Redding

Fairfield County, Connecticut

VIEW 41 COMMUNITY LISTINGS

Founded in 1767 and often referred to as the “Vermont of Connecticut,” Redding is a quiet, rural Fairfield County community.

Redding has been ranked as the No. 1 Small Town in Connecticut by Connecticut Magazine based on its low crime rate, superior school system and exceptional quality of life. Town leaders and residents are committed to preserving its rich New England history, extensive open space and stunning natural resources. Redding has more than 60 miles of trails for hiking, biking, horseback riding and cross-country skiing, and ideal fishing areas are available as well. The town enjoys an active recreation department, community and senior centers, as well as public sports facilities, and is home to the Highstead Arboretum with its lovely, wooded walking trails and on-site museum, sure to delight all ages and interests. There is no shortage of opportunities for recreation, as a private golf and tennis club is located here as well.

Redding has been ranked as the No. 1 Small Town in Connecticut by Connecticut Magazine based on its low crime rate, superior school system and exceptional quality of life. Town leaders and residents are committed to preserving its rich New England history, extensive open space and stunning natural resources. Redding has more than 60 miles of trails for hiking, biking, horseback riding and cross-country skiing, and ideal fishing areas are available as well. The town enjoys an active recreation department, community and senior centers, as well as public sports facilities, and is home to the Highstead Arboretum with its lovely, wooded walking trails and on-site museum, sure to delight all ages and interests. There is no shortage of opportunities for recreation, as a private golf and tennis club is located here as well.

Redding has been ranked as the No. 1 Small Town in Connecticut by Connecticut Magazine based on its low crime rate, superior school system and exceptional quality of life. Town leaders and residents are committed to preserving its rich New England history, extensive open space and stunning natural resources. Redding has more than 60 miles of trails for hiking, biking, horseback riding and cross-country skiing, and ideal fishing areas are available as well. The town enjoys an active recreation department, community and senior centers, as well as public sports facilities, and is home to the Highstead Arboretum with its lovely, wooded walking trails and on-site museum, sure to delight all ages and interests. There is no shortage of opportunities for recreation, as a private golf and tennis club is located here as well.

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Redding is a town unlike any other town in Fairfield County. I am proud to live in a town with such integrity, beauty and commitment to conservation. Truly, the shinning jewel of Fairfield County.
Susan Boone Durkee Resident since 1975

Featured Listings

56 Cross Highway
Redding, CT $1,625,000

56 Cross Highway

Redding, CT

$1,625,000
  • 4 Beds
  • 4 Baths
  • 3,501 Sqft
33 Peaceable Street
Redding, CT $1,599,000

33 Peaceable Street

Redding, CT

$1,599,000
  • 4 Beds
  • 4/1 Baths
  • 4,620 Sqft
27 West Woodland Drive
Redding, CT $699,000

27 West Woodland Drive

Redding, CT

$699,000
  • 4 Beds
  • 2/1 Baths
  • 2,070 Sqft
176 Picketts Ridge Road
Redding, CT $279,000

176 Picketts Ridge Road

Redding, CT

$279,000
  • 2.16 Acres
65b Cross Highway
Redding, CT $2,450/mo

65b Cross Highway

Redding, CT

$2,450/mo
  • 1 Beds
  • 1 Baths
  • 1,044 Sqft
229 Umpawaug Road
Redding, CT $7,495,000

229 Umpawaug Road

Redding, CT

$7,495,000
  • 6 Beds
  • 9/2 Baths
  • 7,528 Sqft
241 Black Rock Turnpike
Redding, CT $4,495,000

241 Black Rock Turnpike

Redding, CT

$4,495,000
  • 6 Beds
  • 7/4 Baths
  • 17,548 Sqft
2 Longwood Drive
Redding, CT $1,849,000

2 Longwood Drive

Redding, CT

$1,849,000
  • 4 Beds
  • 4/1 Baths
  • 6,259 Sqft

Redding

Area Map

Redding is within Fairfield County, Connecticut and borders Bethel, Danbury, Easton, Newtown, Ridgefield, Weston and Wilton.

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Featured Communities Within

Fairfield County

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Redding

Market Snapshot

Units Sold

November 2025

11 TOTAL UNITS

image description -8.3% image description +83.3% since

Median Sales Price

November 2025 - Single Family Homes

$850K
image description -10.3% image description +18.6% since

Percentage of Asking Price

November 2025 Single Family Homes

102%
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102%
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