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$1,849,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 6,259 Sq. Ft.
  • 3 Car Garage
  • Updated 3 days ago
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A refined Connecticut country residence for full-time living or weekend enjoyment, ideal for Westchester and NYC Buyers. Set on nearly three meticulously landscaped acres on a private cul-de-sac drive with only 4 residences, you will enjoy living in one of Redding's most desirable residential enclaves. 2 Longwood Drive offers a safe, secure, and 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 spacious 9-14 foot ceilings, hardwood floors throughout, and an open yet elegant flow ideal for both everyday living and entertaining. A 47' stone-covered front porch, perfect for watching the amazing sunsets, and a 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/Thermador appliances, custom cabinetry, a generous center island, and a butler's pantry, each designed for effortless hosting and daily comfort. The kitchen includes a hexagonal breakfast area with French doors overlooking the rear garden with a 100 foot stone wall.

Full Property Details for 2 Longwood Dr

General

  • Price: $1,849,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24147905
  • Updated: 2/2/2026
  • Added to Site: 31 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Disposal, Washer, Electric Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Bedroom Suite, Ceiling Fan, Full Bath, Whirlpool Tub, Walk-In Closet, Hardwood Floor, 31.3 x 16.1, Upper
  • Bedroom 1: Bedroom - Walk-In Closet, Hardwood Floor, 13 x 16, Upper
  • Bedroom 2: Bedroom - Jack & Jill Bath, Walk-In Closet, Hardwood Floor, 13 x 16, Upper
  • Bedroom 3: Bedroom - Ceiling Fan, Jack & Jill Bath, Walk-In Closet, Hardwood Floor, 13.3 x 16, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Wet Bar, Gas Log Fireplace, Patio/Terrace, Hardwood Floor, 28 x 15.9, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Granite Counters, Wet Bar, Island, Patio/Terrace, Hardwood Floor, 20.4 x 22.11, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, 18 x 13.8, Main
  • Office: Office - 9 ft+ Ceilings, Book Shelves, Built-Ins, Hardwood Floor, 18 x 13.8, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Skylight, Cathedral Ceiling, Ceiling Fan, Hardwood Floor, 15.8 x 38.11, Upper
  • Rec Room: Skylight, Cathedral Ceiling, Ceiling Fan, Hardwood Floor, 15.8 x 38.11, Upper
  • Laundry: Upper Level
  • In-Law/Au Pair Suite: Yes

Exterior

  • Exterior Features: Garden Area, Lighting, Covered Deck, Stone Wall, French Doors, Patio
  • Color: Gray

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Gallows Hill
  • Driving 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.

School Information

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

Community

  • Community Name: Gallows Hill

Heating & Cooling

  • Cooling Type: Ceiling Fans, Central Air, Zoned
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Upright Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Unfinished, Storage, Interior Access, Concrete Floor
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 6,259
  • Above Ground: 6,259 Sq. Ft.
  • Year Built: 1998

Lot Features

  • Lot Size (Acres): 2.72
  • Zoning: R-2
  • Lot Description: Secluded, Lightly Wooded, Dry, Sloping Lot, On Cul-De-Sac, Professionally Landscaped

Green Features

  • Energy Features: Generator, Thermopane Windows

Financial Considerations

  • Assessment Amount: $1,036,500
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 269523

Listed by William Raveis Real Estate, Jeffrey Kaplan

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Listing agent

— 2 Longwood Dr —

  • Jeffrey Kaplan

    William Raveis Real Estate

Agent Contact: (203) 505-3375 Office Contact: (203) 847-6633

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2 Longwood Dr

School Districts:Redding School District, Regional High School District 09
NameGradesDistance
Redding Elementary School
33 Lonetown Road, Redding, CT 06896
PK-40.6 mi
John Read Middle School
486 Redding Road, Redding, CT 06896
5-81 mi
Joel Barlow High School
100 Black Rock Turnpike, Redding, CT 06896
9-122.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2 Longwood Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/05/2026
Listed
$1,849,000
120.12%
MLS
7/17/1998
Sold
$840,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2 Longwood Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$30,618
3%
$1,036,500
—
2023
$29,768
—
$1,036,500
-4%
2023
$29,808
—
$1,076,500
21%
2022
$29,686
-1%
$890,400
-3%
2021
$30,042
—
$914,800
—
2020
$30,042
—
$914,800
—
2019
$30,042
4%
$914,800
—
2018
$29,017
—
$914,800
-7%
2017
$29,042
1%
$980,500
—
2016
$28,670
1%
$980,500
—
2015
$28,346
—
$980,500
—
2014
$28,346
—
$980,500
—
2011
$28,385
—
$980,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by William Raveis Real Estate, Jeffrey Kaplan

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2 Longwood Drive, Redding, CT 06896 (MLS# 24147905) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 2 Longwood Drive is currently listed for $1,849,000 and was received on January 05, 2026. Want to learn more about 2 Longwood Drive? Do you have questions about finding other Single Family real estate for sale in Redding? You can browse all Redding real estate or contact a Coldwell Banker agent to request more information.

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