West of the Trail in Sarasota : Homes for Sale in a Most Prestigious Area

Some of the most prestigious home addresses in Southwest Florida are located West of the Trail, in a large residential area near Downtown Sarasota located west of US 41, also known as the Tamiami Trail.  West of the Trail is a collection of neighborhoods that celebrate Sarasota’s history, residential architecture and quality of life.

The West of the Trail area celebrates the influence of circus magnate John Ringling and his vision of a Sarasota that would resemble the classic urban planning of Italian cities such as Venice and Florence during the Renaissance.  To this end, the spontaneous neighborhood design of Aqualane Estates will appeal to home shoppers looking for waterfront properties.

Bungalow Hill is the only hilltop subdivision in the otherwise flat terrain of Sarasota, and many of the homes in this exclusive neighborhood were built in the Southern Plantation or American Craftsman styles.  A short walk down Bungalow Hill is all it takes for neighbors to be in the heart of Downtown Sarasota and its many parks, art galleries, performance spaces, shops, restaurants, business centers, clinics, hospitals, schools, museums and more.

McClellan Park was already a prestigious neighborhood by the time John Ringling arrived.  This is a very upscale community with Tudor revival mansion, Mediterranean estates and Spanish-style homes.  A similarly exclusive neighborhood is San Remo Estates, which is closer to the water and features some of John Ringling’s visions of lush landscaping and gorgeous public spaces for everyone.  Both McClellan Park and San Remo Estates are just a walk or bike ride away from the heart of Downtown Sarasota.

Since the cream and crop of Florida have been making Southwest Florida their home over the last few decades, neighborhoods such as Cherokee Park have been developed to accommodate them.  As a result, public schools and private academies in Sarasota compete for the enrollment of students, which creates a healthy rivalry in terms of academic excellence.

In essence, the West of the Trail area offers everything a home buyer can hope to find in Florida: Great weather, proximity to gorgeous beaches and pristine nature, fine schools, cultural activities, elegant shopping venues, high quality of life and real estate opportunities ranging from $235K to $9M.

Sarasota’s West of the Trail – Homes for Sale

See all West of the Trail Homes in Sarasota.
(all data current as of 1/3/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.