445 Orange Street - New Haven, CT

$1,999,000

Beds

5.00

Baths

4,016

SqFt

0.22

Acres

Pricing Insight: Originally listed for $1,999,000, the price has remained unchanged for approximately 68 days. This property has been on the market for approximately 68 days.

445 Orange Street, New Haven, CT is a 4-bed, 5-bath, 4,016 square foot home built in 1858 , featuring colonial,other architecture.

This home is within the New Haven school district. Local, with nearby schools including Per Board of Ed.

MLS #: 24181566

Offered Price: $1,999,000

Residence Type: Single Family

Architectural Style: Colonial,Other

Living Area: 4,016 Sq. Ft.

Lot Size: 0.22 Acres

Neighborhood: East Rock

County: New Haven

Year Built: 1858

Design & Construction: Brick

Heating: Hot Air

Cooling: Central Air

Garage Spaces: 0

Price per Sq Ft as listed: $498

Estimated Tax: $20,146

Days on Market: 65

$2,475

2 Beds · 1 Baths · 1,200 Sq Ft

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$1,700

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$2,950

3 Beds · 1 Baths · 2,000 Sq Ft

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$2,250

2 Beds · 1 Baths · 897 Sq Ft

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$3,150

2 Beds · 2 Baths · 1,348 Sq Ft

131 Bradley Street, New Haven

$3,600

3 Beds · 2 Baths · 1,553 Sq Ft

506-508 Orange Street, New Haven

Home Automation: Not specified

Energy Features: Extra Insulation, Programmable Thermostat, Thermopane Windows

Solar Contract: Not specified

Heating Fuel: Natural Gas

Fuel Type: Hot Air

Fuel Tank Location: Not specified

Cooling System: Central Air

Hot Water System: Upright Tank

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $498 / Sq. Ft.

Tax assessed value: $504,140

Estimated Tax: $20,146

Architectural Style: Colonial,Other

Design & Construction: Brick

Residence Type: Single Family

Year Constructed: 1858

Living Area: 4,016 Sq. Ft.

Lot Size: 0.22 Acres

Fuel: Natural Gas

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in New Haven
Statistical modeling algorithms

Local Market Context

Active Listings: 422

Average Price: $102,600

Average DOM: 65 days

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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.

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Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 0.2 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

422

Homes For Sale

$102,600

Average List Price

Mechanicals & Utilities: Hot Air • Natural Gas • Central Air • Public Water Connected water • 4 fireplaces

Exterior Features

Exterior Construction: Brick

Roof Type: Flat

Foundation: Masonry

Garage: Paved

Parking: 12 Total

Utilities: Water: Public Water Connected

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New Haven • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

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445 Orange Street, New Haven, Connecticut

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