New

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$1,999,000

For Sale

8 days ago

445 Orange St, New Haven, CT

House

MLS® 24181566

4 Bed

5 Bath

4016 sqft

12 Parking

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 4016 sqft

Garage

Taxes $19,863

Days Active 7

Lot Size 0.22 Acres

Approx. Age 1858

Avg. Price Per Sqft $497

MLS® Number 24181566

Property Address: 445 Orange St, New Haven, CT, 06511-6202

Average square foot calculated using Size range provided by listing agent.

Description

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 and a large common area. 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. Located right on Yale Shuttle line. 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

MLS® Number24181566

Laundry Level

Central VacNo

FireplaceNo

Acreage

Exterior

Garage

Approx. Age1858

BasementFull, Fully Finished

DrivewayPaved

Garage Spaces

HeatNatural Gas, Hot Air

A/CCentral Air

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Jun 12, 2026List Date

$1,999,000List Price

-End Date

Not Sold YetSold Price

For Rent

Jun 15, 2026List Date

$1,999,000List Price

Commute

Commute

Starting Address

Destination Address

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