Welcome to West of Trail, Sarasota

Sarasota’s Most Timeless Mainland Address (2026 Edition)

Entering the 2026 season, West of Trail has outperformed broader market trends. While other regions saw a pricing plateau, this mainland enclave experienced steady growth, supported by an uncompromising demand for walkability and its proximity to the bayfront. It remains the top choice for buyers who want the sophisticated energy of the city without sacrificing the canopy-covered privacy of a true neighborhood.

What to Love in 2026

• Unrivaled Convenience: Immediate access to Downtown Sarasota, the newly expanded The Bay Park, and the pristine beaches of Siesta and Lido Key.
• Educational Authority: Home to the A-rated Southside Elementary, which continues to be a primary driver for young families and long-term property values in 2026.
• The "Village" Lifestyle: A rare urban-suburban blend where Southside Village acts as a social epicenter, putting boutique shopping and gourmet markets within a five-minute stroll.

The 2026 Local Lifestyle: Wellness & Innovation

Residents enjoy a lifestyle that balances quiet, canopy-covered streets with Sarasota’s most innovative cultural updates. In 2026, the area is buoyed by the Phase 2 expansion of The Bay Park, which has introduced a new resilient shoreline and sunset promenade. This year, the Marie Selby Botanical Gardens has garnered international attention with its nomination for “Best Botanical Garden” in the USA Today 10Best Awards, further cementing the neighborhood’s reputation for world-class beauty.

Dining & Shopping: Southside Village & Beyond

The culinary scene West of Trail is where Sarasota’s locals congregate. In 2026, the highlights include:

• The Green Orchid at Selby Gardens: Now celebrated as the world's first net-positive energy restaurant, offering a true "roof-to-table" experience powered entirely by the sun.
• Southside Village: A curated hub where Morton’s Gourmet Market remains the neighborhood's pantry, and Veronica’s Fish and Oyster provides the definitive 2026 dining experience.
• Culinary Maturity: From artisanal pizzas at Origin to the fusion excellence of Pacific Rim, the Hillview and Osprey corridors offer a higher density of chef-driven concepts than any other mainland neighborhood.

The Medical District Advantage: 2026 Standards

In 2026, Sarasota Memorial Hospital (SMH) has once again been ranked among the nation's 50 best hospitals by U.S. News & World Report and earned a perfect 5-star rating from CMS for the 10th consecutive year. For the surgeons, physicians, and executives who call West of Trail home, this proximity is more than a convenience—it is a cornerstone of the neighborhood's enduring market stability.

Work with the West of Trail Experts

Connect with us today for an unfiltered look at the 2026 West of Trail market.