Oyster Bay Estates Homes for Sale

Oyster Bay Estates Sarasota

Oyster Bay Estates is one of the many West of the Trail neighborhoods in Sarasota that has some of the most desirable beachfront real estate in Florida. Real estate is in demand because of the proximity to immaculate, sandy beaches and downtown Sarasota. The climate is ideal for buyers who want to experience the beach lifestyle all year-round, or those looking for their dream vacation home. Prime real estate in Oyster Bay offers buyers panoramic views of Sarasota Bay and spectacular sunsets. Read More About Oyster Bay Estates.

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Diverse Selection of Homes


Unlike many areas in South Florida in which most of the homes are similar, West of the Trail neighborhoods offers a diverse range of architectural styles. Classic bungalows make lovely vacation or starter homes and have the charm a lot of buyers seek. Modern, airy homes with open floor plans and spectacular oceanfront mansions are available, with something for every taste and lifestyle. 

Oyster Bay has all the charm of the old world, with a variety of classic, Florida ranch-style homes and breathtaking estates that have been lovingly renovated. The imposing locale is on the Sarasota Bay shore. Select homeowners have access to a deep water canal, and many of the homes are on the lakefront. The price range starts at approximately $500,000 and goes to more than $5 million for breathtaking estates on the Florida coast. The homes are open and spacious and range in size from approximately 1,900 to more than 5,000 square feet. 

Nearby Attractions

The Arts and Culture District of Sarasota, dining and shopping, and St. Armand's Circle are readily available from Oyster Bay. The shops at Southside Village and the Siesta Key Beach are nearby. The Intracoastal Waterway and barrier islands make it a sought-after region for boating and yachting enthusiasts. The area is famous for its trend-setting restaurants, museums, and galleries while maintaining the atmosphere of a small, residential neighborhood. 

Oyster Bay Estates is a subdivision with many older homes that have been updated and completely renovated and are ready for new owners. The Field Club on 11 acres offers residents social events and outdoor activities including swimming, tennis, and yachting. 

From Our Blog - West of Trail
Rising Inventories - Market Shifting in Sarasota?

Is this the end of a boom cycle in the real estate market? It is too early to tell but some believe so. Below I provided graphs of inventories levels in Sarasota, Manatee, Longboat Key, Siesta Key, ... Read more

4907 Eastchester Drive - Very Cool House!

I was poking through MLS and found this really great looking home for sale west of the trail in the Museum area of Sarasota. I thought you might enjoy the photos below. Give us a call at 941.822.... Read more

The Hottest Neighborhood in Sarasota?

If you’re looking for luxury with a rich history, established neighborhoods, and an elegant mix of old-world glamour and modern sophistication, living West of the Trail in Sarasota is the ... Read more

Mid Century Modern For Sale

You have to check out this fabulous mid-century modern home for sale in Oyster Bay Estates. I was poking around the MLS this morning and noticed it. This lovely home at 1833 N Lakeshore Drive just ... Read more