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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

1522 N Lake Shore Dr

Sarasota, FL - $3,100,000

Residential, Single Family Home
Oyster Bay Estates
A4442286
  • 4 Beds
  • 5 Baths
  • 4,783 SQFT
  • 106 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...

1818 Lake Shore Dr

Sarasota, FL - $2,449,000

Residential, Single Family Home
Oyster Bay Estates
A4449050
  • 4 Beds
  • 6 Baths
  • 5,968 SQFT
  • 22 DOM
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This Impeccably Built Custom Home In One Of The Premier Neighborhoods In Sarasota Has Everything You Could Want! With Almost 6,000 Square Feet Of Refined Living Space, Coupled With Almost 2,000 Feet Of Outdoor Entertaining Space It Is Fit For Eve...

1409 S Lake Shore Dr

Sarasota, FL - $2,375,000

Land, Residential
Oyster Bay Estates
A4436668
  • 177 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...

1525 N Lake Shore Dr

Sarasota, FL - $1,995,000

Residential, Single Family Home
Oyster Bay Estates
A4443962
  • 4 Beds
  • 4 Baths
  • 4,407 SQFT
  • 87 DOM
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Spectacular Tuscan Masterpiece In Oyster Bay Estates, Sarasota's Most Coveted West-of-the-trail Neighborhood. This Spanish-italian Design Home Was Built In 2006 By Custom-builder Bruce Saba With Impeccable Finishes And The Utmost Attention To Deta...

1400 Kenilworth St

Sarasota, FL - $1,995,000

Residential, Single Family Home
Oyster Bay Landings
A4432539
  • 3 Beds
  • 3 Baths
  • 2,582 SQFT
  • 220 DOM
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This Bayfront Cottage, West Of Trail, In-town Location Of Distinction Seems Worlds Away Yet Enjoys Easy Accessibility To The Very Best Sarasota Has To Offer. Hidden Behind The Gates Of Oyster Bay Landings Is A Winding Tree-canopied Brick Lane That...

1400 Kenilworth St

Sarasota, FL - $1,995,000

Land, Residential
Oyster Bay Landings
A4432440
  • 223 DOM
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This Bayfront, West Of Trail, In-town Location Of Distinction Seems Worlds Away Yet Enjoys Easy Accessibility To The Very Best Sarasota Has To Offer. Hidden Behind The Gates Of Oyster Bay Landings Is A Winding Tree-canopied Brick Lane That Leads T...

4439 Westwood Ln

Sarasota, FL - $1,460,000

Residential, Single Family Home
Oyster Bay Estates
A4425835
  • 4 Beds
  • 4 Baths
  • 3,657 SQFT
  • 283 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...

1511 N Lake Shore Dr

Sarasota, FL - $1,374,900

Residential, Single Family Home
Oyster Bay Estates
N6104544
  • 4 Beds
  • 4 Baths
  • 3,613 SQFT
  • 253 DOM
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Located In The Coveted Oyster Bay Neighborhood This Key West Style Exterior And Contemporary Interior Home Sits On A Half Acre Lot. The Newly Remodeled Open Floor Plan Boasts 12 To 29 Ft. Ceilings And Spacious Well Maintained Rooms. The Home Offer...

1421 Rebecca Lane, Lot #3

Sarasota, FL - $1,200,000

Land, Residential
Oyster Bay Landings
A4439368
  • 139 DOM
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Oyster Bay Landings Where Your Coastal Dream Home Can Come Alive. Rare To Find Mainland, Gated, And Waterfront That Is Just Off Roberts Bay Near The Coveted Field Club Area. On Protected Boating Water, This Beautiful Neighborhood Features Buried U...

1431 Rebecca Lane, Lot #4

Sarasota, FL - $1,175,000

Land, Residential
Oyster Bay Landings
A4439369
  • 139 DOM
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Oyster Bay Landings Where Your Coastal Dream Home Can Come Alive. Tell Your Own Story In This Rare To Find Mainland, Gated, And Waterfront Enclave Just Off Roberts Bay Near The Coveted Field Club Area. On Protected Boating Water, This Beautiful Ne...

1613 Field Rd

Sarasota, FL - $1,100,000

Residential, Single Family Home
Oyster Bay Estates
A4449196
  • 3 Beds
  • 5 Baths
  • 3,292 SQFT
  • 26 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...

1401 Kenilworth St

Sarasota, FL - $1,100,000

Land, Unimproved Land
Oyster Bay Landings
A4431395
  • 223 DOM
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This West Of Trail In-town Location Of Distinction Seems Worlds Away Yet Enjoys Easy Accessibility To The Very Best Sarasota Has To Offer. Hidden Behind The Gates Of Oyster Bay Landings Is A Winding Tree-canopied Brick Lane Leads Through A Small S...

4487 Camino Real

Sarasota, FL - $1,095,000

Residential, Single Family Home
Oyster Bay Estates
A4424993
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 296 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 - $995,000

Land, Unimproved Land
Oyster Bay Estates
A4422136
  • 328 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 - $965,000

Residential, Single Family Home
Oyster Bay Estates
A4419648
  • 3 Beds
  • 3 Baths
  • 2,389 SQFT
  • 359 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...


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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 November 15th, 2019 at 8:30pm EST.