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Oyster Bay Homes For Sale

West of the Trail Real Estate

Welcome to the neighborhood of Oyster Bay which is a waterfront neighborhood West of the Trail in Sarasota, FL.  The following list of Oyster Bay Homes for Sale is arranged by price and is updated daily from the MLS system with prices, descriptions, and photos with virtual tours.  Scroll through this page to see the complete list.

If you are looking for something specific or have any questions about a Oyster Bay home please feel comfortable in calling Sara at (941) 586-4790 or Email her directly at Sara@SaraSellsSarasota.com


Oyster Bay Estates Real Estate Listings

All Listings Under $100,000 $500,000 - $600,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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Sort listings by:Price, Highest First

1441 Rebecca Ln

Sarasota, FL - $4,650,000

Residential, Single Family Home
Oyster Bay Landings
A4455314
  • 4 Beds
  • 6 Baths
  • 5,889 SQFT
  • 81 DOM
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Inspired Coastal Design. Located In The Private Gated Enclave Of Oyster Bay Landings, This Amazing Waterfront Residence Combines Unique Architecture And Incredible Interior Design To Create A Stunning Yet Comfortable And Functional Home. Set On A ...

1522 N Lake Shore Dr

Sarasota, FL - $2,995,000

Residential, Single Family Home
Oyster Bay Estates
A4442286
  • 4 Beds
  • 5 Baths
  • 4,783 SQFT
  • 249 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...

1409 S Lake Shore Dr

Sarasota, FL - $2,375,000

Land, Residential
Oyster Bay Estates
A4436668
  • 320 DOM
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Build Your Dream Property On Prominent South Lake Shore Drive– A Long-established, Highly-regarded Oyster Bay Estates Neighborhood. Tucked Away On Sarasota’s Mainland, This Private Waterside Oasis Spans Almost An Acre Of Beautifully Treed Landscap...

1313 S Lake Shore Dr

Sarasota, FL - $2,300,000

Residential, Single Family Home
Oyster Bay Estates
A4460954
  • 3 Beds
  • 4 Baths
  • 3,003 SQFT
  • 41 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...

1207 N Lake Shore Dr

Sarasota, FL - $2,250,000

Residential, Single Family Home
Oyster Bay Estates
A4458536
  • 5 Beds
  • 5 Baths
  • 5,043 SQFT
  • 65 DOM
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The Motivated Owner Has Positioned This Property To Be One Of The Best Waterfront Opportunities In The Marketplace Today. Located On A Boat Basin In The Beloved Neighborhood Of Oyster Bay, Its Setting Is Magical W/a Large Backyard And Private Dock...

1818 N Lake Shore Dr

Sarasota, FL - $2,250,000

Residential, Single Family Home
Oyster Bay Estates
A4454495
  • 4 Beds
  • 6 Baths
  • 5,968 SQFT
  • 164 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...

1430 Kimlira Ln

Sarasota, FL - $1,700,000

Residential, Single Family Home
Oyster Bay Estates
A4462797
  • 5 Beds
  • 5 Baths
  • 4,460 SQFT
  • 23 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...

4439 Westwood Ln

Sarasota, FL - $1,460,000

Residential, Single Family Home
Oyster Bay Estates
A4425835
  • 4 Beds
  • 4 Baths
  • 3,657 SQFT
  • 426 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...

4487 Camino Real

Sarasota, FL - $1,085,000

Residential, Single Family Home
Oyster Bay Estates
A4424993
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 439 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...

1613 Field Rd

Sarasota, FL - $999,000

Residential, Single Family Home
Oyster Bay Estates
A4449196
  • 3 Beds
  • 5 Baths
  • 3,292 SQFT
  • 169 DOM
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1613 Field Rd. West Of The Trail In The Sought-after Oyster Bay Neighborhood. Featuring 3br/3ba/2hba, Two Story Pool Home With Fully Private Fenced Backyard. Perfect For Entertaining Family And Friends. French Doors In The Living Room Overlook T...

1511 S Lake Shore Dr

Sarasota, FL - $995,000

Land, Unimproved Land
Oyster Bay Estates
A4422136
  • 471 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 ...

1630 N Lakeshore Dr

Sarasota, FL - $839,250

Land, Residential
Oyster Bay Estates
A4445171
  • 215 DOM
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Spectacular Lakefront Lot To Build Your Dream Home In Coveted Oyster Bay Estates, One Of The Most Sought After Neighborhoods In Sarasota, Mature Trees And Landscaping, Riverview High School, The Field Club, And Just Minutes To Siesta Key, Publix...

1421 N Lake Shore Dr

Sarasota, FL - $599,000

Land, Residential
Oyster Bay Estates
A4464107
  • 9 DOM
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Prime West Of Trail Single Family Home (buildable Lot) Located In The Oyster Bay Estates Subdivision. Lot Dimensions Are 100' X 150' (.34 Acre) Major Renovation Required To Update This 1959 3br/2ba Wood Frame Home. Suggested Best Use Is As Teardow...

1421 N Lake Shore Dr

Sarasota, FL - $599,000

Residential, Single Family Home
Oyster Bay Estates
A4464087
  • 3 Beds
  • 2 Baths
  • 2,427 SQFT
  • 9 DOM
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Prime West Of Trail Single Family Home (buildable Lot) Located In The Oyster Bay Estates Subdivision. Lot Dimensions Are 100' X 150' (.34 Acre) Major Renovation Required To Update This 1959 3br/2ba Wood Frame Home. Suggested Best Use Is As Teardow...

1914 Hillsdale Pl

Sarasota, FL - $569,900

Residential, Single Family Home
Oyster Bay East
A4455586
  • 3 Beds
  • 2 Baths
  • 1,596 SQFT
  • 89 DOM
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***oyster Bay East***large Lot***recent Renovations***cul-de-sac Lot***large Pool***screened Pool/lanai Enclosure***immaculate***move In Ready*** Location, Location, Location...this Recently Renovated Property The Lowest Priced Home In One Of Sar...


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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 April 5th, 2020 at 5:45am EDT.