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.
Under contract
$4,995,000
2281 Redding Road, Fairfield, CT 06824
5beds
4,191sqft
Est.:
Single Family Residence
Built in 1941
5.03 Acres Lot
$4,610,900 Zestimate®
$1,192/sqft
$-- HOA
What's special
- 112 days |
- 2,847 |
- 166 |
Zillow last checked: 8 hours ago
Listing updated: December 27, 2025 at 10:21am
Listed by:
Cindy Raney & Team,
Cindy Raney (203)257-8320,
Coldwell Banker Realty 203-227-8424
Source: Smart MLS,MLS#: 24127092
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Music Room, Workshop
Primary bedroom
- Features: Vaulted Ceiling(s), Beamed Ceilings, Built-in Features, Cedar Closet(s), Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Main
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
Bathroom
- Level: Main
Dining room
- Features: Beamed Ceilings, French Doors, Patio/Terrace, Wide Board Floor
- Level: Main
Family room
- Features: Built-in Features, Gas Log Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Beamed Ceilings, Built-in Features, Dining Area, Kitchen Island, Pantry, Wide Board Floor
- Level: Main
Living room
- Features: Wide Board Floor
- Level: Main
Heating
- Forced Air, Natural Gas, Propane
Cooling
- Central Air, Zoned
Appliances
- Included: Gas Range, Convection Oven, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Gas Water Heater, Water Heater, Humidifier
- Laundry: Upper Level
Features
- Sound System, Open Floorplan, Entrance Foyer, Smart Thermostat
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Sump Pump,Storage Space,Garage Access,Partially Finished,Concrete
- Attic: Pull Down Stairs
- Number of fireplaces: 4
Interior area
- Total structure area: 4,191
- Total interior livable area: 4,191 sqft
- Finished area above ground: 3,651
- Finished area below ground: 540
Property
Parking
- Total spaces: 4
- Parking features: Attached, Detached, Garage Door Opener
- Attached garage spaces: 4
Features
- Patio & porch: Patio
- Exterior features: Lighting, Tennis Court(s), Fruit Trees, Garden, Stone Wall, Underground Sprinkler
- Has private pool: Yes
- Pool features: Heated, Pool/Spa Combo, In Ground
- Fencing: Full
- Waterfront features: Beach Access, Water Community
Lot
- Size: 5.03 Acres
- Features: Wetlands, Level, Landscaped
Details
- Additional structures: Barn(s), Greenhouse, Pool House
- Parcel number: 133066
- Zoning: AAA
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Stone, Wood Siding
- Foundation: Concrete Perimeter, Stone
- Roof: Wood
Condition
- New construction: No
- Year built: 1941
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Green energy
- Energy efficient items: Thermostat, Windows
Community & HOA
Community
- Features: Golf, Health Club, Library, Paddle Tennis, Private School(s), Stables/Riding, Tennis Court(s)
- Security: Security System
- Subdivision: Greenfield Hill
HOA
- Has HOA: No
Location
- Region: Fairfield
Financial & listing details
- Price per square foot: $1,192/sqft
- Tax assessed value: $1,267,000
- Annual tax amount: $35,970
- Date on market: 9/18/2025
- Exclusions: Please see attached inclusions/exclusions addendum
Estimated market value
$4,610,900
$4.38M - $4.84M
$8,288/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 12/27/2025 | Pending sale | $4,995,000$1,192/sqft |
Source:  Smart MLS #24127092 Report a problem | ||
| 9/27/2025 | Listed for sale | $4,995,000+137.9%$1,192/sqft |
Source: Smart MLS #24127092 Report a problem | ||
| 2/28/2014 | Sold | $2,100,000-12.3%$501/sqft |
Source: Smart MLS #98535917 Report a problem | ||
| 4/19/2012 | Listed for sale | $2,395,000$571/sqft |
Source: Nicholas H. Fingelly Real Estate, Inc. #98535917 Report a problem | ||
| 11/5/2011 | Listing removed | $2,395,000$571/sqft |
Source: Nicholas H. Fingelly Real Estate, Inc. #98492525 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $35,970 +2.6% | $1,267,000 +0.8% |
| 2024 | $35,052 +1.4% | $1,256,360 |
| 2023 | $34,562 +1% | $1,256,360 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$33,747/mo
Principal & interest
$24964
Property taxes
$7035
Home insurance
$1748
Climate risks
Neighborhood: 06824
Nearby schools
GreatSchools rating
- 8/10Burr Elementary SchoolGrades: K-5Distance: 1.3 mi
- 7/10Tomlinson Middle SchoolGrades: 6-8Distance: 4.2 mi
- 9/10Fairfield Warde High SchoolGrades: 9-12Distance: 3.9 mi
Schools provided by the listing agent
- Elementary: Burr
- Middle: Tomlinson
- High: Fairfield Warde
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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