2 Longwood Drive

Redding, CT
$ 1,599,000 Beds 4 Baths 4.5 Sq 6,259 Virtual Tour
Monthly Estimate* How much can I afford?

NEW PRICE - $1,599,000! Exceptional value for a meticulously maintained 6,259 SF custom Colonial on 2.72 private acres in desirable Redding, CT. Privately set on a quiet cul-de-sac in sought-after Gallows Hill, 2 Longwood Drive offers the space, privacy, quality and flexibility sought by discerning buyers from Fairfield County, Westchester and NYC. Just 8 minutes to the Redding Metro-North station and approximately 1 hour 20 minutes to NYC by car, this quintessential New England country estate provides a peaceful retreat while remaining connected to the metropolitan area. Meticulously maintained by its original owner, this custom home features 9-14' ceilings, hardwood floors, generous room sizes and light-filled living spaces designed for both everyday living and sophisticated entertaining. The gourmet kitchen features Sub-Zero refrigeration, Wolf six-burner gas cooktop, granite countertops, custom cabinetry and a large center island, opening to a spacious family room with gas fireplace, wet bar and French doors leading to the outdoor living spaces. The spacious primary suite features two full bathrooms, abundant closets and a whirlpool tub, complemented by three additional bedrooms and generously sized baths. A standout feature is the finished third-floor private living space with a full ensuite bathroom and steam shower/sauna, offering exceptional flexibility as a 5th bedroom, au pair suite, in-law suite, private guest quarters, home office, gym, media room or retreat. The 5-bedroom septic system adds valuable flexibility beyond the home's current four-bedroom configuration. Additional highlights include a brand-new HVAC system, zoned central air, whole-house generator, thermopane windows and transferable one-year whole-home warranty, providing meaningful peace of mind. The nearly 2,300 SF lower level with 9' ceilings offers abundant storage and significant potential for future finishing, recreation, fitness, media or entertainment space. The 3-car attached garage with 12' ceilings provides exceptional storage and flexibility, including potential for vehicle lifts. Outside, professionally landscaped grounds feature mature trees, classic stone walls, sweeping lawns, garden areas, covered front porch/deck and inviting outdoor living spaces, creating a private New England retreat. Enjoy Redding's highly regarded schools, hiking trails, golf, tennis, paddle facilities, open space and quintessential New England character, with convenient access to Ridgefield, Wilton, Westchester and NYC. The property is also close to the Redding Country Club, Community Center, town green and local events and concerts. At $1,599,000, 2 Longwood Drive represents an exceptional opportunity to own substantial living space, private acreage and remarkable flexibility in one of Redding's most desirable locations. For buyers seeking a country estate with exceptional privacy, turnkey condition, premium finishes and convenient NYC access, this is a rare opportunity. Low inventory and this significant new price adjustment make this property particularly compelling. Schedule your private showing to fully appreciate the scale, setting and versatility of 2 Longwood Drive.

Single Family

  • Price
  • $ 1,599,000
  • City
  • Redding
  • Bedrooms
  • 4
  • Full Bathrooms
  • 4
  • County
  • Fairfield
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 2.72 Acres
  • Zip
  • 06896
  • Sqr Footage
  • 6,259
  • Year Built
  • 1998
  • Taxes
  • $ 31582
  • Style
  • MLS#
  • 24203563
Listed By: Jeffrey Kaplan 203-505-3375 with William Raveis Real Estate. - (203) 847-6633
Data Source: Smart MLS

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 18
Year Built 1998
Style Colonial
Year Built Source Public Records
Energy Features Generator,Thermopane Windows

Interior Features

Cooling System Ceiling Fans,Central Air,Zoned
Total Rooms 9
Basement Description Full,Unfinished,Storage,Interior Access,Concrete Floor

Exterior Features

Water Source Private Well
Lot Description Secluded,Lightly Wooded,Dry,Sloping Lot,On Cul-De-Sac,Professionally Landscaped
Color Gray

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Per Board of Ed Elementary School
Middle School Unknown Middle School
High School Per Board of Ed High School

Price History

9/1/2026 Listed $1,599,000

Property vs Zip Code Average in 06896

Price
AVG $1.39M
$1.6M
Taxes
AVG $19,626
$31,582
Year Built
AVG 1952
1998

2 Longwood Drive Redding, CT is a Single Family Home for sale at $1599000 with 6259 sqft and a lot size of 2.72 Acres Acre(s). 2 Longwood Drive Redding has 4 bedrooms, 4 baths and was built in 1998. The property's zip code is 06896 which is in Redding, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.