About 2281 Redding Road
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.
Features of 2281 Redding Road
| MLS® # | 24127092 |
|---|---|
| Price | $4,995,000 |
| Bedrooms | 5 |
| Bathrooms | 5.00 |
| Full Baths | 4 |
| Half Baths | 1 |
| Square Footage | 4,191 |
| Acres | 5.03 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 2281 Redding Road |
|---|---|
| Area | Greenfield Hill |
| City | Fairfield |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06824 |
Amenities
| Features | Generator, Programmable Thermostat, Thermopane Windows |
|---|---|
| Parking | Attached Garage, Detached Garage |
| # of Garages | 4 |
| Is Waterfront | No |
| Waterfront | Beach Rights, Water Community |
| Has Pool | Yes |
| Pool | Heated, Pool House, Spa, In Ground Pool |
Interior
| 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 |
| Heating | Hot Air, Natural Gas, Propane |
| Cooling | Central Air, Zoned |
| Fireplace | Yes |
| # of Fireplaces | 4 |
| Has Basement | Yes |
| Basement | Full, Sump Pump, Storage, Garage Access, Partially Finished, Concrete Floor |
Exterior
| Exterior | Stone, Wood |
|---|---|
| Exterior Features | Barn, Lighting, French Doors, Patio, Tennis Court, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler |
| Lot Description | Fence - Full, Some Wetlands, Level Lot, Professionally Landscaped |
| Roof | Wood Shingle |
| Foundation | Concrete, Stone |
School Information
| Elementary | Burr |
|---|---|
| Middle | Tomlinson |
| High | Fairfield Warde |
Additional Information
| Date Listed | September 18th, 2025 |
|---|---|
| Days on Market | 19 |
| Zoning | AAA |
| RE / Bank Owned | No |
Listing Details
| Office | Coldwell Banker Realty |
|---|