2 Longwood Drive, Gallows HillRedding, CT 06896MLS Number 24147905

  • Price: $1,849,000
  • Est. Mortgage of $/month
  • 41 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.0% last updated on Mar 5, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
Active
2 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 068962 Longwood Drive Redding CT 06896
QR Code
  • 4Bedrooms
  • 2.72Acreage
  • 5Bathrooms
  • 1998Year Built

Driving Directions

***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.
Listed by Jeffrey Kaplan of William Raveis Real Estate ((203) 505-3375)

Ask A Question

Do not fill in this field:

I agree to receive marketing and customer service calls and text messages from Lorraine Amaral | Sotheby's International Realty | William Pitt. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

More Info

Basic Information

  • MLS Number24147905
  • StatusACT
  • List Price$1,849,000
  • Square Feet6,259
  • Virtual TourView Tour
  • Property TypeSingle Family For Sale

Property

  • Acreage2.72
  • Lot Description
    • Dry
    • Lightly Wooded
    • On Cul-De-Sac
    • Professionally Landscaped
    • Secluded
    • Sloping Lot
  • Parking Spaces

Exterior

  • ColorGray
  • Exterior features
    • Covered Deck
    • French Doors
    • Garden Area
    • Lighting
    • Patio
    • Stone Wall
  • Exterior sidingClapboard

Amenities

  • Amenities
    • Golf Course
    • Library
    • Medical Facilities
    • Paddle Tennis
    • Public Rec Facilities
    • Tennis Courts
  • Other AmenitiesBasement, Fireplace, Golf, Tennis, Waterfront

Water Body

  • Waterfront DescriptionNot Applicable

Tax Information

  • Assessed value$1,036,500
  • Milrate total30
  • Tax YearJuly 2025-June 2026
  • Taxes$30,618

Location

  • StateCT
  • Zip06896
  • CountyFairfield
  • NeighborhoodGallows Hill

Interior

  • Rooms9
  • Interior featuresAuto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Open Floor Plan, Security System
  • RoofAsphalt Shingle
  • Home automation
    • Appliances
    • Electric Outlet(s)
    • Lighting
    • Lock(s)
    • Security System
    • Thermostat(s)

Utilities

  • Waters ourcePrivate Well
  • Cooling SystemCeiling Fans, Central Air, Zoned
  • Hot water descriptionOil, Upright Tank
  • Heating FuelOil
  • Fuel tank locationIn Basement
  • Heat SystemHot Air
  • Sewage systemSeptic

Other

  • Appliances Included
    • Dishwasher
    • Disposal
    • Electric Dryer
    • Freezer
    • Gas Cooktop
    • Icemaker
    • Microwave
    • Range Hood
    • Refrigerator
    • Subzero
    • Washer
    • Wine Chiller
  • Original listprice$1,849,000
  • Remarks addendumThe 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.
  • Date Listed01/29/2026
  • View Count1

School Information

  • Elementary SchoolPer Board of Ed
  • High SchoolPer Board of Ed

Rooms

  • Laundry room location2nd floor hallway.
  • Laundry room infoUpper Level

Building

  • Full Bath4
  • Half Baths1
  • BasementFull, Unfinished, Storage, Interior Access, Concrete Floor
  • Attic descriptionUnfinished, Crawl Space, Access Via Hatch
  • AtticYes
  • Garage Spaces3
  • Bedrooms4
  • Bathroom5
  • Year Built1998
  • Property StyleColonial
  • Energy FeaturesGenerator, Thermopane Windows
  • Fireplaces1
  • FoundationConcrete
  • Garage Parking InfoAttached Garage
  • New construction typeNo/Resale
  • Inlaw apartmentyYes
Sotheby's International Realty | William Pitt
Sotheby's International Realty | William Pitt
Office: 203-796-7700
112 Federal Road
Danbury, CT 06811

The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

I agree to receive marketing and customer service calls and text messages from Lorraine Amaral | Sotheby's International Realty | William Pitt. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.