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$4,995,000

  • For Sale
  • Under Contract
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,191 Sq. Ft.
  • 4 Car Garage
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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.

Full Property Details for 2281 Redding Rd

General

  • Price: $4,995,000
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24127092
  • Updated: 12/27/2025
  • Added to Site: 139 day(s) ago

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Foyer, Greenhouse, Music Room, Workshop
  • Interior Features: Audio System, Auto Garage Door Opener, Humidifier, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Gas Range, Convection Oven, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Partial Bath: Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Vaulted Ceiling, Beams, Built-Ins, Cedar Closet, Full Bath, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Full Bath, Hardwood Floor, Main
  • Bedroom 2: Bedroom - Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Full Bath, Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Wide Board Floor, Main
  • Family Room: Family Room - Built-Ins, Gas Log Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Beams, Built-Ins, Dining Area, Island, Pantry, Wide Board Floor, Main
  • Formal Dining Room: Formal Dining Room - Beams, French Doors, Patio/Terrace, Wide Board Floor, Main
  • Laundry: Upper Level

Additional Information

  • Pool: Yes
  • Pool Description: Heated, Pool House, Spa, In Ground Pool

Exterior

  • Exterior Features: Barn, Lighting, French Doors, Patio, Tennis Court, Fruit Trees, Garden Area, Stone Wall, Underground Sprinkler
  • Color: Beige

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 4
  • Parking: Attached Garage, Detached Garage

Location

  • County: Fairfield
  • Neighborhood: Greenfield Hill
  • Driving Directions: Hulls Farm or Cross Highway to Redding Road

School Information

  • Elementary School: Burr
  • Middle School: Tomlinson
  • High School: Fairfield Warde

Community

  • Community Name: Greenfield Hill

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Natural Gas, Propane
  • Heating Fuel: Natural Gas, Propane
  • Water Heater: Natural Gas, 65 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Stone, Wood
  • Basement Desc.: Full, Sump Pump, Storage, Garage Access, Partially Finished, Concrete Floor
  • Roof: Wood Shingle
  • Attic: Yes
  • Square Feet: 4,191
  • Above Ground: 3,651 Sq. Ft.
  • Below Ground: 540 Sq. Ft.
  • Year Built: 1941

Lot Features

  • Lot Size (Acres): 5.03
  • Zoning: AAA
  • Lot Description: Fence - Full, Some Wetlands, Level Lot, Professionally Landscaped

Water Features

  • Water Front Desc.: Beach Rights, Water Community

Green Features

  • Energy Features: Generator, Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $1,267,000
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Please see attached inclusions/exclusions addendum
  • Property ID: 133066
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 2281 Redding Rd —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 2281 Redding Rd

School District:Fairfield School District
NameGradesDistance
Burr Elementary School
1960 Burr Street, Fairfield, CT 06824
PK-51.3 mi
Tomlinson Middle School
200 Unquowa Road, Fairfield, CT 06824
6-84.2 mi
Fairfield Warde High School
755 Melville Avenue, Fairfield, CT 06825
9-123.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2281 Redding Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/27/2025
Listed
$4,995,000
137.86%
MLS
3/03/2014
Sold
$2,100,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2281 Redding Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$35,970
3%
$1,267,000
1%
2023
$35,052
1%
$1,256,360
—
2023
$34,562
1%
$1,256,360
—
2022
$34,223
1%
$1,256,360
—
2021
$33,897
-1%
$1,256,360
-1%
2020
$34,114
2%
$1,273,370
2%
2019
$33,416
2%
$1,247,330
—
2018
$32,880
2%
$1,247,330
—
2017
$32,206
1%
$1,247,330
—
2016
$31,777
36%
$1,248,590
32%
2015
$23,437
2%
$945,420
—
2014
$23,068
2%
$945,420
—
2011
$22,624
—
$945,420
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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2281 Redding Road, Fairfield, CT 06824 (MLS# 24127092) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 2281 Redding Road is currently listed for $4,995,000 and was received on September 18, 2025. This property is listed by Cindy Raney & Team from our Westport Office.Want to learn more about 2281 Redding Road? Do you have questions about finding other Single Family real estate for sale in Fairfield? You can browse all Fairfield real estate or contact a Coldwell Banker agent to request more information.

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