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West of the Trail

Nestled just west of Tamiami Trail (U.S. 41), this enclave stretches gracefully along Sarasota Bay, just minutes from downtown and Siesta Key. Its location alone gives it rare allure—close to the city’s cultural offerings, yet shaded by old canopies and kissed by the bay breeze.

Property Listings

West of the Trail

West of the Trail is one of Sarasota’s most distinguished residential enclaves. Nestled along Sarasota Bay and just minutes from downtown, this community is defined by its historic character, architectural significance, and enviable location. Here, tree-lined streets frame a graceful mix of early 20th-century homes, Sarasota School of Architecture designs, and modern waterfront estates. The area’s prestige lies not only in its proximity to cultural treasures and white-sand beaches, but also in the timeless sense of refinement it offers.


Ballentine Manor Estate

Ballentine Manor Estate carries the elegance of Sarasota’s golden age. Known for its stately bayfront residences and lush, landscaped grounds, this neighborhood is steeped in history and sophistication. Many of the homes here were constructed during the city’s earliest waves of development, blending Mediterranean Revival influences with spacious floor plans and sweeping water views. Its location just north of downtown places residents close to cultural venues while preserving a private, old-Florida atmosphere.


Indian Beach–Sapphire Shores

Indian Beach–Sapphire Shores is a vibrant and eclectic bayfront neighborhood, celebrated for its artistic flair and architectural diversity. Home to the John and Mable Ringling Museum of Art, it has long drawn creatives, academics, and those seeking a balance of charm and culture. Historic estates and mid-century modern designs sit side by side with contemporary residences, creating a neighborhood as dynamic as its residents. Shaded by mature oaks and overlooking Sarasota Bay, it is among the city’s most picturesque settings—offering both serenity and a deep sense of community.


The Distinction

Together, West of the Trail, Ballentine Manor Estate, and Indian Beach–Sapphire Shores form a tapestry of Sarasota living that is elegant, historic, and enduringly desirable. Whether drawn to the bayfront grandeur of Ballentine, the creative spirit of Sapphire Shores, or the timeless prestige of West of the Trail, each enclave offers a lifestyle defined by beauty, culture, and connection to the water.


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Work With Ashley

In a market where the most desirable opportunities often never reach the public eye, access is everything. As a lifelong St. Petersburg local, I offer more than insight — I bring trusted relationships, private and exclusive listings, and an instinct for the neighborhoods that feel like home. From first meeting to closing, I protect your interests, anticipate challenges, and guide you to a result worth celebrating. Let’s connect and begin your search.

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