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Tucked away in the scenic hills of Fairfield County, Redding, Connecticut is a dream destination for families and homebuyers seeking space, serenity, and strong community roots. Known for its top-rated schools, preserved natural beauty, and low-key luxury, Redding offers a peaceful lifestyle just a short drive from major employment hubs like Stamford and New York City.

Buyers are drawn to Redding’s diverse real estate—from charming Colonials and classic New England farmhouses to spacious custom homes on large wooded lots. It’s a town where kids can play in the yard, neighbors know each other by name, and nature is always just steps away.

With abundant hiking trails, nature preserves, and family-friendly amenities, Redding is the perfect place to plant roots and grow. Whether you're searching for your forever home or investing in a quiet weekend retreat, explore homes for sale in Redding and experience why families are falling in love with this timeless Connecticut town.

Min. Price
Max. Price
Beds
Baths
For Sale
206 Umpawaug Road Redding, CT 06896
7 BD / 8 | 5 BA / 13,094 SQ.FT. $7,725,000
$7,725,000
206 Umpawaug Road,
Redding CT 06896
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For Sale
229 Umpawaug Road Redding, CT 06896
6 BD / 9 | 2 BA / 7,528 SQ.FT. $7,495,000
$7,495,000
229 Umpawaug Road,
Redding CT 06896
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For Sale
63 Turney Road Redding, CT 06896
7 BD / 6 | 1 BA / 9,420 SQ.FT. $7,400,000
$7,400,000
63 Turney Road,
Redding CT 06896
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For Sale
240 Umpawaug Road Redding, CT 06896
6 BD / 5 | 1 BA / 3,264 SQ.FT. $3,950,000
$3,950,000
240 Umpawaug Road,
Redding CT 06896
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For Sale
2 Longwood Drive Redding, CT 06896
4 BD / 4 | 1 BA / 6,259 SQ.FT. $1,795,000
Open House: Jun 20, 2026, 1:00 PM - 3:00 PM
$1,795,000
2 Longwood Drive,
Redding CT 06896
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For Sale
7 Long Meadow Lane Redding, CT 06896
4 BD / 3 | 2 BA / 5,385 SQ.FT. $1,699,000
$1,699,000
7 Long Meadow Lane,
Redding CT 06896
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For Sale
110 Sport Hill Road Redding, CT 06896
5 BD / 5 | 1 BA / 5,308 SQ.FT. $1,695,000
$1,695,000
110 Sport Hill Road,
Redding CT 06896
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For Sale
74 George Hull Hill Road Redding, CT 06896
4 BD / 3 | 2 BA / 4,786 SQ.FT. $1,595,000
$1,595,000
74 George Hull Hill Road,
Redding CT 06896
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For Sale
12 Werf Drive Redding, CT 06896
6 BD / 3 | 2 BA / 4,033 SQ.FT. $1,549,900
$1,549,900
12 Werf Drive,
Redding CT 06896
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For Sale
28 Goodridge Road Redding, CT 06896
5 BD / 4 BA / 4,728 SQ.FT. $1,500,000
$1,500,000
28 Goodridge Road,
Redding CT 06896
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For Sale
74 Black Rock Turnpike Redding, CT 06896
5 BD / 4 | 2 BA / 4,716 SQ.FT. $1,450,000
$1,450,000
74 Black Rock Turnpike,
Redding CT 06896
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For Sale
4 Long Ridge Road Redding, CT 06896
BD / BA / 3 SQ.FT. $1,395,000
$1,395,000
4 Long Ridge Road,
Redding CT 06896
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Min. Price
Max. Price
Beds
Baths
For Sale
2 Longwood Drive Redding, CT 06896
4 BD / 4 | 1 BA / 6,259 SQ.FT. $1,795,000
Open House: Jun 20, 2026, 1:00 PM - 3:00 PM
$1,795,000
2 Longwood Drive,
Redding CT 06896
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For Sale
70 Dayton Road Redding, CT 06896
4 BD / 2 BA / 1,632 SQ.FT. $634,000
Open House: Jun 21, 2026, 2:00 PM - 4:00 PM
$634,000
70 Dayton Road,
Redding CT 06896
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