286 Black Rock Turnpike

Redding, CT 06896

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.

Listing courtesy of Nora Ryan of Houlihan Lawrence WD Office Phone: (203) 787-7800 Broker Contact: (203) 410-5939



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Last checked: 2026-09-10 11:51 PM UTC.