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$1,999,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 1 Full Bath
  • 4 Partial Baths
  • 4,016 Sq. Ft.
  • Updated 2 days ago
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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.

Full Property Details for 445 Orange St

General

  • Price: $1,999,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24181566
  • Updated: 6/18/2026
  • Added to Site: 8 day(s) ago

Interior

  • Number of Rooms: 13
  • Interior Features: Security System
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 1
  • Half Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Bay/Bow Window, Wall/Wall Carpet, 19 x 16, Upper
  • Bedroom 1: Bedroom - Fireplace, Wall/Wall Carpet, 17 x 16, Upper
  • Bedroom 2: Bedroom - Wall/Wall Carpet, 19 x 23, Upper
  • Bedroom 3: Bedroom - Fireplace, Wall/Wall Carpet, 22 x 12, Upper

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, 9 ft+ Ceilings, Wall/Wall Carpet, 20 x 16, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, 12 x 10, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Fireplace, Wall/Wall Carpet, 17 x 14, Main
  • Office: Office - 9 ft+ Ceilings, Wall/Wall Carpet, 9 x 13, Main
  • Study: 9 ft+ Ceilings, Fireplace, Half Bath, Wall/Wall Carpet, 14 x 10, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, 17 x 15, Lower
  • Rec Room: 17 x 15, Lower
  • Other Room 1: Other, 10 x 23, Lower
  • Other Room 2: Other, 17 x 15, Lower

Exterior

  • Color: Red brick

Parking

  • Total Spaces: 12
  • Parking: Paved

Location

  • County: New Haven
  • Neighborhood: East Rock
  • Driving Directions: Trumbull to Orange

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: East Rock

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Upright Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Other
  • Construction Status: No/Resale
  • Exterior Const.: Brick
  • Basement Desc.: Full, Fully Finished
  • Roof: Flat
  • Attic: Yes
  • Square Feet: 4,016
  • Above Ground: 4,016 Sq. Ft.
  • Year Built: 1858

Lot Features

  • Lot Size (Acres): 0.22
  • Zoning: RM2
  • Lot Description: Level Lot

Green Features

  • Energy Features: Extra Insulation, Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $504,140
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1246111

Listed by Pearce Real Estate, Wojtek Borowski and Pearce Real Estate, Bradley Fleming

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Listing agents

— 445 Orange St —

  • Wojtek Borowski

    Pearce Real Estate

  • Bradley Fleming

    Pearce Real Estate

Agent Contact: (203) 314-0571 Office Contact: (203) 776-1899

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 445 Orange St

School District:New Haven School District
NameGradesDistance
East Rock Community Magnet School
133 Nash Street, New Haven, CT 06511
PK-80.8 mi
Wilbur Cross High School
181 Mitchell Drive, New Haven, CT 06511
9-121 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 445 Orange St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/15/2026
Listed
$1,999,000
399.75%
MLS
11/22/2000
Sold
$400,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 445 Orange St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$19,863
2%
$504,140
—
2023
$19,409
3%
$504,140
—
2023
$18,754
-6%
$504,140
—
2022
$20,040
12%
$504,140
24%
2021
$17,852
—
$406,840
—
2020
$17,852
2%
$406,840
—
2019
$17,486
—
$406,840
—
2018
$17,486
11%
$406,840
—
2017
$15,737
—
$406,840
8%
2016
$15,697
—
$377,790
—
2015
$15,697
—
$377,790
—
2014
$15,697
2%
$377,790
—
2011
$15,414
—
$377,790
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Pearce Real Estate, Wojtek Borowski and Pearce Real Estate, Bradley Fleming

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445 Orange Street, New Haven, CT 06511 (MLS# 24181566) is a Single Family property with 4 bedrooms, 1 full bathroom and 4 partial bathrooms. 445 Orange Street is currently listed for $1,999,000 and was received on June 12, 2026. Want to learn more about 445 Orange Street? Do you have questions about finding other Single Family real estate for sale in New Haven? You can browse all New Haven real estate or contact a Coldwell Banker agent to request more information.

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