445 Orange Street | New Haven East Rock

$1,999,000 | 5 Baths (1 Full, 4 Half) | 4,016 Sq. Ft.

Exceptional opportunity to own a distinguished commercial property located in South part of East Rock, on the edge of Downtown. Built in 1858 and attributed to renowned architect Henry Austin for prominent New Haven physician Dr. William DeForest, this landmark Greek Revival brick building combines historic character with outstanding functionality for professional or commercial use. The first floor offers an 11ft ceilings, with a large reception area, elegant offices, conference or meeting rooms, and a kitchen. The second floor includes three spacious offices, including a large conference room that has been wired for high-speed video conferences. The fully finished lower level provides nearly 1,000 square feet of additional usable space with three offices and a large common work area. With 12 off-street parking spaces, a highly visible location, and flexible layout, this property is ideally suited for a law firm, financial services, architectural or engineering practice, medical or consulting offices, nonprofit headquarters, or other professional uses. Its prestigious setting and remarkable architectural character create an exceptional environment for clients and staff alike. Meticulously restored by the current owner, The Winchester House LLC, the property features soaring 11-foot ceilings, original plaster crown moldings, exceptional woodwork, elegant arched openings, bay windows, and a magnificent SmartMLS 24183695

Directions to property: Trumbull to Orange

MLS Listing ID: 
SmartMLS 24183695
Building Details
Details about the building on a property.
Year Built: 
1858
Living Area: 
4,016
Construction
Roof: 
Flat
Room Details
Details about the rooms in the building.
Total Rooms: 
0
Total Bedrooms: 
0
Total Bathrooms: 
5
Total Full-Bathrooms: 
1
Total Half-Bathrooms: 
4
Utilities
Information about utilities available on the property.
Heating System: 
Hot Air
Heating System Fuel: 
Gas In Street
Cooling System: 
Central Air
Water Source: 
Public Water Connected
Sewer: 
Public Sewer Connected
Lot/Land Details
Details about the lots and land features included on the property.
Acres: 
0.22
Waterfront: 
0
Lot Features
Total Parking Spaces: 
12
Garage: 
Paved, Off Street Parking
Public Record
Parcel Number: 
1246111
Annual Tax: 
$19,863.00
Property Zoning: 
RM2
Listing Dates
Dates involved in the transaction.
Listing Entry Date/Time: 
6/15/2026
Contract Details
Details about the listing contract.
Possession: 
Negotialble
Listing Participants
Participants (agents, offices, etc.) in the transaction.
Listing Agent Name: 
Bradley Fleming
Listing Co-Agent Name: 
Wojtek Borowski
Listing Office Name: 
Pearce Real Estate
Listing Co-Office Name: 
Pearce Real Estate