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2 Longwood Drive

Redding, CT 06896
  • $1,849,000
  • STATUS: Active
  • ON SITE: 40 Days
  • MLS #: 24147905
UPDATED: 62 min ago
$1,849,000
  • 4
    BEDS
  • 2.72
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 6,259
    SQFT
  • $295
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1998
County:
Area:

School Information

Elementary School:
High School:

Description

***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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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. Data last updated: 2026-03-11T20:10:24.907.
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2 Longwood Drive Redding, CT 06896

  • Price: $1,849,000
  • Status: Active
  • On Site: 40 Days
  • Updated: 62 min ago
  • MLS #: 24147905
4
Beds
4
Baths
1
½ Baths
2.72
Acres
6,259
SQFT
$295
$/SQFT
1998
Built
Neighborhood:
Gallows Hill
County:
Fairfield
Area:
Redding
Elementary School:
per board of ed
High School:
per board of ed
Property Description
***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.
Exterior Features

Color Gray Direct Waterfront YN No Exterior Features Garden AreaLightingCovered DeckStone WallFrench DoorsPatio Exterior Siding Clapboard Garage And Parking Attached Garage Lot Description SecludedLightly WoodedDrySloping LotOn Cul-De-SacProfessionally Landscaped Nearby Amenities Golf CourseLibraryMedical FacilitiesPaddle TennisPublic Rec FacilitiesTennis Courts Roof Information Asphalt Shingle Style Colonial Swimming Pool YN No Waterfront Description Not Applicable

Interior Features

Appliances Included Gas CooktopMicrowaveRange HoodRefrigeratorFreezerSubzeroIcemakerDishwasherDisposalWasherElectric DryerWine Chiller Attic Description UnfinishedCrawl SpaceAccess Via Hatch Attic YN Yes Basement Description FullUnfinishedStorageInterior AccessConcrete Floor Cooling System Ceiling FansCentral AirZoned Fireplaces Total 1 Heat Type Hot Air Home Automation AppliancesElectric Outlet(s)LightingLock(s)Security SystemThermostat(s) In Law Access Upper Level In Law Apartment Yes Interior Features Auto Garage Door OpenerCable - Pre-wiredCentral VacuumOpen Floor PlanSecurity System Laundry Room Info Upper Level Laundry Room Location 2nd floor hallway. Rooms Kitchen (Main Level 9 ft+ CeilingsGranite CountersWet BarIslandPatio/TerraceHardwood Floor) Rec/Play Room (Upper Level SkylightCathedral CeilingCeiling FanHardwood Floor) Dining Room (Main Level 9 ft+ CeilingsHardwood Floor) Rec/Play Room (Upper Level 9 ft+ CeilingsCeiling FanFull BathSteam/SaunaHardwood Floor) Primary Bedroom (Upper Level Bedroom SuiteCeiling FanFull BathWhirlpool TubWalk-In ClosetHardwood Floor) Bedroom (Upper Level Ceiling FanJack & Jill BathWal Sq Ft Est Heated Above Grade 6259 Sq Ft Est Heated Below Grade 0 Sq Ft Total 6259 Total Rooms 9

Property Features

Agent Owner YN No Bank Owned Property No Energy Features GeneratorThermopane Windows Flood Zone YN No Foundation Type Concrete Fuel Tank Location In Basement Heat Fuel Type Oil Home Owners Assocation No Home Warranty Offered YN Yes Hot Water Description OilUpright Tank New Construction Type No/Resale Potential Short Sale No Radon Mitigation Air YN No Radon Mitigation Water YN No Sewage System Septic Tax Year July 2025-June 2026 Under Agreement Yn No Water Source Private Well Zoning R-2

Listing information © 2026 Smart MLS
Listing provided courtesy of Jeffrey Kaplan of William Raveis Real Estate: (203) 847-6633.


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. Data last updated: 2026-03-11T20:10:24.907.
 
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