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$775,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,945 Sq. Ft.
  • 2 Car Garage
  • Updated 8 hours ago
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Rare historic Wooster Square compound featuring a detached carriage house and private garden retreat. Opportunities like this seldom come to market in New Haven's iconic Wooster Square Historic District. Built in 1870, this distinguished brick residence offers 3 BR, 2 full baths, and a rare blend of architectural character, flexible living space, and private outdoor living. Behind the historic brick facade, soaring ceilings, original details, and two decorative fireplaces evoke the craftsmanship & charm of a bygone era, while thoughtful updates provide modern comfort, including a remod 2nd bath. The unfinished third floor offers expansion potential and a lookout perch overlooking the neighborhood. The walk-out lower level has been transformed into a cozy cabin-inspired retreat, ideal for entertaining or relaxing, with abundant storage. Set on a fenced corner lot, the property lives like a private compound with mature landscaping, intimate garden spaces, and off-street parking-an unexpected retreat in the heart of the city. The detached carriage house has been extensively upgraded into a cigar lounge-inspired home office & fitness studio, offering flexibility and potential Yale Homebuyer Program eligibility, with the option to convert back to a 2-car gar. Just moments from Wooster Square's cherry blossoms, farmers market, world-famous pizza, Union Station,Yale,Yale NH Hospital, downtown, restaurants, and major highways. Historic. Private. Flexible. Walkable.

Full Property Details for 161 Olive St

General

  • Price: $775,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24187215
  • Updated: Today (7/2/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 8
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Electric Cooktop, Convection Oven

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Full Bath, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Book Shelves, Built-Ins, Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Book Shelves, Breakfast Nook, Granite Counters, Tile Floor, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Fireplace, Hardwood Floor, Main
  • Den: Den - Wall/Wall Carpet, Main
  • Study: Wide Board Floor, Other
  • Laundry: Lower Level

Exterior

  • Exterior Features: Porch
  • Color: Red

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Detached Garage, Off Street Parking, Driveway

Location

  • County: New Haven
  • Neighborhood: Wooster Square
  • Driving Directions: State Street to Olive Street

School Information

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

Community

  • Community Name: Wooster Square

Heating & Cooling

  • Cooling Type: Window Unit
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Tank Size Unknown

Utilities

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

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Brick
  • Basement Desc.: Full, Storage, Partially Finished, Walk-out
  • Roof: Asphalt Shingle, Flat
  • Attic: Yes
  • Square Feet: 1,945
  • Above Ground: 1,845 Sq. Ft.
  • Below Ground: 100 Sq. Ft.
  • Year Built: 1870

Lot Features

  • Lot Size (Acres): 0.07
  • Driveway/Sidewalk: Asphalt
  • Zoning: RM2
  • Lot Description: Fence - Chain Link, Corner Lot

Financial Considerations

  • Assessment Amount: $357,910
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Hydrangea bush by driveway
  • Property ID: 1245917

Listed by Re/Max Rise, Seigel Team at RE/MAX Rise, Marc Seigel and Re/Max Rise, Lauren Seigel-Gross

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Listing agents

— 161 Olive St —

  • Marc Seigel

    Re/Max Rise

  • Lauren Seigel-Gross

    Re/Max Rise

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 161 Olive St

School District:New Haven School District
NameGradesDistance
East Rock Community Magnet School
133 Nash Street, New Haven, CT 06511
PK-81 mi
Wilbur Cross High School
181 Mitchell Drive, New Haven, CT 06511
9-121.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 161 Olive St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/02/2026
Listed
$775,000
159.2%
MLS
8/29/2003
Sold
$299,000
—
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 161 Olive St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,102
2%
$357,910
—
2023
$13,780
4%
$357,910
—
2023
$13,314
-6%
$357,910
—
2022
$14,227
36%
$357,910
50%
2021
$10,490
—
$239,050
—
2020
$10,490
2%
$239,050
—
2019
$10,274
—
$239,050
—
2018
$10,274
11%
$239,050
—
2017
$9,246
-9%
$239,050
-2%
2016
$10,119
—
$243,530
—
2015
$10,119
—
$243,530
—
2014
$10,119
2%
$243,530
—
2011
$9,936
—
$243,530
—
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 Re/Max Rise, Seigel Team at RE/MAX Rise, Marc Seigel and Re/Max Rise, Lauren Seigel-Gross

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161 Olive Street, New Haven, CT 06511 (MLS# 24187215) is a Single Family property with 3 bedrooms and 2 full bathrooms. 161 Olive Street is currently listed for $775,000 and was received on July 02, 2026. Want to learn more about 161 Olive Street? Do you have questions about finding other Single 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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