2281 Redding Road
Sold

2281 Redding Road

2281 Redding Road, Fairfield, Connecticut 06824

$4,700,000
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.

5
beds

5
baths

3,651 Sq.Ft. LIVING AREA

5.03 Acres lot

Cindy Raney

Cindy Raney

Features & Amenities

Interior

  • total bedrooms5
  • Total bathrooms5
  • full bathrooms4
  • half bathroom1
  • Laundry room Upper Level
  • APPLIANCES Gas Range, Convection Oven, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • other interior Features Audio System, Auto Garage Door Opener, Humidifier, Open Floor Plan, Security System

Area & Lot

  • Status Sold
  • Date Sold February 9, 2026
  • Living Area3,651 Sq.Ft.
  • Lot Area5.03 Acres
  • MLS® ID24127092
  • TypeOther
  • YEAR BUILT1941
  • Architecture StylesColonial
  • Water FrontageBeach Rights, Water Community
  • Elementary SchoolBurr
  • Middle SchoolTomlinson
  • High SchoolFairfield Warde

Exterior

  • Garage Space4.0
  • water SourcePublic Water Connected
  • PoolHeated, Pool House, Spa, In Ground Pool
  • roofWood Shingle
  • lot featuresFence - Full, Some Wetlands, Level Lot, Professionally Landscaped
  • parkingAttached Garage, Detached Garage
  • HEAT TYPEHot Air
  • AIR CONDITIONINGCentral Air, Zoned
  • sewerSeptic
  • SubstructureConcrete, Stone
  • other exterior FeaturesBarn, Lighting, French Doors, Patio, Tennis Court, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler

Financial

  • Sales Price$4,700,000
  • Real Estate Tax $35,970/yr
  • Zoning AAA

Work With Us

Cindy Raney & Team is an elite boutique real estate team in Fairfield County with extensive industry expertise, having sold over $800 million in luxury real estate. Cindy’s team is deeply focused on the client experience, guiding clients through every step of the home buying or selling process to ensure an exceptional experience from start to finish.

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