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The relatively small Oakenshawe community consists of three areas. The area of greatest density is in the west. where there are apartment buildings of varying sizes -- north of University Parkway are large row houses, constructed before and immediately following World War I, that typify the predominant architectural style of the community, and farther east, near Greenmount Avenue. a number of individual and semi-detached frame structures remain from the Victorian village period in Waverly's history.
Once a site of colonial and nineteenth century estates, the Oakenshawe area was developed for dense residential use between the years 1916 and 1925-later than other portions of this region. Throughout the first half of the 1800s, the affluent merchant James Wilson owned most of this property. After purchasing the tract in 1800, he erected a gambrel-roofed frame house later called "The Cottage," it was located on the south side of today's University Parkway between Calvert Street and Guilford Avenue. At that time University Parkway was an oyster shell surfaced road called Merryman's Lane. named after an early owner of extensive property in the area. Although James Wilson vacated "The Cottage" in 1840 after he purchased a large portion of the nearby "Huntington" estate, it remained standing until 1915 when the Guilford improvement Company demolished it to make room for modern dwellings. After the death of James Wilson in 1851, the old homestead was divided among his children as separate estates named "Roseland" and "Oakenshawe."
Also at mid-century, Henry R. Wilson established "Oakenshawe" upon property which he had inherited from his father north of Merryman's Lane. West of today's Calvin Avenue. it was just south of Arunah S. Abell's "Guilford" estate. Narrow frame individual cottages covered most of the area between Barclay Street and the York Turnpike Road.
Land west of Sumwalt Run, which in this area flowed south roughly along the route of St. Paul Street, was part or Samuel Wyman's 120-acre estate, purchased in 1840 from the Carroll family.
Modern development of the area occurred during the first quarter of the twentieth century. Phillip C. Mueller built the first homes on Guilford Terrace north of University Parkway between 1916 and 1925. Some of the houses in this "Oakenshawe" development were in place by 1917 on the eve of the United States' entry into World War I. The unique row house architecture was of Colonial design, and the houses were to appeal to those who wanted to live in the Guilford area without the expense of a large house. The builders' sales advertisements stressed Oakenshawe's proximity to the Guilford development, its terraced lawns, and the fact that it was a "high class" area. The Mueller Construction Company went on later to build houses in Ednor Gardens at Ellerslie Avenue and 38th Street. Until 1970 when many young families began moving to the community, Oakenshawe ad an unusually high proportion of original homeowners who had been there a half-century.
South of University Parkway, modern development occurred during the same period as the north. Edward J. Storck built gabled and dormered daylight houses with large front porches on the eastern part of the Wyman estate. Thomas W. H. Abbott and E. J. Revell founded the Guilford Building Company. In 1916 they bought the Patterson "Roseland" estate and commenced development. They constructed all the buildings on the block bounded by East University Parkway. Guilford Avenue, 34th and Calvert Streets, as well as houses on other blocks nearby. This block has since been demolished and absorbed by Union Memorial Hospital. The Temple Court Apartments were constructed on the site of the "Roseland" mansion during the 1920s. The Guilford Avenue Garage was built during the 1930s. At one time, the company considered building apartments over the garage, but the plan never materialized.
Most of the apartment buildings and totally-enclosed parking garages date from the 1920s. Union Memorial Hospital opened in 1923 with later additions in 1956 and 1978. The Enoch Pratt Free Library Branch #15 was built in 1970. Other local landmarks include the University Baptist Church and the Alpheus W. Wilson Memorial United Methodist Church on Charles Street. Commercial enterprises exist only along Greenmount Avenue.
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