Active

445 Orange Street

New Haven, CT 06511
Mark as Favorite
Bed 4

Bed

Bath 5

Bath

SqFt4,016

Sqft

Acres0.22

Acre(Lot)

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 Turn pike 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.

Read More Expand

Detail Ic Property Details

Property Type : Residential

Price : $1,999,000

AD Id : 84767820

MLS Id : 24181566

Beds : 4

Lot Size : 0.22 Acre

Living Area Size : 4,016

Year Built : 1858

County : New Haven

  • Map Map

Map

Map What's Nearby

Map Nearby Areas

Feature Features

  • Bedroom Information

    Total beds: 4

    Bathroom Information

    Total Baths: 5 Full Baths: 1 Half Baths: 4

    Room Information

    Rooms Total: 13 Has Basement: Yes Basement: Full, Finished
  • Interior Features

    Appliances: Dishwasher, Microwave, Range, Oven, Refrigerator, Range Hood
  • Heating & Cooling

    Has Heating: Yes Heating: Natural Gas, Forced Air Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 1858 Building Area Total: 4016 Construction Materials: Brick Private Pool: No

  • Lot Information

    Lot Size Acres: 0.22 Lot Description: Level

  • Listing Price Information

    Listing Price: $1999000

  • Tax Information

    Parcel Number: 1246111 Annual Tax: $19863

  • School Information

    Elementary School: Per Board of Ed
    Junior High School:
    Senior High School: Per Board of Ed
  • Location Information

    Direction: Trumbull to Orange WaterSource: Public Security Features: Security System
Sell a home like this and save $119,441 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Images
Loading, please wait...

Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
174 Weybosset Street, New Haven, CT, 06511 $357,000 4 2 1,344 1,344 SqFt
1025 Townsend Avenue, New Haven, CT, 06511 $460,000 4 2 1,555 1,555 SqFt
75 Nash Street, New Haven, CT, 06511 $599,000 3 2 1,200 1,200 SqFt
216 Saint John Street, New Haven, CT, 06511 $899,900 4 3 2,338 2,338 SqFt
125 Linden Street, New Haven, CT, 06511 $795,000 4 3 1,838 1,838 SqFt
29-A Eld Street, New Haven, CT, 06511 $530,000 3 2 1,088 1,088 SqFt
475 Whitney Avenue, New Haven, CT, 06511 $2,100,000 -- -- 6,284 6,284 SqFt
100 York Street #16J, New Haven, CT, 06511 $129,000 1 1 652 652 SqFt
100 York Street #7E, New Haven, CT, 06511 $198,000 2 1 897 897 SqFt
100 York Street #6A, New Haven, CT, 06511 $89,500 1 1 654 654 SqFt

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. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 06/18/2026 @ 05:17

MLS: 24181566 LISTED BY: Bradley Fleming, Pearce Real Estate SOURCE: SmartMLS

Selling? Save $119,441 when you sell a home like this

Tour with a ByOwner Agent