Some West of the Trail communities are more impressive than others, and Oyster Bay Landings Sarasota perfectly fits this definition. Located in the Oyster Bay district of South Sarasota, this neighborhood is of a more recent vintage when compared to others in the West of the Trail area; it consists of 14 home sites that overlook Roberts Bay and Siesta Key, and it is widely considered to be one of the most attractive developments envisioned by renowned Sarasota architect Robert Morris.

Development of Oyster Bay Landings Sarasota started about 30 years ago when Morris purchased the land adjacent to a local marina. The first stage of construction consisted of rezoning the land from commercial to residential use, planting trees and seeding tropical landscaping with native species. Morris’ vision for Oyster Bay Landings came from the paintings of American visual artist Thomas Kinkade, and this explains the nice atmosphere created by the lush landscaping, the old-fashioned street lamps and the wooden piers.

Each property at Oyster Bay Landings has been built as a custom waterfront estate. The American coastal style is predominant, but one of the most interesting properties sold in early 2024 for under $2.9 million was a four-bedroom mansion that had a courtyard style pool area and a boat lift to provide easy access to Sarasota Bay. Latest pricing at Oyster Bay Landings Sarasota will be found below if there is inventory.

Most residents of Oyster Bay Landings are boaters and anglers who enjoy the very generous docking space deeded to each property; this neighborhood is perfect for home buyers who also own large yachts. The Field Club of Sarasota is just outside of the front gate, and a busy shopping district along the Tamiami Trail is just a few blocks away. The beaches of Siesta Key are close enough for a bike ride, but many residents will prefer to take their boats across Roberts Bay for the weekend.