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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
Sold
358 Newtown Turnpike Redding, CT 06896
4 BD / 3 | 2 BA / 4,365 SQ.FT. SOLD: $1,325,000
358 Newtown Turnpike,
Redding CT 06896
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Sold
9 Brick School Drive Redding, CT 06896
4 BD / 3 BA / 3,284 SQ.FT. SOLD: $865,000
9 Brick School Drive,
Redding CT 06896
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Sold
187/185 Umpawaug Road Redding, CT 06896
7 BD / 6 | 3 BA / 9,720 SQ.FT. SOLD: $11,500,000
187/185 Umpawaug Road,
Redding CT 06896
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Sold
27 Old Hattertown Road Redding, CT 06896
6 BD / 7 | 1 BA / 9,587 SQ.FT. SOLD: $3,800,000
27 Old Hattertown Road,
Redding CT 06896
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Sold
118 Mountain Road Redding, CT 06896
5 BD / 5 | 2 BA / 7,162 SQ.FT. SOLD: $3,750,000
118 Mountain Road,
Redding CT 06896
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Sold
45 Sanfordtown Road Redding, CT 06896
5 BD / 3 | 2 BA / 8,998 SQ.FT. SOLD: $3,100,000
45 Sanfordtown Road,
Redding CT 06896
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Sold
45 Sidecut Road Redding, CT 06896
4 BD / 2 | 1 BA / 5,160 SQ.FT. SOLD: $2,900,000
45 Sidecut Road,
Redding CT 06896
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Sold
4 Longwood Drive Redding, CT 06896
7 BD / 5 | 2 BA / 10,197 SQ.FT. SOLD: $2,600,000
4 Longwood Drive,
Redding CT 06896
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1 Chestnut Woods Road Redding, CT 06896
3 BD / 3 BA / 2,783 SQ.FT. SOLD: $2,500,000
1 Chestnut Woods Road,
Redding CT 06896
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Sold
30 Mark Twain Lane Redding, CT 06896
4 BD / 5 | 1 BA / 6,300 SQ.FT. SOLD: $2,225,000
30 Mark Twain Lane,
Redding CT 06896
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Sold
60 Topstone Road Redding, CT 06896
3 BD / 2 | 2 BA / 2,483 SQ.FT. SOLD: $2,200,000
60 Topstone Road,
Redding CT 06896
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Sold
Undisclosed Redding, CT 06896
4 BD / 3 | 1 BA / 4,001 SQ.FT. SOLD: $2,075,000
Undisclosed,
Redding CT 06896
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Min. Price
Max. Price
Beds
Baths
For Sale
61 Marchant Road Redding, CT 06896
4 BD / 3 | 1 BA / 4,146 SQ.FT. $1,565,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$1,565,000
61 Marchant Road,
Redding CT 06896
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For Sale
16 Black Rock Turnpike Redding, CT 06896
4 BD / 3 | 2 BA / 4,140 SQ.FT. $1,300,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$1,300,000
16 Black Rock Turnpike,
Redding CT 06896
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For Sale
28 Sunnyview Drive Redding, CT 06896
4 BD / 2 | 1 BA / 4,182 SQ.FT. $1,299,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$1,299,000
28 Sunnyview Drive,
Redding CT 06896
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For Sale
86 Pocahontas Road Redding, CT 06896
5 BD / 3 BA / 2,200 SQ.FT. $789,000
Open House: Sep 20, 2025, 12:00 PM - 2:00 PM
$789,000
86 Pocahontas Road,
Redding CT 06896
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For Sale
22 Lonetown Road Redding, CT 06896
5 BD / 3 BA / 2,458 SQ.FT. $769,000
Open House: Sep 21, 2025, 1:00 PM - 3:00 PM
$769,000
22 Lonetown Road,
Redding CT 06896
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