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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 $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

1409 S Lake Shore Dr

Sarasota, FL - $4,950,000

Residential, Single Family Home
Oyster Bay Estates
A4405978
  • 4 Beds
  • 4 Baths
  • 5,193 SQFT
  • 215 DOM
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Pre-construction: To Be Built. This Incredibly Beautiful Home Will Be Built On Prestigious South Lake Shore Drive– A Long-established, Highly-regarded Oyster Bay Estates Neighborhood. Tucked Away On Sarasota’s Mainland, This Private Waterside Oas...

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
  • 110 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...

1409 S Lake Shore Dr

Sarasota, FL - $2,400,000

Land, Single Family Use
Oyster Bay Estates
A4208320
  • 354 DOM
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Build Your Dream Property On Prestigious 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 Landsc...

1235 N Lake Shore Dr

Sarasota, FL - $2,395,000

Residential, Single Family Home
Oyster Bay Estates
A4213972
  • 4 Beds
  • 3 Baths
  • 3,535 SQFT
  • 301 DOM
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Water Views In The Front And Back Of This 4br Plus Family And Bonus Rooms Oyster Bay Home Create An Idyllic Backdrop For An Easygoing Family Lifestyle. This Private Residence Is Surrounded By Lush Manicured Foliage, With A Charming Courtyard Entry...

1818 N Lake Shore Dr

Sarasota, FL - $2,250,000

Residential, Single Family Home
Oyster Bay Estates
A4414868
  • 3 Beds
  • 6 Baths
  • 5,968 SQFT
  • 106 DOM
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This Oyster Bay Estates Residence Designed By Accomplished Architect, Thorning Little, Embodies Classic Italianate Design With Moorish Influences. Framed By Mature Palms And Lush Hedges, This West Of The Trail Home Exudes Palm Beach Garden Glamour...

1410 Ladue Ln

Sarasota, FL - $1,150,000

Residential, Single Family Home
Oyster Bay / Ladue
A4404790
  • 4 Beds
  • 4 Baths
  • 3,570 SQFT
  • 228 DOM
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Ladue Lane...charming Street In Sought After Location By The Field Club In The Oyster Bay Area. Traditional Family Home With Many Inviting Spaces With 4 Bedrooms, 3 ½ Baths, (3570 Sf), The Guest House Above The Garage Has A Large Open Space, Small...

1616 N Lake Shore Dr

Sarasota, FL - $1,125,000

Residential, Single Family Home
Oyster Bay Estates
A4419648
  • 3 Beds
  • 3 Baths
  • 2,389 SQFT
  • 56 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 - $1,125,000

Land, Residential
Oyster Bay Estates
A4419652
  • 56 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...

1511 S Lake Shore Dr

Sarasota, FL - $1,100,000

Land, Unimproved Land
Oyster Bay Estates
A4422136
  • 25 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 ...

4557 Camino Real

Sarasota, FL - $995,000

Residential, Single Family Home
Oyster Bay
A4215896
  • 4 Beds
  • 5 Baths
  • 3,771 SQFT
  • 636 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
  • 74 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
  • 237 DOM
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Move In Ready And 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 Etc., Built Of High Quality Construction And Former Model Home. An Open...


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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 January 16th, 2019 at 7:30pm EST.