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.
Listed by Cindy Raney
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Coldwell Banker Realty
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(203) 257-8320
Last updated October 16, 2025
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Source: SmartMLS #24127092
Listing Facts
TypeSingle-family
NeighborhoodGreenfield Hill
Bedrooms5
Bathrooms5
Days on Prevu34
Taxes$35,970/year
Size4,191 sqft
Price per sqft$1,192
Location
Mortgage Calculator
Listing History
09/28/2025
Status changed to Active
$4,995,000
09/27/2025
Status changed to Removed from Feed
$4,995,000
09/18/2025
Listed by Coldwell Banker Realty
$4,995,000
Property Details for 2281 Redding Road
Exterior
Construction
New Construction: No/Resale
Roof: Wood Shingle
Year Built: 1941
Year Built Details: Public Records
Architectural Style: Colonial
Construction Materials: Frame
Exterior Features: Barn, Lighting, French Doors, Patio, Tennis Court, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler
Features
Pool Features: Heated, Pool House, Spa, In Ground Pool
Pool Private: Yes
Waterfront Features: Beach Rights, Water Community
Measurements
Lot Features: Fence - Full, Some Wetlands, Level Lot, Professionally Landscaped
Lot Size Acres: 5.03
Financial
Taxes
Parcel Number: 133066
Tax Annual Amount: $35,970.00
Tax Year: 25
Interior
Features
Appliances: Gas Range, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
Exclusions: Please see attached inclusions/exclusions addendum
Parking
Parking
Attached Garage: Attached Garage, Detached Garage
Garage Spaces: 4
Schools
Elementary School
Elementary School: Burr
High School
High School: Fairfield Warde
Middle or Junior School
Middle Or Junior School: Tomlinson
Utilities
Equipment
Cooling: Central Air, Zoned
Heating: Hot Air
Laundry Features: Upper Level
Sewer: Septic
Water Source: Public Water Connected
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