North of Bay Road and South of Mound Street

West of the Trail

The McClellan Sisters c. 1910. Sarasota County History Center

Located and named for the Southside Elementary School District and Southside Village, which are reason enough to buy a home in this area, many consider this the 'best place to live in Sarasota.'  It is considered the most 'walkable' and residential part of the city without BEING IN the city.  Wonderful canopied streets and a huge variety of homes, all within walking distance of Southside Village, a place filled with cafes, shops, offices, etc.  All this and 5 minutes to Siesta going south, 5 minutes to Downtown going north. 

Southside Area

Southside Elementary School

Southside Elementary first opened its doors open in 1926, has a wonderful history (Watch the video here) and today people have been known to move to this area just to enroll their children here.  Located a few blocks south of Southside Village, Southside, which has  a mandatory uniform policy in place, has accomplished an A level grade, year after year!  In 2007, a building addition was completed to accommodate up to 630+ students, To find out more or set up a tour, please visit the Southside School Website.  Voted Best Elementary 2016 by Herald Tribune!

Southside Village

At the intersection of Osprey Avenue and Hillview Street, the Village offers those lucky enough to live here a location to walk to, to meet friends for lunch or to run errands, with numerous shops, cafes and fine dining restaurants that will suit any taste! Morton’s Gourmet Market is the Heart of Southside Village with fresh produce, prepared foods, wine, cheese and a butcher shop has been a local mainstay of Sarasota for many years.  Stop in and you’ll be welcomed like you’ve been a customer for years!  Power lunch (or Brunch) at Libby's and across the intersection of Hillview and Osprey Avenue you'll join the hipsters at Perq Coffee Bar.

architectual diversity

Sarasota is especially proud of the variety of architectural styles and there’s nowhere better will see that spectrum than West of the Trail. Sweet Florida Bungalow with overgrown thickets of swaying bamboo, bougainvillea and jasmine will hold their own next to a stately, new Spanish Style ‘palace’ or an Ultra Modern manse with manicured grass, Traveller’s Palms and up-lighting, that’s next to the 1950s Mid-Century Modern artist studio tucked away under grand 100 year old Florida Oak trees and bromilliads. West of the Trail is the farthest from the typical “Florida Subdivision on a Golf Course” where all the homes are exactly alike. If visions of apricot colored rows of the same home street after street makes you queasy, then West of the Trail may be just what you are looking for. Because of all the architectural styles, because of the proximity to downtown and the beaches, because this neighborhood attracts and welcomes every type of home owner, you will get an area as diverse as its residents!


 You want history?  West of the Trail is chock full of it!  There is a pre-historic ‘Indian’ mound, called “School Mound,” located in McClellan Park,  predating the Seminole Indians that made the shores of Sarasota Bay home.  The area saw Spanish explorers in the 15th Century followed by European hunters and fishermen who set up camps up until the days when ‘cowboys’ in the 1800s set up ranches.  Soon, the city folk arrived, finally taming the wild by developing the town into a small city.  The Ringling Brothers and their circus made this their Winter Home and you’ll see many Circus-themed influences on our city today.  To find out more about Sarasota wonderful History, visit the Sarasota County History Center OR visit this terrific website dedicated to Sarasota’s History!

Sarasota Memorial Hospital

Voted one of America’s Best Hospitals by US World Reports for the past 6 years, what became S.M.H. first opened in 1925 and has grown (and is still growing!) into South West Florida’s choice for superior healthcare.  Many physicians and their families chose to live West of the Trail as well as open their practices in the medical facilities here that use the hospital.  For more information on Sarasota Memorial visit their WEBSITE.