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Oyster Bay Real Estate

Oyster Bay real estate in Sarasota Florida is a part of a lushly landscaped and carefully cared for "West of the Trail" community, located a few blocks south of Bee Ridge Road between Roberts Bay and the Tamiami Trail. The neighborhood features a wide variety of home styles from classic "Old-Florida" homes and updated ranches to executive mansions on over-sized lots. This older Sarasota neighborhood has the established landscaping and mature trees that only time can provide.

Discover more about the Oyster Bay, Sarasota's homes for sale or browse the currently available real estate listing below.

Oyster Bay Real Estate Listings

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Photo of Listing #A4414590

1329 N Lake Shore Dr, Sarasota, FL - $2,495,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 3,160 SQFT
  • 209 DOM
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Introducing This Private 1-acre Old Florida Style Waterfront Estate Property With Open Views Of Sarasota Bay In One Of Sarasota’s Most Beloved Neighborhoods, Oyster Bay. This Property Enjoys 100 Feet On The Water And Old Oaks And Tropical Flora Se...

1329 N Lake Shore Dr, Sarasota, FL - $2,495,000

Land, Residential
  • 61 DOM
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Introducing This Private 1-acre Old Florida Style Waterfront Estate Property In One Of Sarasota’s Most Beloved Neighborhoods, Oyster Bay. This Property Enjoys 100 Feet On The Water And Old Oaks And Tropical Flora Serve As The Backdrop For A Charmi...

Photo of Listing #A4414868

1818 N Lake Shore Dr, Sarasota, FL - $1,995,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,968 SQFT
  • 205 DOM
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Could This Be The Best Priced Opportunity In Sarasota? Absolutely. With A Price Reduction Of Half A Million Dollars And All Serious Offers Considered, This Property Is Firmly On The Radar Of The Savvy Buyer. Delivering Not Only In Value, Scale And...

4439 Westwood Ln, Sarasota, FL - $1,650,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,657 SQFT
  • 79 DOM
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Warm, Inviting And In A Stellar Location! Enter Through The Stunning, Arched Wood Doorway, You Will Be Met With A True Sense Of Serenity. Every Detail Has Been Carefully Thought Of In This Substantial Mediterranean Revival Home. Grand Columns Acce...

Photo of Listing #A4426164

1418 Ladue Ln, Sarasota, FL - $1,224,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 3,674 SQFT
  • 82 DOM
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Competitively Priced Below Appraisal. Tucked Away In A Prime Position In Sarasota’s West Of Trail Area, This Updated Two-story Home Is A Place For Families And Friends To Make Lasting Memories. Surrounded By Natural Beauty And Positioned Next To T...

Photo of Listing #A4424993

4487 Camino Real, Sarasota, FL - $1,170,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 92 DOM
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Beautiful West Of The Trail Contemporary Home In The Sought-after Oyster Bay Area And Walking Distance To The Field Club. It’s Situated On ½ Acre With Beautiful Gardens Surrounding The Home Featuring Exotic And Lush Tropical Landscaping With A La...

1511 S Lake Shore Dr, Sarasota, FL - $1,100,000

Land, Unimproved Land
  • 124 DOM
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Located In One Of The Most Sought-after Neighborhoods In Sarasota, Oyster Bay Estates, This Lake Front Lot Features Nearly 30,000 Square Feet Of Cleared, Buildable Land. The Perfect Site To Build Your Dream Home Awaits You And Includes A Complete ...

Photo of Listing #A4419652

1616 N Lake Shore Dr, Sarasota, FL - $985,000

Land, Residential
  • 155 DOM
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Nearly ½ Acre Lake Front Lot In Coveted Oyster Bay Estates! This Is The Perfect West Of The Trail Location To Build Your Dream Home. Or, For Those That Love The Mid-century Style, Work To Revive This 1954 One Story 2400 Sq. Ft. Home. An Updated Su...

Photo of Listing #A4419648

1616 N Lake Shore Dr, Sarasota, FL - $985,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,389 SQFT
  • 155 DOM
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Nearly ½ Acre Lake Front Lot In Coveted Oyster Bay Estates! This Is The Perfect West Of The Trail Location To Build Your Dream Home. Or, For Those That Love The Mid-century Style, Work To Revive This 1954 One Story 2400 Sq. Ft. Home. An Updated Su...

Photo of Listing #A4403669

1906 Hillsdale Pl, Sarasota, FL - $630,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,126 SQFT
  • 317 DOM
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West Of The Trail In The Fabulous Neighborhood Of Oyster Bay East! Casually Elegant Updated Home With Stunning Pool And Outdoor Living Space Situated On A Quiet Cul De Sac. Renovated In 2012 With New Roof, Ac, Sliding Doors, Windows Etc. An Open ...

Photo of Listing #A4430615

1801 Field Rd, Sarasota, FL - $479,000

Residential, Single Family Home
  • 2 Beds
  • 2 Baths
  • 1,682 SQFT
  • 39 DOM
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** Must See ** Seller Motivated, Bring An Offer ** Oyster Bay Estates Presents A Botanical Paradise In This Fantastic 2 Bed, 2 Bath Pool Home. Sitting On A 15,500ft2 (.35 Acres) Lot, Native Plantings, Blooming Flowers, Soaring Palms, Plush Grass A...

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Oyster Bay Homes

There are approximately 170 homes in Oyster Bay. Homes for sale in the neighborhood vary in architectural styles, from classic Florida ranches and two-story residences in the interior sections to lavish Oyster Bay Estate mansion estates directly on Roberts Bay. Some older homes have been fully remodeled and restored. Others have been torn down and replaced by larger homes. The dwellings range in size from just under 2,000 to more than 6,000 sq ft. , Some of the larger Oyster Bay Estates homes are directly on Roberts Bay. Others are on deep water canals with no bridges to limit sailboat access to the Bay and the Gulf of Mexico, while others overlook two small lakes.

Modest properties in Oyster Bay are priced in the $400,000 range while executive estates sitting directly on the bay sell for as much as $5.0 million. 

Oyster Bay Estates

Oyster Bay Estate is the gated community portion of the community. Here you will find styles ranging from modern mansions and Spanish-style villas to Mediterranean estates, The neighborhood contains a friendly mix of young professionals, new families, and retirees living along tree-lined streets. Located only minutes from some of the barrier islands that line the coast of Sarasota, Oyster Bay Estates is practically a beach community of its own.

The Field Club

The Field Club, located within Oyster Bay Estates, is one of the most prestigious yacht clubs in Sarasota. Originally the home of the the Fields family, of the Marshall Field retail stores in Chicago, it was converted from a private residence into a yacht club in 1957. Members of the club have access to the tennis courts, pools, boating activities, and social activities the club offers.

Why Choose An Oyster Bay Home?

Residents of Oyster Bay and Oyster Bay Estates enjoy living in a prime location. They are spoiled with convenient access to all of the arts and cultural amenities of downtown Sarasota as well as the soft, white sands of Siesta Key's beaches.

If you love sailing or motor boating or you're just seeking a comfortable close-to-downtown-Sarasota location, Oyster Bay real estate will meet your dreams as well as your needs.

If you are interested in seeing these gorgeous homes in person, I would be happy to arrange a tour of this charming Sarasota waterfront community - Call me on my direct line at 941-928-3424 or contact me online.

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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.

Listing information last updated on April 24th, 2019 at 6:44pm EDT.