West of Trail

West of Trail is an upscale community nestled located West of the “Tamiami Trail” (a.k.a. Highway 41) right in the heart of Sarasota, offering easy access to prime areas such as Downtown Sarasota, picturesque beaches, terrific restaurants, and other top-notch amenities.

Considered one of the most historic residential areas in Sarasota, West of Trail consists of some of the most desirable historical Old Florida neighborhoods in the city such as Avondale, Cherokee Park, Desoto Park, Harbor Acres, and McClellan Park, among others.

West of Trail also offers easy access to the award-winning Sarasota Memorial Hospital which is known for providing the highest-quality healthcare and patient experience in the country.

Due to its terrific location, West of Trail is the perfect community for anyone looking to enjoy the benefits of living close to Downtown Sarasota, along with the tranquility and tight-knit community atmosphere.


Southside Elementary School
Brookside Middle School
Sarasota High School
Riverview High School
Suncoast Polytechnical School


Sarasota Opera
Asolo Theater
Morton’s Gourmet Market
Marina Jacks
Marie Selby Botanical Gardens
Sarasota Bay


Lido Beach
Biking and Jogging
Siesta Key Beach

West of Trail


Some of the neighborhoods that are part of the West of Trail area date back to the early 1900s.

McClellan Park, in particular, is one of the oldest neighborhoods in Sarasota. Established in 1913, the neighborhood sits on the original settlement that eventually became the city of Sarasota itself. Other historical neighborhoods such as Cherokee Park and Avondale were developed in the 1920s, and are two of the most prominent neighborhoods in West of Trail today.



Marie Selby Botanical Gardens

Marie Selby Botanical Gardens provides 45 acres of bayfront sanctuaries connecting people with air plants of the world, native nature, and our regional history. Established by forward thinking women of their time, Selby Gardens is composed of the 15-acre Downtown Sarasota campus and the 30-acre Historic Spanish Point campus in the Osprey area of Sarasota County, Florida.

Dining Options

Planning to dine out with the family? Be sure to visit some of the top-rated restaurants in and around the West of Trail community such as Libby’s, Veronica Fish & Oyster, Pacific Rim, Morton’s Gourmet Market, and Owen’s Fish Camp.

Siesta Key Beach

Siesta Key Beach is a few minutes away from the West of Trail community, giving residents easy access to its fine quartz-crystal shores kissed by gentle waves. It was recently named #1 beach in the U.S. and #11 in the world in 2020 by the TripAdvisor Travelers’ Choice awards.


Things To Do In Sarasotaby John Brink

This guide has been carefully curated by our Broker Owner John Brink who is a long-time Sarasota resident and a passionate boater. Discover top restaurants, unique places, boating attractions and major cultural events in the area. Please enter your information below so we can send you this amazing guide!

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