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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...

7858 Sanderling Rd, Sarasota, FL - $10,900,000

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...

1356 Point Crisp Rd, Sarasota, FL - $7,999,000

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...

Photo of Listing #A4116794

8501 Midnight Pass Rd, Sarasota, FL - $7,500,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,158 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 #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 #A4138095

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...

7208 Point Of Rocks Road, Sarasota, FL - $6,675,000

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 7,145 SQFT
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Timeless Design, Panoramic Gulf Of Mexico Views And A Private, Secluded Beach Make This Newer Coastal Home One To Cherish For Generations. It Is Perfectly Situated On A Nearly One Acre Site In The Historic Point Of Rocks Area, At The Southern Tip...

4205 Higel Ave, Sarasota, FL - $6,499,900

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 8,571 SQFT
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Welcome To “villa Del Paradiso”, A Luxurious Private Estate Located On The World-renowned Siesta Key, Yet Reminiscent Of The Palladian Villas Of The Veneto. This Venetian Inspired Estate Home Sits On The Protected Waters Of Roberts Bay With Direct...

145 Beach Rd, Sarasota, FL - $6,000,000

Residential, Single Family Home
  • 6 Beds
  • 6 Baths
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Rare Siesta Key Mutifamily Property / 5 Units "protected Full Gulf Views", The Property Comes With An Additional Parcel @ #146 Avenida Veneccia, Siesta Key, Florida, 34242 Which Is Contiguous. So Many Options: Single Family Residence, Rental Prope...

9230 Blind Pass Rd, Sarasota, FL - $5,995,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 8,230 SQFT
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Paradise Found. All That You Could Desire Is Yours To Experience From This Exclusive Southern Siesta Key Gulf Front Estate. Here You’ll Find The Best Of Both Worlds, A Rare Island Property With Dockage And Direct Access To The Gulf Of Mexico, Alon...

Photo of Listing #A3996493

4740 Ocean Blvd, Sarasota, FL - $5,790,000

Land, Single Family Use
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Located On The Northern End Of Siesta Key On Sarasota's Big Pass, Approved By The County For A 4 Story, 6 Unit Condo This Spectacular Gulf-front Development Site Is Comprised Of Approximately One Acre With 400 Feet Of Waterfront Protected By A Har...

Photo of Listing #A4155531

7152 Point Of Rocks Cir, Sarasota, FL - $5,499,000

Residential, Single Family Home
  • 6 Beds
  • 5 Baths
  • 4,464 SQFT
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Siesta Key Gulf Front Perfection~perched 14.2' Above Mean Sea Level On Point Of Rocks This Home Provides Spectacular Gulf Views To The W, N & S. This Is The Best Single Family Gulf Front Home On Siesta Key. The Original Home Was Gutted To 3 Exteri...

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 May 28th, 2016 at 11:33pm EDT.