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445 Orange Street, New Haven, CT 06511

Single Family For Sale

$1,999,000
$498/sqft
445 Orange Street, New Haven, CT
Active
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4
Bedrooms
5
Bathrooms
4,016
Sq Ft
0.22
Acres
1858
Year Built

About This Home

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.

Listed by Bradley Fleming (203) 314-0571 with Pearce Real Estate (203) 776-1899

Listing Snapshot

Price $1,999,000 Days on Our Site 4 days
Property Tax $19,863/yr Style Colonial,Other
Year Built 1858 Total Sq Ft 4,016
Lot Size 0.22 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 1
Total Rooms 13 Half Baths 4

Key Features

Interior
  • Security System
Appliances
  • Oven/Range
  • Microwave
  • Range Hood
  • Refrigerator
  • Dishwasher
Nearby
  • Library
  • Medical Facilities
  • Park
  • Public Transportation
  • Tennis Courts
  • Walk to Bus Lines

Structure & Parking

Construction Brick
Roof Flat
Garage Type Paved

Systems & Utilities

Heat Hot Air
Fuel Natural Gas
Cooling Central Air
Hot Water Upright Tank
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $1,655/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Jun 12, 2026 Listed $1,999,000

Frequently Asked Questions

How much does 445 Orange Street in New Haven, CT cost?
This property is listed at $1,999,000, which works out to $498 per square foot.
How many bedrooms does 445 Orange Street have?
This home has 4 bedrooms and 5 bathrooms.
What is the square footage of 445 Orange Street?
The home is 4,016 square feet, situated on 0.22 acres.
When was 445 Orange Street in New Haven built?
This property was built in 1858.
Is 445 Orange Street, New Haven, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 445 Orange Street, New Haven in?
This home is served by the New Haven public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 445 Orange Street, New Haven, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Bradley Fleming · (203) 314-0571

Pearce Real Estate · (203) 776-1899

MLS# 24181566 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Jun 15, 2026 4:05 AM UTC