NOT LISTED FOR SALE

4 Longwood Dr Redding, CT 06896

Estimated Value: $2,395,779 - $2,615,000

7 Beds
7 Baths
10,197 Sq Ft
$247/Sq Ft Est. Value

Last Sold July 25, 2025

Last sale price $2,600,000 $255 Per Sq Ft

Est. 3% decrease in value since last sale

Current estimated payment $16,297/month

45 Days on Market

Highlights

  • Wine Cellar
  • Pool House
  • Open Floorplan
  • Redding Elementary School Rated A
  • 3.75 Acre Lot
  • Cape Cod Architecture

About This Home

As of July 2025

Welcome to 4 Longwood Drive, a quintessential New England retreat set on 3.75 serene acres of amenity filled living spaces. This exquisite property provides an idyllic lifestyle amidst natural beauty, making it a perfect haven for families and individuals seeking comfort, elegance, and tranquility. The stone and shingle exterior of this elegant, custom-designed colonial residence was influenced by the former dean of the Yale School of Architecture, Robert A. Stern and presents an unparalleled blend of sophistication and warmth, designed to cater to the most discerning homeowners. Step inside and relax within a recently updated and expansive open concept living space including a luxurious first-floor primary suite with a spa-like ensuite bathroom with a soaking tub, dual vanities, a separate shower, a dedicated sitting room, and a private home office with built-in cabinetry, providing the perfect environment for remote work. The heart of the home features a gourmet kitchen with a large center island perfect for meal preparation and entertainment, ample cabinet space, a butler pantry, and a cozy sunlit breakfast nook overlooking the private backyard.

Last Agent to Sell the Property

Jeffrey Kaplan

William Raveis Real Estate License #RES.0783899 Listed on: 02/01/2025

William Raveis Real Estate

Last Buyer's Agent

Kathleen Usherwood

Compass Connecticut, LLC License #RES.0813653

Compass Connecticut, LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $37,374

Year Built

  • Built in 2000

Lot Details

  • 3.75 Acre Lot
  • Garden
  • Property is zoned R-2

Home Design

  • Cape Cod Architecture
  • Colonial Architecture
  • Concrete Foundation
  • Stone Frame
  • Frame Construction
  • Asphalt Shingled Roof
  • Cedar Siding
  • Shake Siding
  • Stone Siding
  • Stone

Interior Spaces

  • Open Floorplan
  • Built In Speakers
  • Sound System
  • 2 Fireplaces
  • Thermal Windows
  • French Doors
  • Mud Room
  • Entrance Foyer
  • Wine Cellar
  • Sitting Room
  • Bonus Room
  • Home Gym

Kitchen

  • Gas Cooktop
  • Range Hood
  • Microwave
  • Ice Maker
  • Dishwasher
  • Smart Appliances

Bedrooms and Bathrooms

  • 7 Bedrooms

Laundry

  • Laundry Room
  • Laundry on main level
  • Electric Dryer
  • Washer

Attic

  • Storage In Attic
  • Pull Down Stairs to Attic
  • Unfinished Attic

Finished Basement

  • Heated Basement
  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry
  • Basement Storage

Home Security

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

Parking

  • 3 Car Garage
  • Automatic Garage Door Opener

Eco-Friendly Details

  • Energy-Efficient Lighting
  • Pre-Wired For Photovoltaic Solar

Pool

  • Pool House
  • Cabana
  • Heated In Ground Pool
  • Spa
  • Gunite Pool
  • Pool has a Solar Cover

Outdoor Features

  • Balcony
  • Patio
  • Gazebo
  • Outdoor Grill
  • Rain Gutters

Location

  • Property is near a golf course

Utilities

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

Listing and Financial Details

  • Assessor Parcel Number 269525

Home Details

Home Type

Single Family

Est. Annual Taxes

$37,374

Year Built

Built in 2000

Lot Details

0

Listing Details

  • Neighborhood: Gallows Hill
  • Property Type: Single Family For Sale
  • Style: Cape Cod, Colonial
  • Sq Ft Est Heated Above Grade: 6343
  • Sq Ft Est Heated Below Grade: 3854
  • Total Sq Ft: 10197
  • Year Built: 2000
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Library, Playground/Tot Lot, Tennis Courts
  • In Law Access: LOWER,ENTRY
  • Remarks Public Addendum: The kitchen opens to a grand living room with 20-foot-high ceilings and a wood burning fireplace, and a stately formal dining room that is perfect for hosting large gatherings. The fully finished and expansive lower level has direct outdoor access, 9-foot ceilings and features a half bath, home gym, media room, living room with a stone fireplace, and wet bar. Relax outside in your private oasis including a large stone patio for entertaining, huge firepit, inground pool, spa, and cabana.
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Directions: 107 to 53 to Gallows Hill to Longwood. House is last home down private road at end of Cul-de-sac.
  • Financing Used: VA
  • In Law Apartment: Possible
  • Street Type: Drive
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 7
  • Total Bathrooms: 7
  • Full Bathrooms: 5
  • Half Bathrooms: 2
  • Fireplaces: 2
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Basement Description: Full, Heated, Storage, Fully Finished, Cooled, Interior Access, Walk-out
  • Interior Amenities: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
  • Appliances: Gas Cooktop, Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Electric Dryer
  • Additional Rooms: Bonus Room, Exercise Room, Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
  • Laundry Room Location: 1st floor
  • Laundry Room Info: Main Level
  • Attic: Yes
  • Home Automation: Appliances, Built In Audio, Lighting, Lock(s), Security System, Thermostat(s)

Exterior Features

  • Exterior Features: Cabana, Gutters, Hot Tub, French Doors, Patio, Balcony, Grill, Gazebo, Garden Area
  • Exterior Siding: Shake, Cedar, Stone
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: Yes
  • Pool: Gunite, Heated, Pool House, Spa, Solar Cover, In Ground Pool
  • Construction Description: Frame, Stone

Garage/Parking

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

Utilities

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

Schools

  • Intermediate School: Per Board of Ed

Green Features

  • Energy Features: Thermopane Windows

Lot Info

  • Acres: 3.75
  • Lot Description: Secluded Golf Course Frontage Treed On Cul-De-Sac Professionally Landscaped
  • Zoning: R-2
  • Parcel #: 269525

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 37374

MLS Schools

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

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
Feb 1, 2025
Closed on
Jul 25, 2025
Sold by
Gregory S Young Ret and Young
Bought by
Natal Jason and Natal Diana
Seller's Agent
Jeffrey Kaplan
William Raveis Real Estate
Buyer's Agent
Kathleen Usherwood
Compass Connecticut, LLC
List Price
$2,499,000
Sold Price
$2,600,000
Premium/Discount to List
$101,000
4.04%
Views
104
Current Estimated Value
$2,515,945

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$84,055
Avg. Annual Appreciation
-7.36%
Original Mortgage
$2,685,800
Outstanding Balance
$2,676,580
Interest Rate
6.81%
Mortgage Type
Future Advance Clause Open End Mortgage
Estimated Equity
-$160,635

Purchase Details

Closed on
Mar 22, 2010
Sold by
Young Gregory S
Bought by
Gregory S Young Ret and Young

Purchase Details

Closed on
Nov 30, 1998
Sold by
20 Gallows Hill Llc
Bought by
Young Laura A
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Buyer Sale Price Title Company
Natal Jason $2,600,000 --
Gregory S Young Ret -- --
Gregory S Young Ret -- --
Young Laura A $270,000 --
Young Laura A $270,000 --
Source: Public Records

Mortgage History

Date Status Borrower Loan Amount
Open Natal Jason $2,685,800
Previous Owner Young Laura A $1,650,000
Previous Owner Young Laura A $110,000
Previous Owner Young Laura A $1,265,000
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
07/25/2025 07/25/25 Sold $2,600,000 +4.0% $255 / Sq Ft
03/18/2025 03/18/25 Pending -- -- --
02/01/2025 02/01/25 For Sale $2,499,000 0.0% $245 / Sq Ft
10/28/2016 10/28/16 Rented $7,250 -3.3% --
09/28/2016 09/28/16 Under Contract -- -- --
07/23/2016 07/23/16 For Rent $7,500 -- --
Source: SmartMLS

Tax History Compared to Growth

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 $37,374 $1,265,200 $205,900 $1,059,300
2024 $36,337 $1,265,200 $205,900 $1,059,300
2023 $35,033 $1,265,200 $205,900 $1,059,300
2022 $37,918 $1,137,300 $220,500 $916,800
2021 $37,349 $1,137,300 $220,500 $916,800
2020 $37,349 $1,137,300 $220,500 $916,800
2019 $37,349 $1,137,300 $220,500 $916,800
2018 $36,075 $1,137,300 $220,500 $916,800
2017 $35,568 $1,200,800 $263,400 $937,400
2016 $35,111 $1,200,800 $263,400 $937,400
2015 $34,715 $1,200,800 $263,400 $937,400
2014 $34,715 $1,200,800 $263,400 $937,400
Source: Public Records

Agents Affiliated with this Home

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Map

Source: SmartMLS

MLS Number: 24072075

SmartMLS

APN: REDD-000014-000000-000013