Oakland, MO

Tucked right alongside Kirkwood and Webster Groves in St. Louis County, Oakland is a quiet, leafy enclave of around 1,500 residents. Originally named after a historic local estate and railroad depot, the community chose to incorporate back in 1920 to preserve its independent, small-town feel. Today, it remains an almost entirely residential neighborhood framed by tree-lined streets, character-filled homes, and corridors like Lockwood Avenue and Sappington Road. While Oakland itself is peaceful and low-key, residents are only minutes away from the bustling downtown districts, farmers markets, and local dining of neighboring Kirkwood, with downtown St. Louis an easy drive to the east.

Families moving here benefit from top-tier public education through the Kirkwood School District, along with Ursuline Academy, a historic all-girls Catholic high school located right in town. Everyday errands and activities are simple, with the Oak Bend branch library down the road and leafy neighborhood parks for walking the dog. With its quiet residential streets, great schools, and quick connections to the rest of the metro area, Oakland gives newcomers a relaxed neighborhood feel right in the heart of St. Louis County.