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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
172 Umpawaug Road Redding, CT 06896
5 BD / 4 | 1 BA / 6,099 SQ.FT. $10,500
$10,500
172 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. $8,600,000
$8,600,000
63 Turney 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
2 Longwood Drive Redding, CT 06896
4 BD / 4 | 1 BA / 6,259 SQ.FT. $1,849,000
$1,849,000
2 Longwood Drive,
Redding CT 06896
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For Sale
12 Werf Drive Redding, CT 06896
6 BD / 3 | 2 BA / 4,033 SQ.FT. $1,750,000
$1,750,000
12 Werf Drive,
Redding CT 06896
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For Sale
34 Fox Run Road Redding, CT 06896
5 BD / 4 | 2 BA / 7,833 SQ.FT. $1,550,000
$1,550,000
34 Fox Run Road,
Redding CT 06896
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For Sale
41 Deer Hill Road Redding, CT 06896
4 BD / 3 | 1 BA / 3,912 SQ.FT. $1,199,000
$1,199,000
41 Deer Hill Road,
Redding CT 06896
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For Sale
299 Redding Road Redding, CT 06896
4 BD / 3 | 1 BA / 4,234 SQ.FT. $979,000
Open House: Jan 31, 2026, 12:00 PM - 2:00 PM
$979,000
299 Redding Road,
Redding CT 06896
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For Sale
2 Brick School Drive Redding, CT 06896
4 BD / 2 | 1 BA / 2,560 SQ.FT. $925,000
$925,000
2 Brick School Drive,
Redding CT 06896
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For Sale
24 Costa Lane Redding, CT 06896
BD / BA / 8.24 SQ.FT. $615,000
$615,000
24 Costa Lane,
Redding CT 06896
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For Sale
145 Limekiln Road Redding, CT 06896
BD / BA / 9.31 SQ.FT. $599,000
$599,000
145 Limekiln Road,
Redding CT 06896
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For Sale
71 Picketts Ridge Road Redding, CT 06896
2 BD / 1 BA / 930 SQ.FT. $539,000
$539,000
71 Picketts Ridge Road,
Redding CT 06896
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Min. Price
Max. Price
Beds
Baths
For Sale
299 Redding Road Redding, CT 06896
4 BD / 3 | 1 BA / 4,234 SQ.FT. $979,000
Open House: Jan 31, 2026, 12:00 PM - 2:00 PM
$979,000
299 Redding Road,
Redding CT 06896
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