Cheshire

Shoreline, Connecticut

VIEW 206 COMMUNITY LISTINGS

The town of Cheshire in New Haven County offers all the benefits of a small community, with its charming New England landscape, historic sites, vibrant downtown, and nationally ranked school system.

Although the New Haven County town of Cheshire is perhaps most famously known for its “Bedding Plant Capital of Connecticut” moniker, as it is home to several major flower farms and nurseries, this charming community of about 28,700 also boasts a vibrant town center featuring eclectic boutiques, shops and eateries, as well as several retail malls.
Its quaint, New England character is evident throughout, and the town’s Historic District comprises more than 50 buildings in the center of town in the area of the Town Green. Cheshire, which spans 33.4 square miles, also once had copper mines, first found in 1712, and barite mines from 1838 through 1877. Throughout Cheshire, one will find a plethora of dining establishments as well as cozy cafes. The town is home to an active Chamber of Commerce and boasts an educational system with numerous awards and national rankings. The town’s Watch Factory complex, originally the site of the Cheshire Watch Company, is also home to numerous businesses.
Visitors and residents alike take pride in local attractions, including The Barker Character, Comic & Cartoon Museum, where more than 80,000 antique toys and collectibles delight the young and young-at-heart. The Audubon Society’s Riverbound Farm and Sanctuary nature preserve, the town park, CPFA Artsplace and the spectacular Roaring Brook Falls along the Quinnipiac Trail in the southwest corner of town, are among the town’s coveted places to visit.
A wealth of things to do and places to explore await, whether visiting, shopping, recreating or residing in this scenic community.

Although the New Haven County town of Cheshire is perhaps most famously known for its “Bedding Plant Capital of Connecticut” moniker, as it is home to several major flower farms and nurseries, this charming community of about 28,700 also boasts a vibrant town center featuring eclectic boutiques, shops and eateries, as well as several retail malls.
Its quaint, New England character is evident throughout, and the town’s Historic District comprises more than 50 buildings in the center of town in the area of the Town Green. Cheshire, which spans 33.4 square miles, also once had copper mines, first found in 1712, and barite mines from 1838 through 1877. Throughout Cheshire, one will find a plethora of dining establishments as well as cozy cafes. The town is home to an active Chamber of Commerce and boasts an educational system with numerous awards and national rankings. The town’s Watch Factory complex, originally the site of the Cheshire Watch Company, is also home to numerous businesses.
Visitors and residents alike take pride in local attractions, including The Barker Character, Comic & Cartoon Museum, where more than 80,000 antique toys and collectibles delight the young and young-at-heart. The Audubon Society’s Riverbound Farm and Sanctuary nature preserve, the town park, CPFA Artsplace and the spectacular Roaring Brook Falls along the Quinnipiac Trail in the southwest corner of town, are among the town’s coveted places to visit.
A wealth of things to do and places to explore await, whether visiting, shopping, recreating or residing in this scenic community.

Although the New Haven County town of Cheshire is perhaps most famously known for its “Bedding Plant Capital of Connecticut” moniker, as it is home to several major flower farms and nurseries, this charming community of about 28,700 also boasts a vibrant town center featuring eclectic boutiques, shops and eateries, as well as several retail malls.
Its quaint, New England character is evident throughout, and the town’s Historic District comprises more than 50 buildings in the center of town in the area of the Town Green. Cheshire, which spans 33.4 square miles, also once had copper mines, first found in 1712, and barite mines from 1838 through 1877. Throughout Cheshire, one will find a plethora of dining establishments as well as cozy cafes. The town is home to an active Chamber of Commerce and boasts an educational system with numerous awards and national rankings. The town’s Watch Factory complex, originally the site of the Cheshire Watch Company, is also home to numerous businesses.
Visitors and residents alike take pride in local attractions, including The Barker Character, Comic & Cartoon Museum, where more than 80,000 antique toys and collectibles delight the young and young-at-heart. The Audubon Society’s Riverbound Farm and Sanctuary nature preserve, the town park, CPFA Artsplace and the spectacular Roaring Brook Falls along the Quinnipiac Trail in the southwest corner of town, are among the town’s coveted places to visit.
A wealth of things to do and places to explore await, whether visiting, shopping, recreating or residing in this scenic community.

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Featured Listings

351-363 South Meriden Road
Cheshire, CT $3,500,000

351-363 South Meriden Road

Cheshire, CT

$3,500,000
  • 4 Beds
  • 2/1 Baths
  • 4,143 Sqft
351-363 South Meriden Road
Cheshire, CT $3,500,000

351-363 South Meriden Road

Cheshire, CT

$3,500,000
  • 33.00 Acres
219 South Main Street
Cheshire, CT $950,000

219 South Main Street

Cheshire, CT

$950,000
  • 3,955 Sqft
630 Cook Hill Road
Cheshire, CT $2,200,000

630 Cook Hill Road

Cheshire, CT

$2,200,000
  • 5 Beds
  • 4/1 Baths
  • 3,174 Sqft
9 Melrose Drive #6
Cheshire, CT $1,600,000

9 Melrose Drive #6

Cheshire, CT

$1,600,000
  • 4 Beds
  • 3/1 Baths
  • 5,159 Sqft
0 Whispering Oaks, Lot 16
Cheshire, CT $1,532,822

0 Whispering Oaks, Lot 16

Cheshire, CT

$1,532,822
  • 5 Beds
  • 4/1 Baths
  • 4,766 Sqft
226 Maple Avenue
Cheshire, CT $1,450,000

226 Maple Avenue

Cheshire, CT

$1,450,000
  • 1/3 Baths
  • 5,179 Sqft
8 Empire Court #5
Cheshire, CT $1,350,000

8 Empire Court #5

Cheshire, CT

$1,350,000
  • 5 Beds
  • 4/1 Baths
  • 4,785 Sqft

Cheshire

Area Map

Cheshire is within Shoreline, Connecticut and borders Hamden.

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Featured Communities Within

Shoreline

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Cheshire

Market Snapshot

Units Sold

May 2024

36 TOTAL UNITS

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Median Sales Price

May 2024 - Single Family Homes

$493K
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Percentage of Asking Price

May 2024 Single Family Homes

106%
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106%
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106%
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106%
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Cheshire-CT