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$3,725,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 8 Total Beds
  • Updated 7 hours ago
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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.

Full Property Details for 99 Orange St

General

  • Price: $3,725,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24158335
  • Updated: Today (3/9/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 17

Rooms

Bathrooms

  • Total Bathrooms: 8
  • Full Bathrooms: 8

Bedrooms

  • Total Bedrooms: 8

Other Rooms

  • Laundry: Washer/Dryer Some Units

Exterior

  • Exterior Features: Awnings

Location

  • County: New Haven
  • Neighborhood: Wooster Square
  • Driving Directions: GPS

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Community Name: Wooster Square

Heating & Cooling

  • Cooling Type: Heat Pump, Zoned
  • Heating Type: Hot Air, Electric, Natural Gas
  • Heating Fuel: Electric, Natural Gas
  • Water Heater: Domestic

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Units on different Floors
  • Construction Status: No/Resale
  • Exterior Const.: Brick
  • Basement Desc.: Full, Full With Walk-Out
  • Roof: Flat
  • Square Feet: 11,545
  • Above Ground: 11,545 Sq. Ft.
  • Year Built: 1900

Unit Information

Unit 1

  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 2

  • Total Bathrooms: 1

Unit 3

  • Total Bathrooms: 1
  • Bedrooms: 1

Unit 4

  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 5

  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 6

  • Total Bathrooms: 1

Unit 7

  • Full Bathrooms: 1
  • Bedrooms: 1

Unit 8

  • Total Bathrooms: 1
  • Full Bathrooms: 1
  • Bedrooms: 1

Lot Features

  • Lot Size (Acres): 0.08
  • Zoning: BD1
  • Lot Description: City Views

Financial Considerations

  • Assessment Amount: $1,168,860
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1248473

Listed by Real Broker CT, Vantagepoint Properties at Real Broker, Michael Spindler

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Listing agent

— 99 Orange St —

  • Michael Spindler

    Real Broker CT

Agent Contact: (347) 419-2250 Office Contact: (413) 231-6114

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 99 Orange St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/09/2026
Listed
$3,725,000
70.87%
MLS
3/31/2022
Sold
$2,180,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 99 Orange St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$47,514
—
$1,168,860
—
2023
$47,561
3%
$1,168,860
—
2023
$45,983
-6%
$1,168,860
—
2022
$48,964
6%
$1,168,860
16%
2021
$46,189
—
$1,006,950
—
2020
$46,189
2%
$1,006,950
—
2019
$45,283
—
$1,006,950
—
2018
$45,283
16%
$1,006,950
—
2017
$38,949
2%
$1,006,950
9%
2016
$38,241
—
$920,360
—
2015
$38,241
—
$920,360
—
2014
$38,241
2%
$920,360
—
2011
$37,551
—
$920,360
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Real Broker CT, Vantagepoint Properties at Real Broker, Michael Spindler

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99 Orange Street, New Haven, CT 06510 (MLS# 24158335) is a Multi-Family property with 9 units containing 8 bedrooms and 8 full bathrooms. 99 Orange Street is currently listed for $3,725,000 and was received on March 09, 2026. Want to learn more about 99 Orange Street? Do you have questions about finding other Multi-Family real estate for sale in New Haven? You can browse all New Haven real estate or contact a Coldwell Banker agent to request more information.

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