Welcome to Oyster Bay
Oyster Bay is a prominent Sarasota neighborhood located just south of the West of Trail neighborhood and bordered by a western presence on Roberts Bay. All 168 homes in Oyster Bay are located within a mile or two of Siesta Key. Charm, sophistication, and deep-rooted tradition are hallmarks of the area.
The neighborhood features 100-year-old live oaks, silver and royal palms, fruit cedar trees, canopied promenades, deep sailboat waterways, lush landscaping and sizeable lots compared to similar properties in many of Sarasota’s other upscale neighborhoods. Homes here have long been known for their old Florida charm and variety of architectural styles.
​​​​​​​Camino Real runs parallel to the Roberts Bay, travels throughout the Oyster Bay neighborhood, and provides access to discreet, high-end enclaves including Oyster Bay Landings, North Lake Shore Drive and South Lake Shore Drive. Oyster Bay Landings’ private peninsula of fourteen large estate homes are hidden behind an elaborate wrought iron gate with beautiful brick pavers and ornamental lighting. Noted local appraiser Don Saba placed North and South Lake Shore Drives in the top grouping of luxurious streets in a Herald-Tribune article referencing premiere addresses in Sarasota.
Insider Tips
Family Friendly:
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Kids enjoy Red Rock Park for its two, age-specific playgrounds, expansive ball field, and recreational area. Parents appreciate its ample parking and central location within Oyster Bay.
Recreation / Culture:
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Oyster Bay has long been known for its “old money”, “summers in Nantucket” feel. It is home to the Field Club, one of Sarasota’s most esteemed private clubs. Generations of families have enjoyed tennis, boating, swimming, fine dining and a variety social of activities since it opened in 1957. The Field Club is a great place for members to bond with neighbors and other members, make contacts, entertain the kids and meet new friends. It also offers marina slips with Roberts Bay and Gulf of Mexico access.
Favorite Restaurants:
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Walt’s Fish Market is a legendary Sarasota fish market and restaurant that has been in business for over 30 years. The restaurant was renovated in 2012 and now offers a dedicated dining room, takeout fish counter, lively tiki bar and outside dining.
​​​​​​​Alpine Steakhouse, established in 1975, is casually referred to by locals as a “cultural landmark”. While it has received multiple “Best of” Sarasota Magazine awards for its prime dry-aged steaks, it is also a charming, old-school eatery that functions as both a restaurant, and a meat and specialty grocery store. As part of its charm, Alpine is the only restaurant in Florida to sell the TurDucKen, made famous by football legend John Madden during Thanksgiving NFL broadcasts.
