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.
Listing Provided Courtesy of Wojtek Borowski at Pearce Real Estate
Property Details
Price:
$1,999,000
MLS #:
24181566
Status:
Active
Beds:
4
Baths:
5
Type:
Single Family
Neighborhood:
eastrock
Listed Date:
Jun 12, 2026
Finished Sq Ft:
4,016
Lot Size:
9,583 sqft / 0.22 acres (approx)
Year Built:
1858
See this Listing
Schools
Elementary School:
Per Board of Ed
High School:
Per Board of Ed
Interior
Exterior
Financial
Map
Community
- Address445 Orange New Haven CT
- NeighborhoodEast Rock
- CityNew Haven
- CountyNew Haven
- Zip Code06511
Subdivisions in New Haven
Market Summary
Current real estate data for Single Family in New Haven as of Aug 07, 2026
87
Single Family Listed
71
Avg DOM
261
Avg $ / SqFt
$463,344
Avg List Price
Property Summary
- 445 Orange New Haven CT is a Single Family for sale in New Haven, CT, 06511. It is listed for $1,999,000 and features 4 beds, 5 baths, and has approximately 4,016 square feet of living space, and was originally constructed in 1858. The current price per square foot is $498. The average price per square foot for Single Family listings in New Haven is $261. The average listing price for Single Family in New Haven is $463,344. To schedule a showing of MLS#24181566 at 445 Orange in New Haven, CT, contact your Century 21 AllPoints Realty agent at (203) 802-7252.
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445 Orange
New Haven, CT


