Proximity to Kirkwood amenities and the local country club
Though one of the many municipalities in St. Louis County, Oakland offers a primarily suburban feel. Walkable to Kirkwood and the Westborough Country Club, the community keeps amenities and entertainment at its fingertips while staying just far enough away to allow for larger lot sizes and more diverse architecture than in neighboring cities. Home to less than 1,400 people, Oakland preserves its small-town atmosphere, even with the City of St. Louis just 12 miles northeast. With summer temperatures in the high 80s, it’s not uncommon to see neighbors walking along the narrow sidewalks or relaxing at local parks; however, in the winter, lows hover around the 20s, so homeowners stay prepared for freezing temperatures and occasional snowfall.
Oakland is close to the Westborough Country Club.
Downtown Kirkwood is a popular shopping and dining destination for residents in Oakland.
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Mix of architectural styles north of Interstate 44
Oak, evergreen and black walnut trees line the sidewalks and serve as a backdrop for homes. Because years of construction vary throughout Oakland, architectural styles range from Tudor to colonial, giving the neighborhood a more varied appearance than in master-planned communities. With lot sizes up to half an acre and a veil of greenery tucked between properties, homes maintain a little privacy despite being in a small city. Homes with about 1,500 square feet cost between $250,000 and $285,000, while homes closer to 2,000 square feet hover between $300,000 and $450,000. For homes over 3,000 square feet, prices can extend over $650,000 and even over $1 million, depending on the year constructed and proximity to Kirkwood.
Colonial revival homes can be found in Oakland.
Tudor style homes are varied and common in Oakland.
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Kirkwood schools and Ursuline Academy
Students can attend the Kirkwood District, starting with North Glendale Elementary, a school receiving an A from Niche. From here, they can transition to Nipher Middle, another A-graded school, and Kirkwood High, an A-plus school with a 98% graduation rate. Kirkwood High also earned a National Blue Ribbon Award in 2022. For a private option, Ursuline Academy is located in Oakland, though it is an all-girls school.
Nipher Middle School serves the community.
North Glendale Elementary School provides educational opportunities for resident children
Kirkwood High School on Essex Road ranks consistently among the best high schools in the state.
Oakland schools rank highly in the state.
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A quick walk from Westborough Country Club
Westborough Country Club is in the northeastern corner of Oakland, inviting golf lovers to hit the fairways and tennis players to practice their swing. Oakland has a couple of pocket parks, like Backstoppers and Loewnau, but Kirkwood Park is only 2 miles west, a green space equipped with playgrounds, pickleball courts and walking paths. Though required to pay a membership, residents can use the pool at the Kirkwood Aquatic Center, also housed within Kirkwood Park, just off Geyer Road.
Sports courts are available for residents.
The country club is walkable from Oakland.
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Amenities along Kirkwood Road and in surrounding cities
A primarily residential community, Oakland doesn’t include many stores of its own. Fortunately, grocery stores such as Aldi and Walmart Supercenter are less than 2 miles west along Kirkwood Road, easily accessible via Big Bend Road. Because the neighborhood is centered between multiple municipalities, Oakland allows locals to decide between dining at spots like Olive + Oak in Webster Groves or grabbing a bite at Billy G’s, a spot local Red Key Realty agent Sarah Bernard calls “a gathering place for friends.”
Billy G's in Kirkwood is a relaxed local spot.
Olive and Oak is a delicious dining option for Oakland residents in Webster Groves.
For groceries, Aldi is very close to Oakland in Kirkwood.
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Ramps to Interstate 44 close to home
Sidewalks extend throughout the neighborhood, including along East Monroe, but with most amenities over a mile away, most homeowners prefer to drive around the area. Bordered by Interstate 44 and only about 12 miles southwest of downtown St. Louis, Oakland offers commuter-friendly access to major employers throughout the St. Louis metropolitan area. Though not a common way to get into the big city, there are bus stops in the neighborhood that connect to the Shrewsbury Transit Center, a station that offers buses direct to downtown.
STAGES productions and other local events
Though the city of St. Louis has a wealth of entertainment within driving distance, Kirkwood keeps events even closer to Oakland. “It has the ever-popular STAGES professional theater productions, live theater produced in Kirkwood since the late 1980s,” Bernard says. Other events in Kirkwood include a farmers market, summer concert series and Fall Wine Walk.
Photography Contributed By
Dana Dieckmann
Video By
Mallory Nolte
Interested in learning more about homes in this area?
Reach out to
Hayley Tomazic,
an experienced agent in this area.
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