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Siesta Key Real Estate

Siesta Key real estateSiesta Key, a gorgeous island off the coast of Sarasota, FL, lies along a captivating eight-mile long barrier area. Voted the Best Beach in America, Siesta Key’s Crescent Beach is famous for its cool, sugary-white sands and wide beachfront. Whether you are looking for a simple vacation cottage, a luxury condo, or a single-family home on the beach or by a canal, homebuyers will find a wide variety of offerings here at Siesta Key. Check out current listings below or find out more about Siesta Key.

Siesta Key Homes & Condos for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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7712 Sanderling Rd, Sarasota, FL - $18,000,000

Residential, Single Family Home
  • 3 Beds
  • 5 Baths
  • 11,112 SQFT
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A Soul-stirring Statement Of Beachfront Living, Aquadisia Is A Landmark Gulf-to-lagoon Property Nestled On Almost Four Acres Behind The Gates Of The Exclusive Sanderling Club On Siesta Key. With An Extraordinary 529 Ft. On The Gulf Of Mexico And 1...

Photo of Listing #A4171273

8218 Sanderling Rd, Sarasota, FL - $13,900,000

Residential, Single Family Home
  • 7 Beds
  • 8 Baths
  • 10,624 SQFT
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Welcome To Unparalleled Tropical Splendor In The Prestigious Sanderling Club, The Only Gated Single-family Home Community On Gorgeous Siesta Key. Sprawling From The Shimmering Waters Of The Gulf Of Mexico To The Serenity Of Heron Lagoon, This Worl...

1300 Hidden Harbor Way, Sarasota, FL - $11,900,000

Residential, Single Family Home
  • 6 Beds
  • 5 Baths
  • 6,850 SQFT
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Situated On 1.5 Acres On A Private Peninsula, Also, 3 Dedicated Building Lots, Hidden Harbor Is A Waterfront Mediterranean Villa Minutes From Downtown Sarasota, Yet Decades Away From It. Adorned With Vined Trellises And Coral Walkways, This Home ...

Photo of Listing #A3957336

7858 Sanderling Rd, Sarasota, FL - $9,800,000

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 6,312 SQFT
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Majestically Poised Along The Shimmering Gulf Of Mexico Waters Bordering Siesta Key, This Masterfully Designed Retreat Invokes Distinctive Asian-inspired Aesthetics To Achieve A Unique Harmony With Nature. A Feeling Of Tranquility Prevails As This...

8423 Midnight Pass Rd, Sarasota, FL - $9,800,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 6,553 SQFT
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This Extraordinary Waterfront Estate On World-famous Siesta Key Epitomizes The Very Best Of Refined Island Living. Majestically Poised Along The Shimmering Waters Of The Intracoastal Waterway Sits This Masterfully Redesigned And Meticulously Renov...

Photo of Listing #A4158589

3975 Shell Rd, Sarasota, FL - $8,845,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,079 SQFT
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Siesta Key Estates - The Rarest And Most Desirable Parcel In Sarasota Fl. 105,000 Total Sq Ft With 264ft Directly On A Private And Unobstructed Access To One Of The Best Beaches In The Country. A Unique And Exclusive Feature Of The Estate Is A Dee...

Photo of Listing #A4158009

7940 Sanderling Rd, Sarasota, FL - $7,950,000

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 5,203 SQFT
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Romantic And Supremely Private, This Magnificent Gulf Front Residence On A Sandy Walking Beach Is Nestled On 1.8 Acres In Siesta Key’s Exclusive Sanderling Club. The Property Extends To Heron Lagoon, A Pristine Body Of Water Ideal For Fishing, Kay...

3975 S Shell Rd, Sarasota, FL - $7,495,000

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 7,263 SQFT
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Pre Construction - To Be Built Discover The Extraordinary Oppritunity To Own An Iconic, Custom Gulf-front Home Sited On 132.5 Ft Of Secluded Beach, On One Acre Of Supreme Siesta Key Land. The Coveted North End Of The Key Sets The Stage For This ...

Photo of Listing #A4104031

4011 Shell Rd, Sarasota, FL - $7,400,000

Residential, Single Family Home
  • 5 Beds
  • 9 Baths
  • 9,202 SQFT
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A Stunning Statement Of Refinement And Comfort, This Impeccably-designed, Lushly-landscaped Estate Sits On Nearly An Acre At The Coveted North End Of Siesta Key Directly On The Gulf Of Mexico. Here Residential Bliss Comes To Life With Spectacular ...

Photo of Listing #A4116794

8501 Midnight Pass Rd, Sarasota, FL - $6,950,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 12,444 SQFT
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The Cumulative Age Of The Majestic Oaks That Stand Guard Over This One-of-a-kind Property Must Surely Reach Into The Thousands, Each Telling A Story And Creating A Special Ambiance One Can Only Understand By Being There. These Oaks Together With A...

Photo of Listing #T2802200

1356 Point Crisp Rd, Sarasota, FL - $6,950,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 7,443 SQFT
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This Spectacular Siesta Key Estate Has The Unique Feature Of Direct Water Access From Both The Front And Back Yards To Sarasota Bay. This Impressive Home Has 7443 Square Feet Of Living Area And Just Over 14000 Square Feet Of Total Covered Areas Wh...

125 Big Pass Ln, Sarasota, FL - $6,870,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 4,000 SQFT
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Pre-construction. To Be Built. Oversized Gulf Front Parcel And A Extraordinary Rare Find On The Famous North End Of Siesta Key. Located On Almost An Acre Lot Directly On The Gulf Of Mexico At Big Pass Is The Perfect Place For This Phenomenal Guy P...

Siesta Key

One of several barrier islands off the Sarasota mainland, Siesta Key offers casual island living at its best—the name alone says it all. Siesta Key, FL homes for sale give residents access to a multitude of luxury housing options. The community is home to an eclectic mix of homeowners and real estate includes everything from exclusive waterfront penthouses and estates, to private and secluded neighborhood enclaves, to vacation townhomes and villas, and even historic cottages and bungalows.

The Siesta Key Village is a favorite spot among residents and visitors alike for nightlife and dining, with everything from casual seafood restaurants to fine dining. With a slightly more relaxed atmosphere than Longboat Key further up north, people flock to Siesta Key for the beaches and the casual Siesta Village lifestyle, where you can always find people strolling between restaurants, cafes, pubs, ice cream parlors and parks. And with the Sarasota Bay to the east and the Gulf of Mexico to the west, there's plenty of water for all types of active recreation.

Siesta Key History

Siesta Key has quite the history to boast about. As early as 1513, European cartographers designated Siesta Key on maps as “Sarasota Key.” But until the early 20th century, only a handful of families lived on the island, but in 1906 Captain Louis Roberts and his wife, Ocean Hansen Roberts, expanded their home and opened it up as a hotel. Ocean, for whom Ocean Blvd is named, became the resident chef and was famous for her great cooking, especially her clam chowder. Over time, their hotel, dubbed the Siesta Inn, was frequented by an impressive guest list, including the likes of Oscar B. DeMille, Charleton Heston, Bette Davis, Dorothy Lamour, Agnes Moorehead, Cornel Wilde and Betty Hutton.

Captain Roberts joined forces with Harry Higel, then mayor of Sarasota, and others to form the Siesta Key Land Company. Higel began to plat the land and dredge canals. He also opened his own hotel, called Higelhurst, in 1914, and he ferried guests back and forth from the mainland to the island. In 1917, a bridge was constructed from the Key to the mainland, and in 1927, the southern bridge at Stickney Point was built.

While the Depression slowed development for a time, the post-war years began a time of growth. Today, about 24,000 people call Siesta Key home, but the island itself is a major vacation spot, attracting as many as 350,000 visitors annually.

Map of Siesta Key, FL

Siesta Key Resources


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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 December 8th, 2016 at 12:48am EST.