$1,599,000

Estimated payment $11,660/month

Total Views 2,001
4 Beds
4.5 Baths
6,259 Sq Ft
$255 Price per Sq Ft

Highlights

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

About This Home

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.

Listing Agent

Jeffrey Kaplan

William Raveis Real Estate Brokerage Phone: (203) 505-3375 License #RES.0783899 Listed on: 09/01/2026

William Raveis Real Estate

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $31,582

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
  • Wolf Appliances
  • Smart Appliances
  • Disposal

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Soaking Tub
  • Steam Shower

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
  • 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

$31,582

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: 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.
  • 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
  • Estimated Annual Heat Cost: 6468

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 2026-June 2027
  • Property Tax: 31582

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
09/01/2026 09/01/26 For Sale $1,599,000 -- $255 / 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 --
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
Source: Public Records

Source: SmartMLS

MLS Number: 24203563

SmartMLS

APN: REDD-000014-000000-000089

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