Cheshire, CT Homes

• 

  $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 $210,138

  Last Listing Agent Amanda Albert Coldwell Banker Realty

  40 Southwick Ct Unit 106, Cheshire, CT 06410
• 

  Est $399,779 Not Listed For Sale

  1147 King Rd, Cheshire, CT 06410

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1938

  1147 King Rd, Cheshire, CT 06410

  Last Sold Summary

  • 21% Above List Price
  • $308/SF
  • 3 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Alaina Capasso Advise Realty Services
• 

  

  /2

  $1,815,000 Pending

  • 6 Beds
  • 8 Baths
  • 6,008 Sq Ft

  21 Melrose Dr Unit Lot 2, Cheshire, CT 06410

  A truly SPECTACULAR house plan on a truly PICTURESQUE lot! This to be built home will be simply breathtaking at just over 6,000 sq ft.

  Dori Degennaro William Raveis Real Estate

  21 Melrose Dr Unit Lot 2, Cheshire, CT 06410
• 

  $680,000 Sold Jun 06, 2025

  166 Mixville Rd, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,764 Sq Ft
  • Built 1966

  Last Sold Summary

  • 13% Above List Price
  • $246/SF
  • 4 Days On Market

  Current Estimated Value $690,226

  Last Listing Agent Tiziana Tremblay Real Broker CT, LLC

  166 Mixville Rd, Cheshire, CT 06410
• 

  Est $466,654 Not Listed For Sale

  100 Brentwood Dr, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1969

  100 Brentwood Dr, Cheshire, CT 06410

  Last Sold Summary

  • 18% Above List Price
  • $317/SF
  • 3 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Cindy Forlenzo Coldwell Banker
• 

  

  /20

  $540,000

  • 3 Beds
  • 3 Baths
  • 1,288 Sq Ft

  35 Mountain Edge Ct, Cheshire, CT 06410

  Welcome to this beautiful raised ranch nestled on a quiet cul-de-sac, offering the perfect combination of space, versatility, and comfort. Featuring 3 spacious bedrooms and 3 full bathrooms, this home is ideal for both everyday living and entertaining. Don't miss this unique opportunity!

  Donald Proko Coldwell Banker Realty

  35 Mountain Edge Ct, 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 $353,972

  Last Listing Agent Thomas Scott Coldwell Banker Realty

  114 Spring St, Cheshire, CT 06410
• 

  Est $531,584 Not Listed For Sale

  20 Brentwood Dr, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • Built 1969

  20 Brentwood Dr, Cheshire, CT 06410

  Last Sold Summary

  • 3% Below List Price
  • $300/SF
  • 4 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Cindy Forlenzo Coldwell Banker
• 

  

  /3

  $1,299,000 Pending

  • 4 Beds
  • 5 Baths
  • 4,011 Sq Ft

  17 Melrose Dr Unit Lot 3, Cheshire, CT 06410

  A beautiful new construction home!! Only 2 lots remain in the desirable Orchard View subdivision. Introducing the expanded Essex plan at 4,011 square feet. A very spacious home with 9 ft ceilings on the main level, a generous sized kitchen, and a beautiful cathedral ceiling in the Family Room that perfectly highlights the propane fireplace. A very functional mudroom area right off the 3 car

  Dori Degennaro William Raveis Real Estate

  17 Melrose Dr Unit Lot 3, Cheshire, CT 06410
• 

  $670,000 Sold Dec 15, 2025

  4 Brookfield Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $291/SF
  • 39 Days On Market

  Current Estimated Value $672,739

  Last Listing Agent Brette Stern Calcagni Real Estate

  4 Brookfield Ct, Cheshire, CT 06410
• 

  Est $446,219 Not Listed For Sale

  5 Rockview Dr, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,976 Sq Ft
  • Built 1950

  5 Rockview Dr, Cheshire, CT 06410

  Last Sold Summary

  • 5% Above List Price
  • $215/SF
  • 60 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Lauren Freedman Coldwell Banker Realty
• 

  

  /40

  $649,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,498 Sq Ft

  34 Nathan Hale Ct, Cheshire, CT 06410

  Welcome to this expansive Colonial nestled on almost 2 secluded acres in one of Cheshire's sought-after neighborhoods. Presenting 4 bedrooms (potential for a 5th) each with its own walk-in closet, this home provides exceptional space and flexibility. Step into the grand foyer, highlighted by a beautiful chandelier and a newer window that fills the entry with natural light. The main level offers a

  Stephanie Plaza Lamacchia Realty

  34 Nathan Hale Ct, Cheshire, CT 06410
• 

  $565,000 Sold Feb 19, 2026

  975 Wolf Hill Rd, Cheshire, CT 06410

  • 3 Beds
  • 3 Baths
  • 1,882 Sq Ft
  • Built 1947

  Last Sold Summary

  • 2% Below List Price
  • $300/SF
  • 10 Days On Market

  Current Estimated Value $560,505

  Last Listing Agent Rachel Wardwell Calcagni Real Estate

  975 Wolf Hill Rd, Cheshire, CT 06410
• 

  Est $429,607 Not Listed For Sale

  39 Green Hill Ln, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft
  • Built 1954

  39 Green Hill Ln, Cheshire, CT 06410

  Last Sold Summary

  • 5% Above List Price
  • $248/SF
  • 51 Days On Market

  Last Sold Price $411,000

  Last Listing Agent Mary Tirozzi Century 21 AllPoints Realty
• 

  

  /40

  $639,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,344 Sq Ft

  88 Nob Hill Rd, Cheshire, CT 06410

  Homes like this are hard to find in today's market! Located in the new Barnum Elementary School district, this classic 4-bedroom, 2.5-bath Colonial sits on over an acre in one of Cheshire's desirable neighborhoods. Home offers 9 spacious rooms with major updates completed within the past 10 years, including roof, siding, gutters, HVAC and more. Hardwood flooring flows throughout, with a layout

  Heidi Weed Lamacchia Realty

  88 Nob Hill Rd, Cheshire, CT 06410
• 

  $381,000 Sold Jul 01, 2025

  48 Warren St, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,198 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Above List Price
  • $318/SF
  • 39 Days On Market

  Current Estimated Value $390,001

  Last Listing Agent Kelly Ryan William Raveis Real Estate

  48 Warren St, Cheshire, CT 06410
• 

  Est $434,922 Not Listed For Sale

  32 Rockview Dr, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,576 Sq Ft
  • Built 1954

  32 Rockview Dr, Cheshire, CT 06410

  Last Sold Summary

  • 2% Above List Price
  • $270/SF
  • 19 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Melanie Ricci Coldwell Banker
• 

  

  /36

  $399,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,725 Sq Ft

  767 Ives Row, Cheshire, CT 06410

  HIGHEST AND BEST 4/12 7PM Welcome to this beautifully maintained 3-bedroom, 1.5-bath ranch nestled in one of Cheshire's most desirable neighborhoods-where comfort, functionality, and location come together effortlessly. From the moment you arrive, you'll appreciate the inviting curb appeal and pride of ownership throughout. Step inside to discover gleaming hardwood floors, with additional

  Agnes Nawrocki William Raveis Real Estate

  767 Ives Row, Cheshire, CT 06410
• 

  $785,000 Sold Jul 17, 2025

  33 Roxbury Ct, Cheshire, CT 06410

  • 5 Beds
  • 4.5 Baths
  • 3,671 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $214/SF
  • 121 Days On Market

  Current Estimated Value $797,670

  Last Listing Agent Kori Gauvin KW Legacy Partners

  33 Roxbury Ct, Cheshire, CT 06410
• 

  Est $458,972 Not Listed For Sale

  120 Rockview Dr, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,496 Sq Ft
  • Built 1955

  120 Rockview Dr, Cheshire, CT 06410

  Last Sold Summary

  • 19% Above List Price
  • $257/SF
  • 63 Days On Market

  Last Sold Price $384,900

  Last Listing Agent Todd Regan Redfin Corporation
• 

  

  /12

  $198,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  Unlisted Address

  Second floor-Two Bedroom Condo at Birchwood Condominiums, Upgraded Kitchen-Available Immediately. HEAT, HOT WATER, & WATER IS INCLUDED in the monthly Condo fee. One full bath and spacious bedrooms, There is coin operated laundry with an extremely reasonable price for usage and a storage area for the unit in the basement. Located on approximately 50 acres! Centrally located in town, walk to

  Marty Rauch Marty Rauch Real Estate

  Unlisted Address
• 

  $646,500 Sold Mar 13, 2026

  25 Goldenrod Ct, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $280/SF
  • 171 Days On Market

  Current Estimated Value $664,199

  Last Listing Agent Mark Gracia William Raveis Real Estate

  25 Goldenrod Ct, Cheshire, CT 06410
• 

  Est $448,450 Not Listed For Sale

  165 Rockview Dr, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,334 Sq Ft
  • Built 1955

  165 Rockview Dr, Cheshire, CT 06410

  Last Sold Summary

  • 18% Above List Price
  • $285/SF
  • 46 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Stacey Deangelis Calcagni Real Estate
• 

  

  /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
• 

  $710,000 Sold Jun 30, 2025

  671 Cortland Cir, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,750 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Above List Price
  • $258/SF
  • 3 Days On Market

  Current Estimated Value $703,934

  Last Listing Agent Cheri Paulsen Advise Realty Services

  671 Cortland Cir, Cheshire, CT 06410
• 

  Est $481,547 Not Listed For Sale

  195 Green Hill Ln, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Built 1953

  195 Green Hill Ln, Cheshire, CT 06410

  Last Sold Summary

  • 9% Above List Price
  • $335/SF
  • 4 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Pat DelVento III Coldwell Banker Realty
• 

  

  /40

  $619,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,167 Sq Ft

  365 Maple Ave, Cheshire, CT 06410

  Welcome to 365 Maple Ave, a quintessential Cheshire Colonial where timeless New England charm meets you at the front door & is the backdrop of every room. Curb appeal abounds with crisp white siding, a brand-new roof (1.5 yrs), and iconic red accents. Once you step inside, you won't be able to stop yourself from wanting to wander & immerse yourself in each and every room! The heart of the home is

  Suzy Couture Better Homes and Gardens Real Estate Executive Real Estate

  365 Maple Ave, Cheshire, CT 06410
• 

  $400,000 Sold Dec 04, 2025

  1325 Avon Blvd, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,316 Sq Ft
  • Built 1953

  Last Sold Summary

  • $304/SF
  • 69 Days On Market

  Current Estimated Value $396,949

  Last Listing Agent Cindy Forlenzo Coldwell Banker Realty

  1325 Avon Blvd, Cheshire, CT 06410
• 

  Est $304,857 Not Listed For Sale

  315 S Brooksvale Rd, Cheshire, CT 06410

  • 2 Beds
  • 1.5 Baths
  • 1,725 Sq Ft
  • Built 1962

  315 S Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 2% Above List Price
  • $174/SF
  • 3 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Kara Chappell eXp Realty
• 

  

  /40

  $1,300,888

  • 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
• 

  $790,000 Sold May 21, 2025

  25 Soderman Way, Cheshire, CT 06410

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

  Last Sold Summary

  • $266/SF
  • 58 Days On Market

  Last Listing Agent Kathleen Maloney Coldwell Banker Realty

  25 Soderman Way, Cheshire, CT 06410
• 

  Est $259,297 Not Listed For Sale

  311 S Brooksvale Rd, Cheshire, CT 06410

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1962

  311 S Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 31% Above List Price
  • $172/SF
  • 8 Days On Market

  Last Sold Price $198,000

  Last Listing Agent James Bulger Calcagni Real Estate
• 

  

  /13

  $674,900 Pending

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

  88 Shea Cir Unit 88, Cheshire, CT 06410

  Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy, offer

  Michael Helmuth EG Group Realty LLC

  88 Shea Cir Unit 88, Cheshire, CT 06410
• 

  $710,000 Sold Jan 08, 2026

  440 Mount Sanford Rd, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 3,816 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $186/SF
  • 16 Days On Market

  Last Listing Agent Sam Ratner Keller Williams Realty Prtnrs.

  440 Mount Sanford 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
• 

  

  /40

  $950,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,300 Sq Ft

  776 Bethany Mountain Rd, Cheshire, CT 06410

  Tucked away on 4 private wooded acres, this charming Dutch Colonial offers the perfect blend of peaceful country living and modern comfort, just minutes from town. Inside, the home offers 3,300 SF of inviting living space filled with natural light, warm wood floors, exposed beams and lovely built-ins. The recently updated spacious kitchen with new wood flooring, new quartz countertops and new

  Rose Ciardiello William Raveis Real Estate

  776 Bethany Mountain 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

  Current Estimated Value $515,608

  Last Listing Agent Elise Kamp Press/Cuozzo Realtors

  236 Mountain 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
• 

  

  /38

  $499,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,998 Sq Ft

  25 Stonegate Cir, Cheshire, CT 06410

  A rare opportunity to own the Reverend John Hull House at Stonegate, a 55+ community in Cheshire. This home was originally built in 1764 but was gutted and restored for today's living in 2005, still keeping all it's historic charm and features such as original wide plank flooring, exposed hand-hewn beams and 4 fireplaces (3 functioning w gas). The spacious Living Room w large gas FP creates a

  Phil Giampietro Coldwell Banker Realty

  25 Stonegate Cir, 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 $282,238

  Last Listing Agent Julie Luchina Coldwell Banker Realty

  40 Southwick Ct Unit 201, Cheshire, CT 06410

Showing Results 241 - 280, Page 7 of 18