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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 #A4442286

1522 N Lake Shore Dr, Sarasota, FL - $2,895,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,783 SQFT
  • 341 DOM
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Tucked Away On Lakeshore Drive In A Storybook Lakefront Setting, This Exquisite Estate Embodies Tropical Elegance And Style. Luxurious Appointments, State-of-the-art Amenities, And A Romantic Water View Present An Artful Backdrop For Living. Beaut...

Photo of Listing #A4454495

1818 N Lake Shore Dr, Sarasota, FL - $2,250,000

Residential, Single Family Residence
  • 3 Beds
  • 6 Baths
  • 5,968 SQFT
  • 240 DOM
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Set In Oyster Bay Estates And Remarkable In Every Way Is Villa Lidia, A Stunning Example Of Architectural Mastery And Creatively Imagined By Acclaimed Architect Thorning Little. Impressive In Both Indoor And Outdoor Living Space As Well As Its Cla...

Photo of Listing #A4460954

1313 S Lake Shore Dr, Sarasota, FL - $2,150,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,003 SQFT
  • 100 DOM
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Mid-century Modern, Canal-front Home On Over 1/2 Acre In Desirable Oyster Bay Estates. Easy Access To Roberts Bay/intracoastal. Partial Westerly Views Provide For Breathtaking Sunsets From The Expansive Backyard. Over 165' Of Concrete Seawall Wi...

1145 N Lake Shore Dr, Sarasota, FL - $2,100,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 6,963 SQFT
  • 115 DOM
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Priced At Land Value, The Seller Has Positioned This Waterfront Property For An Immediate Sale. Situated In Oyster Bay, One Of Sarasota’s Most Revered Neighborhoods, And Close To The Field Club, The Central Location And Tropical Setting Along The ...

1430 Kimlira Ln, Sarasota, FL - $1,700,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 4,460 SQFT
  • 115 DOM
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Stunning Oyster Bay 4460 Sq.ft. Estate Has Been Carefully Designed To Blend Into The Natural Setting Of This Secluded ½ Acre Property. Beautifully Imagined And Masterfully Constructed Home Features 5 Bedrooms And 5 Baths. A Mix Of Hand Scraped Woo...

Photo of Listing #A4424993

4487 Camino Real, Sarasota, FL - $1,085,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 476 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...

Photo of Listing #A4422136

1511 S Lake Shore Dr, Sarasota, FL - $995,000

Land, Unimproved Land
  • 563 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 #A4471239

1810 N Lake Shore Dr, Sarasota, FL - $850,000

Residential, Single Family Residence
  • 5 Beds
  • 3 Baths
  • 3,224 SQFT
  • 4 DOM
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One Or More Photo(s) Has Been Virtually Staged. Prime West Of Trail Location In Oyster Bay Estates Near The Field Club. Spacious And Private 5 Br/3ba Heated Pool Family Ranch Home (or Buildable Lot On Over A Third Of An Acre). This Home Has An Ea...

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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 DBA Stellar MLS.

Listing information last updated on July 6th, 2020 at 6:00am EDT.