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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
83 Sherman Turnpike Redding, CT 06896
4 BD / 2 BA / 2,463 SQ.FT. $805,000
$805,000
83 Sherman Turnpike,
Redding CT 06896
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For Sale
87 Giles Hill Road Redding, CT 06896
3 BD / 2 BA / 2,115 SQ.FT. $747,500
$747,500
87 Giles Hill Road,
Redding CT 06896
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For Sale
248 Simpaug Turnpike Redding, CT 06896
4 BD / 2 BA / 2,004 SQ.FT. $724,900
$724,900
248 Simpaug Turnpike,
Redding CT 06896
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For Sale
22 Great Pasture Road Redding, CT 06896
3 BD / 2 BA / 2,140 SQ.FT. $699,999
$699,999
22 Great Pasture Road,
Redding CT 06896
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For Sale
268 Umpawaug Road Redding, CT 06896
4 BD / 2 | 2 BA / 3,922 SQ.FT. $675,000
Open House: Nov 1, 2026, 1:00 PM - 3:00 PM
$675,000
268 Umpawaug Road,
Redding CT 06896
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For Sale
85 Mountain Road Redding, CT 06896
5 BD / 3 BA / 1,859 SQ.FT. $668,000
$668,000
85 Mountain Road,
Redding CT 06896
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For Sale
3 Long Wall Road Redding, CT 06896
3 BD / 2 BA / 1,092 SQ.FT. $629,000
Open House: Oct 31, 2026, 12:00 PM - 2:00 PM
$629,000
3 Long Wall Road,
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
0 Black Rock Turnpike Redding, CT 06896
BD / BA / 16.47 SQ.FT. $599,999
$599,999
0 Black Rock Turnpike,
Redding CT 06896
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For Sale
85 Lonetown Road Redding, CT 06896
2 BD / 2 BA / 1,126 SQ.FT. $539,000
$539,000
85 Lonetown Road,
Redding CT 06896
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For Sale
19 Olmstead Road Redding, CT 06896
2 BD / 2 BA / 1,125 SQ.FT. $499,900
$499,900
19 Olmstead Road,
Redding CT 06896
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For Sale
65 Umpawaug Road Redding, CT 06896
BD / BA / 8.89 SQ.FT. $499,000
$499,000
65 Umpawaug Road,
Redding CT 06896
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Min. Price
Max. Price
Beds
Baths
For Sale
3 Long Wall Road Redding, CT 06896
3 BD / 2 BA / 1,092 SQ.FT. $629,000
Open House: Oct 31, 2026, 12:00 PM - 2:00 PM
$629,000
3 Long Wall Road,
Redding CT 06896
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For Sale
123 Cross Highway Redding, CT 06896
4 BD / 3 | 1 BA / 3,525 SQ.FT. $995,000
Open House: Nov 1, 2026, 12:00 PM - 2:00 PM
$995,000
123 Cross Highway,
Redding CT 06896
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For Sale
268 Umpawaug Road Redding, CT 06896
4 BD / 2 | 2 BA / 3,922 SQ.FT. $675,000
Open House: Nov 1, 2026, 1:00 PM - 3:00 PM
$675,000
268 Umpawaug Road,
Redding CT 06896
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