People dining outside a New Haven restaurant near Olive & Wooster

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Convenient Living in an Idyllic Locale


In the Charming Oasis of Wooster Square

One of New Haven’s most storied neighborhoods is now home to an exceptional rental living experience. Spend your day relaxing under the cherry blossoms in the square. Dine on authentic New Haven pizza in Little Italy—and once and for all end the Sally’s v Pepe’s debate. Enjoy a night out of live music at neighborhood institutions. All of this in a little “slice” of paradise conveniently located near downtown, Yale campus, and the medical district.


Explore New Haven

Conveniently located within walking distance of downtown New Haven, the Yale New Haven Hospitals, Wooster Square, Yale University, and the New Haven-State Street Shore Line CT Rail station, Olive & Wooster is your sanctuary in the middle of it all.

  • Parks
  • Restaurants
  • Transit
  • Retail
  • Medical District
  • Collegiate


A New Chapter in New Haven

New Haven is undergoing a 21st-century renaissance and Olive & Wooster is excited to be joining the fray of the many exciting developments taking place in the greater New Haven area. The City of New Haven’s Downtown Crossing infrastructure investment is tying the city’s neighborhoods back together through a system of urban boulevards that will reestablish New Haven’s grids while promoting walkability and new commercial development. One such project at 101 College Street is already taking shape and will support new science and bio-tech firms in a 500,000 square foot facility in the Downtown Crossing project area.

The development will help tie together previously disparate portions of New Haven, knitting together parts of downtown with the Yale University Medical School campus, and Hill Neighborhood. The project includes partnerships with New Haven Public Schools, Southern Connecticut State University, and Gateway Community College and will bring 700 – 1,000 new jobs to the area once complete.

Nearby, the Yale-New Haven Hospital’s St. Raphael Campus is undergoing an $838 million expansion for its planned Neurosciences Center, which will make the facility a leading center in the research of and care for brain-related disorders. The planned center will add capacity to the Yale University’s New Haven Hospital network while fostering job growth in medical research and health sciences.

Increased development requires greater connectivity and New Haven is responding to its growth with a $100 million investment in the Tweed New Haven airport. In what will becoming the largest investment in the airport’s history, the planned upgrades will bring a new terminal, longer runways, and flyer improvements, along with the arrival of Avelo Airlines, which plans to make Tweed-New Haven Airport its East Coast base in the months to come.

It’s a new chapter in New Haven’s history.