In Sarasota, the distinguished West of the Trail neighborhoods are often considered to offer the best real estate in Southwest Florida, and this is certainly the case with Cherokee Park, a stately residential district that has featured lavish mansions since the 1920s. Located north of Spring Creek Drive and west of Osprey Avenue, Cherokee Park extends out to the waterfront, and it also features a canal that connects boaters to the Sarasota Bay and the Gulf of Mexico.
Cherokee Park is both a district and a subdivision; even though there are only 94 homes in this large neighborhood, each one manages to be more spectacular than the other. In 2019, pricing of most properties starts at a million dollars, and quite a few are mansions that are candidates to enter the National Register of Historic Places. The architectural styles range from Southern Plantation to Old Florida mansions and from Key West Homes to imposing Mediterranean estates.
Half acre home sites are the norm at Cherokee Park, and quite a few are larger. As befits a stately neighborhood in Southwest Florida, lush vegetation and mature trees line the ample sidewalks and streets. For $739K, you can get a four-bedroom and three bathroom Southern Plantation originally built in the 1960s, but a more enticing listing in 2019 consists of a five-bedroom Mediterranean mansion located right at the corner where the neighborhood’s canal meets the Sarasota Bay; this gorgeous property has extras such as private docking space, bayfront balconies, wine room, heated swimming pool, spa, summer kitchen, and much more for $$4,79 million.
Cherokee Park is a community where homeowners never have to worry about real estate downturns, and this has a lot to do with location. Residents and their guests can ride their bikes to Nora Patterson Bay Island Park and Siesta Key Beach. Suburban comforts near Cherokee Park include two shopping districts, a CineBistro, and the restaurant district just south of Sarasota Memorial Hospital.
Homes for Sale at Cherokee Park in Sarasota
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(all data current as of
8/23/2025)
Listing information deemed reliable but not guaranteed. Read full disclaimer.
