About Olive and Wooster Olive and Wooster, nestled in the heart of Wooster square, not only offers a variety of floor plans, but lease term options built just for you. Traditional apartments are rented on a joint-and-several lease agreement. Lease terms vary by floor plan and lease start date. Looking for something different? In our Collective Living or Co-Living units, you will be on an individual lease agreement and only responsible for your personal rent. Enjoy your space with friends new or old and say goodbye to the days of Venoming your roommates to pay rent. Collective Living Bedroom Pricing Starting at: $1,200. Studio - Four Bedroom Apartments Townhomes Starting at: $1,850 - $6,000. Olive and Wooster is an apartment community located in New Haven County and the 06511 ZIP Code. This area is served by the New Haven attendance zone.