$1,795,000

2 Longwood Dr Redding, CT 06896

Estimated payment $12,228/month

Total Views 5,607
4 Beds
4.5 Baths
6,259 Sq Ft
$287 Price per Sq Ft

Highlights

  • Sub-Zero Refrigerator
  • Open Floorplan
  • Attic
  • Redding Elementary School Rated A
  • Colonial Architecture
  • 1 Fireplace

About This Home

Newly Priced at $1,795,000 *** Exceptional Luxury Value in Redding's Limited Inventory Market. In today's market, where luxury inventory in Redding remains extremely limited, 2 Longwood Drive presents a rare opportunity to own a meticulously maintained custom estate offering exceptional square footage, privacy, flexibility, and long term value in one of Connecticut's most desirable communities. Privately set on nearly three professionally landscaped acres on a private drive at the end of a quiet cul-de-sac with only four luxury homes, this property offers over 6,200 square feet of thoughtfully designed living space rarely available at this price point. Located in one of Redding's most sought after neighborhoods, the home is ideally positioned close to the Redding Community Center, Mark Twain Library, Redding Country Club, hiking trails, parks, concerts and events on the historic town green, and the Metro-North train station with direct access to Grand Central. Buyers relocating from New York City, Westchester, or neighboring Fairfield County towns are increasingly drawn to Redding for its exceptional quality of life, natural beauty, strong sense of community, and highly regarded schools. Thoughtfully designed and impeccably maintained by its original owner, this custom built colonial combines timeless New England architecture with the spaciousness and flexibility today's luxury buyers demand.

Listing Agent

Jeffrey Kaplan

William Raveis Real Estate Brokerage Phone: (203) 505-3375 License #RES.0783899 Listed on: 05/21/2026

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

  • Gas Cooktop
  • Range Hood
  • Microwave
  • Sub-Zero Refrigerator
  • Ice Maker
  • Dishwasher
  • Wine Cooler
  • 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

2.72 Acres

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: Inside, soaring 9-14 foot ceilings, hardwood floors throughout, oversized windows, and beautifully scaled living spaces create a bright, elegant atmosphere ideal for both entertaining and everyday living. A dramatic 47-foot covered stone front porch welcomes guests and provides breathtaking sunset views overlooking the manicured grounds and surrounding natural beauty. The chef's kitchen serves as the heart of the home, featuring premium Sub-Zero, Wolf, and Thermador appliances, custom cabinetry, large center island, butler's pantry, and a sun-filled breakfast area with French doors opening to the private backyard setting. The spacious family room with gas fireplace and custom wet bar flows seamlessly to the outdoor entertaining area, creating the indoor-outdoor lifestyle buyers are searching for. Additional main level highlights include a private home office with custom built-ins, formal dining room, oversized mudroom, and an oversized three-car garage with impressive 12-foot ceilings, ideal for car enthusiasts, storage, or future lift installation. The luxurious primary suite offers dual full bathrooms, separate dressing areas, and generous closet space, while three additional bedrooms and a large recreation room complete the second level. One of the home's most valuable and versatile features is the finished third floor with a full ensuite bathroom and steam shower, serviced by a five bedroom septic system. This incredible space can function as a private 5th bedroom, au pair suite, guest suite, in-law suite, home office, media room, or fitness retreat - offering flexibility rarely found in today's market. The nearly 2,300 square foot unfinished lower level with impressive 9-foot ceilings provides extraordinary future potential for a home theater, golf simulator, gym, wine cellar, or additional recreational living space. Outside, expansive lawns, mature landscaping, natural privacy, and classic New England stone walls create a peaceful resort-like setting with room for a future pool (buyers to independently verify). Now offered at the newly adjusted price of $1,795,000, this is a compelling opportunity to own a luxury estate offering exceptional space, privacy, flexibility, and long-term value in one of Connecticut's premier towns known for its top-ranked schools, natural beauty, and exceptional lifestyle. Sale includes a full home warranty.
  • Direct Waterfront: No
  • Home Warranty Offered: Yes
  • 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

Schools

  • Intermediate School: Per Board of Ed

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
  • Middle Jr High 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

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

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

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
05/21/2026 05/21/26 For Sale $1,795,000 -- $287 / Sq Ft
Source: SmartMLS

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

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

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

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: 24177771

SmartMLS

APN: REDD-000014-000000-000089

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