445 Orange Street, New Haven, CT 06511
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FOR SALE
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445 Orange Street
New Haven, CT 06511

East Rock
  • 4 Beds
  • 3 Baths
  • 4,016 sqft

$1,999,000

Est. Mortgage $13,910/mo*
Get Pre-Qualified

$1,999,000

Est. Mortgage $13,910/mo*
Get Pre-Qualified
4 Beds
3 Baths
4,016 sqft

Home Highlights

Parking
12 Parking Spaces
Climate Control
Heating & Cooling
Price/Sqft
$498
Listed
45 days ago

Local Information

  • Map ViewExplore the area around 445 Orange Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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. 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

Home Details for 445 Orange Street

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 13Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Office, Other, Rec Play Room, Study
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 1Number of Bathrooms (half): 4
Dimensions and Layout
Living Area: 4016 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Water HeaterDishwasherMicrowaveRefrigerator
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 4Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: FlatFoundation: MasonryNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking Spaces: 12Parking: Paved
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4016 Square Feet

Days on Market

Days on Market: 45

Property Information

Year Built
Year Built: 1858
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Other
Building
Construction Materials: BrickNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1246111

Price & Status

Price
List Price: $1,999,000Price Per Sqft: $498
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: New HavenCommunity: East Rock
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Listing Agent
Listing ID: 24181566

Building

Building Area
Building Area: 4016 Square Feet

Community

Community Features: Library, Medical Facilities, Park, Near Public Transport, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 9583.2 sqft

Energy

Energy Efficiency Features: Insulation, Thermostat, Windows

Miscellaneous

BasementMls Number: 24181566Attic: Walk-upAttribution Contact: (203) 314-0571Above Grade Unfinished Area: 4016Activation Date: Mon Jun 15 2026

Additional Information

LibraryMedical FacilitiesParkNear Public TransportTennis Court(s)
Last check for updates: about 6 hours ago
Listing courtesy of Wojtek Borowski, (203) 314-0571
Pearce Real Estate, (203) 314-0571
Bradley Fleming, (203) 314-0571
Pearce Real Estate, (203) 776-1899
Source: Smart MLS, MLS#24181566
Also Listed on Smart MLS.

Market trends in New Haven

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$321K
$20.17KMoM
Sale-to-List Price
100.3%
0.3%MoM
Price per sq ft
$236
$11MoM
Available listings
153
5MoM

Price History for 445 Orange Street

DatePriceEventSource
06/15/2026$1,999,000Listed For SaleSmart MLS #24181566

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Comparable Sales for 445 Orange Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
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Sqft
43 Lincoln Street, New Haven, CT
0.12
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$1,400,000
05/29/26
5
4.5
3,472
12 Lincoln Street, New Haven, CT
0.08
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$1,525,000
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2
2.5
2,585
188 Bishop Street, New Haven, CT
0.35
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$1,630,000
11/07/25
6
3.5
3,799
178 Bradley Street, New Haven, CT
0.04
Single-Family Home
$850,000
07/07/26
2
2
2,116
192 Bishop Street, New Haven, CT
0.35
Single-Family Home
$1,550,000
08/29/25
5
5
3,743
38 Eld Street, New Haven, CT
0.09
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$1,010,000
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3
2
2,344
118 Edwards Street, New Haven, CT
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Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 445 Orange Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

East Rock
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about East Rock

At least 68 Trulia users voted on each feature.

  • 93 % Say there are sidewalks

  • 86 % Say it's dog friendly

  • 80 % Say it's walkable to restaurants

  • 75 % Say kids play outside

  • 74 % Say it's walkable to grocery stores

  • 73 % Say parking is easy

  • 72 % Say streets are well-lit

  • 71 % Say there's holiday spirit

  • 62 % Say yards are well-kept

  • 60 % Say people would walk alone at night

  • 55 % Say car is needed

  • 55 % Say neighbors are friendly

  • 42 % Say there's wildlife

  • 40 % Say there are community events

  • 39 % Say it's quiet

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Fairhaven is a section of New Haven. I live and work near this section. It is not friendly, but they did recently put some speed humps down so that helps with the speeders. "
    2
    Flag
  • Trulia User
    "This area feels very safe and lots of people walk to commute. I love living here, and feel safe as a young woman."
    0
    Flag
  • Trulia User
    "you don't see too many people walking their dogs like you would in East rock, but there are sidewalks for safety. "
    1
    Flag
  • Nike B.
    " I lived in area an also went to school there. The people are very welcome and friendly I baseball and parks are lovely"
    3
    Flag
  • Penelope L.
    "Plenty of other dog owners walking their dogs and a big dog park under trees and with gravel so not so messy, and my dog loves getting her zoomies out and since there are dogs in the neighborhood she usually has a playmate"
    0
    Flag
  • Abigail L.
    "A lot of pedestrians at all times of day & throughout the year (joggers, dog walkers, etc.). The neighborhood feels very safe even for single people living alone and there are a lot of “eyes on the street.” The neighborhood is older, so sidewalk cracks and some peeling paint is common, but despite the high number of rentals, the houses tend to be well-maintained. Mostly residential, but still plenty to do (a few restaurants/cafes, coffee shops, beer hall, gym, laundromats). Much quieter than downtown. Most street parking doesn’t require a permit. "
    0
    Flag
  • Frank1721
    "you'll be paying $15,000 a year for property taxes and they going to go up more great area for the rest of the city not so great"
    3
    Flag
  • Amelia F.
    "Peace and quiet and it feel safe. But new neighbors are becoming a problem with music. But cops always respond very fast "
    0
    Flag
  • Amelia F.
    "They love that I pick up after my dog and my dog is very quiet and it’s very friendly and most of all that my dog love kids and love chasing squirrels"
    0
    Flag
  • Nikia
    "Neighborhood markets and little shops along with everyone always being out and friendly in the neighborhood. "
    1
    Flag
  • Tradewindllc1
    "The neighborhood is great, it has easy access to restaurants and East Rock Park. Several new businesses have opened within walking distance. East Rock Brewing Company will be opening soon, mActivity Fitness Center on Nicoll St and 136 Restaurant is on Willow St. It has excellent food. The area is filled with professionals, grad students and people who really enjoy living in this area."
    12
    Flag
  • Ctpkrose
    "Sort of pet friendly and easy access to restaurants and easy rock park. Not as friendly as some say crime is on the periphery. So there is a false sense of feeling safe. "
    12
    Flag
  • Ctpkrose
    "Dog friendly... but they lie, only if you sedate your dog could you even exist here. Restaurants are expensive here too. Hubgrub is your friend"
    4
    Flag
  • Ctpkrose
    "Italian and mixed population. Awesome small shops. Good restaurants Lots of trees soooo lonnngggg"
    1
    Flag

LGBTQ Local Legal Protections

Wojtek Borowski, Pearce Real Estate, (203) 314-0571
Agent Phone: (203) 314-0571
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.
445 Orange Street, New Haven, CT 06511 is a 4 bedroom, 5 bathroom, 4,016 sqft single-family home built in 1858. 445 Orange Street is located in East Rock, New Haven. This property is currently available for sale and was listed by Smart MLS on Jun 12, 2026. The MLS # for this home is MLS# 24181566.