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
·
Coldwell Banker Realty
·
(203) 257-8320
Last updated November 02, 2025
·
Source: SmartMLS #24127092
Listing Facts
TypeSingle-family
NeighborhoodGreenfield Hill
Bedrooms5
Bathrooms5
Days on Prevu84
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
Frequently Asked Questions
How many bedrooms and bathrooms does this single-family home have?
There are 5 bedrooms and 5 bathrooms in this single-family home at 2281 Redding Road.
What schools are nearby to 2281 Redding Road?
Nearby schools include the Burr Elementary School, Tomlinson Middle School, and Fairfield Warde High School.
Does this single-family home have parking?
Yes, there are 4 parking spaces available for 2281 Redding Road.
What are the annual taxes for 2281 Redding Road?
Annual taxes for this single-family home are estimated at $35,970.
How does 2281 Redding Road compare to other single-family homes in Greenfield Hill?
This single-family home is listed 172% above the average price for single-family homes in Greenfield Hill and has been on the market for 80 more days than the typical home in this area.
What is the square footage on this single-family home?
According to the MLS, this listing is 4,191 sqft.
2281 Redding Road is a 5-bedroom, 5-bath single-family home for sale in Fairfield CT 06824. Listed on Prevu for 84 days at $4,995,000. This residence features 4,191 square feet of living space, located in Fairfield County. The median listing price for single-family homes in this area is $1,835,000. Nearby schools include Burr Elementary School, Tomlinson Middle School, and Fairfield Warde High School. View other single-family home listings in Fairfield County.
The data relating to real estate for sale on this website appears in part through the
SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property
listing data between licensed real estate brokerage firms, and is provided by SMARTMLS
through a licensing agreement. Listing information is from various brokers who participate
in the SMARTMLS IDX program and not all listings may be visible on the site. The property
information being provided on or through the website is for the personal, non-commercial
use of consumers and such information may not be used for any purpose other than to identify
prospective properties consumers may be interested in purchasing. Some properties which appear
for sale on the website may no longer be available because they are for instance, under
contract, sold or are no longer being offered for sale. Property information displayed is
deemed reliable but is not guaranteed. Copyright 2025 SmartMLS, Inc.
Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.
