West of the Trail in Sarasota, Florida

Real Estate Agent with Michael Saunders & Co.

West of the Trail home in Sarasota, Florida



When you’re selecting a home in Sarasota, one area that mustn’t be overlooked are neighborhoods West of the Trail.  Any local can tell you that West of the Trail homes carry a certain distinction. These homes are coveted by many for their waterfront properties, boating access, historic and/or restored homes, charm and character, low commute times, proximity to the hospital and great schools, high value on community, pedestrian and cycling traffic, cozy parks and thoughtful planning. West of the Trail addresses offer in-town living mingled with Sarasota’s best shops, markets, cafés, restaurants, schools and health care. Featuring Sarasota School of Architecture condominiums, villas, luxury homes, historic buildings and waterfront estates, West of the Trail neighborhoods showcase a variety of beautiful and exclusive styles. For a neighborhood with personality, taste and sure-fire staying power, the choices West of the Trail are unmatched.


Moving just south of downtown you’re sure to find what you need in lovely Cherokee Park or Harbor Acres. Residents here can enjoy quick, easy access to St Armand’s Circle, with boutique shopping and casual or fine dining opportunities. The premier golf courses at Palmer Ranch are also a short drive away, as well as the pristine, 99% quartz sand beaches of Siesta Key and Crescent Beach. Possibly one of the most convenient locations, these neighborhoods are just minutes from the world-class care of Sarasota Memorial Hospital, not to mention Southside Elementary School, one of the area’s best elementary schools, which lies across the street from Cherokee Park and a short drive from Harbor Acres.


Thinking about living on the water? San Remo Estates is on the mainland just before Siesta Key’s north bridge. Featuring large lots, this beautiful neighborhood is minutes from one of the best beaches in the country, Siesta Key. Likewise, downtown is only a short drive down Osprey Ave, past famous Morton’s Market in Southside Village, both options being renowned for their dining and shopping venues.


For secure living at it’s finest, The Landings is a brilliantly planned gated and deed restricted community with long, winding streets through regulated, manicured landscaping. Located conveniently in central Sarasota there’s a shopping center at the entrance, numerous restaurants, and the Westfield Sarasota Square Mall for plenty of shops just minutes away. Likewise, downtown is still only about a ten minute drive up the Trail for even more inspiring dining and shopping opportunities.


The area in and around the Landings and the Oyster Bay area have an interesting history. Robert Jeffcott was the first individual owner of the land area of Oyster Bay Estates, having purchased the land for $1.00 per acre in 1881. The land changed hands a couple of times (Potter Palmer Jr. bought the land in 1921 and sold it in 1923 to Fred & Ede Wooley), but it eventually became the Bispham Dairy Farm and occupied the property adjacent to the south where The Landings Shopping Center is now located. The Bisphams owned 60-70 Guernsey and Jersey dairy cattle at the time. The leased the land from the Wooley’s for grazing and pastureland and paid one quart of milk per day, delivered to Mr. Wooley’s home, in exchange.


Finally purchased by Robert W. Newman in 1951 and since retaining the layout given by him, this neighborhood (now devoid of any Guernsey or Jersey cattle) still retains a lovely tranquil, laid back atmosphere, with mature oaks hanging over the streets, winding past beautifully manicured gardens and lawns. Many of the homes are also situated directly on Sarasota Bay or canals that offer breathtaking vistas and boat dock-age. The kicker to this neighborhood is the Field Club, one of the city’s most revered private clubs, situated inside Oyster Bay and offering boating, tennis & swimming, as well as renowned dining and social activities.


Contact Jaime Carrion at 941-928-8892 if you would like to buy a home West of the Trail in Sarasota, Florida or with any questions you may have.


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Jaime Carrion

Sarasota Real Estate
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