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: | 12 |
| Average Price: | $5,970,500 |
| Highest Price: | $26,400,000 |
| Lowest Price: | $1,895,000 |
| Average Size: | 4,531 ft² |
| Average Price Per Square Foot: | $1,138 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...
Under Construction. 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 Ex...
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 Entertaining. With A Prime Position On Sarasota Bay, Th...
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 2025 Custom Residence Offers 5 Bedrooms, 5 Full And 2 Half Baths—all On One Thoughtfully Designe...
Pre-construction. To Be Built. Step Into The Pinnacle Of Modern Luxury With This Stunning Home Located In The Prestigious Oyster Bay Estates Built By The Holliday Group. Nestled On A Generous 18,991 Sq Ft Lot With 71 Feet Of Serene Lake Frontage, ...
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...
**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 Offers Desired Privacy And Extensive Updates. Attention ...
Welcome To This Stunning, Fully Reimagined Residence In One Of Sarasota’s Most Sought-after Neighborhoods West Of The Trail. No Detail Has Been Overlooked In This Comprehensive Luxury Renovation, Offering The Perfect Blend Of Timeless Coastal Eleg...
Construction Now Complete! Prepare To Be Impressed With Artful Expressions Of Design, Beautifully Tailored Interiors And An Open Brightness Filling The Home And Welcoming You To Further Explore The Many Subtle Nuances And Brilliant Examples Of Exc...
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...
Welcome To This Beautifully Appointed Estate Located At 4505 Camino Real In Sarasota — A Private, Fully Walled-in Enclave Designed For Both Elegance And Everyday Comfort. This Unique Residence Offers A 3-bedroom, 3.5-bath Main House Where Every Ro...
It Just Doesn't Get Any More Charming Than This Home. Beautifully Updated 4-bedroom, 3.5-bathroom Residence Nestled In The Highly Sought-after Oyster Bay Area. Perfectly Positioned West Of The Trail, Outside Of A Flood Zone, This Charming Residenc...
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 December 14th, 2025 at 10:13am EST.
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.
