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About This Home
This 4-bedroom, 5-bathroom single family at 445 Orange Street in New Haven, CT is listed for $1,999,000 ($498 per sqft). Built in 1858, the home offers 4,016 sqft of living space on a 0.22 acres lot.
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.
Key Features
- Built in 1858
- 0.22 acre lot
- 12 parking spaces
- Fireplace
Property Details
Amenities
Monthly Cost Estimate
$10,691/mo
20% down · 6.5% · 30 years
Estimates only. Actual payments may vary.
Location
445 Orange Street
New Haven, CT 06511
Features & Amenities
Interior Features
Property Details
Cooling
Appliances
Questions & Answers
This 4-bedroom, 5-bathroom single family at 445 Orange Street is listed at $1,999,000 ($498/sqft). The estimated monthly payment is $8,662 based on 20% down at 6.5% interest.
Key features include: Built in 1858, 0.22 acre lot, 12 parking spaces, Fireplace. Interior Features: Security System.
This property is listed by Bradley Fleming and can be reached at 2033140571 or bfleming@hpearce.com.



