friendly neighborhood. Thoughtfully designed for today's lifestyle, the home features white oak flooring and 9-foot ceilings throughout the main level, creating a bright and inviting atmosphere. The updated eat-in kitchen flows seamlessly into the family room,

    Brette Stern Calcagni Real Estate

    80 Orleton Ct, 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 $371,370

    Last Listing Agent Mela Veltri Case KW Legacy Partners

    67 Southwick Ct Unit 67, Cheshire, CT 06410
    • 86 Hawthorne Dr, Cheshire, CT 06410

      Est $562,445 Not Listed For Sale

      86 Hawthorne Dr, Cheshire, CT 06410

      • 4 Beds
      • 3 Baths
      • 2,449 Sq Ft
      • Built 1955
      86 Hawthorne Dr, Cheshire, CT 06410

      Last Sold Summary

      • 3% Below List Price
      • $237/SF
      • 4 Days On Market

      Last Sold Price $580,000

      Last Listing Agent Brian DePodesta Coldwell Banker

  • 443 E Mitchell Ave, Cheshire, CT 06410
    443 E Mitchell Ave, Cheshire, CT 06410
    443 E Mitchell Ave, Cheshire, CT 06410
    /14

    $144,900

    • 1 Bed
    • 1 Bath
    • 853 Sq Ft

    443 E Mitchell Ave, Cheshire, CT 06410

    Hillside Village, age restricted community 62+. One level living, 1 bedroom with an additional living space that could be used as a 2nd bedroom (no closet). Slider to patio and yard area, stackable washer/dryer. Condo fees include heat and hot water. Close to restaurants, shopping, public library, and highways. Sold in as is condition, needs work and updating.

    Phil Giampietro Coldwell Banker Realty

    443 E Mitchell Ave, 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 $515,693

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

    1324 Notch Rd, Cheshire, CT 06410
    • 1222 Long Hill Rd, Cheshire, CT 06410

      Est $474,193 Not Listed For Sale

      1222 Long Hill Rd, Cheshire, CT 06410

      • 3 Beds
      • 1 Bath
      • 1,344 Sq Ft
      • Built 1956
      1222 Long Hill Rd, Cheshire, CT 06410

      Last Sold Summary

      • 10% Above List Price
      • $320/SF
      • 6 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Dawn D'Auria Coldwell Banker

  • 54 Soderman Way Unit 54, Cheshire, CT 06410

    $711,050 Sold Apr 30, 2025

    54 Soderman Way Unit 54, Cheshire, CT 06410

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

    Last Sold Summary

    • 2% Above List Price
    • $239/SF
    • 277 Days On Market

    Last Listing Agent Jason Helton EG Group Realty LLC

    54 Soderman Way Unit 54, Cheshire, CT 06410
    • 8 Inverness Ct, Cheshire, CT 06410

      Est $783,643 Not Listed For Sale

      8 Inverness Ct, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 2,868 Sq Ft
      • Built 1968
      8 Inverness Ct, Cheshire, CT 06410

      Last Sold Summary

      • 17% Above List Price
      • $234/SF
      • 3 Days On Market

      Last Sold Price $670,000

      Last Listing Agent Laureen Kennedy Coldwell Banker

  • 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 $537,527

    Last Listing Agent Brette Stern Calcagni Real Estate

    70 Royalwood Ct, Cheshire, CT 06410
    • 18 Chamberlain Ct, Cheshire, CT 06410

      Est $1,088,084 Not Listed For Sale

      18 Chamberlain Ct, Cheshire, CT 06410

      • 4 Beds
      • 2.5 Baths
      • 3,751 Sq Ft
      • Built 2001
      18 Chamberlain Ct, Cheshire, CT 06410

      Last Sold Summary

      • 24% Above List Price
      • $235/SF
      • 34 Days On Market

      Last Sold Price $879,900

      Last Listing Agent Jan Broga Coldwell Banker

  • 968 Coleman Rd, Cheshire, CT 06410

    $600,000 Sold May 20, 2025

    968 Coleman Rd, Cheshire, CT 06410

    • 5 Beds
    • 2.5 Baths
    • 1,995 Sq Ft
    • Built 1959

    Last Sold Summary

    • 4% Above List Price
    • $301/SF
    • 15 Days On Market

    Current Estimated Value $614,689

    Last Listing Agent Patrick Combs Dan Combs Real Estate

    968 Coleman Rd, Cheshire, CT 06410
    • 65 Abrams Rd, Cheshire, CT 06410

      Est $1,493,733 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

      • 21% Above List Price
      • $152/SF
      • 163 Days On Market

      Last Sold Price $1,230,888

      Last Listing Agent Mark Gracia William Raveis Real Estate

  • 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 $344,373

    Last Listing Agent Sandra Wagner Calcagni Real Estate

    320 Highland Ave, Cheshire, CT 06410
    • 647 Tamarack Rd, Cheshire, CT 06410

      Est $884,536 Not Listed For Sale

      647 Tamarack Rd, Cheshire, CT 06410

      • 4 Beds
      • 4 Baths
      • 3,703 Sq Ft
      • Built 1997
      647 Tamarack Rd, Cheshire, CT 06410

      Last Sold Summary

      • 7% Above List Price
      • $223/SF
      • 33 Days On Market

      Last Sold Price $824,900

      Last Listing Agent Cheryl Rosadino Berkshire Hathaway Home Services

  • 104 Ridgeview Place, Cheshire, CT 06410

    $685,000 Sold May 09, 2025

    104 Ridgeview Place, Cheshire, CT 06410

    • 4 Beds
    • 2.5 Baths
    • 2,625 Sq Ft
    • Built 2012

    Last Sold Summary

    • 1% Above List Price
    • $261/SF
    • 6 Days On Market

    Current Estimated Value $691,722

    Last Listing Agent Brette Stern Calcagni Real Estate

    104 Ridgeview Place, Cheshire, CT 06410
    • 5 Wildlife Ct, Cheshire, CT 06410

      Est $564,291 Not Listed For Sale

      5 Wildlife Ct, Cheshire, CT 06410

      • 2 Beds
      • 2.5 Baths
      • 2,048 Sq Ft
      • Built 2010
      5 Wildlife Ct, Cheshire, CT 06410

      Last Sold Summary

      • 19% Above List Price
      • $232/SF
      • 30 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Karen Brimberg William Raveis Real Estate

  • 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 $357,197

    Last Listing Agent Nicholas Greene eXp Realty

    253 Elmwood Cir, Cheshire, CT 06410
    • 36 Wildlife Ct, Cheshire, CT 06410

      Est $668,300 Not Listed For Sale

      36 Wildlife Ct, Cheshire, CT 06410

      • 3 Beds
      • 2.5 Baths
      • 2,672 Sq Ft
      • Built 2010
      36 Wildlife Ct, Cheshire, CT 06410

      Last Sold Summary

      • 17% Above List Price
      • $213/SF
      • 4 Days On Market

      Last Sold Price $570,000

      Last Listing Agent Barbara Podlisny William Raveis Real Estate

  • 131 Shea Cir Unit 131, Cheshire, CT 06410

    $545,340 Sold Feb 13, 2026

    131 Shea Cir Unit 131, Cheshire, CT 06410

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2026

    Last Sold Summary

    • 10% Above List Price
    • $295/SF
    • 49 Days On Market

    Last Listing Agent Jason Helton EG Group Realty LLC

    131 Shea Cir Unit 131, Cheshire, CT 06410
    • 30 Bramble Way, Cheshire, CT 06410

      Est $557,559 Not Listed For Sale

      30 Bramble Way, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 3,176 Sq Ft
      • Built 2006
      30 Bramble Way, Cheshire, CT 06410

      Last Sold Summary

      • 25% Above List Price
      • $140/SF
      • 13 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Melissa Lawson Dow Della Valle

  • 278 Wiese Rd, Cheshire, CT 06410

    $365,000 Sold Nov 26, 2025

    278 Wiese Rd, Cheshire, CT 06410

    • 2 Beds
    • 1 Bath
    • 765 Sq Ft
    • Built 1938

    Last Sold Summary

    • 7% Above List Price
    • $477/SF
    • 5 Days On Market

    Current Estimated Value $357,100

    Last Listing Agent Joseph Snell Luxe Realty LLC

    278 Wiese Rd, Cheshire, CT 06410
    • 28 Wildlife Ct, Cheshire, CT 06410

      Est $523,892 Not Listed For Sale

      28 Wildlife Ct, Cheshire, CT 06410

      • 2 Beds
      • 2 Baths
      • 1,563 Sq Ft
      • Built 2010
      28 Wildlife Ct, Cheshire, CT 06410

      Last Sold Summary

      • 19% Above List Price
      • $282/SF
      • 2 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Beverly Welch Calcagni Real Estate

  • 751 W Main St Unit G, Cheshire, CT 06410

    $330,000 Sold Mar 23, 2026

    751 W Main St Unit G, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $204/SF
    • 125 Days On Market

    Last Listing Agent Cynthia Ortiz LAER Realty Partners

    751 W Main St Unit G, Cheshire, CT 06410
    • 15 Wildlife Ct, Cheshire, CT 06410

      Est $637,142 Not Listed For Sale

      15 Wildlife Ct, Cheshire, CT 06410

      • 3 Beds
      • 2.5 Baths
      • 2,639 Sq Ft
      • Built 2010
      15 Wildlife Ct, Cheshire, CT 06410

      Last Sold Summary

      • 9% Above List Price
      • $222/SF
      • 14 Days On Market

      Last Sold Price $585,000

      Last Listing Agent Barbara Lehrer Coldwell Banker Realty

  • 20 Club Ln, Cheshire, CT 06410

    $528,000 Sold Sep 05, 2025

    20 Club Ln, Cheshire, CT 06410

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1976

    Last Sold Summary

    • 13% Above List Price
    • $423/SF
    • 4 Days On Market

    Current Estimated Value $526,328

    Last Listing Agent James Bulger Calcagni Real Estate

    20 Club Ln, Cheshire, CT 06410

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