286 Black Rock Turnpike

Redding, CT
$ 1,329,000 Beds 5 Baths 4.5 Sq 4,158 Virtual Tour
Monthly Estimate* How much can I afford?

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. The beautifully landscaped grounds provide a private retreat enhanced by brick walkways, stone retaining walls, mature trees, and a gated driveway with additional parking. A spectacular 1,000-square-foot stone patio with a working stone fireplace offers an exceptional setting for outdoor entertaining, dining, and relaxation. The property's 720-square-foot barn with loft provides three-car garage capacity, workshop space, storage, and potential for a studio or hobby area. Additional amenities include a storage shed and basketball court, adding to the property's versatility and appeal. Meticulously maintained and thoughtfully updated, the home features oil-fired forced-air heat, central air conditioning, a new oil tank, updated 200 amp electrical service, new balcony roof, and new cedar fencing enhancing privacy and curb appeal. This extraordinary Greek Revival estate offers a rare combination of historic character, modern comfort, privacy, and exceptional outdoor amenities. Move-in ready and rich in history, it presents a unique opportunity to own one of Connecticut's treasured historic properties while enjoying the conveniences of today's lifestyle. Located in Fairfield County, Redding is a picturesque New England community known for its natural beauty, privacy, and strong sense of community. Surrounded by rolling hills, preserved open space, and miles of scenic trails, Redding offers a peaceful country lifestyle with convenient access to excellent schools, local amenities, neighboring towns, and commuter routes to New York City.

Single Family

  • Price
  • $ 1,329,000
  • City
  • Redding
  • Bedrooms
  • 5
  • Full Bathrooms
  • 4
  • County
  • Fairfield
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 2.37 Acres
  • Zip
  • 06896
  • Sqr Footage
  • 4,158
  • Year Built
  • 1708
  • Taxes
  • $ 25982
  • Style
  • MLS#
  • 24191583
Listed By: Nora Ryan 203-410-5939 with Houlihan Lawrence WD. - (203) 787-7800
Data Source: Smart MLS

Features

General

Zoning R-2
Neighborhood Redding Center
County Fairfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 2.37
Directions GPS friendly.
High School Joel Barlow
City Redding
Elementary School Redding
Sq Ft Total 4158
DOM 65
Year Built 1708
Exclusions Please see inclusion/exclusion form.
Style Antique
Year Built Source Public Records
Energy Features Extra Insulation,Generator Ready,Programmable Thermostat,Storm Doors

Interior Features

Cooling System Ceiling Fans,Central Air,Whole House Fan,Zoned
Total Rooms 12
Basement Description Full,Heated,Storage,Interior Access,Partially Finished,Liveable Space,Full With Walk-Out

Exterior Features

Water Source Private Well
Lot Description Fence - Wood,Fence - Partial,Fence - Rail,Treed,Dry,Sloping Lot,Professionally Landscaped
Color Tan

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Redding Elementary School
Middle School Unknown Middle School
High School Joel Barlow High School

Price History

7/15/2026 Listed $1,329,000

Property vs Zip Code Average in 06896

Price
AVG $1.39M
$1.33M
Taxes
AVG $19,626
$25,982
Year Built
AVG 1952
1708

286 Black Rock Turnpike Redding, CT is a Single Family Home for sale at $1329000 with 4158 sqft and a lot size of 2.37 Acres Acre(s). 286 Black Rock Turnpike Redding has 5 bedrooms, 4 baths and was built in 1708. The property's zip code is 06896 which is in Redding, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.