3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose.
Have you ever dreamed of owning a small farm? This home feels like your own private B&B, a sophisticated country farmhouse beautifully & impeccably restored and modernized for today’s lifestyle. Sherwood Family Farm is only 55 miles from Manhattan and is currently used as a home and farm, producing honey & growing vegetables for local restaurants. Farm-use keeps taxes low and provides a wonderful lifestyle minutes from town & train. Property also includes a charming restored Guest Cottage, original English Barn (As-is), 2-horse Paddock, Chicken Coop and 16+ acres that feel like your own personal Audubon in the backyard. Some wetlands, 1-2 horses ideal! Perfect as a year-round home or summer/weekend retreat, enjoy Fairfield’s downtown restaurant, music and art scene as well as its five beaches.
Smart MLS #99183145
Oct 10, 2017
Listing Removed
—
Apr 26, 2017
Listed
$1,599,000
$297/sq ft
Public Records
Oct 2, 2007
Sold
$1,150,000
$214/sq ft
Smart MLS #98343087
Sep 25, 2007
Listing Removed
—
Jul 26, 2007
Listed
$1,399,000
$260/sq ft
Smart MLS #98343084
Jul 26, 2007
Listed
$1,399,000
$260/sq ft
Smart MLS #98330758
Jul 25, 2007
Listing Removed
—
May 2, 2007
Listed
$1,399,000
$260/sq ft
Smart MLS #98330774
Jul 25, 2007
Listing Removed
—
May 2, 2007
Listed
$1,399,000
$260/sq ft
Public Records
Aug 21, 1992
Sold
$200,000
$37/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$30,000 (+1.0%)
$709,290 + $381,220
$1,090,510
2022
$29,705 (+1.0%)
$709,290 + $381,220
$1,090,510
2021
$29,422 (+0.8%)
$709,290 + $381,220
$1,090,510
2020
$29,185 (+0.8%)
$732,480 + $356,930
$1,089,410
2019
$28,964 (+76.5%)
$732,480 + $348,670
$1,081,150
2018
$16,414 (+2.1%)
$274,010 + $348,670
$622,680
2017
$16,078 (+1.5%)
$274,010 + $348,670
$622,680
2016
$15,847 (+3.9%)
$274,010 + $348,670
$622,680
2014
$15,259
$304,210 + $321,160
$625,370
Public record
Beds
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Lot size
16.76 Acres
Year renovated
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Finished Sq. Ft.
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Unfinished Sq. Ft.
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Total Sq. Ft.
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Year built
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Style
Other
County
Fairfield County
APN
129845
Parking Spaces
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Last updated by owner on Jul 13, 2023.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 98° expected this year, 15 days in 30 years
6/10 Wind Factor
27% chance of strong winds in next 30 years
4/10 Air Factor
5 unhealthy days expected this year, 7 days in 30 years
Provided by First Street
Historical weather
Fairfield, CT • 06824
Average low and high temperatures (°F)
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75
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66
48
55
38
40
27
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Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Provided by Shadowmap
Redfin Estimate for 3808 Redding Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $1,400,000 and $2,750,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $1.4M to $2.8M.