2 Longwood Dr

Redding, CT 06896

$1,849,000
Price
4
Beds
6,259 Sq. Ft.
$295 / Sq. Ft.
6,259
Sq. Ft.
$295
per Sq. Ft.
front view of a house with a yard
a front view of a house with a yard table and chairs
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a front view of a house with a yard
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a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop a refrigerator a stove top oven and a dining table with wooden floor
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a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
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Description

A refined Connecticut country residence for full-time living or weekend enjoyment, ideal for Westchester and NYC Buyers. Set on nearly three private, landscaped acres in one of Redding's most desirable residential enclaves, 2 Longwood Drive offers a 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...A refined Connecticut country residence for full-time living or weekend enjoyment, ideal for Westchester and NYC Buyers. Set on nearly three private, landscaped acres in one of Redding's most desirable residential enclaves, 2 Longwood Drive offers a 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 9-foot ceilings, hardwood floors throughout, and an open yet elegant flow ideal for both everyday living and entertaining. A stone-covered entry and 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, and Thermador appliances, custom cabinetry, a generous center island, and a butler's pantry, all designed for effortless hosting and daily comfort. 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 French doors and relax outside on the stunning stone patio, all overlooking the serene, manicured grounds.
  1. Listed by Jeffrey Kaplan • William Raveis Real Estate
    P: (203)-505-3375 C: (203)-505-3375 Jeff.Kaplan@raveis.com

Property Details for 2 Longwood Drive

Basement Description
Full, Unfinished, Storage, Interior Access, Concrete Floor
Direct Waterfront
No
Garages Number
3
Neighborhood
Gallows Hill
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
No
LISTING UPDATED: 01/29/2026 07:28 PM

Property Details for 2 Longwood Drive

StatusActive
MLS #24147905
Days on Market27
Taxes$30,618 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1998
Lot Size2.72 AC / 118,483 SF
CountyFairfield County

Location

Listing Courtesy of William Raveis Real Estate, Jeffrey Kaplan
Add your commute

Building Information for 2 Longwood Drive

Stories-Year Built1998Building Size-Lot Size2.72 AC / 118,483 SF

Payment Calculator

$11,563 per month

30 year fixed, 6.15% Interest

Principal and Interest

$9,012

Property Taxes

$2,552

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 2 Longwood Drive

Summary
Property and Location
  • Acres Source: Public Records
  • 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.
  • Elementary School: Per Board of Ed
  • Flood Zone: No
  • High School: Per Board of Ed
  • Latitude: 41.317097
  • Longitude: -73.38982
  • Neighborhood Amenities: Golf Course, Library, Medical Facilities, Paddle Tennis, Public Rec Facilities, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $30,618
Interior and Exterior Features
Exterior Features
  • Exterior Features: Garden Area, Lighting, Covered Deck, Stone Wall, French Doors, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Cooktop, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Disposal, Washer, Electric Dryer, Wine Chiller
  • Attic Description: Unfinished, Crawl Space, Access Via Hatch
  • Cooling System: Ceiling Fans, Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Home Automation: Appliances, Electric Outlet(s), Lighting, Lock(s), Security System, Thermostat(s)
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Open Floor Plan, Security System
  • Laundry Room Info: Upper Level
  • Laundry Room Location: 2nd floor hallway.
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Wet Bar,Gas Log Fireplace,Patio/Terrace,Hardwood Floor
  • Room Length: 28.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 15.9
Room 2
  • Room Entry Order: 10
  • Room Features: 9 ft+ Ceilings,Ceiling Fan,Full Bath,Steam/Sauna,Hardwood Floor
  • Room Length: 34.11
  • Room Level: Upper
  • Room Type: Rec/Play Room
  • Room Width: 39.11
Room 3
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 13.8
Room 4
  • Room Entry Order: 3
  • Room Features: Bedroom Suite,Ceiling Fan,Full Bath,Whirlpool Tub,Walk-In Closet,Hardwood Floor
  • Room Length: 31.3
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 16.1
Room 5
  • Listing Key: 47E3BA78AD4306F2E063E201100ABD04
  • Room Entry Order: 4
  • Room Features: Walk-In Closet,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 6
  • Room Entry Order: 5
  • Room Features: Jack & Jill Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 7
  • Room Entry Order: 6
  • Room Features: Ceiling Fan,Jack & Jill Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 13.3
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 8
  • Room Entry Order: 7
  • Room Features: 9 ft+ Ceilings,Granite Counters,Wet Bar,Island,Patio/Terrace,Hardwood Floor
  • Room Length: 20.4
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 22.11
Room 9
  • Listing Key: 47E3BA78AD4306F2E063E201100ABD04
  • Room Entry Order: 8
  • Room Features: 9 ft+ Ceilings,Book Shelves,Built-Ins,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 13.8
Room 10
  • Room Entry Order: 9
  • Room Features: Skylight,Cathedral Ceiling,Ceiling Fan,Hardwood Floor
  • Room Length: 15.8
  • Room Level: Upper
  • Room Type: Rec/Play Room
  • Room Width: 38.11
Property
Property and Assessments
  • Color: Gray
  • Construction Description: Frame
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1998
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Upper Level
  • In Law Apartment: Yes
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 6259
Lot Information
  • Lot Description: Secluded, Lightly Wooded, Dry, Sloping Lot, On Cul-De-Sac, Professionally Landscaped
  • Parcel Number: 269523
  • Sq Ft Est Heated Above Grade: 6259.0
  • Sq Ft Total: 6259.0
  • Zoning: R-2
Utilities
  • Energy Features: Generator, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Upright Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 2 Longwood Drive

DateEvent & SourcePriceAppreciation
Jul 17, 1998

Closed (Public Record)

Public Record #91143060

$840,000—
DateEvent & SourcePrice
07/17/1998

Closed (Public Record)

Public Record #91143060

$840,000

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

Public Records for 2 Longwood Drive

Taxable ValueLand$191,800Additions$844,700Total$1,036,500
Tax Record2024$30,618 ($2,552 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt6,259 SqFtAbove Grade Finished SqFt6,259 SqFtStories2Lot Size118,483 SqFtStyleSingle Family ResidenceYear Built1998ZoningR-2CountyFAIRFIELDAPNREDD M:14 L:89Fireplace TypeHas Fireplace

Schools near 2 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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More information about 2 Longwood Drive, Redding, CT 06896

2 Longwood Drive is a single family home for sale in Redding, CT 06896. This property was listed for sale on January 5, 2026 by William Raveis Real Estate, it's currently listed at $1,849,000. It has been on the market for a total of 27 days and was last sold on July 17, 1998. This listing's school districts are Redding School District, Regional School District 09. Nearby schools include Redding Elementary School, John Read Middle School and Joel Barlow High School. 2 Longwood Drive is a 4-bed, 5-bath, 6,259 sqft single family home built in 1998.

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.