$1,849,000

2 Longwood Dr Redding, CT 06896

Estimated payment $12,163/month

Total Views 13,247
4 Beds
4.5 Baths
6,259 Sq Ft
$295 Price per Sq Ft

Highlights

  • Sub-Zero Refrigerator
  • Open Floorplan
  • Wolf Appliances
  • Redding Elementary School Rated A
  • Colonial Architecture
  • Attic

About This Home

A refined Connecticut country residence for full-time living or weekend enjoyment, ideal for Westchester and NYC Buyers. 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 just beyond the city. 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.

Listing Agent

Jeffrey Kaplan

William Raveis Real Estate Brokerage Phone: (203) 505-3375 License #RES.0783899 Listed on: 01/05/2026

William Raveis Real Estate

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $30,618

Year Built

  • Built in 1998

Lot Details

  • 2.72 Acre Lot
  • Stone Wall
  • Garden
  • Property is zoned R-2

Home Design

  • Colonial Architecture
  • Concrete Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Clap Board Siding

Interior Spaces

  • 6,259 Sq Ft Home
  • Open Floorplan
  • Central Vacuum
  • Ceiling Fan
  • 1 Fireplace
  • Thermal Windows
  • French Doors
  • Concrete Flooring

Kitchen

  • Butlers Pantry
  • Gas Cooktop
  • Range Hood
  • Microwave
  • Sub-Zero Refrigerator
  • Ice Maker
  • Dishwasher
  • Wine Cooler
  • Wolf Appliances
  • Smart Appliances
  • Disposal

Bedrooms and Bathrooms

  • 4 Bedrooms

Laundry

  • Laundry on upper level
  • Electric Dryer
  • Washer

Attic

  • Unfinished Attic
  • Attic or Crawl Hatchway Insulated

Unfinished Basement

  • Basement Fills Entire Space Under The House
  • Interior Basement Entry
  • Crawl Space
  • Basement Storage

Home Security

  • Home Security System
  • Smart Lights or Controls
  • Smart Locks
  • Smart Thermostat

Parking

  • 3 Car Garage
  • Automatic Garage Door Opener

Outdoor Features

  • Covered Deck
  • Patio
  • Exterior Lighting

Utilities

  • Zoned Heating and Cooling
  • Heating System Uses Oil
  • Power Generator
  • Private Company Owned Well
  • Oil Water Heater
  • Fuel Tank Located in Basement
  • Cable TV Available

Additional Features

  • Modified Wall Outlets
  • Energy-Efficient Lighting
  • Property is near golf course

Listing and Financial Details

  • Assessor Parcel Number 269523

Home Details

Home Type

Single Family

Est. Annual Taxes

$30,618

Year Built

Built in 1998

Lot Details

0

Listing Details

  • Neighborhood: Gallows Hill
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 6259
  • Total Sq Ft: 6259
  • Year Built: 1998
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Library, Medical Facilities, Paddle Tennis, Public Rec Facilities, Tennis Courts
  • In Law Access: Upper Level
  • Remarks Public Addendum: 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, complemented by three additional bedrooms, a large recreation room, and a thoughtfully placed laundry 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 to add a pool. With a whole-house generator, and proximity to the Redding Country Club, town amenities, and commuting routes, 2 Longwood Drive presents a distinguished country residence defined by thoughtful scale, refined layout, and enduring quality, whether enjoyed full-time or on weekends. If you feel like getting outside, visit the nearby shops and restaurants in Ridgefield, Bethel, and Georgetown, or take-in the July 4th / Labor fireworks from one of the outdoor patios.
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: No
  • Radon Mitigation Water Ynu: No
  • 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.
  • In Law Apartment: Yes
  • Street Type: Drive
  • Office Attribution Contact: (203) 847-6633
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 4
  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Fireplaces: 1
  • Attic Description: Unfinished, Crawl Space, Access Via Hatch
  • Basement Description: Full, Unfinished, Storage, Interior Access, Concrete Floor
  • Interior Amenities: Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Open Floor Plan, Security System
  • Appliances: Gas Cooktop, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Disposal, Washer, Electric Dryer, Wine Chiller
  • Laundry Room Location: 2nd floor hallway.
  • Laundry Room Info: Upper Level
  • Attic: Yes
  • Home Automation: Appliances, Electric Outlet(s), Lighting, Lock(s), Security System, Thermostat(s)

Exterior Features

  • Exterior Features: Garden Area, Lighting, Covered Deck, Stone Wall, French Doors, Patio
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: No
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 3
  • Garage And Parking: Attached Garage

Utilities

  • Cooling System: Ceiling Fans, Central Air, Zoned
  • Heat Type: Hot Air
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Oil, Upright Tank
  • Water Source: Private Well
  • Sewer: Septic

Green Features

  • Energy Features: Generator, Thermopane Windows

Lot Info

  • Acres: 2.72
  • Lot Description: Secluded Lightly Wooded Dry Sloping Lot On Cul-De-Sac Professionally Landscaped
  • Flood Zone: No
  • Zoning: R-2
  • Parcel #: 269523

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 30618

MLS Schools

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Map

Range of Values:

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Value Increase
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Percent Increase
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Adjusted for Inflation
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $30,618 $1,036,500 $191,800 $844,700
2024 $29,768 $1,036,500 $191,800 $844,700
2023 $29,808 $1,076,500 $191,800 $884,700
2022 $29,686 $890,400 $206,400 $684,000
2021 $4,610 $914,800 $206,400 $708,400
2020 $30,042 $914,800 $206,400 $708,400
2019 $5,783 $914,800 $206,400 $708,400
2018 $29,017 $914,800 $206,400 $708,400
2017 $29,042 $980,500 $246,600 $733,900
2016 $28,670 $980,500 $246,600 $733,900
2015 $28,346 $980,500 $246,600 $733,900
2014 $28,346 $980,500 $246,600 $733,900
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
01/05/2026 01/05/26 For Sale $1,849,000 -- $295 / Sq Ft
Source: SmartMLS

Purchase History

Date Type Sale Price Title Company
Quit Claim Deed -- --
Warranty Deed $840,000 --
Warranty Deed $840,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $550,800 Stand Alone Refi Refinance Of Original Loan
Previous Owner $640,000 No Value Available
Previous Owner $649,900 No Value Available
Previous Owner $650,000 Purchase Money Mortgage
Source: Public Records

Source: SmartMLS

MLS Number: 24147905

SmartMLS

APN: REDD-000014-000000-000089

Connecticut Fairfield County Redding 06896

2 Longwood Dr, Redding, CT

For Sale

Detached

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Listing Agent
Jeffrey Kaplan
Section Image
William Raveis Real Estate
(475) 281-3613