Cherokee Park
One of Sarasota’s most storied West of the Trail enclaves, Cherokee Park blends grand oak canopies with architect-designed homes—ranging from lovingly preserved 1920s residences to sleek new builds—some with boatable water on Hudson Bayou leading to Sarasota Bay. Residents enjoy a short hop to the bayfront, the cultural core downtown, and iconic green spaces like Marie Selby Botanical Gardens and The Bay’s waterfront promenades curated by The Bay Park. Daily conveniences are equally close: the boutiques and eateries of Southside Village include neighborhood mainstays such as Morton’s Gourmet Market, while world-class care is just up the road at Sarasota Memorial Hospital.
Families value the strong public-school pipeline supported by Sarasota County Schools, with nearby options that commonly serve the area, including Southside Elementary School, Brookside Middle School, and Sarasota High School. Weekends bring paddle sessions along the bayou, sunset strolls at the marina, and easy dining in adjacent Harbor Acres. Gulf beaches and the laid-back vibe of Siesta Key are within a quick drive, while civic amenities across Sarasota County keep errands efficient and recreation abundant.
If you’re considering a move into or out of Cherokee Park, Agent Pronto can quickly connect you with a top local real estate expert—tailored to your price point, timeline, and goals—for both buying and selling.