2 Longwood Drive
Redding, Connecticut 06896
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 6,259
- Acres
- 2.72
- Year Built
- 1998
- Neighborhood
- Gallows Hill
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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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.
Key Facts
- City/Town
- Redding
- Neighborhood
- Gallows Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1998
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 4 full · 1 half
- Living Area
- 6,259 sq ft
- Lot Size
- 2.72 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $31,582 / Annually
Market Snapshot
The Redding Market
Single Family · trailing 12 months
Active Listings
23
14 under contract
Median List Price
$1.15M
23 active listings
Median Closed Price
$955,000
99 sales
Median Days on Market
68
23 active listings
Median $ / Sq Ft
$284
23 active listings
Sale-to-List Ratio
100.0%
99 sales
How this home compares
List Price
$1.60M
vs $1.15M median
39.0% above median
Price / Sq Ft
$255
vs $284 median
10.2% below median
Days on Market
0 days
vs 68 days median
68 days fresher than median
Based on 23 active and 99 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of September 1, 2026.
Location
2 Longwood Drive, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$8,220
- Property Taxes$2,632
- Insurance$533
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Redding
- Neighborhood
- Gallows Hill
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1998
- New Construction
- No/Resale
- Living Area
- 6,259 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral AirZoned
- Fireplaces
- 1
- Laundry
- Upper Level
- Laundry Location
- 2nd floor hallway.
- Appliances
- Gas CooktopMicrowaveRange HoodRefrigeratorFreezerSubzeroIcemakerDishwasherDisposalWasherElectric DryerWine Chiller
- Basement
- FullUnfinishedStorageInterior AccessConcrete Floor
- In-Law Apartment
- YesUpper Level
- Interior Features
- Auto Garage Door OpenerCable - Pre-wiredCentral VacuumOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 2.72 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Garden AreaLightingCovered DeckStone WallFrench DoorsPatio
- Lot Description
- SecludedLightly WoodedDrySloping LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $31,582 / Annually
- Days on Market
- 0
- MLS #
- 24203563
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/1/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/1/2026 at 6:21 PM UTC.