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$950,000

  • Sold
  • Closed
  • Multi-Family
  • 5 Total Beds
See This Home
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See This Home
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Step into timeless elegance at 99 Olive Street, a rare Queen Anne Victorian style three-family in the heart of Wooster Square! This striking brick home showcases the best of 19th-century craftsmanship, with its intricate detailing, patterned facade, and beautifully preserved historic character. This lovingly maintained, legal 3 family with a bonus office space, has been thoughtfully updated. The property features a newer roof, rebuilt chimney, updated mechanicals, and recent repointing of the whole brick exterior, preserving its beauty and ensuring long-term integrity! Inside, each spacious unit offers high ceilings, hardwood floors, fireplaces, and large windows that fill the rooms with natural light. Private backyard with garden boxes and community grill is great for entertaining and relaxing in the heart of the city. Separate utilities and flexible layouts make it ideal for both investors and owner-occupants. Enjoy everything Wooster Square has to offer right outside your door- the park, weekend farmers market, cafes, and the legendary Sally's and Pepe's Apizza. Just minutes to Yale, downtown, and Union Station, this home perfectly blends Queen Anne elegance with modern reliability and city convenience. A true Wooster Square gem, full of charm, character, and opportunity.

Full Property Details for 99 Olive St

General

  • Sold For: $950,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24136128
  • Added to Site: 80 day(s) ago

Interior

  • Number of Rooms: 17
  • Fireplace: Yes
  • Number of Fireplaces: 4

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Washer/Dryer All Units

Exterior

  • Color: Brick

Parking

  • Parking: None

Location

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

School Information

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

Community

  • Community Name: Wooster Square

Heating & Cooling

  • Cooling Type: Central Air, Split System, Window Unit
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Tankless Hotwater

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, Unfinished, Storage, Hatchway Access, Interior Access, Concrete Floor, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,885
  • Above Ground: 2,885 Sq. Ft.
  • Year Built: 1870

Unit Information

Unit 1

  • Square Feet: 1152
  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 2

  • Square Feet: 1152
  • Total Bathrooms: 1
  • Bedrooms: 2

Unit 3

  • Square Feet: 921
  • Total Bathrooms: 1
  • Bedrooms: 1

Lot Features

  • Lot Size (Acres): 0.07
  • Zoning: RM2
  • Lot Description: City Views

Financial Considerations

  • Assessment Amount: $477,190
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1245751

Listed by eXp Realty, John Daikus
Sold by Pearce Real Estate, Edgehill Team at Pearce Real Estate, Miguel Perez

Listing agent

— 99 Olive St —

  • John Daikus

    eXp Realty

Agent Contact: (203) 228-3554 Office Contact: (866) 828-3951

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

Schools serving 99 Olive St

School District:New Haven School District
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 99 Olive St

Date
Details
Price
Change
Source
12/05/2025
Sold
$950,000
5.56%
MLS
10/27/2025
Listed
$899,999
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by eXp Realty, John Daikus
Sold by Pearce Real Estate, Edgehill Team at Pearce Real Estate, Miguel Perez

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99 Olive Street, New Haven, CT 06511 (MLS# 24136128) is a Multi-Family property that was sold at $950,000 on December 05, 2025. Want to learn more about 99 Olive 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.