286 Black Rock Turnpike
Redding, Connecticut 06896
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,158
- Acres
- 2.37
- Year Built
- 1708
- Neighborhood
- Redding Center
- 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
The Rebecca Denison Homestead, established in 1708 with the present Greek Revival residence built in 1824, is a rare historic offering that beautifully combines architectural significance with modern-day living. Listed with the Connecticut State Historical Commission, this exceptional property is privately situated on 2.37 park-like acres and showcases timeless craftsmanship, meticulous maintenance, and thoughtful updates throughout. Offering more than 4,100 square feet of living space, this distinguished 12 room residence features 5 bedrooms, 4 updated full baths, and an updated half bath. Details include the original historic front door, exposed beams, paned windows, hardwood floors, five fireplaces (one gas fireplace in the family room and four wood-burning fireplaces), and abundant natural light throughout. Designed for both elegant entertaining and comfortable everyday living, the home offers gracious living and dining spaces with exceptional versatility, including a private entrance to a potential home office, study, or guest suite with Jotul cast iron gas stove. The chef's kitchen serves as the heart of the home, featuring high-end appliances, modern finishes, a large center island, generous pantry with prep sink, additional refrigerator, and abundant workspace. The kitchen flows seamlessly to the expansive deck, creating a wonderful indoor-outdoor living experience.
Key Facts
- City/Town
- Redding
- Neighborhood
- Redding Center
- Property / Style
- Single Family · Antique
- Year Built
- 1708
- Days on Market
- 13 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 4,158 sq ft
- Lot Size
- 2.37 acres
- Garage / Parking
- 3 garage · 8 total
- Property Taxes
- $25,189 / 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
$1.33M
vs $1.26M median
5.5% above median
Price / Sq Ft
$320
vs $296 median
8.1% above median
Days on Market
13 days
vs 54 days median
41 days fresher 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
286 Black Rock Turnpike, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$6,776
- Property Taxes$2,099
- Insurance$443
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Redding
- Neighborhood
- Redding Center
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Antique
- Year Built
- 1708
- New Construction
- No/Resale
- Living Area
- 4,158 sq ft
- Below Grade
- 370 sq ft
Schools
- Elementary
- Redding
- Middle
- Per Board of Ed
- High
- Joel Barlow
Interior
- Heating
- Hot Air
- Heat Fuel
- OilPropane
- Cooling
- Ceiling FansCentral AirWhole House FanZoned
- Fireplaces
- 5
- Laundry
- Lower Level
- Appliances
- Gas RangeMicrowaveRange HoodRefrigeratorSubzeroDishwasherWasherDryer
- Basement
- FullHeatedStorageInterior AccessPartially FinishedLiveable SpaceFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - AvailableCentral Vacuum
Exterior & Lot
- Lot Size
- 2.37 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spaces8 total parking spacesBarnDetached GaragePavedOff Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Tan
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- BarnLightingPatioBalconyShedFruit TreesPorchDeckGarden Area
- Lot Description
- Fence - WoodFence - PartialFence - RailTreedDrySloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $25,189 / Annually
- Days on Market
- 13
- MLS #
- 24191583
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
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 5:25 AM UTC.