2 Longwood Drive Redding, CT $ 1,675,000
2 Longwood Drive
$ 1,675,000
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2 Longwood Drive

Redding, CT, 06896
$ 1,675,000
Bedrooms4 Baths4.1 Sq 6,259

Monthly Estimate*

$ 10,576

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Single Family Home for sale in Redding, CT

for $1,675,000 with 4 bedrooms and 4 full baths, 1 half bath. This 6,259 square foot home was built in 1998 on a lot size of 2.72.

***NEW PRICE*** $1,675,000! MORE HOUSE. MORE LAND. MORE PRIVACY. EXCEPTIONAL VALUE. If you've been searching Westchester or Fairfield County for a quintessential country estate that gives you substantial space without sacrificing access to the NYC metropolitan area, this exceptional custom built Redding Colonial deserves your attention. Offering 6,259 square feet, 2.72 private acres, 4 bedrooms, 4 full and 1 half baths, a 3-car attached garage, and a 5-bedroom septic system, this meticulously maintained single-owner home delivers an extraordinary amount of property and high-end living space for the price. And the location makes the lifestyle especially compelling: just 8 minutes to the Redding Metro-North station and a drive time of approximately 1 hour and 20 minutes to New York City. Enjoy the privacy, greenery, space, and tranquility of Fairfield County while remaining connected to NYC, Westchester, and the surrounding metropolitan area. Set privately on a cul-de-sac in desirable Gallows Hill, this classic New England Colonial has been meticulously maintained by its original owner and offers an ideal combination of timeless character and modern convenience. Inside, nine-foot ceilings, hardwood floors, generous room sizes, and flexible living spaces create an exceptional environment for both everyday life and entertaining. The gourmet kitchen is designed for serious cooking and gathering, featuring Sub-Zero refrigeration, a Wolf six-burner gas cooktop, granite countertops, and a large center island, with an open connection to the gas fireplaced living room and multiple French doors leading to the outdoor stone patio areas. The spacious primary suite includes 2 bathrooms, abundant closets and a whirlpool tub, joined by three additional bedrooms and generously sized baths. Two upper-level recreation rooms provide tremendous flexibility, including one with a full bath and steam sauna. The third-floor space offers additional possibilities for a home office, gym, media room, guest space, extended family, or in-law use. The 5-bedroom septic system adds valuable flexibility beyond the home's current four-bedroom configuration. A full unfinished basement provides abundant storage. For today's buyer, the infrastructure and finishes are particularly compelling. The home features a brand-new HVAC system, zoned central air, whole-house generator, thermopane windows, and a one-year whole-home warranty, offering meaningful peace of mind and helping minimize near-term unexpected expenses. Outside, the property truly comes to life. 2.72 acres of professionally landscaped grounds, mature trees, stone walls, sweeping lawns, garden areas, a covered front deck, and patio create a private New England retreat. There's room to entertain, relax, garden, play, and enjoy the outdoors, while still being close to everything you need. Redding offers an exceptional quality of life with highly regarded schools, hiking trails, golf, tennis, paddle facilities, and quintessential New England scenery, with convenient access to Ridgefield, Wilton, Westport, Westchester, and NYC. Consider what $1,675,000 delivers here: 6,259 SF, 2.72 acres, 4 bedrooms, 4.5 baths, a 5-bedroom septic system, 3-car garage, exceptional entertaining spaces, brand-new HVAC, whole-house generator, and a one-year whole-home warranty, all in a private, beautiful setting. If you've been waiting for the opportunity to have significantly more home, land, privacy, and lifestyle without giving up your connection to New York, this is the one to see. Schedule your private showing or come experience it at the next open house. You truly need to walk the property to fully appreciate the scale, setting, and floorplan.

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Single Family Active

Price

$ 1,675,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 31,582

Style

Lot Size

2.72

Year Built

1998

Town/City

Redding

MLS | Web ID

24177771

Features
General
Zoning R-2
Neighborhood Gallows Hill
County Fairfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 2.72
Directions Gallows Hill Road to Longwood Drive. Drive around cul-de-sac to enter private drive. 2nd home on right. Park in driveway by garage. There is no "for sale" sign on property.
High School Per Board of Ed
City Redding
Elementary School Per Board of Ed
Sq Ft Total 6259
DOM 86
Year Built 1998
Style Colonial
Year Built Source Public Records
Energy Features Generator Thermopane Windows
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Interior
Cooling System Ceiling Fans Central Air Zoned
Total Rooms 9
Basement Description Full Unfinished Storage Interior Access Concrete Floor
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Exterior
Water Source Private Well
Lot Description Secluded Lightly Wooded Dry Sloping Lot On Cul-De-Sac Professionally Landscaped
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* Excluded Features
List By
Jeffrey Kaplan

Listing Agent

William Raveis Real Estate

Broker

Jeff.Kaplan@raveis.com

Email

Affordability Calculator

$13,208
Per Month
80%
20%
0%
Monthly Principal & Interest
$10,576
Monthly Property Taxes
$2,632
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
8/12/2026$1,675,000 -4.01% Price Down
6/26/2026$1,745,000 -2.79% Price Down
5/22/2026$1,795,000 Listed Price

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2 Longwood Drive, Redding, CT, 06896 is a Single Family Home for sale at $1,675,000 with 6,259 sqft and a lot size of 2.72. 2 Longwood Drive has 4 bedrooms, 4.1 baths, and was built in 1998. The property's zip code is 06896 which is in Redding, CT