2 Longwood Dr Redding, CT 06896
Redding AreaEstimated payment $11,660/month
Highlights
- Sub-Zero Refrigerator
- Open Floorplan
- Wolf Appliances
- Redding Elementary School Rated A
- Colonial Architecture
- Attic
About This Home
NEW PRICE - $1,599,000! Exceptional value for a meticulously maintained 6,259 SF custom Colonial on 2.72 private acres in desirable Redding, CT. Privately set on a quiet cul-de-sac in sought-after Gallows Hill, 2 Longwood Drive offers the space, privacy, quality and flexibility sought by discerning buyers from Fairfield County, Westchester and NYC. Just 8 minutes to the Redding Metro-North station and approximately 1 hour 20 minutes to NYC by car, this quintessential New England country estate provides a peaceful retreat while remaining connected to the metropolitan area. Meticulously maintained by its original owner, this custom home features 9-14' ceilings, hardwood floors, generous room sizes and light-filled living spaces designed for both everyday living and sophisticated entertaining. The gourmet kitchen features Sub-Zero refrigeration, Wolf six-burner gas cooktop, granite countertops, custom cabinetry and a large center island, opening to a spacious family room with gas fireplace, wet bar and French doors leading to the outdoor living spaces. The spacious primary suite features two full bathrooms, abundant closets and a whirlpool tub, complemented by three additional bedrooms and generously sized baths. A standout feature is the finished third-floor private living space with a full ensuite bathroom and steam shower/sauna, offering exceptional flexibility as a 5th bedroom, au pair suite, in-law suite, private guest quarters, home office, gym, media room or retreat. The 5-bedroom septic system adds valuable flexibility beyond the home's current four-bedroom configuration. Additional highlights include a brand-new HVAC system, zoned central air, whole-house generator, thermopane windows and transferable one-year whole-home warranty, providing meaningful peace of mind. The nearly 2,300 SF lower level with 9' ceilings offers abundant storage and significant potential for future finishing, recreation, fitness, media or entertainment space. The 3-car attached garage with 12' ceilings provides exceptional storage and flexibility, including potential for vehicle lifts. Outside, professionally landscaped grounds feature mature trees, classic stone walls, sweeping lawns, garden areas, covered front porch/deck and inviting outdoor living spaces, creating a private New England retreat. Enjoy Redding's highly regarded schools, hiking trails, golf, tennis, paddle facilities, open space and quintessential New England character, with convenient access to Ridgefield, Wilton, Westchester and NYC. The property is also close to the Redding Country Club, Community Center, town green and local events and concerts. At $1,599,000, 2 Longwood Drive represents an exceptional opportunity to own substantial living space, private acreage and remarkable flexibility in one of Redding's most desirable locations. For buyers seeking a country estate with exceptional privacy, turnkey condition, premium finishes and convenient NYC access, this is a rare opportunity. Low inventory and this significant new price adjustment make this property particularly compelling. Schedule your private showing to fully appreciate the scale, setting and versatility of 2 Longwood Drive.
Listing Agent
William Raveis Real Estate Brokerage Phone: (203) 505-3375 License #RES.0783899 Listed on: 09/01/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $31,582
Year Built
- Built in 1998
Lot Details
- 2.72 Acre Lot
- Stone Wall
- Garden
- Property is zoned R-2
Home Design
- Colonial Architecture
- Concrete Foundation
- Frame Construction
- Asphalt Shingled Roof
- Clap Board Siding
Interior Spaces
- 6,259 Sq Ft Home
- Open Floorplan
- Central Vacuum
- Ceiling Fan
- 1 Fireplace
- Thermal Windows
- French Doors
- Concrete Flooring
Kitchen
- Gas Cooktop
- Range Hood
- Microwave
- Sub-Zero Refrigerator
- Ice Maker
- Dishwasher
- Wine Cooler
- Wolf Appliances
- Smart Appliances
- Disposal
Bedrooms and Bathrooms
- 4 Bedrooms
- Soaking Tub
- Steam Shower
Laundry
- Laundry on upper level
- Electric Dryer
- Washer
Attic
- Unfinished Attic
- Attic or Crawl Hatchway Insulated
Unfinished Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
- Crawl Space
- Basement Storage
Home Security
- Home Security System
- Smart Lights or Controls
- Smart Locks
- Smart Thermostat
Parking
- 3 Car Garage
- Automatic Garage Door Opener
Outdoor Features
- Covered Deck
- Patio
- Exterior Lighting
Utilities
- Zoned Heating and Cooling
- Heating System Uses Oil
- Power Generator
- Well
- Oil Water Heater
- Fuel Tank Located in Basement
- Cable TV Available
Additional Features
- Modified Wall Outlets
- Energy-Efficient Lighting
- Property is near golf course
Listing and Financial Details
- Assessor Parcel Number 269523
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| 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 | $30,618 | $1,036,500 | $191,800 | $844,700 |
| 2024 | $29,768 | $1,036,500 | $191,800 | $844,700 |
| 2023 | $29,808 | $1,076,500 | $191,800 | $884,700 |
| 2022 | $29,686 | $890,400 | $206,400 | $684,000 |
| 2021 | $4,610 | $914,800 | $206,400 | $708,400 |
| 2020 | $30,042 | $914,800 | $206,400 | $708,400 |
| 2019 | $5,783 | $914,800 | $206,400 | $708,400 |
| 2018 | $29,017 | $914,800 | $206,400 | $708,400 |
| 2017 | $29,042 | $980,500 | $246,600 | $733,900 |
| 2016 | $28,670 | $980,500 | $246,600 | $733,900 |
| 2015 | $28,346 | $980,500 | $246,600 | $733,900 |
| 2014 | $28,346 | $980,500 | $246,600 | $733,900 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 09/01/2026 09/01/26 | For Sale | $1,599,000 | -- | $255 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | -- | -- | |
| Warranty Deed | $840,000 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $550,800 | Stand Alone Refi Refinance Of Original Loan | |
| Previous Owner | $640,000 | No Value Available | |
| Previous Owner | $649,900 | No Value Available |
Source: SmartMLS
MLS Number: 24203563
APN: REDD-000014-000000-000089
- 9 Deacon Abbott Ln S
- 22 Deacon Abbott Ln S
- 28 Winding Brook Ln
- 162 Lonetown Rd
- 33 Old Stagecoach Rd
- 22 Great Pasture Rd
- 24 Costa Ln
- 16 Shady Ln
- 380 Black Rock Turnpike
- 5 Dry River Ct
- 123 Cross Hwy
- 451 Newtown Turnpike
- 471 Newtown Turnpike
- 24 Mark Twain Ln
- 268 Umpawaug Rd
- 286 Black Rock Turnpike
- 31 Granite Ridge Rd
- 206 Umpawaug Rd
- 281 Newtown Turnpike
- 148-B Putnam Park Rd
- 11 John Read Rd
- 150A Lonetown Rd
- 80 Turkey Plain Rd
- 11 van Campen Ln
- 142 Seventy Acre Rd
- 26 Chalburn Rd
- 26 Chalburn Rd
- 8 Winthrop Rd
- 21 Old Redding Rd
- 64 Chestnut St Unit 2
- 36 Kingswood Place
- 16 South St Unit 2
- 9 South St Unit B
- 320 Valley Rd
- 168 Greenwood Ave
- 64 Knollwood Dr Unit 64 Knollwood Drive
- 69 Carol St
- 7 Golden Hill St Unit 2nd floor
- 232 Greenwood Ave Unit 3
- 1 Knollwood Dr
Ask me questions while you tour the home.