Welcome to West of Trail
There are several different areas and communities that comprise West of Trail’s large footprint, with each offering a unique style and appeal. Harbor Acres is located on Sarasota Bay and is one of Sarasota’s most desirable mainland neighborhoods. It has waterfront homes that offer views of the Ringling Bridge, Bird Key, Big Pass and Downtown Sarasota, and private docks and boating access to Sarasota Bay and the Gulf of Mexico. Harbor Acres has two peninsulas that stretch out into Sarasota Bay: Hillview and Harbor Drives. Hillview Drive has 35 of its 37 homes with direct access to Sarasota Bay, while Harbor Drive is experiencing a building spree of elaborate new mansions that now decorate the northwest side of the peninsula.
Insider Tips
Family Friendly:
​​Marie Selby Botanical Gardens is a gorgeous bayfront sanctuary of enchanting gardens and exhibitions. It features the Children’s Rainforest Garden as a favorite spot for children to explore nature. Selby Gardens offers fun, educational programs for the kids year-round. Be sure to check out Selby Spooktacular, the annual Halloween event that attracts families of all ages, as well as Lights in Bloom, the annual open-air holiday light show that illuminates the gardens in December each year.
The Cherokee Park community is conveniently located down the street from Southside Elementary School. It is well-known for its residents’ annual Halloween party. The event attracts families from across Sarasota for an early evening of trick-or-treating, haunted houses, music, spookily inspired streets and homes decorated for the occasion. The adults get in on the fun donning costumes and walking between homes with coolers full of refreshments.​​​​​​​
Favorite Restaurants:
Southside Village provides a wide variety of options for breakfast, lunch or dinner.
​​​​​​​
Libby’s Neighborhood Brasserie serves a delicious weekend brunch. It is also a local favorite for business lunch meetings. The space was redesigned in 2019 with a contemporary appeal. Veronica Fish and Oyster Bar offers fresh seafood in a sleek modern setting. It has an open dining room, a beautiful marble raw bar and a full-service bar where patrons love to enjoy craft cocktails. Southside Deli, a neighborhood staple, attracts locals who enjoy its comfort food including traditional breakfast items, sandwiches and delicious desserts. Morton’s Gourmet Market provides shoppers a local, high-end convenience market selling prepared foods, organic produce and baked goods
Recreation/Culture:
West of Trail residents enjoy the proximity of newly-opened Sarasota Art Museum Ringling College Museum Campus. It is located across the street on the north side of Tamiami Trail. The museum totals 20,000 square-feet, and was repurposed from Sarasota High School’s historical buildings and connecting courtyard. The space masterfully incorporates the school’s legacy brick and industrial feel with white spaces and modern updates. It is the region’s first museum dedicated to contemporary art.
​​​​​​​Marie Selby Botanical Gardens hosts one of the marquee social calendar events of the year. Selby’s Orchid Ball, voted Best Gala of the Year by SRQ Magazine, is an annual event held on its grounds. The event sells out every year, and attracts over 500 guests for a black-tie affair with music, dancing and dining under a large tent.
