Oakland, arguably one of St. Louis County’s best-kept secrets, is a small fourth class city of approximately 1,350 residents. Its 7.5 miles of tree-lined streets are nestled between Webster Groves to its east, Crestwood to its south, Kirkwood to its west, and Glendale to its north.

Oakland is a community of great architectural diversity. Not only will you find homes designed by such mid-century architects as Harris Armstrong, Robert Schutt and Paul Marti (all of whom are former Oakland residents) but also turn of the century houses and arts and crafts-styled cottages. Oakland has a fascinating history, explored in the book Oakland: A History of the People & Their Homes written by Oakland resident Suzanne Stewart Bolten and summarized here.

Oakland is primarily a residential community, but within its city limits you will find Westborough Country Club, Ursuline Academy, a private Catholic girls’ high school, Bethesda Dilworth, one of the largest long term care facilities in Missouri, Webster Groves Christian Church and Oak Bend Library, a branch of St. Louis County Library.  It is also the future home to Perennial on the Trail, a tasting room featuring Perennial Brewing company's beer and blended spirits which will be located in the current Pedego St. Louis building next to Grant's Trail and Backstoppers Park of Oakland. 

You will also find three city parks. Loewnau Park is located on the corner of Sappington Road and Oakland and is named for the late Adolph Loewenau, Oakland’s former longtime city clerk. Backstoppers Park of Oakland is located at the trailhead of Grant’s Trail, part of the Gravois Greenway and is named for the non-profit organization that supports families of fallen first responders.  Minturn Park, centered on Gravois Creek in the north end of town, features the oft-photographed Paul and Audie Marti bridge. City parks provide wonderful green spaces within our community.