2 Longwood Drive Redding, CT $ 1,849,000
2 Longwood Drive
$ 1,849,000
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2 Longwood Drive

Redding, CT, 06896
$ 1,849,000
Bedrooms4 Baths4.1 Sq 6,259

Monthly Estimate*

$ 11,385

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Single Family Home for sale in Redding, CT

for $1,849,000 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.

***Exceptional Value in Redding CT*** A refined Connecticut country residence for full-time living or weekend enjoyment. Set on nearly three meticulously landscaped acres on a private cul-de-sac drive with only 4 residences, you will enjoy living in one of Redding's most desirable residential enclaves. 2 Longwood Drive offers a safe, secure, and sophisticated country lifestyle that resonates naturally with buyers seeking space, privacy, and enduring quality. Commuters into NYC enjoy a reasonable 1.5 hour drive or can take the Redding train directly to Grand Central if preferred. Thoughtfully designed and meticulously maintained by its original owner, this custom-built colonial blends classic New England architecture with modern luxury, creating a residence equally suited for full-time living or refined weekend use. Spanning 6,259 square feet, the home features beautifully proportioned interiors with spacious 9-14 foot ceilings, hardwood floors throughout, and an open yet elegant flow ideal for both everyday living and entertaining. A 47' stone-covered front porch, perfect for watching the amazing sunsets, and a central foyer introduce the main level, where light-filled spaces unfold seamlessly from room to room. The sunlit chef's kitchen serves as the centerpiece of the home, appointed with premium Sub-Zero/Wolf/Thermador appliances, custom cabinetry, a generous center island, and a butler's pantry, each designed for effortless hosting and daily comfort. The kitchen includes a hexagonal breakfast area with French doors overlooking the rear garden with a 100 foot stone wall. Enjoy time together in the spacious family room around the gas fireplace and pour cocktails at the wet bar, featuring a wine refrigerator and ice maker. Open the family room doors and relax outside on the 2nd stunning stone patio, all overlooking the serene, manicured grounds. A formal dining room offers elegant entertaining, while a dedicated home office with custom built-ins provides an ideal remote-work environment. An oversized mudroom with multiple points of entry connects the oversized 3-car garage (with a 12' ceiling to accommodate several lifts), 2nd front entry, and a rear patio adds the practicality expected in a well-designed country residence. The second level is anchored by a serene primary suite offering the rare luxury of two full bathrooms with separate closets and dressing areas, complemented by three additional bedrooms and a large recreation room. A dramatic third-level finished living space, served by a five-bedroom septic, functions beautifully as a fifth bedroom, in-law suite, guest suite, or private retreat, complete with a full bath and steam shower. An unfinished lower level of nearly 2,300 square feet provides exceptional flexibility for future living, fitness, or entertainment space. Outdoor living is equally considered, with two stone patios surrounded by mature plantings, classic stone walls, and a huge sunny lawn space with plenty of room to add a pool (rendering shown/new owner must independently verify). This home is a short drive to Redding public schools, rated as one of the top school systems in the United States, near the Redding Country Club and Redding Community Center, and a 10 minute drive to the Redding train station. If you feel like getting outside, visit the nearby shops and restaurants in Redding, Ridgefield, and Georgetown, or take-in the July 4th / Labor fireworks from one of the outdoor patios. The home includes a "whole house" automatic generator and a one-year "full home" warranty - covering all appliances and roof to provide additional peace of mind for the new owner. Home photographs indicate if virtually staged with new interior paint, new lighting fixtures, new carpets, and new furniture. All photos show the existing floors, windows, cabinets, countertops, sinks, and appliances.

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Single Family Active

Price

$ 1,849,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 30,618

Style

Lot Size

2.72

Year Built

1998

Town/City

Redding

MLS | Web ID

24147905

Features
General
Zoning R-2
Neighborhood Gallows Hill
County Fairfield
Tax Year July 2025-June 2026
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 62
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

$13,936
Per Month
82%
18%
0%
Monthly Principal & Interest
$11,385
Monthly Property Taxes
$2,552
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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
3/5/2026$1,849,000 Listed Price

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2 Longwood Drive, Redding, CT, 06896 is a Single Family Home for sale at $1,849,000 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