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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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Photo of Listing #A4203264

7712 & 7660 Sanderling Rd, Sarasota, FL - $15,500,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 8,496 SQFT
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Escape To Aquadisia, A Serene Tropical Sanctuary Perfectly Positioned On Just Over 3-acres With 542 Feet Of Private Gulf Of Mexico Frontage. Located Behind The Gates Of The Coveted Sanderling Club On Siesta Key, This Brilliantly Designed Estate Co...

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...

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...

3975 Shell Rd, Sarasota, FL - $8,250,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,079 SQFT
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One-of-a-kind Beachfront Parcel On Siesta Key. 2.4 Acres With 264ft Directly On The Beach. Western Exposure For Stunning Sunsets. Siesta Key's North Bridge Provides Extremely Quick Access To Downtown Sarasota And St. Armand's Circle Letting You Av...

4137-4153 Higel Ave, Sarasota, FL - $7,990,000

Land, Single Family Use
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The Best Of All Worlds – A Rare, Spectacular North Siesta Key Gulf-front Estate-sized Parcel. Build Your Custom Estate And Create A Special Island Lifestyle. This Lot Offers 240 Feet Of Gulf-front Living With Panoramic Water Views On This 2.52-acr...

125 Big Pass Ln, Sarasota, FL - $7,800,774

Residential, Single Family Home
  • 4 Beds
  • 5 Baths
  • 4,472 SQFT
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Pre-construction To Be Built. Two Options - 1. The Mindera Model Of John Cannon Homes With Nearly 4500 Square Feet Of Living Area (6658 Sf Under Roof) Has 4 Bedrooms, Den, Bonus Room, 3-car Garage, Outdoor Kitchen All Overlooking The Big Pass With...

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

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 5,079 SQFT
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Pre Construction - To Be Built Discover The Extraordinary Opportunity 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 #A4158009

7940 Sanderling Rd, Sarasota, FL - $7,450,000

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 1.5 Acres In Siesta Key’s Exclusive Sanderling Club. The Property Extends To Heron Lagoon, A Pristine Body Of Water Ideal For Fishing, Kay...

Photo of Listing #A4183773

16 Sandy Hook Rd S, Sarasota, FL - $7,200,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 6,343 SQFT
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Direct Gulf Front Custom Built 2008 Home With All The Luxuries That You Would Expect In A Newer Home. Enjoy The Breath Taking Views From Most All The Rooms Plus 21' Ceilings In The Living Room, Family Room And Library. The Chefs Kitchen Has Top...

Photo of Listing #A4161697

4136 Roberts Point Cir, Sarasota, FL - $6,500,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 7,309 SQFT
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Sophisticated Elegance To Please The The Most Discerning Palate ! This One Of A Kind European Inspired, Contemporary Masterpiece. Amazing Details Of Chamfered Stone Entrance, Custom Solid Mahogany Door, Thirty Tons Of Select European Marble, Zebr...

Photo of Listing #A4177149

7208 Point Of Rocks Rd, Sarasota, FL - $6,295,000

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

Photo of Listing #N5913541

1250 Hidden Harbor Way, Sarasota, FL - $6,200,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 7,505 SQFT
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Luxurious And Contemporary Custom-built Family Home On A Private Half Acre+ Tip Lot In Hidden Harbor. This Lush, Tropical, Private Upscale Waterfront Neighborhood Consisting Of Only 36 Exclusive Residences Is One Of Siesta Key's And Sarasota's Bes...

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 15th, 2017 at 2:19pm EST.