Cheshire, CT Homes

• 

  $525,000 Sold Aug 21, 2025

  • 1,866 Sq Ft
  • $281/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1934

  345 Spring St, Cheshire, CT 06410

  Once upon a time, there wa s a home that looked like it was plucked straight from the pages of a storybook. With its gingerbread charm and inviting warmth, this house wasn't just a place to live-it was a place to dream. Inside, the story unfolds with beautiful hardwood floors that guide you through a welcoming living room, where a fireplace takes center stage, hinting at cozy evenings to come.

  Christy Lindsay Coldwell Banker Realty

  345 Spring St, Cheshire, CT 06410
• 

  Est $392,987 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,236 Sq Ft

  158 Crescent Cir, Cheshire, CT 06410

  158 Crescent Cir, Cheshire, CT 06410
• 

  

  

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  $449,900 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,704 Sq Ft

  25 Hidden Place, Cheshire, CT 06410

  UNIQUE OPPORTUNITY! Improved price...Contractors, Investors, flippers or DIY persons, take notice. Here is your opportunity to purchase a home in Cheshire, in a desired neighborhood, on a cul-de-sac, for half the value cost. Unfortunately this home suffered a fire in April. Return this home to its original beauty, but you will need to be patient and put the time and money into this project. At

  Laura Maturo William Raveis Real Estate

  25 Hidden Place, Cheshire, CT 06410
• 

  $640,000 Sold Aug 20, 2025

  • 2,758 Sq Ft
  • $232/SF
  • 91 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1997

  40 Nathan Hale Ct, Cheshire, CT 06410

  Welcome to this beautifully maintained 4-bedroom Colonial, perfectly nestled on over 3 acres in a serene cul-de-sac setting. A dramatic two-story foyer sets the tone for a home that blends comfort, style, and thoughtful design. The warm, inviting living room with custom built-ins connects seamlessly to the family room via a stunning two-sided wood-burning fireplace-ideal for entertaining or

  Brette Stern Calcagni Real Estate

  40 Nathan Hale Ct, Cheshire, CT 06410
• 

  Est $895,142 Not Listed For Sale

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

  75 Winding Trail, Cheshire, CT 06410

  75 Winding Trail, Cheshire, CT 06410
• 

  

  /38

  $619,800 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,637 Sq Ft

  2 Tunxis Place, Cheshire, CT 06410

  NEW PRICE !!! Exceptional, rare, COPPER HILL Stand Alone Ranch..Most desirable, private, charming community. This 3/4 BR, 2.1 bath is distinguished with detailed features throughout...Custom bookshelves and cabinetry fill this special home. Natural light fills the rooms..Vaulted ceilings, stunning kitchen with Corian countertops, subzero refrigerator, double oven, cook top, bar area, wine cooler,

  Gary Damato Press/Cuozzo Realtors

  2 Tunxis Place, Cheshire, CT 06410
• 

  $557,000 Sold Aug 19, 2025

  • 2,141 Sq Ft
  • $260/SF
  • 41 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1965

  622 Wiese Rd, Cheshire, CT 06410

  Don't miss this gorgeous 4-bedroom, 2.5-bath colonial set on a pristine, beautifully landscaped lot. Hardwood floors flow throughout the home, adding timeless charm. The bright and sunny living room features a welcoming wood-burning fireplace and a large bay window. Enjoy meals in the elegant dining room with bay window and classic moldings. The expansive kitchen offers granite countertops, tile

  Stacey Deangelis Calcagni Real Estate

  622 Wiese Rd, Cheshire, CT 06410
• 

  Est $870,866 Not Listed For Sale

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

  39 Winding Trail, Cheshire, CT 06410

  39 Winding Trail, Cheshire, CT 06410
• 

  $700,000 Sold Aug 18, 2025

  • 1,724 Sq Ft
  • $406/SF
  • 13 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1954

  60 Brook Ln, Cheshire, CT 06410

  Like New Construction but With All the Custom Upgrades at No Extra Cost! Luxuriate in this stunning, fully renovated contemporary ranch-style home. Designed with an open floor plan, this home features gleaming hardwood floors, quartz countertops, a spacious center island, and state-of-the-art stainless-steel appliances. Custom built-ins throughout--including a beautifully designed

  Iris Meyer William Raveis Real Estate

  60 Brook Ln, Cheshire, CT 06410
• 

  Est $972,709 Not Listed For Sale

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

  30 Winding Trail, Cheshire, CT 06410

  30 Winding Trail, Cheshire, CT 06410
• 

  $750,000 Sold Aug 18, 2025

  • 3,114 Sq Ft
  • $241/SF
  • 25 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1997

  20 Autumn Ct, Cheshire, CT 06410

  Highest and Best 7pm 7/22. Gracious Colonial in Cheshire's South End. Set on a cul de sac, in a neighborhood setting complete with sidewalks, this 4 bedroom 2 1/2 bathroom is a breath of fresh air with it's curb appeal, brand new roof , level lot, sprinkler system and underground utilities. Valuable updates include a new furnace (2023), roof (2025) and a/c condenser (2024). Step through the brand

  Kathleen Maloney Coldwell Banker Realty

  20 Autumn Ct, Cheshire, CT 06410
• 

  Est $911,412 Not Listed For Sale

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

  25 Winding Trail, Cheshire, CT 06410

  25 Winding Trail, Cheshire, CT 06410
• 

  $670,000 Sold Aug 15, 2025

  • 2,403 Sq Ft
  • $279/SF
  • 45 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1958

  262 Patton Dr, Cheshire, CT 06410

  Located in the highly sought-after center of town, this gorgeously renovated 4-bedroom Colonial blends timeless charm with modern luxury. Just a short stroll from Cheshire High School, Bartlem Park, and the scenic Farmington Canal Trail, this prime location offers the ultimate in convenience and community. Inside, a beautifully designed custom kitchen showcases granite countertops, a center

  Philip Degennaro Coldwell Banker Realty

  262 Patton Dr, Cheshire, CT 06410
• 

  Est $582,653 Not Listed For Sale

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

  374 N Brooksvale Rd, Cheshire, CT 06410

  374 N Brooksvale Rd, Cheshire, CT 06410
• 

  $589,900 Sold Aug 15, 2025

  • 1,908 Sq Ft
  • $309/SF
  • 45 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1970

  677 Wiese Rd, Cheshire, CT 06410

  Great opportunity to make this well cared for 3 Bedroom, 2.5 Bath Colonial your new home! The bright, inviting Living Room contains a wood burning fireplace for added comfort on chilly evenings. Enjoy cozy family dinners in the Dining Room with a beautiful bow window, flooding the room with natural light. The spacious Kitchen features ample cabinetry, Corian counters, a large island with storage

  Phil Giampietro Coldwell Banker Realty

  677 Wiese Rd, Cheshire, CT 06410
• 

  Est $788,358 Not Listed For Sale

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

  295 Towpath Ln, Cheshire, CT 06410

  295 Towpath Ln, Cheshire, CT 06410
• 

  $651,000 Sold Aug 12, 2025

  • 1,974 Sq Ft
  • $330/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  320 Spruce St, Cheshire, CT 06410

  Welcome to 320 Spruce, Cheshire, CT, a beautifully updated and meticulously cared-for home set on a prime corner lot in one of the area's most desirable neighborhoods. From the moment you arrive, you'll notice the curb appeal and thoughtful landscaping. Inside, the home features a stylishly renovated kitchen opening seamlessly to the dining area and an expansive cathedral-ceiling family room that

  Sam Ratner Keller Williams Realty Prtnrs.

  320 Spruce St, Cheshire, CT 06410
• 

  Est $480,618 Not Listed For Sale

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

  879 Farmington Dr, Cheshire, CT 06410

  879 Farmington Dr, Cheshire, CT 06410
• 

  $790,000 Sold Aug 11, 2025

  • 2,450 Sq Ft
  • $322/SF
  • 275 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  65 Soderman Way Unit 65, Cheshire, CT 06410

  Carriage home complete with designer appointed finishes! Available in the Summer of 2025. Carriage Home is stylish and sophisticated, yet every bit as warm, our Carriage homes provide the perfect mix of luxury, function, and comfort. You'll feel its charm upon entering the foyer, which leads to the heart of the home. A bright, open kitchen overlooks the dining area and wow-factor, the 2-story

  Jason Helton EG Group Realty LLC

  65 Soderman Way Unit 65, Cheshire, CT 06410
• 

  Est $492,382 Not Listed For Sale

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

  499 Sharon Dr, Cheshire, CT 06410

  499 Sharon Dr, Cheshire, CT 06410
• 

  $340,000 Sold Aug 08, 2025

  • 1,406 Sq Ft
  • $242/SF
  • 43 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1850

  114 Spring St, Cheshire, CT 06410

  This three-bedroom vintage home was built circa 1850. The style and architecture reflect the era. Lots of potential and possible room to expand. Hardwood floors. Large corner lot. Short walk to downtown Cheshire. Property being sold "As-Is". Great value - priced to sell!

  Thomas Scott Coldwell Banker Realty

  114 Spring St, Cheshire, CT 06410
• 

  Est $368,435 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  280 N Brooksvale Rd, Cheshire, CT 06410

  280 N Brooksvale Rd, Cheshire, CT 06410
• 

  $420,000 Sold Aug 08, 2025

  • 1,572 Sq Ft
  • $267/SF
  • 78 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  1813 Peck Ln, Cheshire, CT 06410

  Stunning Renovated Contemporary Ranch in Prime Commuter Location Welcome to this beautifully renovated contemporary ranch, ideally situated on a level corner lot directly across from the scenic Farmington Canal Rail-to-Trail. Perfectly blending style and functionality, this home offers exceptional convenience and sophisticated living. Step inside to discover engineered hardwood floors throughout

  Beth Santos Showcase Realty, Inc.

  1813 Peck Ln, Cheshire, CT 06410
• 

  Est $484,342 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  15 Rosemary Ln, Cheshire, CT 06410

  15 Rosemary Ln, Cheshire, CT 06410
• 

  $640,000 Sold Aug 05, 2025

  • 1,910 Sq Ft
  • $335/SF
  • 30 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  5 Smith Place, Cheshire, CT 06410

  Welcome to this beautifully maintained 4-bedroom Colonial nestled on a peaceful cul-de-sac. Set on a generous lot with a large, private backyard - perfect for outdoor entertaining and play - this home offers space, comfort and style. Step inside to find a thoughtfully renovated kitchen featuring modern finishes, updated appliances, and ample cabinet space. The main level boasts a traditional

  James Bulger Calcagni Real Estate

  5 Smith Place, Cheshire, CT 06410
• 

  Est $515,608 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,076 Sq Ft

  31 Rosemary Ln, Cheshire, CT 06410

  31 Rosemary Ln, Cheshire, CT 06410
• 

  $315,000 Sold Jul 30, 2025

  • 1,052 Sq Ft
  • $299/SF
  • 63 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  148 Fairway Dr Unit 148, Cheshire, CT 06410

  This sunny, 2 bedroom, 1.5 bath townhouse condo built 1986 in leafy Cheshire is well-updated and ready for you! Country Village Condos in Cheshire is a gem: a secluded, quiet, and orderly 80-unit condo complex of cute townhouses with an outdoor pool, clubhouse, basketball court, and oodles of parking. This bright and sunny unit's first floor offers a large living room, half bath and kitchen with

  Amy Lapierre Coldwell Banker Realty

  148 Fairway Dr Unit 148, Cheshire, CT 06410
• 

  Est $498,388 Not Listed For Sale

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

  120 Hilltop Rd, Cheshire, CT 06410

  120 Hilltop Rd, Cheshire, CT 06410
• 

  $680,000 Sold Jul 30, 2025

  • 3,156 Sq Ft
  • $215/SF
  • 84 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1992

  319 Redstone Dr, Cheshire, CT 06410

  Spacious and grand contemporary colonial on a spectacular level one acre lot in a desirable, well-regarded neighborhood. This custom designed home offers a 2-story foyer and kitchen, 10-foot ceilings throughout most of first floor, and so much character. The grandiose entryway greets you with a curved double staircase leading to a bridged balcony overlooking the kitchen and foyer. The great room

  Brette Stern Calcagni Real Estate

  319 Redstone Dr, Cheshire, CT 06410
• 

  Est $559,799 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,601 Sq Ft

  28 Hilltop Rd, Cheshire, CT 06410

  28 Hilltop Rd, Cheshire, CT 06410
• 

  $315,000 Sold Jul 28, 2025

  • 1,052 Sq Ft
  • $299/SF
  • 1 Day On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  107 Greens Loop, Cheshire, CT 06410

  Location! Location! Location! Easiest in and out from Country Club Rd entrance (Fairway Dr), just a few feet to mail, pool, clubhouse, basketball courts. Expansive rear yard. Beautifully updated, featuring new hardwood floors and carpet. Refreshed kitchen cabinets with marble counters and new GE appliances. New bathroom floors, toilets, and vanities. Freshly painted throughout. Great location

  Joel Grossman Huntsman,Meade & Partners Comp

  107 Greens Loop, Cheshire, CT 06410
• 

  Est $806,297 Not Listed For Sale

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

  940 Ward Ln, Cheshire, CT 06410

  940 Ward Ln, Cheshire, CT 06410
• 

  $586,960 Sold Jul 25, 2025

  • 1,850 Sq Ft
  • $317/SF
  • 272 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  116 Shea Cir Unit 116, Cheshire, CT 06410

  DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious townhome in a desirable location. This maintenance-free community will have a pavilion, fire pit, walking loop, and trails. A convenient location offers endless restaurants nearby,

  Jason Helton EG Group Realty LLC

  116 Shea Cir Unit 116, Cheshire, CT 06410
• 

  Est $611,475 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  864 Mountain Rd, Cheshire, CT 06410

  864 Mountain Rd, Cheshire, CT 06410
• 

  $421,000 Sold Jul 24, 2025

  • 1,717 Sq Ft
  • $245/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  80 Quarry Village Rd, Cheshire, CT 06410

  SPACIOUS BRIGHT RANCH/SPLIT LEVEL END UNIT WITH LOTS OF SPACE, 1717 Sq. Ft Total. LIVING ROOM, DINING ROOM, EAT-IN KITCHEN, MASTER BEDROOM AND BEDROOM ALL WITH HARDWOOD FLOORING, LARGE FAMILY ROOM AND THIRD BEDROOM IN ADDITION. 3 BEDROOMS AND 2 FULL BATHS. NEW LAMINATE WOOD FLOORING IN KITCHEN AND THIRD BEDROOM, STAINLESS STEEL APPLIANCES ONLY 4 YEARS OLD. GAS HEAT AND CENTRAL AIR. MASTER BEDROOM

  Joan Kranyak Coldwell Banker Realty

  80 Quarry Village Rd, Cheshire, CT 06410
• 

  Est $1,172,907 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 6,063 Sq Ft

  50 Inverness Ct, Cheshire, CT 06410

  50 Inverness Ct, Cheshire, CT 06410
• 

  $585,000 Sold Jul 23, 2025

  • 2,835 Sq Ft
  • $206/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1978

  180 Round Hill Rd, Cheshire, CT 06410

  Welcome to 180 Round Hill Road. A Turn-Key Ranch in very desirable neighborhood, with 4 Bedrooms and 3 Full Bathrooms. One floor living with handicap accessible full bath and ramp to enter in garage. Plenty of room to entertain in the kitchen which leads to both a 3 season sunroom and large deck. Or to enjoy your morning coffee overlooking a level backyard. Adjacent dining room also opens to the

  Patti Langevin Century 21 Clemens Group

  180 Round Hill Rd, Cheshire, CT 06410
• 

  Est $977,014 Not Listed For Sale

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

  779 Foster Ct, Cheshire, CT 06410

  779 Foster Ct, Cheshire, CT 06410
• 

  $650,000 Sold Jul 22, 2025

  • 2,356 Sq Ft
  • $276/SF
  • 24 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  248 Harrison Rd, Cheshire, CT 06410

  Welcome home to this beautifully updated four-bedroom Colonial in a prime South Cheshire location. A convenient floor plan, a multitude of updates, and an abundance of natural light put this home at the top of your list. The first floor features a flexible floor plan with a very efficient use of space. Light, neutral colors with natural hardwood floors offer a perfect palette for your design

  Michael O'Neill LPT Realty

  248 Harrison Rd, Cheshire, CT 06410
• 

  Est $980,114 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 5,545 Sq Ft

  630 Tudor Ct, Cheshire, CT 06410

  630 Tudor Ct, Cheshire, CT 06410

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