Oyster Bay Estates Real Estate

Oyster Bay Estates Sarasota

Find all of the newest West of the Trail Oyster Bay Estates homes for sale and real estate listings in Sarasota, FL below! One drive through Oyster Bay Estates in Sarasota and this will quickly become one of your favorite neighborhoods. This is an eclectic community of diverse homes sitting on large lots with mature and lush landscaping. Here you can find anything from an older ranch style home, a modern structure designed with Sarasota School of Architecture themes, Key West style as well as Spanish Mediterranean designs.

The feeling of ‘Old Sarasota’ from the 1910’s and 1920’s shines through in Oyster Bay Estates. Many of the original homes from this community have been torn down to make room for condominiums , however this neighborhood stays true to it’s historical roots. The tropical landscaping and beautiful waterfront estates give charm to this historic Sarasota development. Receive information about West of the Trail Oyster Bay Estates neighborhood properties for sale or to make a private showing or home tour home please contact your Sarasota, Florida DWELL real estate agent today!

Homes for Sale in Oyster Bay West of Trail Sarasota

All Listings $800,000 - $900,000 Over $1,000,000
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4487 Camino Real, Sarasota $1,295,000

  • 3 Beds
  • 3.0 Baths
  • 2,765 SqFt
  • 0.52 Acres

West Of Trail Directly Across From The Field Club, This Stunning Contemporary Beautiful Home In Sought-after Oyster Bay. Situated On 1/2 Acre With Beautiful Gardens Surrounding The Home Featuring Exotic And Lush Tropical Landscaping With A Lap Pool With Lot...

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1615 S Lake Shore Dr, Sarasota $2,250,000

  • 3 Beds
  • 4.0 Baths
  • 4,642 SqFt
  • 0.57 Acres

Beautiful Lake Front Address In Oyster Bay! Wooded Setting With Tall Pines And Old Oaks On Over ½ An Acre Sets The Scene For This Custom-built Home Fronting Onto A Peaceful Spring-fed Lake Where You Are Transported To The Carolinas. Contemporary Styling In...

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1451 Rebecca Ln, Sarasota $2,475,000

  • 4 Beds
  • 5.0 Baths
  • 4,683 SqFt
  • 0.23 Acres

You Will Be At Once Captivated By This Custom Masterpiece Residence Located West Of Trail In Oyster Bay Landings. Featuring A Deeded Boat Dock With 15,000 Lb Lift, 4,700 +/- Sq Ft Of Living Area, And Newer Construction With The Finest Architectural Details ...

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1865 N Lake Shore Dr, Sarasota $1,494,500

  • 5 Beds
  • 4.0 Baths
  • 3,937 SqFt
  • 0.53 Acres

Rarely Available 5 Bedroom Home West Of Trail In Oyster Bay Estates, Situated Amongst Stately Oaks On Over Half An Acre. This Extraordinary John Cannon Built Two-story Residence Boast Magnificent Square Footage. The Open Kitchen Includes Wood Cabinets, Gran...

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1833 N Lake Shore Dr, Sarasota $1,295,000

  • 4 Beds
  • 3.0 Baths
  • 3,323 SqFt
  • 0.36 Acres

Don't Miss The Opportunity Own This Unique And Exquisite Design Of This Mid-century Modern Home By Jack West Complete With All The Things You Would Expect.... Ocala Block, Disappearing Glass Walls, Clean Lines And More. Enter Through The Private Gated Entry...

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Want to purchase a Oyster Bay Estates home West of Trail? Call your Sarasota, Florida real estate team, DWELL Real Estate (941) 822-0708. Your neighborhood Oyster Bay Estates REALTORS® and agents are here to help with the West of the Trail Sarasota, FL housing market.

View Sold Homes in Oyster Bay Estates

Oyster Bay Estates Real Estate Market

Oyster Bay Estates is located West of the Trail and sits on the Sarasota bay. Some of the streets include North and South Lakeshore Drive, Camino Real and Field Road. This is an exclusive community with a fabulous location. Boaters will appreciate deep canals and stunning views of the bay. Oyster Bay is also very convenient to area beaches including the world famous Siesta Key beach, shopping, restaurants, downtown Sarasota and all of the arts and culture amenities of the city.

Oyster Bay is located in the heart of Sarasota’s diverse shopping destinations, notable locations such as the Southgate Mall, many Southside Village shops and the Hyde Park area gourmet market are all within short driving distance.

The Field Club

One of Sarasota’s most prestigious clubs is also located near the Oyster Bay community, The Field Club. Members enjoy boating, swimming, tennis, and a variety of other social activities.

The historic subdivision of Oyster Bay features some of the finest old Florida real estate in Sarasota. Located centrally to all the best that Sarasota has to offer. Oyster Bay real estate is an attractive investment to the potential Sarasota home buyer.

Location of Oyster Bay Estates Subdivision


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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 28th, 2017 at 2:18am EDT.