2281 Redding Rd Fairfield, CT, 06824

single family home
$ 4,995,000 For Sale Active Sep 18, 2025
  • 5 beds
  • 5 baths
  • 4,191 sq ft
  • 5.03 acres
  • 1941 year built
  • pool house
  • 4 cars garage

About the Home

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.

Rooms & Interior

5 bedrooms beds
4 full + 1 half baths
4,191 square feet sq ft

Room Details

  • Bedroom (Upper Level) Full Bath, Hardwood Floor
  • Eat In Kitchen (Main Level) Beams, Built-Ins, Dining Area, Island, Pantry, Wide Board Floor
  • Primary Bedroom (Upper Level) Vaulted Ceiling, Beams, Built-Ins, Cedar Closet, Full Bath, Hardwood Floor
  • Bedroom (Upper Level) Hardwood Floor
  • Bedroom (Main Level) Full Bath, Hardwood Floor
  • Bedroom (Upper Level) Full Bath, Hardwood Floor
  • Eat In Kitchen (Main Level) Beams, Built-Ins, Dining Area, Island, Pantry, Wide Board Floor
  • Primary Bedroom (Upper Level) Vaulted Ceiling, Beams, Built-Ins, Cedar Closet, Full Bath, Hardwood Floor
  • Bedroom (Upper Level) Hardwood Floor
  • Bedroom (Main Level) Full Bath, Hardwood Floor
  • Bedroom (Upper Level) Hardwood Floor
  • Living Room (Main Level) Wide Board Floor
  • Formal Dining Room (Main Level) Beams, French Doors, Patio/Terrace, Wide Board Floor
  • Family Room (Main Level) Built-Ins, Gas Log Fireplace, Hardwood Floor
  • Half Bath (Main Level)
  • Other Rooms Foyer, Greenhouse, Music room, Workshop

Home Features

Heating

  • Fireplaces: 4
  • Heating: hot air
  • Heat fuel type: natural gas, propane
  • Fuel tank: in ground

Cooling

  • Central air
  • Zoned

Interior Features

  • Audio system
  • Auto garage door opener
  • Humidifier
  • Open floor plan
  • Security system

Appliances

  • Gas range
  • Convection oven
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
  • Wine chiller

Home Automation

  • Lighting
  • Security system
  • Thermostat(s)

Attic

  • Pull-down stairs

Basement

  • Full
  • Sump pump
  • Storage
  • Garage access
  • Partially finished
  • Concrete floor

Laundry

  • Upper level

Energy Features

  • Generator
  • Programmable thermostat
  • Thermopane windows

Exterior Features

  • Barn
  • Lighting
  • French doors
  • Patio
  • Tennis court
  • Fruit trees
  • Garden area
  • Stone wall
  • Underground sprinkler

Property Details

Parking

  • Garage spaces: 4
  • Attached garage
  • Detached garage

Swimming Pool

  • Heated
  • Pool house
  • Spa
  • In ground pool

Waterfront

  • Beach rights
  • Water community

Lot Details

  • Lot surface: 5.03 acres
  • Fence - full
  • Some wetlands
  • Level lot
  • Professionally landscaped

Utilities

  • Water: public water connected
  • Sewage: septic

Near-by Amenities

  • Golf course
  • Health club
  • Library
  • Paddle tennis
  • Private school(s)
  • Stables/riding
  • Tennis courts

Construction Details

Style
colonial

Construction year
1941

Exterior Siding
stone, wood

Foundation
concrete, stone

Roof
wood shingle


Area & Town

This home is located in Greenfield Hills neighborhood, in the town of Fairfield.

Finance & Listing Info

Status Active
Listing date September 18, 2025
List price $ 4,995,000
Current price $ 4,995,000
Tax amount $ 35,970
Tax year july 2025-june 2026
MLS ID #24127092
List Agent Cindy Raney
List Office Coldwell Banker Realty

2281 Redding Road Home Photos

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