Real Estate Agent in Connecticut and Western Massachusetts

2281 Redding Road
Fairfield, Connecticut

Single Family For Sale

5

Bedrooms

4 (full) / 1 (half)

Bathrooms

4,191

Sq Ft

$ 4,995,000

Price

2281 Redding Road
Fairfield, Connecticut

Fairfield, Connecticut

Description:

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.

Listing Courtesy of Coldwell Banker Realty

Meet Our Team

Our team consists of dedicated real estate professionals passionate about helping our clients achieve their goals. Every client receives personalized attention, expert guidance, and unparalleled service. Meet our team:

Alison Malkin
Alison Malkin

Broker/Owner

860-214-8008

Email
Alison Malkin
Nicole Malkin James

Broker/Owner

843-614-7222

Email
Alison Malkin
Luis Torres

Associate Broker

860-383-5211

Email
Alison Malkin
Debra Pliego

Realtor®

860-919-7376

Email
Alison Malkin
Madison Wells

Realtor®

860-538-7567

Email
Alison Malkin
Lori Sierpinski

Realtor®

860-222-4692

Email
Alison Malkin
Jim Murkette

Realtor®

860-539-5009

Email
Alison Malkin
Leah Pliego

Realtor®

860-681-7373

Email
Alison Malkin
Shaissa Acosta

Realtor®

860-249-1641

Email

Acres : 5.03
Appliances Included : Gas Range, Convection Oven, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
Attic : Pull-Down Stairs
Basement : Full, Sump Pump, Storage, Garage Access, Partially Finished, Concrete Floor
Full Baths : 4
Half Baths : 1
Baths Total : 5
Beds Total : 5
City : Fairfield
Cooling : Central Air, Zoned
County : Fairfield
Elementary School : Burr
Fireplaces : 4
Foundation : Concrete, Stone
Fuel Tank Location : In Ground
Garage Parking : Attached Garage, Detached Garage
Garage Slots : 4
Description : Fence - Full, Some Wetlands, Level Lot, Professionally Landscaped
Middle School : Tomlinson
Amenities : Golf Course, Health Club, Library, Paddle Tennis, Private School(s), Stables/Riding, Tennis Courts
Neighborhood : Greenfield Hill
Parcel : 133066
Pool Description : Heated, Pool House, Spa, In Ground Pool
Postal Code : 06824
Roof : Wood Shingle
Additional Room Information : Foyer, Greenhouse, Music Room, Workshop
Sewage System : Septic
Total SqFt : 4191
Tax Year : July 2025-June 2026
Total Rooms : 9
Watersource : Public Water Connected
weeb : RPR, IDX Sites, Realtor.com

Phone

860-384-7624

Address

20 Hopmeadow St, Unit 821, Weatogue, CT 06089


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