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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 $400,000 - $500,000 $600,000 - $700,000
$700,000 - $800,000 $900,000 - $1,000,000 Over $1,000,000
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Sort listings by:Price, Highest First

1404 Kenilworth St

Sarasota, FL - $4,595,000

Residential, Single Family Home
Oyster Bay Landings
A4424301
  • 4 Beds
  • 5 Baths
  • 5,428 SQFT
  • 43 DOM
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Art You Can Live In! World Renowned And Acclaimed Architect, Guy Peterson, Designed Another Modern Masterpiece Of Remarkable Craftsmanship And Pure Minimalist Aesthetic. It All Began With A Vision, An Ambitious Dream To Imagine And Design The Cons...

1329 N Lake Shore Dr

Sarasota, FL - $2,495,000

Land, Residential
Oyster Bay Estates
A4428336
  • 29 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...

1329 N Lake Shore Dr

Sarasota, FL - $2,495,000

Residential, Single Family Home
Oyster Bay Estates
A4414590
  • 3 Beds
  • 3 Baths
  • 3,160 SQFT
  • 177 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...

1818 N Lake Shore Dr

Sarasota, FL - $1,995,000

Residential, Single Family Home
Oyster Bay Estates
A4414868
  • 4 Beds
  • 6 Baths
  • 5,968 SQFT
  • 173 DOM
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Incredible Value, As Seller Has Reduced By $500,000! This Oyster Bay Estates Residence Designed By Architect, Thorning Little, Embodies Classic Italianate Design Right Down To The Exterior Appearance Of A Century Old Manse. Built To The Highest St...

4439 Westwood Ln

Sarasota, FL - $1,650,000

Residential, Single Family Home
Oyster Bay Estates
A4425835
  • 4 Beds
  • 4 Baths
  • 3,657 SQFT
  • 47 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 - $1,195,000

Residential, Single Family Home
Oyster Bay Estates
A4424993
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 60 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...

1410 Ladue Ln

Sarasota, FL - $1,150,000

Residential, Single Family Home
Oyster Bay / Ladue
A4404790
  • 4 Beds
  • 4 Baths
  • 3,570 SQFT
  • 295 DOM
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Ladue Lane...charming Private Street In Sought After Location By The Field Club In The Oyster Bay Area. Traditional Family Home With So Many Inviting Spaces! The Main House Has 4 Bedrooms, 3 ½ Baths, The Guest House Above The Garage Has A Large Op...

1511 S Lake Shore Dr

Sarasota, FL - $1,100,000

Land, Unimproved Land
Oyster Bay Estates
A4422136
  • 92 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 ...

1616 N Lake Shore Dr

Sarasota, FL - $1,000,000

Residential, Single Family Home
Oyster Bay Estates
A4419648
  • 3 Beds
  • 3 Baths
  • 2,389 SQFT
  • 123 DOM
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Perfect West Of The Trail Location To Build Your Dream Home. A True Tropical Haven, And One Of The Most Sought After Neighborhoods In Sarasota - Oyster Bay Estates Abuts Sarasota Bay And Is Located Next To The Distinguished The Field Club; A Priva...

1616 N Lake Shore Dr

Sarasota, FL - $1,000,000

Land, Residential
Oyster Bay Estates
A4419652
  • 123 DOM
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Perfect West Of The Trail Location To Build Your Dream Home. A True Tropical Haven, And One Of The Most Sought After Neighborhoods In Sarasota - Oyster Bay Estates Which Abuts Sarasota Bay And Is Located Next To The Distinguished The Field Club; A...

4557 Camino Real

Sarasota, FL - $949,000

Residential, Single Family Home
Oyster Bay
A4215896
  • 4 Beds
  • 5 Baths
  • 3,771 SQFT
  • 703 DOM
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This Charming Four-bedroom Oyster Bay Home Is Spacious And Built With Custom Details. Located “west Of The Trail” In A Wonderfully Central Spot, Only Minutes From Downtown Sarasota’s Bustling City Life And Unforgettable Gulf Beaches At Siesta And ...

1525 Kenilworth St

Sarasota, FL - $789,000

Residential, Single Family Home
Oyster Bay
A4417849
  • 3 Beds
  • 2 Baths
  • 2,183 SQFT
  • 141 DOM
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Stunning Renovation West Of The Trail! This Light And Bright California Contemporary Has Walls Of Windows And Cathedral Ceilings Making It Feel As One With The Outdoors. The Expansive Floor Plan Features A Separate Dining Room And Huge Great Room ...

1906 Hillsdale Pl

Sarasota, FL - $630,000

Residential, Single Family Home
Oyster Bay East
A4403669
  • 3 Beds
  • 3 Baths
  • 2,126 SQFT
  • 304 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 ...

1801 Field Rd

Sarasota, FL - $499,000

Residential, Single Family Home
Oyster Bay Estates
A4430615
  • 2 Beds
  • 2 Baths
  • 1,682 SQFT
  • 7 DOM
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** Must See ** 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 And Charming Shadows Make This One Of...


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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 March 23rd, 2019 at 12:45pm EDT.