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3808 Redding Road

Fairfield, Connecticut 06824

ACTIVE$2,275,000

Reduced from $2,595,000

Beds
4
Baths
4 | 1
SqFt
5,376
Acres
16.76
Year Built
1769
Matt Caiola

Matt Caiola

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Guest House2-Car Garage3 FireplacesPrice Reduced

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

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,717

per 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

Similar Properties

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Listed By

Cindy Raney

(203) 625-1820

Coldwell Banker Realty

(203) 227-8424

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.