The Exquisite West of the Trail Neighborhoods in Sarasota

When you ask Sarasota residents about life on the western side of the Tamiami Trail, you are bound to hear them mention the names of prestigious neighborhoods such as Oyster Bay, McClellan Park, Cherokee Park, Bayview Heights, and Harbor Acres; these are neighborhoods with more than just attractive real estate, they evoke feelings of regal and stately homes located in the most desirable part of town.

The prestige associated with West of the Trail neighborhoods dates back to the late 1800s, a time when Sarasota was known by its original name of “Sara Sota.” The first major road of this city ran between the McClellan Park and Bayview districts, which used to be citrus farms until a few visionary developers started building cottages and Nantucket-style homes in this area. After the Great Depression, people associated with the New York publishing industry began making Sarasota their winter homes, and they predominantly settled in neighborhoods situated around the old downtown district, which today is where Sarasota Memorial Hospital sits.

From a real estate point of view, house-hunting in the West of the Trail neighborhoods is an adventure you will certainly enjoy; this is an area filled with character and Old Florida history. Here is where you will find some of the most exquisite and refined properties in Southwest Florida; instead of gated communities with tract housing, West of the Trail offers leafy subdivisions with custom homes built in Mediterranean, Contemporary, Spanish Colonial, Key West, Caribbean, and American Craftsman styles.

The suburban planning that has shaped this part of Sarasota has resulted in a very desirable place to live. In these neighborhoods you will find mature trees and inviting public spaces surrounded by upscale markets, cafés and restaurants. The heart of the West of the Trail residential district is Morton’s Gourmet Market on South Osprey Avenue, not far from the Memorial Hospital; Morton’s is legendary in terms of its organic and gourmet products, and it is located just down the street from landmarks such as Gecko’s Grill and the Five O’Clock Club.

Depending on the West of the Trail neighborhood you choose, you could be within walking or biking distance from museums, performance spaces, art galleries, trendy boutiques, marinas, and the Siesta Key beaches. This is the kind of residential district where all homeowners are property investors since the homes tend to appreciate even when the regional market slows down.

Whether you are looking for a historic home, a small condo or a spectacular waterfront mansion with private docking space and views of the Sarasota Bay, you can rest assured that you will be able to find your dream home in the West of the Trail neighborhoods of Sarasota.

Homes for Sale West of the Trail in Sarasota

See all West of the Trail Homes in Sarasota.
(all data current as of 2/3/2023)

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