99 Orange Street
New Haven, Connecticut 06510
- Beds
- 8
- Baths
- 8
- SqFt
- 11,545
- Acres
- 0.08
- Year Built
- 1900
- Neighborhood
- Wooster Square
- Property Type
- Multi-Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
69
62 under contract
Median List Price
$575,000
69 active listings
Median Closed Price
$480,000
297 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: indicative defaultsper 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
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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.