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99 Orange Street

New Haven, Connecticut 06510

ACTIVE$3,725,000
Beds
8
Baths
8
SqFt
11,545
Acres
0.08
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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About This Home

Welcome to The Orange Street Collection, a mixed-use hospitality and residential investment opportunity located in the heart of Downtown New Haven. Positioned steps from Yale University, this asset combines immediate income with meaningful long-term upside in one of the city's most active corridors. The property features over 5,000 square feet of restaurant space across the main and lower levels, including two full kitchens and a flexible layout suited for a flagship dining concept, dual operators, or a hospitality-driven reposition. The lower level offers additional potential for lounge, speakeasy, or private event use. Above, eight residential units provide stabilized income and consistent cash flow, creating built-in diversification and downside protection. This is a rare opportunity to acquire a true mixed-use downtown asset with lease-up potential, strategic location advantages, and strong fundamentals driven by proximity to Yale University, surrounding retail, and vibrant nightlife. Ideal for investors, 1031 exchange buyers, or owner-operators seeking both income and long-term positioning in a growing urban corridor.

Key Facts

City/Town
New Haven
Neighborhood
Wooster Square
Property / Style
Multi-Family · Units on different Floors
Year Built
1900
Days on Market
170 days
Beds
8
Baths
8 full
Living Area
11,545 sq ft
Lot Size
0.08 acres
Property Taxes
$49,270 / Annually

Market Snapshot

The New Haven Market

Multi-Family · trailing 12 months

Median Days on Market

43

69 active listings

Median $ / Sq Ft

$202

69 active listings

Sale-to-List Ratio

100.1%

297 sales

How this home compares

List Price

$3.73M

vs $575,000 median

6.5× the median

Price / Sq Ft

$323

vs $202 median

59.9% above median

Days on Market

170 days

vs 43 days median

127 days longer than median

Based on 69 active and 297 closed sales (trailing 12 mo) of multi-family in New Haven. Source: SmartMLS · As of August 26, 2026.

Location

99 Orange Street, New Haven, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: indicative defaults
$24,479

per month

  • Principal & Interest$19,131
  • Property Taxes$4,106
  • Insurance$1,242
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
New Haven
Neighborhood
Wooster Square
County
New Haven

Residence

Property Type
Multi-Family
Subtype
Other
Style
Units on different Floors
Year Built
1900
New Construction
No/Resale
Living Area
11,545 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
ElectricNatural Gas
Cooling
Heat PumpZoned
Laundry
Washer/Dryer Some Units
Basement
FullFull With Walk-Out

Exterior & Lot

Lot Size
0.08 acres
Zoning
BD1
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Brick
Roof
Flat
Foundation
Concrete
Exterior Features
Awnings
Lot Description
City Views

Listing & Financials

Property Taxes
$49,270 / Annually
Days on Market
170
MLS #
24158335
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Michael Spindler

(347) 419-2250

Real Broker CT

(413) 231-6114

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/26/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 8/26/2026 at 9:01 PM UTC.