$1,999,000

445 Orange St New Haven, CT 06511

East Rock Neighborhood

Estimated payment $12,547/month

Total Views 28,426
4 Beds
5 Baths
4,016 Sq Ft
$498 Price per Sq Ft

Highlights

  • Colonial Architecture
  • Attic
  • Thermal Windows
  • Property is near public transit and bus stop
  • 4 Fireplaces
  • Crown Molding

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.

Listing Agent

Wojtek Borowski

Pearce Real Estate Brokerage Phone: (203) 314-0571 License #REB.0758965 Listed on: 06/12/2026

Pearce Real Estate

Co-Listing Agent

Bradley Fleming

Pearce Real Estate Brokerage Phone: (203) 314-0571 License #RES.0834375

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $19,863

Year Built

  • Built in 1858

Lot Details

  • 9,583 Sq Ft Lot
  • Level Lot
  • Property is zoned RM2

Parking

  • 12 Parking Spaces

Home Design

  • Colonial Architecture
  • Flat Roof Shape
  • Brick Exterior Construction
  • Flat Tile Roof
  • Masonry Siding
  • Masonry

Interior Spaces

  • 4,016 Sq Ft Home
  • Crown Molding
  • 4 Fireplaces
  • Thermal Windows
  • Finished Basement
  • Basement Fills Entire Space Under The House
  • Home Security System

Kitchen

  • Oven or Range
  • Range Hood
  • Microwave
  • Dishwasher

Bedrooms and Bathrooms

  • 4 Bedrooms

Attic

  • Walkup Attic
  • Unfinished Attic

Utilities

  • Central Air
  • Heating System Uses Natural Gas
  • Programmable Thermostat

Additional Features

  • Energy-Efficient Insulation
  • Property is near public transit and bus stop

Community Details

  • Public Transportation

Listing and Financial Details

  • Assessor Parcel Number 1246111

Home Details

Home Type

Single Family

Est. Annual Taxes

$19,863

Year Built

Built in 1858

Lot Details

9,583 Sq Ft Lot

Listing Details

  • Neighborhood: East Rock
  • Property Type: Single Family For Sale
  • Style: Colonial, Other
  • Sq Ft Est Heated Above Grade: 4016
  • Total Sq Ft: 4016
  • Year Built: 1858
  • New Construction: No/Resale
  • Nearby Amenities: Library, Medical Facilities, Park, Public Transportation, Tennis Courts, Walk to Bus Lines
  • Remarks Public Addendum: Beyond, the elegant front parlor is enhanced by an arched alcove and bay window that fills the room with natural light. Additional formal rooms provide outstanding spaces for living, entertaining, or offices. The main level also includes a kitchen and two additional offices. The second floor offers three expansive offices, including an impressive conference room, each featuring the same remarkable scale and architectural character found throughout the home. The fully finished lower level adds nearly 1,000 square feet of functional space with three additional offices and a large common area. Outside, the property offers the rare convenience of twelve off-street parking spaces, an exceptional amenity for either residential or professional use. Ideally located just minutes from Yale University, downtown New Haven, East Rock Park, hospitals, museums, and acclaimed restaurants, the property also provides easy access to I-95, I-91, Union Station, and Tweed New Haven Airport. New York City is approximately 90 minutes away by rail or car. Located right on Yale Shuttle line. Combining architectural significance, meticulous restoration, modern functionality, and an exceptional location, this is a truly one-of-a-kind offering. See MLS 24183695 for commercial listing
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Directions: Trumbull to Orange
  • Street Type: Street
  • Office Attribution Contact: (203) 776-1899
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 4
  • Total Bathrooms: 5
  • Full Bathrooms: 1
  • Half Bathrooms: 4
  • Fireplaces: 4
  • Attic Description: Unfinished, Walk-up
  • Basement Description: Full, Fully Finished
  • Interior Amenities: Security System
  • Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher
  • Attic: Yes

Exterior Features

  • Exterior Siding: Brick
  • Foundation Type: Masonry
  • Roof Information: Flat
  • Waterfront Description: Not Applicable
  • Swimming Pool: No
  • Construction Description: Brick

Garage/Parking

  • Total Parking Spaces: 12
  • Garage And Parking: Paved

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Upright Tank
  • Water Source: Public Water Connected
  • Sewer: Public Sewer Connected

Green Features

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

Lot Info

  • Acres: 0.22
  • Lot Description: Level Lot
  • Zoning: RM2
  • Parcel #: 1246111

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 19863

MLS Schools

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

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
06/15/2026 06/15/26 For Sale $1,999,000 -- $498 / Sq Ft
Source: SmartMLS

About the Listing Agent

Wojtek Borowski
Wojtek Borowski

Pearce Real Estate

(475) 335-8825

Section Image

Wojtek has been a New Haven resident for over 30 years. He has over 22 years of real estate experience helping sellers and buyers with their real estate needs. His personal approach, close attention to detail and clients’ personal needs are his top priorities.

Professional

Wojtek specializes in communities in Greater New Haven and along the shoreline. His expertise in historic/antique homes, contemporary architecture, multi-family, condominiums, investment real estate, and rentals

View Wojtek's Profile

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Source: SmartMLS

MLS Number: 24181566

SmartMLS
Connecticut New Haven County New Haven 06511 East Rock

445 Orange St, New Haven, CT

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

SmartMLS IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Wojtek Borowski
Wojtek Borowski
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Pearce Real Estate
(475) 335-8825
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