In 1909, under the auspices of G.G. Nesbit, Brown and von Beren Architects was commissioned to build a freestanding masonry structure with structural steel girders and concrete floors to function as a garage adjacent to New Haven’s burgeoning Chapel District. Over the next hundred years, and up to the present, 39/41 High Street has stood the test of time and programmatic changes, representing what is one of High Street’s oldest standing structures. Fire insurance Sanborn maps from 1930 indicate that the building was a four story, 70-car garage, with concrete floors, that was heated via steam. These records also indicate that, perhaps due to its nature as housing a car rental/taxi business, a 1000 gallon gasoline tank was buried beneath what is presently the entrance to the 39 High Street portion.



Though it is one building, the placards on the door lintels indicate two separate addresses 39 and 41 High Street. This ornamentation has to do that for much of its life the building had separate commercial programs operating within its structure, though often in a symbiotic relationship.  When it was erected, the new garage housed The Blue Ribbon Garage and the New Have taxi Cab Companies. Originally a freestanding structure, the structure was joined with its ancillary wing sometime around 1913. This is indicated because the 1911 Atlas of New Haven shows the structure standing alone but the 1913 phone directory lists a 45 High Street that houses the Maynyard W.A. & Co Automobiles shop. Through its lifespan the building underwent several name and ownership changes but remained programmatically constant, always servicing the automobile industry in some form.  By the early 1920s New Haven Taxi Cab Co. had left to be replaced by H&P Motor Livery and Combined Auto Crafts Co., the latter of which is listed as occupying 41-45 High Street. In the mid to late 1920s some of the auto shops were taken over by New Haven Car Renting Co. Henceforth from the 1930s until 1987 the building was known as the High Street Garage (with a brief exception in the early 1960s when it was known as the Palace Garage). No pictures exist of the garage in its past configurations.



The garage changed owners a couple of times. City records indicated that in 1951 Frank Nuzzo was the owner and for some time in the mid-50s a rental car company called "U-Drive it of New Haven" also occupied the building. When the garage changed ownership in the early 1960s, the rental car company either went out of business or moved somewhere else. The building was bought in 1986 by Barbara Wareck in conjunction with its two story 45 High Street Neighbor. Her son John Wareck now owns the property under the company Wareck D’Ostilio. Throughout late 1987 the building was cleared from its previous uses and remodeled for a total cost of $1.2 million (1987 dollars). In the late 1980s its current tenants moved in: Pelli Clarke Pelli and Chapel Investment. Its last major upgrade was in 1995 when 39 High Street was cleared via permit for a restaurant remodel totaling $110,000 (1996 dollars). This is the space that would go on to house Ibiza and currently Olea which opened in 2015.



As of September 2015 the building was granted a permit to redo its roofing for a total cost of $366,000, for which construction has yet to begin as of October 2015.