Cherokee Park is one of the historic neighborhoods south of downtown Sarasota noted for upscale vintage residences. It counts among the high-end neighborhoods that realtors classify highly as “West of the Trail” with their superb location in-between Sarasota Bay and south Tamiami Trail (U.S. 41) corridor.
This community, formerly orange grove, was first platted sometime in the mid-1920s by its developer, James C. Brown. A Scottish silk merchant, Brown also built a large house for himself in the neighborhood. This he called Cherokee Lodge, and it featured a Mediterranean Revival architectural design that he wanted to be the template for the other residences in the property.
Brown set three entrances to the community on South Osprey Avenue, which were marked by stucco gate posts with a Cherokee rose depicted in decorative tiles. These markers were erected off Osprey on North, Cherokee and South Drives and still stand today.
Updated Houses and New Builds
The development of Brown’s subdivision, however, didn’t materialize in full mainly due to the housing market’s crash leading up to the 1930s Great Depression. Cherokee Park came into full bloom only after World War II during the 1950s and early 1960s when this neighborhood’s 94 lots were filled out with ranch-style houses and bungalows.
Many of the durable residences of this era here have been extensively updated or renovated. Some were demolished, including Brown’s original house, and new houses were built. These new builds came out quite grand and larger, thanks to this neighborhood’s spacious lots 200 feet deep and frontage of 100 feet.
Today, Cherokee Park is one the most beautiful and sough-after communities in Sarasota.
The North, South and Cherokee Drives leading into this neighborhood are boulevards with charming center islands lined with ancient oak trees. All residences of Cherokee Park nestle amidst lush and mature landscaping.
Market Activity Hums Smooth
The market for Cherokee Park properties for sale is relatively active with three residences sold in this neighborhood in 2017 and two still available to buyers. Pricing for these sales listings during the year range from the upper $800s up to a quote at $2.7 million.
Cherokee Park residents consist of a mix of retirees, empty nesters, and young professionals. Families with kids are also drawn to this neighborhood because of its proximity to local schools. Southside Elementary, for instance, is just across the street from North Drive. Other nearby district schools include Sarasota High and Brookside Middle.
The community is also conveniently close to the Sarasota Memorial Hospital and the Southside Village, which has Morton’s Market and a wide selection of restaurants. Taking a short drive south opens access to even more shopping and dining opportunities at the rebranded commercial hub of Westfield Siesta Key on Siesta Drive.
The same road corridor also notably extends west to the pristine white sands of the Siesta Key beaches. Via the Tamiami Trail just a block east of this community, its residents are but some 10 minutes away from downtown Sarasota and its various points of interest which have helped shape Cherokee Park as a choice neighborhood to live in.