2281 Redding Road - Fairfield, CT

$4,995,000

Beds

5.00

Baths

4,191

SqFt

5.03

Acres

Pricing Insight: Originally listed for $4,995,000, the price has remained unchanged for approximately 131 days. This property has been on the market for approximately 131 days. MLS reports 90 Days on Market (DOM) before it went under contract.

2281 Redding Road, Fairfield, CT is a 5-bed, 5-bath, 4,191 square foot home built in 1941 , featuring colonial architecture.

This home is within the Fairfield school district. Local, with nearby schools including Burr.

MLS #: 24127092

Offered Price: $4,995,000

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 4,191 Sq. Ft.

Lot Size: 5.03 Acres

Neighborhood: Greenfield Hill

County: Fairfield

Year Built: 1941

Design & Construction: Frame

Heating: Hot Air

Cooling: Central Air,Zoned

Garage Spaces: 4

Price per Sq Ft as listed: $1,192

Estimated Tax: $35,970

Days on Market: 90

Home Automation: Lighting, Security System, Thermostat(s)

Energy Features: Generator, Programmable Thermostat, Thermopane Windows

Solar Contract: Not specified

Heating Fuel: Natural Gas, Propane

Fuel Type: Hot Air

Fuel Tank Location: In Ground

Cooling System: Central Air, Zoned

Hot Water System: Natural Gas, 65 Gallon Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $1,192 / Sq. Ft.

Tax assessed value: $1,267,000

Estimated Tax: $35,970

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1941

Living Area: 4,191 Sq. Ft.

Lot Size: 5.03 Acres

Fuel: Natural Gas,Propane

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Fairfield
Statistical modeling algorithms

Local Market Context

Active Listings: 184

Average Price: $922,591

Average DOM: 90 days

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Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's kitchen opens to elegant dining and living areas, with French doors to a bluestone terrace designed for candlelit dinners under the stars. A first-floor guest suite with a full bath provides flexibility and privacy, while upstairs, four additional bedrooms-including a serene primary suite-offer refined comfort and room to breathe. Beyond the home, the grounds unfold like a private resort. A two-story pool house features a full kitchen, bath, and playful loft. A climate-controlled barn houses a Trackman 4 golf simulator, sauna, and space for training or unwinding. Outdoors, discover a saltwater pool and spa, sport court, vegetable gardens, wildflower meadow with carved walking trails, orchard of apple, cherry, and peach trees, and a cider press-all with a private path leading to the Patterson Club. Whether for weekends or a lifetime, this estate elevates every season and every gathering-minutes from town, yet a world apart.

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Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 5.0 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

184

Homes For Sale

$922,591

Average List Price

Mechanicals & Utilities: Hot Air • Natural Gas,Propane • Central Air,Zoned • Public Water Connected water • 4 fireplaces

Exterior Features

Exterior Construction: Stone,Wood

Roof Type: Wood Shingle

Foundation: Concrete,Stone

Garage: Attached Garage,Detached Garage (4 car)

Patio/Deck: Barn,Lighting,French Doors,Patio,Tennis Court,Fruit Trees,Garden Area,Stone Wall,Underground Sprinkler

Pool: Heated,Pool House,Spa,In Ground Pool

Utilities: Water: Public Water Connected

Outbuildings: Barn,Lighting,French Doors,Patio,Tennis Court,Fruit Trees,Garden Area,Stone Wall,Underground Sprinkler

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"Local Market Expert"

Steve Simos

Real Estate Advisor

Fairfield • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

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(800) 555-0003

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2281 Redding Road, Fairfield, Connecticut

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