BuySellBlogBrowse Listings

2281 Redding RoadFairfield, CT 06824

For Sale

$4,995,000

Smart Buyer Rebate $49,950

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 October 16, 2025

·

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
  • Fireplaces Total: 4
  • Interior Features: AUDIO, DROPEN, HUMID, OPEN, SECURESY

Measurements

  • Living Area: 3,651

Rooms

  • Basement: Full, Sump Pump, Storage, Garage Access, Partially Finished, Concrete Floor
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 5
  • Rooms Total: 9

Other

General

  • 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

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.

Full MLS Disclaimers

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.