The Allure of Oyster Bay Estates
Oyster Bay is a highly sought-after community located west of the Trail in Sarasota, offering easy access to stunning beaches, shopping, and entertainment. The neighborhood features approximately 163 homes situated on spacious, tree-lined lots, contributing to its mature and inviting atmosphere.
Residents, whether newcomers or families who have lived here for generations, enjoy a waterfront lifestyle with breathtaking bay views, private docks, and direct access to the Gulf of Mexico. This area beautifully blends the charm of Old Florida with modern elegance, showcasing lush landscaping and ample space that ensures both privacy and tranquility.
In addition to its historic character and privacy, Oyster Bay Estates offers a variety of amenities that enhance its appeal. Boaters appreciate the numerous docking options available on the lake, canals, and bayfront, as well as at The Field Club. The beaches, shopping malls, Southside Village, and downtown Sarasota—with its restaurants and cultural venues—are all just a 10-minute drive away.
Spotlight: The Field Club
Situated along Roberts Bay, the Field Club is more than just a private club; it serves as a living connection to Sarasota's golden era. In the 1920s, the area was originally used as a grazing pasture for cattle.
In 1925, Stanley and Sara Field, from the Marshall Field retail stores in Chicago, built a Spanish villa styled after 18th-century architecture on the water in Oyster Bay. The couple enjoyed spending their winters there until they decided to retire back to Illinois permanently in their 80s.
Constructed in 1927 as the winter estate of Stanley and Clara Field—part of Chicago's renowned Marshall Field & Company retail dynasty—the property embodies the glamour and sophistication of the Roaring Twenties. It features sweeping bayfront views, Mediterranean Revival architecture, and lush tropical gardens, quickly becoming a showcase of refined coastal living.
In 1957, the estate began a new chapter when it was transformed into a private club, carefully preserving its historic character while adding modern amenities. Today, the Field Club reflects the elegance of its past while offering a vibrant and active lifestyle for its members.
As one of Sarasota's oldest private clubs, it currently serves around 600 members, many of whom are from Oyster Bay, making it a prestigious and historic cornerstone of the community. The Field Club provides a full-service marina with quick access to the Gulf of Mexico, as well as waterfront dining, well-maintained tennis and pickleball courts, a swimming pool, and state-of-the-art fitness facilities. The Field Club remains one of Sarasota's most prestigious addresses—a place where tradition meets modernity, and every visit feels like stepping into a timeless retreat.
For those seeking a timeless waterfront lifestyle, Oyster Bay Estates represents a rare opportunity to live in one of Sarasota's most distinguished communities.
Explore Oyster Bay Estates here.
