Cheshire, CT Homes

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  /19

  $74,995

  • Land
  • 27,007 Sq Ft
  • $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
• 

  $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 $363,554

  Last Listing Agent Joseph Snell Luxe Realty LLC

  278 Wiese Rd, Cheshire, CT 06410
• 

  Est $450,124

  Not Listed For Sale

  36 Lewis Rd, Cheshire, CT 06410

  • 4 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • Built 1954

  36 Lewis Rd, Cheshire, CT 06410

  Last Sold Summary

  • 22 Days On Market
• 

  

  

  /37

  $529,900

  Under Contract

  • 6 Beds
  • 3 Baths
  • 2,015 Sq Ft

  405 Sheridan Dr, Cheshire, CT 06410

  Charming 6 bedroom Cape in great neighborhood! Home offered for sale for the first time. The property's original owner has loved and cared for this home for the past 56 years. Nice layout with generous room size. Living room w/fireplace, formal dining room, eat-in kitchen, sunroom, 6 bedrooms and 3 full baths. Lovely yard with lots of flowers, plantings and charm. Full basement with ample storage

  Sarah Kolman The Heritage Group, LLC

  405 Sheridan Dr, 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
• 

  Est $398,146

  Not Listed For Sale

  158 Crescent Cir, Cheshire, CT 06410

  • 3 Beds
  • 1 Bath
  • 1,236 Sq Ft
  • Built 1955

  158 Crescent Cir, Cheshire, CT 06410

  Last Sold Summary

  • 45 Days On Market
• 

  

  /36

  $499,900

  • 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
• 

  $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 $523,433

  Last Listing Agent James Bulger Calcagni Real Estate

  20 Club Ln, Cheshire, CT 06410
• 

  Est $871,298

  Not Listed For Sale

  75 Winding Trail, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 3,574 Sq Ft
  • Built 1998

  75 Winding Trail, Cheshire, CT 06410

  Last Sold Summary

  • 16 Days On Market
• 

  /2

  $249,900

  Coming Soon

  • 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
• 

  $225,000

  Sold Jul 08, 2025

  316 Jinny Hill Rd, Cheshire, CT 06410

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

  Last Sold Summary

  • 7% Above List Price
  • $183/SF
  • 2 Days On Market

  Current Estimated Value $263,238

  Last Listing Agent Stephanie Oliver Dave Jones Realty, LLC

  316 Jinny Hill Rd, Cheshire, CT 06410
• 

  Est $858,963

  Not Listed For Sale

  39 Winding Trail, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,979 Sq Ft
  • Built 1998

  39 Winding Trail, Cheshire, CT 06410

  Last Sold Summary

  • 33 Days On Market
• 

  

  /40

  $549,900

  $89K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,554 Sq Ft

  80 Pound Ridge Rd, Cheshire, CT 06410

  Highest and Best offer by tonight, June 8, 2026, by 8pm! Spacious 4-bedroom, 2.1-bath Colonial located on a desirable sidewalk-lined cul-de-sac in sought-after South Cheshire. This classic center-hall floor plan offers a bright kitchen, spacious living and dining rooms with hardwood floors throughout, and an expansive family room featuring a beautiful custom fireplace mantelpiece. Finished lower

  Robert Murphy Station Cities

  80 Pound Ridge Rd, Cheshire, CT 06410
• 

  $538,000

  Sold Nov 25, 2025

  4 Blueberry Place, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • Built 1983

  Last Sold Summary

  • 5% Above List Price
  • $255/SF
  • 17 Days On Market

  Current Estimated Value $538,585

  Last Listing Agent Elizabeth Urbanski Coldwell Banker Realty

  4 Blueberry Place, Cheshire, CT 06410
• 

  Est $947,448

  Not Listed For Sale

  30 Winding Trail, Cheshire, CT 06410

  • 4 Beds
  • 3 Baths
  • 3,098 Sq Ft
  • Built 1998

  30 Winding Trail, Cheshire, CT 06410

  Last Sold Summary

  • 6 Days On Market
• 

  

  /40

  $579,900

  • 5 Beds
  • 2.5 Baths
  • 2,613 Sq Ft

  151 Braemar Dr, Cheshire, CT 06410

  Spacious 5-bedroom, 2.5-bath Colonial offering two levels of comfortable living space and endless potential. Hardwood floors run throughout the home, which features a large living room with a wood-burning fireplace and beautiful bay window, formal dining room, kitchen, family room, half bath with laundry, and a private office/den. The first floor also includes two bedrooms, one with direct access

  Katie Smith Berkshire Hathaway NE Prop.

  151 Braemar Dr, Cheshire, CT 06410
• 

  $1,075,000

  Sold Jul 07, 2025

  1161 Sperry Rd, Cheshire, CT 06410

  • 3 Beds
  • 5 Baths
  • 8,558 Sq Ft
  • Built 1953

  Last Sold Summary

  • 39% Below List Price
  • $126/SF
  • 133 Days On Market

  Current Estimated Value $1,017,848

  Last Listing Agent Derek Greene Derek Greene

  1161 Sperry Rd, Cheshire, CT 06410
• 

  Est $884,711

  Not Listed For Sale

  25 Winding Trail, Cheshire, CT 06410

  • 4 Beds
  • 4 Baths
  • 3,773 Sq Ft
  • Built 1999

  25 Winding Trail, Cheshire, CT 06410

  Last Sold Summary

  • 34 Days On Market
• 

  

  /14

  $134,900

  $15K PRICE DROP Pending

  • 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
• 

  $520,000

  Sold Oct 16, 2025

  497 Maple Ave, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Above List Price
  • $217/SF
  • 6 Days On Market

  Current Estimated Value $540,585

  Last Listing Agent Monique Jacobs RE/MAX RISE

  497 Maple Ave, Cheshire, CT 06410
• 

  Est $572,818

  Not Listed For Sale

  374 N Brooksvale Rd, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,915 Sq Ft
  • Built 1986

  374 N Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 31 Days On Market
• 

  

  /35

  $559,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,057 Sq Ft

  375 Sycamore Ln, Cheshire, CT 06410

  Charming colonial located in a sought-after neighborhood in Cheshire. This 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and functionality. The eat-in kitchen features stainless steel appliances and flows into an inviting dining room that opens to the living room, with hardwood floors in both rooms creating a warm and welcoming atmosphere. Just off the kitchen is a spacious

  Cheryl Rosadino Berkshire Hathaway NE Prop.

  375 Sycamore Ln, Cheshire, CT 06410
• 

  $530,000

  Sold Nov 24, 2025

  1213 Avon Blvd, Cheshire, CT 06410

  • 4 Beds
  • 2 Baths
  • 2,312 Sq Ft
  • Built 1954

  Last Sold Summary

  • 9% Above List Price
  • $229/SF
  • 11 Days On Market

  Current Estimated Value $554,440

  Last Listing Agent Jill Nathanson-Zaengel Press/Cuozzo Realtors

  1213 Avon Blvd, Cheshire, CT 06410
• 

  Est $755,374

  Not Listed For Sale

  295 Towpath Ln, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 2,956 Sq Ft
  • Built 1976

  295 Towpath Ln, Cheshire, CT 06410

  Last Sold Summary

  • 7 Days On Market
• 

  

  /38

  $689,900

  Under Contract

  • 5 Beds
  • 3.5 Baths
  • 3,170 Sq Ft

  463 Payne Dr, Cheshire, CT 06410

  Immaculate and exceptionally versatile, 3,000+ sq ft Colonial, perfectly suited for multi-generational living. Nestled in the highly sought-after Nob Hill neighborhood, this home offers an ideal blend of space, comfort, and thoughtful design. The main level features a rare extended living setup above the garage with a 5th bedroom, full bath, and slider to the deck- a perfect retreat for in-laws,

  Vasco Silva Great Estates, CT

  463 Payne Dr, Cheshire, CT 06410
• 

  $525,000

  Sold Apr 03, 2026

  8 Soderman Way Unit 8, Cheshire, CT 06410

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

  Last Sold Summary

  • 3% Below List Price
  • $284/SF
  • 54 Days On Market

  Last Listing Agent Tracey Fiasconaro Berkshire Hathaway NE Prop.

  8 Soderman Way Unit 8, Cheshire, CT 06410
• 

  Est $468,352

  Not Listed For Sale

  879 Farmington Dr, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft
  • Built 1963

  879 Farmington Dr, Cheshire, CT 06410

  Last Sold Summary

  • 49 Days On Market
• 

  

  /40

  $379,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft

  129 Pleasant Dr, Cheshire, CT 06410

  Opportunity awaits at 129 Pleasant Drive! This 3-bedroom, 2 full bath Cape offers 1,663 square feet of living space and is set on a .47-acre lot in a desirable location. The first floor features a kitchen with stackable washer and dryer, dining room with sliders leading to a deck overlooking the private backyard, spacious front-to-back living room w/ fireplace, den, and a full bath. While the

  The Sally Bowman Team Berkshire Hathaway NE Prop.

  129 Pleasant Dr, Cheshire, CT 06410
• 

  $190,000

  Sold Nov 20, 2025

  0 S Meriden Rd Unit 3, Cheshire, CT 06410

  • Land
  • 9.81 Acres
  • $19,368 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 136 Days On Market

  Last Listing Agent James Bulger Calcagni Real Estate

  0 S Meriden Rd Unit 3, Cheshire, CT 06410
• 

  Est $506,200

  Not Listed For Sale

  499 Sharon Dr, Cheshire, CT 06410

  • 3 Beds
  • 1.5 Baths
  • 1,620 Sq Ft
  • Built 1962

  499 Sharon Dr, Cheshire, CT 06410

  Last Sold Summary

  • 9 Days On Market
• 

  $320,000

  Sold Jan 15, 2026

  315 Greens Loop Unit 315, Cheshire, CT 06410

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

  Last Sold Summary

  • 1% Below List Price
  • $304/SF
  • 84 Days On Market

  Current Estimated Value $305,932

  Last Listing Agent Mark Tavares Mark Tavares Realty, LLC

  315 Greens Loop Unit 315, Cheshire, CT 06410
• 

  Est $374,038

  Not Listed For Sale

  280 N Brooksvale Rd, Cheshire, CT 06410

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1958

  280 N Brooksvale Rd, Cheshire, CT 06410

  Last Sold Summary

  • 7 Days On Market
• 

  $209,000

  Sold May 21, 2026

  80 Southwick Ct Unit 201, Cheshire, CT 06410

  • 1 Bed
  • 1 Bath
  • 807 Sq Ft
  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • $259/SF
  • 26 Days On Market

  Current Estimated Value $206,754

  Last Listing Agent Rebecca Bower Forever Homes Real Estate LLC

  80 Southwick Ct Unit 201, Cheshire, CT 06410
• 

  Est $483,811

  Not Listed For Sale

  120 Hilltop Rd, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft
  • Built 1955

  120 Hilltop Rd, Cheshire, CT 06410

  Last Sold Summary

  • 55 Days On Market
• 

  $570,000

  Sold Oct 27, 2025

  1016 Split Rock Rd, Cheshire, CT 06410

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1968

  Last Sold Summary

  • 10% Below List Price
  • $352/SF
  • 73 Days On Market

  Current Estimated Value $567,424

  Last Listing Agent Heidi Weed Lamacchia Realty

  1016 Split Rock Rd, Cheshire, CT 06410
• 

  Est $785,913

  Not Listed For Sale

  940 Ward Ln, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 3,446 Sq Ft
  • Built 1999

  940 Ward Ln, Cheshire, CT 06410

  Last Sold Summary

  • 50 Days On Market
• 

  $500,000

  Sold Feb 24, 2026

  25 Mountain Brook Dr, Cheshire, CT 06410

  • 4 Beds
  • 2.5 Baths
  • 4,630 Sq Ft
  • Built 1979

  Last Sold Summary

  • 32% Below List Price
  • $108/SF
  • 100 Days On Market

  Current Estimated Value $546,972

  Last Listing Agent Anthony Greco Anthony J Greco JR Real Estate

  25 Mountain Brook Dr, Cheshire, CT 06410
• 

  Est $1,635,880

  Not Listed For Sale

  764 Bethany Mountain Rd, Cheshire, CT 06410

  • 4 Beds
  • 3.5 Baths
  • 7,762 Sq Ft
  • Built 2005

  764 Bethany Mountain Rd, Cheshire, CT 06410

  Last Sold Summary

  • 200 Days On Market
• 

  $330,000

  Sold Nov 24, 2025

  8 Currier Ct Unit 8, Cheshire, CT 06410

  • 2 Beds
  • 1.5 Baths
  • 1,712 Sq Ft
  • Built 1976

  Last Sold Summary

  • 2% Above List Price
  • $193/SF
  • 2 Days On Market

  Current Estimated Value $329,723

  Last Listing Agent Melissa Mesite Coldwell Banker Realty

  8 Currier Ct Unit 8, Cheshire, CT 06410
• 

  Est $949,842

  Not Listed For Sale

  779 Foster Ct, Cheshire, CT 06410

  • 3 Beds
  • 2.5 Baths
  • 3,056 Sq Ft
  • Built 1978

  779 Foster Ct, Cheshire, CT 06410

  Last Sold Summary

  • 32 Days On Market

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