445 Orange Street

A rare opportunity to own one of New Haven's most distinguished mid-19th century landmarks. Believed to have been designed by renowned architect Henry Austin for prominent New Haven physician Dr. William DeForest in 1858, this stately Greek Revival brick residence occupies a prominent site in the southern section of the coveted East Rock neighborhood. Meticulously restored by the current owner, The Winchester House LLC, the property showcases exceptional craftsmanship and an extraordinary collection of original architectural details. Soaring 11-foot ceilings, original plaster crown moldings, impeccable millwork, elegant arched openings, and graceful bay windows reflect the grandeur of the period. The remarkable grand staircase, relocated from the historic Eli Whitney House on Hartford Turnpike in Hamden, serves as a dramatic architectural centerpiece. Historically, the exterior was finished in scored stucco designed to resemble finely cut ashlar stone, a distinctive detail that speaks to the sophistication of the original design. Currently configured as an elegant law office, the property could be readily returned to a magnificent single-family residence while also offering exceptional potential for professional offices, institutional use, or a live/work environment, subject to applicable zoning requirements. The impressive formal entry foyer opens to a gracious reception hall centered around an intricate period fireplace. Beyond, the elegant front parlor is enhanced by an arched alcove and bay window that fills the room with natural light. Additional formal rooms provide outstanding spaces for living, entertaining, or offices. The main level also includes a kitchen and two additional offices. The second floor offers three expansive offices, including an impressive conference room, each featuring the same remarkable scale and architectural character found throughout the home. The fully finished lower level adds nearly 1,000 square feet of functional space with three additional offices, a large common area, and a unique circular room ideally suited for a wine cellar, tasting room, archives, or private retreat. Outside, the property offers the rare convenience of twelve off-street parking spaces, an exceptional amenity for either residential or professional use. Ideally located just minutes from Yale University, downtown New Haven, East Rock Park, hospitals, museums, and acclaimed restaurants, the property also provides easy access to I-95, I-91, Union Station, and Tweed New Haven Airport. New York City is approximately 90 minutes away by rail or car. Combining architectural significance, meticulous restoration, modern functionality, and an exceptional location, this is a truly one-of-a-kind offering. See MLS 24183695 for commercial listing