2 Longwood Drive
Redding, Connecticut 06896
Reduced from $1,795,000
- 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
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
***Rare turn-key opportunity at an unbeatable price point*** For buyers seeking exceptional craftmanship, serenity, a strong sense of community, award winning schools and uncompromised value. 2 Longwood Drive is a rare opportunity to purchase a 6,200+ square foot luxury home in southern Redding below recent comparable sales. Experience the exceptional lifestyle that has made Redding one of Fairfield County's most desirable towns for discerning buyers. Known for its scenic landscapes, extensive open space, award-winning parks, the Redding Country Club, and highly regarded public schools, Redding offers an unmatched quality of life just over an hour from Manhattan. With convenient access to Metro-North stations in Westport, Wilton, and West Redding, commuting and weekend travel are effortless. This 6,259 square foot custom built and meticulously maintained colonial is a must see, perfectly positioned on 2.72 professionally landscaped acres in one of Redding's most sought-after neighborhoods. Surrounded by mature trees, rolling lawns, and classic New England charm, the property provides a peaceful retreat while remaining just minutes from Redding schools, hiking trails, top-rated restaurants, shopping, cultural attractions, and the neighboring towns of Ridgefield, Westport, and Wilton.
Key Facts
- City/Town
- Redding
- Neighborhood
- Gallows Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1998
- Days on Market
- 67 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
- $30,618 / Annually
Market Snapshot
The Redding Market
Single Family · trailing 12 months
Active Listings
24
24 under contract
Median List Price
$1.26M
24 active listings
Median Closed Price
$947,500
96 sales
Median Days on Market
54
24 active listings
Median $ / Sq Ft
$296
24 active listings
Sale-to-List Ratio
100.0%
96 sales
How this home compares
List Price
$1.75M
vs $1.26M median
38.5% above median
Price / Sq Ft
$279
vs $296 median
5.7% below median
Days on Market
67 days
vs 54 days median
13 days longer than median
Based on 24 active and 96 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of July 28, 2026.
Location
2 Longwood Drive, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$8,897
- Property Taxes$2,552
- Insurance$582
- 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
- $30,618 / Annually
- Days on Market
- 67
- MLS #
- 24177771
- 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 7/28/2026. 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 7/28/2026 at 6:15 AM UTC.