3808 Redding Road
Fairfield, Connecticut 06824
Reduced from $2,595,000
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 5,376
- Acres
- 16.76
- Year Built
- 1769
- Neighborhood
- Greenfield Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
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.
Key Facts
- City/Town
- Fairfield
- Neighborhood
- Greenfield Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1769
- Days on Market
- 88 days
- Beds
- 4
- Baths
- 4 full · 1 half
- Living Area
- 5,376 sq ft
- Lot Size
- 16.76 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $28,313 / Annually
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
88
109 under contract
Median List Price
$1.59M
88 active listings
Median Closed Price
$1.16M
567 sales
Median Days on Market
33
88 active listings
Median $ / Sq Ft
$496
88 active listings
Sale-to-List Ratio
101.9%
567 sales
How this home compares
List Price
$2.27M
vs $1.59M median
43.4% above median
Price / Sq Ft
$423
vs $496 median
14.7% below median
Days on Market
88 days
vs 33 days median
55 days longer than median
Based on 88 active and 567 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of July 27, 2026.
Location
3808 Redding Road, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$11,600
- Property Taxes$2,359
- Insurance$758
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Fairfield
- Neighborhood
- Greenfield Hill
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1769
- New Construction
- No/Resale
- Living Area
- 5,376 sq ft
Schools
- Elementary
- Burr
- High
- Fairfield Warde
Interior
- Heating
- Hot AirWood/Coal Stove
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Main Level
- Appliances
- Gas RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedStorageInterior Access
- In-Law Apartment
- YesDetached
- Additional Rooms
- Bonus RoomLaundry Room
Exterior & Lot
- Lot Size
- 16.76 acres
- Zoning
- AAA
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water In Street
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- ShingleWood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedFruit TreesBarnGarden AreaGuest House
- Lot Description
- Some WetlandsTreedFarm Land
Listing & Financials
- Property Taxes
- $28,313 / Annually
- Days on Market
- 88
- MLS #
- 24171406
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/27/2026 at 8:10 PM UTC.