This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
$2,600,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
Property 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 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.
Full Property Details
Full Property Details for 4 Longwood Dr
General
- Sold For: $2,600,000
- Taxes: (July 2025-June 2026)
- Status: Closed
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24072075
- Added to Site: 349 day(s) ago
Interior
- Number of Rooms: 14
- Rooms/Areas: Bonus Room, Exercise Room, Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
- Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Gas Cooktop, Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Electric Dryer
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 5
- Half Bathrooms: 2
- Primary Bathroom: Primary Bath - Remod, 15 x 12, Main
Bedrooms
- Total Bedrooms: 7
- Primary Bedroom: Primary Bedroom - Remodeled, 9 ft+ Ceilings, Bedroom Suite, Built-Ins, Walk-In Closet, Hardwood Floor, 23 x 18, Main
- Bedroom 1: Bedroom - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Bedroom Suite, Full Bath, Hardwood Floor, 13 x 16, Upper
- Bedroom 2: Bedroom - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Full Bath, Hardwood Floor, 16 x 15, Upper
- Bedroom 3: Bedroom - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Full Bath, Hardwood Floor, 16 x 24, Upper
- Bedroom 4: Bedroom - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Hardwood Floor, 18 x 15, Upper
- Bedroom 5: Bedroom - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Balcony/Deck, Jack & Jill Bath, Hardwood Floor, 18 x 15, Upper
- Bedroom 6: Bedroom - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Hardwood Floor, 18 x 17, Upper
Other Rooms
- Living Room: Living Room - Remodeled, Cathedral Ceiling, Built-Ins, Fireplace, French Doors, Hardwood Floor, 21 x 28, Main
- Kitchen: Kitchen - 9 ft+ Ceilings, Granite Counters, Double-Sink, Wet Bar, Pantry, Hardwood Floor, 19 x 17, Main
- Eat In Kitchen: Eat-In Kitchen - Bay/Bow Window, 9 ft+ Ceilings, Balcony/Deck, Hardwood Floor, 14 x 8, Main
- Formal Dining Room: Formal Dining Room - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Balcony/Deck, French Doors, Hardwood Floor, 20 x 17, Main
- Office: Office - Remodeled, Bay/Bow Window, 9 ft+ Ceilings, Balcony/Deck, Built-Ins, Hardwood Floor, 20 x 12, Main
- Game room: Yes
- Game Room: Rec/Play Room - Remodeled, 9 ft+ Ceilings, Wet Bar, Fireplace, French Doors, Hal, 29 x 28, Lower
- Rec Room: Remodeled, 9 ft+ Ceilings, Wet Bar, Fireplace, French Doors, Half Bath, 29 x 28, Lower
- Theater/Media: Media Room - Remodeled, 9 ft+ Ceilings, Hardwood Floor, 21 x 21, Lower
- Laundry: Main Level
Additional Information
- Pool: Yes
- Pool Description: Gunite, Heated, Pool House, Spa, Solar Cover, In Ground Pool
Exterior
- Exterior Features: Cabana, Gutters, Hot Tub, French Doors, Patio, Balcony, Grill, Gazebo, Garden Area
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Parking: Attached Garage
Location
- County: Fairfield
- Neighborhood: Gallows Hill
- Driving Directions: 107 to 53 to Gallows Hill to Longwood. House is last home down private road at end of Cul-de-sac.
School Information
- Elementary School: Per Board of Ed
- Middle School: Per Board of Ed
- Intermediate School: Per Board of Ed
- High School: Per Board of Ed
Community
- Community Name: Gallows Hill
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Hot Air, Radiant, Zoned, Oil
- Heating Fuel: Oil
- Water Heater: Oil, Tank Size Unknown
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Cape Cod, Colonial
- Construction Status: No/Resale
- Exterior Const.: Shake, Cedar, Stone
- Basement Desc.: Full, Heated, Storage, Fully Finished, Cooled, Interior Access, Walk-out
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 10,197
- Above Ground: 6,343 Sq. Ft.
- Below Ground: 3,854 Sq. Ft.
- Year Built: 2000
Lot Features
- Lot Size (Acres): 3.75
- Zoning: R-2
- Lot Description: Secluded, Golf Course Frontage, Treed, On Cul-De-Sac, Professionally Landscaped
Green Features
- Energy Features: Thermopane Windows
Financial Considerations
- Assessment Amount: $1,265,200
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 269525
Listed by William Raveis Real Estate, Jeffrey Kaplan
Sold by Compass Connecticut, LLC, Kathleen Usherwood
Get Pre-Approved Today
Schools
Schools serving 4 Longwood Dr
School Districts:Redding School District, Regional High School District 09
| Name | Grades | Distance |
|---|---|---|
Redding Elementary School 33 Lonetown Road, Redding, CT 06896 | PK-4 | 0.7 mi |
John Read Middle School 486 Redding Road, Redding, CT 06896 | 5-8 | 1.1 mi |
Joel Barlow High School 100 Black Rock Turnpike, Redding, CT 06896 | 9-12 | 3 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 4 Longwood Dr
Date
Details
Price
Change
Source
7/25/2025
Sold
$2,600,000
4.04%
MLS
2/01/2025
Listed
$2,499,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
4 Longwood Drive, Redding, CT 06896 (MLS# 24072075) is a Single Family property that was sold at $2,600,000 on July 25, 2025. Want to learn more about 4 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.

