4 Longwood Dr

Redding, CT 06896

$2,600,000
Last Sold Price
7
Beds
10,197 Sq. Ft.
$255 / Sq. Ft.
10,197
Sq. Ft.
$255
per Sq. Ft.
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Closed 7/25/25
Closed 7/25/25
a green field with lots of flowers

Description

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...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.
  1. Listed by Jeffrey Kaplan • William Raveis Real Estate
    P: (203)-505-3375 C: (203)-505-3375 Jeff.Kaplan@raveis.com

Property Details for 4 Longwood Drive

Basement Description
Full, Heated, Storage, Fully Finished, Cooled, Interior Access, Walk-out
Direct Waterfront
No
Garages Number
3
Neighborhood
Gallows Hill
Style
Cape Cod, Colonial
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 07/25/2025 02:47 PM

Property Details for 4 Longwood Drive

StatusClosed
MLS #24072075
Days on Market44
Taxes$37,374 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built2000
Lot Size3.75 AC / 163,350 SF
CountyFairfield County
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Location

Listing Courtesy of William Raveis Real Estate, Jeffrey Kaplan

Sold By Compass Connecticut, LLC, Kathleen Usherwood

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Building Information for 4 Longwood Drive

Stories-Year Built2000Building Size-Lot Size3.75 AC / 163,350 SF

Payment Calculator

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$15,786 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,672

Property Taxes

$3,115

HOA Dues

$0

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Property Information for 4 Longwood Drive

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: 107 to 53 to Gallows Hill to Longwood. House is last home down private road at end of Cul-de-sac.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.318375
  • Longitude: -73.39106
  • Middle Jr High School: Per Board of Ed
  • Neighborhood Amenities: Golf Course, Library, Playground/Tot Lot, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $37,374
Interior and Exterior Features
Exterior Features
  • Exterior Features: Cabana, Gutters, Hot Tub, French Doors, Patio, Balcony, Grill, Gazebo, Garden Area
  • Pool Description: Gunite, Heated, Pool House, Spa, Solar Cover, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Cooktop, Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Electric Dryer
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air, Radiant, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Home Automation: Appliances, Built In Audio, Lighting, Lock(s), Security System, Thermostat(s)
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: 1st floor
  • Rooms Additional: Bonus Room, Exercise Room, Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
  • Rooms Total: 14
Room 1
  • Room Entry Order: 1
  • Room Features: Remodeled,Cathedral Ceiling,Built-Ins,Fireplace,French Doors,Hardwood Floor
  • Room Length: 21.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 28.0
Room 2
  • Room Entry Order: 10
  • Room Features: 9 ft+ Ceilings,Granite Counters,Double-Sink,Wet Bar,Pantry,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 17.0
Room 3
  • Room Entry Order: 11
  • Room Features: Bay/Bow Window,9 ft+ Ceilings,Balcony/Deck,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 8.0
Room 4
  • Room Entry Order: 12
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Balcony/Deck,Built-Ins,Hardwood Floor
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 12.0
Room 5
  • Listing Key: 2D07ED163F177FFDE0631401100AC3DD
  • Room Entry Order: 13
  • Room Features: Remodeled,9 ft+ Ceilings,Wet Bar,Fireplace,French Doors,Half Bath
  • Room Length: 29.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 28.0
Room 6
  • Room Entry Order: 14
  • Room Features: Remodeled,9 ft+ Ceilings,Hardwood Floor
  • Room Length: 21.0
  • Room Level: Lower
  • Room Type: Media Room
  • Room Width: 21.0
Room 7
  • Room Entry Order: 15
  • Room Features: Remodeled,Granite Counters,Double-Sink,Full Bath,Marble Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Primary Bath
  • Room Width: 12.0
Room 8
  • Room Entry Order: 2
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Balcony/Deck,French Doors,Hardwood Floor
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Formal Dining Room
  • Room Width: 17.0
Room 9
  • Listing Key: 2D07ED163F177FFDE0631401100AC3DD
  • Room Entry Order: 3
  • Room Features: Remodeled,9 ft+ Ceilings,Bedroom Suite,Built-Ins,Walk-In Closet,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 18.0
Room 10
  • Room Entry Order: 4
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Balcony/Deck,Jack & Jill Bath,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 11
  • Room Entry Order: 5
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Full Bath,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 24.0
Room 12
  • Room Entry Order: 6
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Full Bath,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 13
  • Room Entry Order: 7
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Bedroom Suite,Full Bath,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 14
  • Room Entry Order: 8
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Built-Ins,Jack & Jill Bath,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 15
  • Room Entry Order: 9
  • Room Features: Remodeled,Bay/Bow Window,9 ft+ Ceilings,Built-Ins,Jack & Jill Bath,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 17.0
Property
Property and Assessments
  • Construction Description: Frame, Stone
  • Exterior Siding: Shake, Cedar, Stone
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2000
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level, Separate Entry
  • In Law Apartment: Possible
  • Sq Ft Description: Total 1st/2nd floor sf per floorplan measurements. Floorplans included in listing documentation.
  • Sq Ft Est Heated Below Grade: 3854
  • Living Area SQFT Per Public Records: 6343
Lot Information
  • Lot Description: Secluded, Golf Course Frontage, Treed, On Cul-De-Sac, Professionally Landscaped
  • Parcel Number: 269525
  • Sq Ft Est Heated Above Grade: 6343.0
  • Sq Ft Total: 10197.0
  • Zoning: R-2
Utilities
  • Energy Features: Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Tank Size Unknown
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 4 Longwood Drive

DateEvent & SourcePriceAppreciation
Jul 25, 2025

Closed (Public Record)

Public Record #1908629049

$2,600,000

+161.9% / yr

Mar 22, 2010

Closed (Public Record)

Public Record #327052156

$1—
Aug 4, 2008

Closed (Public Record)

Public Record #327051998

$1

-72.5% / yr

Nov 30, 1998

Closed (Public Record)

Public Record #91143148

$270,000—
DateEvent & SourcePrice
07/25/2025

Closed (Public Record)

Public Record #1908629049

$2,600,000

+161.9% / yr

03/22/2010

Closed (Public Record)

Public Record #327052156

$1
08/04/2008

Closed (Public Record)

Public Record #327051998

$1

-72.5% / yr

11/30/1998

Closed (Public Record)

Public Record #91143148

$270,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 4 Longwood Drive

Taxable ValueLand$205,900Additions$1,059,300Total$1,265,200
Tax Record2024$37,374 ($3,114 / month)
Home Facts
Beds5Baths6Total Finished SqFt6,343 SqFtAbove Grade Finished SqFt6,343 SqFtStories2Lot Size163,350 SqFtStyleSingle Family ResidenceYear Built2000ZoningR-2CountyFAIRFIELDAPNREDD M:14 L:13Fireplace TypeHas Fireplace

Schools near 4 Longwood Drive

This home is within Redding School District.
Rating
School
Type
Grades
Distance
Redding Elementary School
Public - PK to 4
John Read Middle School
Public - 5 to 8
Joel Barlow High School
Public - 9 to 12
Rating
School
Distance
Redding Elementary School
PublicPK to 4

John Read Middle School
Public5 to 8

Joel Barlow High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Jeffrey Kaplan

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.