Cheshire, CT Homes

• 

  

  

  /25

  $375,000

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft

  393 S Meriden Rd, Cheshire, CT 06410

  Discover this charming two-bedroom ranch located in the heart of Cheshire. As you step inside, you'll immediately be impressed by the hardwood floors that span the living room, family room, and both bedrooms. Beautiful built-in bookshelves and crown molding add a classic touch. The master bedroom has its own private full bathroom, ensuring convenience and privacy. On those rainy days, retreat to

  Stacey Deangelis Calcagni Real Estate

  393 S Meriden Rd, Cheshire, CT 06410
• 

  $507,500

  Sold Oct 09, 2025

  236 Mountain Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 1,619 Sq Ft
  • Built 1948

  Last Sold Summary

  • 4% Below List Price
  • $313/SF
  • 54 Days On Market

  Last Listing Agent Elise Kamp Press/Cuozzo Realtors

  236 Mountain Rd, Cheshire, CT 06410
• 

  Est $466,742

  Not Listed For Sale

  957 Coleman Rd, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1956

  957 Coleman Rd, Cheshire, CT 06410

  Last Sold Summary

  • 35 Days On Market
• 

  

  

  /39

  $779,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,474 Sq Ft

  19 E Ridge Ct, Cheshire, CT 06410

  Exceptional, beautifully built, updated and maintained, custom center hall Colonial on over 1 acre of private, professionally maintained gardens and yard. Property abuts open space. Bluestone steps and stone walls surround this magnificent home. Hardwood floors throughout. Newer granite, tiled kitchen features large island,wet bar, wine cooler and window seat with storage. Kitchen by Gedney.

  Karen Brimberg William Raveis Real Estate

  19 E Ridge Ct, Cheshire, CT 06410
• 

  $285,000

  Sold Jan 27, 2026

  40 Southwick Ct Unit 201, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 954 Sq Ft
  • Built 2000

  Last Sold Summary

  • $299/SF
  • 52 Days On Market

  Current Estimated Value $283,517

  Last Listing Agent Julie Luchina Coldwell Banker Realty

  40 Southwick Ct Unit 201, Cheshire, CT 06410
• 

  Est $632,576

  Not Listed For Sale

  968 Coleman Rd, Cheshire, CT 06410

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

  968 Coleman Rd, Cheshire, CT 06410

  Last Sold Summary

  • 15 Days On Market
• 

  

  /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
• 

  $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 $574,056

  Last Listing Agent Julie Corrado Coldwell Banker Realty

  100 Lynwood Drive Extension, Cheshire, CT 06410
• 

  Est $263,724

  Not Listed For Sale

  316 Jinny Hill Rd, Cheshire, CT 06410

  • 1 Bed
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1953

  316 Jinny Hill Rd, Cheshire, CT 06410

  Last Sold Summary

  • 2 Days On Market
• 

  

  /40

  $1,080,888

  $220K PRICE DROP Under Contract

  • 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
• 

  $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
• 

  Est $499,203

  Not Listed For Sale

  425 Radmere Rd, Cheshire, CT 06410

  • 4 Beds
  • 2 Baths
  • 1,551 Sq Ft
  • Built 1959

  425 Radmere Rd, Cheshire, CT 06410

  Last Sold Summary

  • 5 Days On Market
• 

  

  /38

  $549,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,678 Sq Ft

  115 Oak Ave, Cheshire, CT 06410

  ****Best and Final offers due Wednesday July 15th at Noon. ****Welcome home to this beautifully maintained Cape offering 4 bedrooms, 2 full baths, and 1,678 square feet of comfortable living space on a level .48-acre lot. The inviting main level features a spacious family room with hardwood flooring that opens to the beautifully updated kitchen with granite countertops, creating the perfect space

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  115 Oak Ave, 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 $506,281

  Last Listing Agent Paulo Salgado RE/MAX RISE

  31 Roslyn Dr, Cheshire, CT 06410
• 

  Est $481,658

  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
• 

  

  /26

  $579,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  836 Wolf Hill Rd, Cheshire, CT 06410

  Classic style and timeless charm are found in this 4 bedroom Colonial. Remodeled eat-in kitchen complete with granite countertops, tile backsplash and stainless appliance opens to the step-down family room with dramatic 18' vaulted ceiling and floor to ceiling brick, raised hearth fireplace. The two skylights offer loads of light. From the family room slider step outside to a beautifully crafted

  Roberta Havlick William Raveis Real Estate

  836 Wolf Hill Rd, 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 $526,789

  Last Listing Agent Betsy Purtell Purtell Realty LLC

  265 Lancaster Way, Cheshire, CT 06410
• 

  Est $662,710

  Not Listed For Sale

  164 N Brooksvale Rd, Cheshire, CT 06410

  • 5 Beds
  • 3.5 Baths
  • 2,566 Sq Ft
  • Built 1920

  164 N Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 57 Days On Market
• 

  

  /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
• 

  $251,000

  Sold Jun 22, 2026

  422 N Brooksvale Rd, Cheshire, CT 06410

  • 3 Beds
  • 1,562 Sq Ft
  • Built 1860

  Last Sold Summary

  • 12% Above List Price
  • $161/SF
  • 35 Days On Market

  Current Estimated Value $220,500

  Last Listing Agent Phil Giampietro Coldwell Banker Realty

  422 N Brooksvale Rd, Cheshire, CT 06410
• 

  Est $640,790

  Not Listed For Sale

  230 Sharon Dr, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,618 Sq Ft
  • Built 1978

  230 Sharon Dr, Cheshire, CT 06410

  Last Sold Summary

  • 51 Days On Market
• 

  

  /39

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  479 Blacks Rd, Cheshire, CT 06410

  This expansive Cape Cod is filled with charm, character, and plenty of space to make your own. The spacious eat-in kitchen offers abundant storage and cooking space, along with flexible room for a dining table, breakfast bar, or both. Step outside to the large Trex deck, where you can enjoy your morning coffee while overlooking the private, peaceful wooded yard. A charming screened porch provides

  Brette Stern Calcagni Real Estate

  479 Blacks Rd, 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 $458,675

  Last Listing Agent Carly Kirsch Lamacchia Realty

  851 Ward Ln, Cheshire, CT 06410
• 

  Est $1,103,835

  Not Listed For Sale

  95 Jinny Hill Rd, Cheshire, CT 06410

  • 5 Beds
  • 5 Baths
  • 5,845 Sq Ft
  • Built 2006

  95 Jinny Hill Rd, Cheshire, CT 06410

  Last Sold Summary

  • 212 Days On Market
• 

  

  /40

  $814,900

  Under Contract

  • 5 Beds
  • 3.5 Baths
  • 3,455 Sq Ft

  921 Bethany Mountain Rd, Cheshire, CT 06410

  Set on 2.3 beautifully landscaped acres in Cheshire's desirable south end, this exceptional 5-bedroom, 3.5-bath Colonial offers the perfect blend of privacy, comfort, and flexibility for modern living. Bordered by Cheshire Land Trust property, the setting is peaceful and picturesque, with mature peonies, hydrangeas, and trees. Inside, the home features 2,920 sq ft plus a finished walkout lower

  Melissa Mesite Coldwell Banker Realty

  921 Bethany Mountain Rd, 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 $613,225

  Last Listing Agent Catherine Leake Coldwell Banker Realty

  1296 Deer Run Cir, Cheshire, CT 06410
• 

  Est $873,640

  Not Listed For Sale

  40 Brittany Ct, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 3,338 Sq Ft
  • Built 1986

  40 Brittany Ct, Cheshire, CT 06410

  Last Sold Summary

  • 36 Days On Market
• 

  

  /29

  $329,888

  Under Contract

  • 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
• 

  $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 $359,146

  Last Listing Agent Mela Veltri Case KW Legacy Partners

  67 Southwick Ct Unit 67, Cheshire, CT 06410
• 

  Est $406,613

  Not Listed For Sale

  1071 King Rd, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1971

  1071 King Rd, Cheshire, CT 06410

  Last Sold Summary

  • 13 Days On Market
• 

  

  /19

  $49,995

  $25K PRICE DROP

  • Land
  • 27,007 Sq Ft
  • $80,637 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
• 

  $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 $523,928

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

  1324 Notch Rd, Cheshire, CT 06410
• 

  Est $974,237

  Not Listed For Sale

  1043 Sperry Rd, Cheshire, CT 06410

  • 4 Beds
  • 3.5 Baths
  • 3,060 Sq Ft
  • Built 2016

  1043 Sperry Rd, Cheshire, CT 06410

  Last Sold Summary

  • 113 Days On Market
• 

  

  /36

  $479,900

  $20K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 1,928 Sq Ft

  1757 Musso View Ave, Cheshire, CT 06410

  Searching for a 4-bed home in Cheshire, CT, with flexible living space and room for extended family? This versatile 4-bedroom, 3.5-bath home offers 1,928 square feet of living space on a .46-acre lot. It features a legal in-law apartment with its own private entrance and separate driveway, making it ideal for multigenerational living, guests, or added privacy. (The in-law apartment contains 1 bed

  Joe Cafasso mygoodagent

  1757 Musso View Ave, 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 $545,119

  Last Listing Agent Brette Stern Calcagni Real Estate

  70 Royalwood Ct, Cheshire, CT 06410
• 

  Not Listed For Sale

  802 S Main St, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 2,228 Sq Ft
  • Built 1930

  802 S Main St, Cheshire, CT 06410

  Last Sold Summary

  • 106 Days On Market
• 

  

  /13

  $209,000

  $41K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  1117 Waterbury Rd Unit 1B, Cheshire, CT 06410

  This rare 3-bedroom, 2-full-bath, first-floor unit offers the convenience of main-level living and peaceful surroundings at Bayberry Knoll. Step inside and discover a spacious layout filled with natural light and endless potential to make it your own. The generously sized living areas provide comfortable everyday living and an ideal space for entertaining. The primary bedroom features its own

  Nicole Staples Coldwell Banker Realty

  1117 Waterbury Rd Unit 1B, Cheshire, CT 06410
• 

  $1,125,000

  Sold Jul 02, 2026

  15 Shire Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 4,437 Sq Ft
  • Built 2007

  Last Sold Summary

  • $254/SF
  • 61 Days On Market

  Current Estimated Value $1,105,807

  Last Listing Agent Iris Meyer William Raveis Real Estate

  15 Shire Ct, Cheshire, CT 06410
• 

  Est $478,933

  Not Listed For Sale

  70 Lewis Rd, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,896 Sq Ft
  • Built 1955

  70 Lewis Rd, Cheshire, CT 06410

  Last Sold Summary

  • 3 Days On Market
• 

  $930,000

  Sold Jun 30, 2026

  305 Richmond Glen Dr, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,625 Sq Ft
  • Built 2016

  Last Sold Summary

  • 11% Above List Price
  • $354/SF
  • 3 Days On Market

  Current Estimated Value $834,679

  Last Listing Agent Beverly Welch Calcagni Real Estate

  305 Richmond Glen Dr, Cheshire, CT 06410

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