161 Olive Street

New Haven, CT
$ 775,000 Beds 3 Baths 2 Sq 1,945
Monthly Estimate* How much can I afford?

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 sophisticated 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.

Single Family

  • Price
  • $ 775,000
  • City
  • New Haven
  • Bedrooms
  • 3
  • Full Bathrooms
  • 2
  • County
  • New Haven
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 0.07 Acres
  • Zip
  • 06511
  • Sqr Footage
  • 1,945
  • Year Built
  • 1870
  • Taxes
  • $ 14303
  • Style
  • MLS#
  • 24187215
Listed By: Marc Seigel 203-494-3888 with RE/MAX RISE. - (203) 806-1435
Data Source: Smart MLS

Features

General

Zoning RM2
Neighborhood Wooster Square
County New Haven
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Under Contract - Continue to Show
Acres 0.07
Directions State Street to Olive Street
High School Per Board of Ed
City New Haven
Elementary School Per Board of Ed
Sq Ft Total 1945
DOM 53
Year Built 1870
Exclusions Hydrangea bush by driveway
Style Colonial
Year Built Source Public Records

Interior Features

Cooling System Window Unit
Total Rooms 8
Basement Description Full,Storage,Partially Finished,Walk-out

Exterior Features

Water Source Public Water Connected
Lot Description Fence - Chain Link,Corner Lot
Color Red

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Per Board of Ed Elementary School
Middle School Unknown Middle School
High School Per Board of Ed High School

Price History

6/30/2026 Listed $775,000

Property vs Zip Code Average in 06511

Price
AVG $640K
$780K
Taxes
AVG $10,403
$14,303
Year Built
AVG 1919
1870

161 Olive Street New Haven, CT is a Single Family Home for sale at $775000 with 1945 sqft and a lot size of 0.07 Acres Acre(s). 161 Olive Street New Haven has 3 bedrooms, 2 baths and was built in 1870. The property's zip code is 06511 which is in New Haven, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.