Below are all of the homes for sale in the Oyster Bay Estates neighborhood of Sarasota Florida. All real estate listings are updated daily from the Multiple Listing Service (MLS).
To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!
… Read More| Total Listings: | 14 |
| Average Price: | $6,202,357 |
| Highest Price: | $26,400,000 |
| Lowest Price: | $1,975,000 |
| Average Size: | 4,807 ft² |
| Average Price Per Square Foot: | $1,168 per ft² |
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Welcome To Villa Meraviglia - A Home Beyond Imagination. An Extraordinary Neo-classical Italian Renaissance Estate Set On 1.22 Bayfront Acres In Sarasota’s Exclusive Oyster Bay Estates. Featuring 146 Feet Of Pristine, Direct Frontage Along The Spa...
Tucked Behind The Gates Of Oyster Bay Landings, The Only Gated Community In Oyster Bay Estates, This One-of-a-kind 2024 Sweet Sparkman–designed Residence Offers Exceptional Privacy And Boating Access In A Premier West Of Trail Location. One Of Jus...
One Or More Photo(s) Has Been Virtually Staged. Located West-of-trail In One Of Sarasota’s Sought-after Neighborhoods, Oyster Bay Estates, This Stunning Waterfront Home Is Designed For Those Who Appreciate Breathtaking Views And Effortless Enterta...
The Windemere Ii Is An Extraordinary Luxury Custom Home Meticulously Crafted By Heritage Builders. This Coastal Contemporary Residence With Clean Lines Is Situated On A Very Rare West-of-trail Lakefront Estate Home Site. The Exquisite Two-level Re...
A Residence Of Sophistication And Luxury, This Exceptional Home Was Thoughtfully Designed To Bring Family And Friends Together—sharing Good Food, Meaningful Connection, And The Enjoyment Of Elevated Everyday Living. Ideally Located Just 8 Miles Fr...
One Or More Photo(s) Has Been Virtually Staged. Experience Luxury West-of-trail Living In Sarasota’s Coveted Oyster Bay Neighborhood. This Newly Built 2026 Custom Residence Offers 5 Bedrooms, 5 Full And 2 Half Baths—all On One Thoughtfully Designe...
Privately Positioned In Gated Oyster Bay Landings With Water Views Stretching Down A Short Canal To Sarasota Bay, This Stunning Iconic Masterpiece From World-renowned Architect Guy Peterson Is A Breathtaking Example Of The Sarasota School Of Archi...
Perfectly Positioned On A Spacious, Private Lot In The Prestigious And Highly Sought-after Oyster Bay Estates Community, The Residence Embodies Exceptional Design, Architectural Intention, And Refined Livability. Custom Designed And Built By Disti...
Experience Refined Modern Living In This Oyster Bay Estates, Stunning Five-bedroom, Four-and-a-half-bath Residence Thoughtfully Designed And Custom Built With Exceptional Craftsmanship, Elevated Finishes, And Sophisticated Smart-home Technology. E...
Under Construction. Estimated Completion July 2026. You Have To See This One In Person To Understand. Prestigious Oyster Bay Estates Modern Design Built By The Holliday Group. Nestled On A Generous 18,991 Sq Ft Lot With 71 Feet Of Serene Lake Fro...
**brilliantly Updated And Meticulously Maintained Estate In Oyster Bay, A Coveted, West Of Trail Neighborhood** Situated On A Large Corner Lot, This 4-bed, 3 Full And 1 Half Bath Residence Is Being Sold Furnished And Offers Desired Privacy And Ex...
Welcome To This Stunning, Fully Reimagined Residence In One Of Sarasota’s Most Sought-after Neighborhoods West Of The Trail. Comprehensive Back To Studs Renovation With An Effective Build Date To Florida Building Codes Of 2020. No Detail Has Been ...
This Oyster Bay Residence With Well Known Address Of “north Lakeshore Dr.”….west Of Trail Perfect Location…..close To Siesta Key And The Activities And Also Near The Renowned “field Club”. The Grand Entrance Is Deserving Of The Compliments You Wil...
Located In The Sought-after West Of Trail Neighborhood Of Oyster Bay Estates, This Beautifully Updated Residence Sits On Nearly One-third Of An Acre Just Around The Corner From The Historic Field Club. The Home Blends Timeless Architectural Chara...
All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.
Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.
Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on April 22nd, 2026 at 8:53am EDT.
Framed in the lifestyle and "old world" charm of Sarasota, Oyster Bay Estates is a mature and distinguished neighborhood nestled along the shores of the Sarasota Bay, just minutes from downtown Sarasota. There are 168 single family homes in the neighborhood. Residents enjoy well shaded and spacious home sites on the bay, lakefront or interior lots.
The history of this established west of the trail neighborhood that dates back many years. The area has an eclectic array of architectural styles including, classic "Old-Florida", ranch style, 2-story, and large estates just to name a few. With today's homeowners focused on innovations and designs, many of the older homes have been renovated and restored to look better than new. Homes range anywhere from 1,914 to 5,615 square feet. Prices range from around $500,000 to over $5 million.
With location being a key factor, select homeowners have private canal access to deep sailboat waters while the rest of the community is privileged to be neighbors with the prestigious Field Club. Encompassing 11 acres of plush landscaping, this highly exclusive club provides 600 members with tennis, yachting and social events. Conveniently located, residents of Oyster Bay can choose to join this club for their ample amenities or simply indulge in a variety of urban activities surrounding Sarasota. Siesta Key Beaches, St Armands Circle, Downtown Main Street, the Arts and Culture District are all within minutes.
Whether you want to relax in your quiet sanctuary, sail the Bay waters, or meander the streets of Sarasota, the choice is yours in alluring Oyster Bay.
