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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 $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 - $4,385,000

Residential, Single Family Home
Oyster Bay Landings
A4424301
  • 4 Beds
  • 5 Baths
  • 5,428 SQFT
  • 107 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
  • 93 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
  • 241 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 - $2,375,000

Land, Residential
Oyster Bay Estates
A4436668
  • 5 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...

1400 Kenilworth St

Sarasota, FL - $2,100,000

Residential, Single Family Home
Oyster Bay Landings
A4432539
  • 3 Beds
  • 3 Baths
  • 2,582 SQFT
  • 48 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 - $2,100,000

Land, Residential
Oyster Bay Landings
A4432440
  • 51 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...

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
  • 237 DOM
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This Property Should Be Firmly On The Radar Of The Savvy Buyer Seeking The Utmost In Quality Construction With A Classic Thorning Little Architectural Design. Delivering Not Only In Value, Scale And Style, The Home Is Located In One Of The Area’s ...

4439 Westwood Ln

Sarasota, FL - $1,650,000

Residential, Single Family Home
Oyster Bay Estates
A4425835
  • 4 Beds
  • 4 Baths
  • 3,657 SQFT
  • 111 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...

1401 Kenilworth St

Sarasota, FL - $1,200,000

Land, Unimproved Land
Oyster Bay Landings
A4431395
  • 51 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 - $1,170,000

Residential, Single Family Home
Oyster Bay Estates
A4424993
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 124 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 - $1,100,000

Land, Unimproved Land
Oyster Bay Estates
A4422136
  • 156 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 ...

Lot 14 Kenilworth St

Sarasota, FL - $1,000,000

Land, Unimproved Land
Oyster Bay Landings
A4431400
  • 51 DOM
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Tucked Away In The Exclusive West Of Trail Area Of Sarasota, Oyster Bay Landings Is A Secluded Waterfront Enclave Of 14 Homesites. Bring Your Own Builder To This Waterfront Property And Make Your Dreams Come Alive! Level Lot, Set On Protected Boat...

1616 N Lake Shore Dr

Sarasota, FL - $985,000

Residential, Single Family Home
Oyster Bay Estates
A4419648
  • 3 Beds
  • 3 Baths
  • 2,389 SQFT
  • 187 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...

1616 N Lake Shore Dr

Sarasota, FL - $985,000

Land, Residential
Oyster Bay Estates
A4419652
  • 187 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...

1525 Kenilworth St

Sarasota, FL - $789,000

Residential, Single Family Home
Oyster Bay
A4417849
  • 3 Beds
  • 2 Baths
  • 2,183 SQFT
  • 205 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 ...


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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 May 26th, 2019 at 5:30pm EDT.