Oyster Bay Estates
Real Estate Listings & Community Guide
Oyster Bay Real Estate in Sarasota, FL
Oyster Bay Estates homes for sale are located within a very desirable neighborhood of 143 homes located West of the Trail in Sarasota. The single-family residences are surrounded by mature tropical landscaping with scenic views of the waterways and the bright blue Florida sky. The home designs range from Spanish Mediterranean, Key West, Ranch and Contemporary built from 1952 to current. Even though there are many older homes, they are been updated and tastefully remodeled by the current homeowners. Read more
Oyster Bay Homes Overview

Community Info:
# of Homes: | 143 |
Year Built: | 1952 – Present |
Gated: | No |
Pool: | No |
Fences: | Yes |
Yard Care: | No |
HOA Fee: | Yes |
CDD Fee: | No |
Min. Lease: | 1 Month |
# of Leases: | 12 /Year |
Amenities:
- Waterfront
HOA Fee Includes:
- Common Maintenance
Category: Sarasota West of Trail Homes for Sale
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Transactions
400+
Sales
1/4 Billion
5-Star Reviews
150+

HONESTY · Reputation · Experience
Top 3% Home Sales Team in Sarasota & Manatee County
Current Homes For Sale in Oyster Bay

Receive New Listing Alerts For This Neighborhood
Insight For Oyster Bay Neighborhood
Pros:
- Waterfront community
- Short walk to historic downtown Palm Harbor
- Reasonable home prices
Considerations:
- Some homes may be older and in need of updating
Lifestyle:
- Pinellas Trail offers running biking and walking paths
- Quiet area but close to everything
- Top-rated schools and entertainment
Shopping:
- Grocery store is 3.6 miles
- UTC Mall is 10.9 miles
- Costco is 6.8 miles
Beach:
- Siesta Key Beach is 5.2 miles
- Closest beach is Siesta Key
Downtown:
- 2.1 miles
- 7 minute drive
Photos of Oyster Bay | Sarasota, FL
Additional Oyster Bay Neighborhood Information
Homes range from 1,500 to 7,000 square feet with deep water boat docks and other homes are on the lakefront. The homes were built on large lots with some of these executive and mansion style estates situated on Sarasota Bay. Many of these special homes have beautiful balconies, private lanais, tropical gardens, pools and plenty of space for entertaining family and guests. The nearby prestigious and historic Field Club on Roberts Bay was originally built as a residence in the 1920’s and was offered as a club in 1957. The Field Club now offers the Oyster Bay community a variety of membership privileges such as a clubhouse, boat docks with water access, community pool, tennis courts, park, and fine dining. The neighborhood is located near top-rated schools. Pets are always welcome. The annual HOA fee is very reasonable.
Location
Oyster Bay Estates is a great location close to Southside Village with its many shops and restaurants, Morton’s Gourmet Market, Publix, medical facilities and Sarasota Memorial Hospital. Spend the day relaxing on the beautiful powdery sand of Siesta Key Beach watching dolphins jumping through the waves and taking in the breathtaking sunset. If you enjoy shopping, the UTC Mall and St. Armand’s Circle will keep you busy. In a few minutes you can be in downtown Sarasota for an evening of fine dining along with theatrical performances and cultural venues. Golf enthusiasts have numerous public and semi-private challenging courses throughout the area. The Sarasota Airport is conveniently located for greeting upcoming guests to the Sunshine State.
Oyster Bay Estates homes for sale offer a relaxing Florida experience with that “Old World Charm”. Take advantage of a great opportunity to live in a very sought-after Sarasota neighborhood.

Oyster Bay Real Estate
Frequently Asked Questions
Oyster Bay is about 143 homes, built between 1952 – present.
No, Oyster Bay does not have a community pool.
No, Oyster Bay is not a gated community.
The HOA maintains the common areas of the community, however homeowners are responsible for their own yard care.
No, Oyster Bay does not have a CDD. (CDD stands for “Community Development District”. It is an additional tax assessment included on a property’s annual real estate tax bill, which pays for the initial and ongoing infrastructure cost for community development.)
Yes, some homes in Oyster Bay have fencing, however there may be HOA restrictions regarding which lot locations may have a fence, or the size or type of fence allowed. It is important to check HOA rules for specific fencing requirements prior to making a purchase decision.
Oyster Bay is located about 3.5 miles from downtown Sarasota.
Oyster Bay is located about 6.5 miles from Holmes Beach.
Oyster Bay is located about 7.5 miles from the Sarasota International Airport.
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.