Oyster Bay Estates

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Overview

Below are all of the homes for sale in the Oyster Bay Estates neighborhood of Sarasota Florida. All real estate listings are updated daily from the Multiple Listing Service (MLS).

To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!

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MLS® Listing Statistics

Total Listings: 11
Average Price: $1,499,350
Highest Price: $3,100,000
Lowest Price: $614,000
Average Size: 3,488 ft²
Average Price Per Square Foot: $433 per ft²

Explore Other West of the Trail Communities

Listings for Sale in Oyster Bay

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1522 N Lake Shore Dr, Sarasota, FL - $3,100,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,783 SQFT
  • 53 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...

Image 1: A4432539

1400 Kenilworth St, Sarasota, FL - $2,100,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,582 SQFT
  • 167 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...

Image 2: A4445676

1145 N Lake Shore Dr, Sarasota, FL - $2,000,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,963 SQFT
  • 12 DOM
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Priced Below Market For Immediate Sale. Located In One Of Sarasota’s Most Revered Neighborhoods And Tucked In On A Quiet Cul-de-sac Street, This Waterfront Gem Has A Boat Dock And Lift, Good Boating Water And Views Overlooking The Basin. The Home ...

Image 3: A4443962

1525 N Lake Shore Dr, Sarasota, FL - $1,995,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 4,407 SQFT
  • 34 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...

4439 Westwood Ln, Sarasota, FL - $1,650,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,657 SQFT
  • 230 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...

Image 5: N6104544

1511 N Lake Shore Dr, Sarasota, FL - $1,374,900

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 3,613 SQFT
  • 200 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...

Image 6: A4424993

4487 Camino Real, Sarasota, FL - $1,095,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,765 SQFT
  • 243 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...

Image 7: A4419648

1616 N Lake Shore Dr, Sarasota, FL - $965,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,389 SQFT
  • 306 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...

1630 N Lakeshore Dr, Sarasota, FL - $899,950

Residential, Single Family Home
  • 4 Beds
  • 3 Baths
  • 2,821 SQFT
  • 19 DOM
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Seldom Available And A Hidden Gem "west Of The Trail" And On The Lake In Oyster Bay, One Of The Most Sought Out Areas In Sarasota. The Value Of This Property Is In The Land. The Buyers Wishing To Create Their Own Dream Home The Property Offers Unl...

Image 9: A4432827

1555 Eastbrook Dr, Sarasota, FL - $699,000

Residential, Single Family Home
  • 4 Beds
  • 2 Baths
  • 1,889 SQFT
  • 166 DOM
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Begin Your Dream Home West Of The Trail. This Charming Four-bedroom Pool Home Is Situated On A Corner Parcel Spanning Nearly A Quarter-acre Of Lush, Manicured Property. Waiting For You To Renovate Or Begin A New Build, The Open Layout Offers Tile ...

Image 10: A4442428

1828 N Lake Shore Dr, Sarasota, FL - $614,000

Residential, Single Family Home
  • 3 Beds
  • 3 Baths
  • 2,503 SQFT
  • 45 DOM
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One Or More Photo(s) Has Been Virtually Staged. West Of The Trail In Oyster Bay. Location, Location And Beautiful Grounds Is The Hallmark Of This Home. 3 Bedrooms, 2 Of Which Are On Suites With Private Baths For Visitors Or The Family’s Young Adul...

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 September 22nd, 2019 at 2:45pm EDT.

Oyster Bay Estates Description (continued)

Framed in the lifestyle and "old world" charm of Sarasota, Oyster Bay Estates is a mature and distinguished neighborhood nestled along the shores of the Sarasota Bay, just minutes from downtown Sarasota. There are 168 single family homes in the neighborhood. Residents enjoy well shaded and spacious home sites on the bay, lakefront or interior lots.

The history of this established west of the trail neighborhood that dates back many years. The area has an eclectic array of architectural styles including, classic "Old-Florida", ranch style, 2-story, and large estates just to name a few. With today's homeowners focused on innovations and designs, many of the older homes have been renovated and restored to look better than new. Homes range anywhere from 1,914 to 5,615 square feet. Prices range from around $500,000 to over $5 million.

With location being a key factor, select homeowners have private canal access to deep sailboat waters while the rest of the community is privileged to be neighbors with the prestigious Field Club. Encompassing 11 acres of plush landscaping, this highly exclusive club provides 600 members with tennis, yachting and social events. Conveniently located, residents of Oyster Bay can choose to join this club for their ample amenities or simply indulge in a variety of urban activities surrounding Sarasota. Siesta Key Beaches, St Armands Circle, Downtown Main Street, the Arts and Culture District are all within minutes.

Whether you want to relax in your quiet sanctuary, sail the Bay waters, or meander the streets of Sarasota, the choice is yours in alluring Oyster Bay.

Map of Oyster Bay Estates

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