Siesta Key Real Estate

Siesta Key real estate

Take one meander down the powdery white sandy beaches of Siesta Key or a boat tour around the key and you will understand why this is such a desirable place to live. Siesta Key Beach continually ranks as one of the world's prettiest beaches.

The island has a good mix of working professionals, retirees and second home owners who venture down in the winter time to enjoy the beautiful weather. Many who purchase Siesta Key real estate do so for vacationing purposes, with the goal of eventually retiring to this island paradise.

There are a number of options for Siesta Key homes–everything from a modest abode to a luxurious bay or beach front mansion. Waterfront homes in Siesta Key that can accommodate boats and are within a short walk to the beach are the most popular properties on the key. Read more about Siesta Key

If you like Longboat Key you should also explore Casey KeyBird KeyLido Key and Longboat Key

Homes & Condos For Sale on Siesta Key

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19 Whispering Sands Dr # 206, Sarasota $649,999

  • 2 Beds
  • 2.0 Baths
  • 1,282 SqFt

Private Gulf Front Beach In The Middle Of All Of Siesta Key Action. Walking Distance To Village, Public Transportation And The #1 Beach. Vacation Now And Eventually Retire To This Amenity Packed, Impeccably Manicured Playground. Friends And Family Welcome 4...

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4874 Commonwealth Dr, Sarasota $835,000

  • 3 Beds
  • 3.0 Baths
  • 2,648 SqFt
  • 0.24 Acres

Opportunity Is Knocking! Are You Ready? This Siesta Key, Canal Front Home , Is A Diamond In The Rough, But Presents Endless Opportunities To The Buyer With Vision. The Property Has Long Canal Views, Perfect For Enjoying The Sky At Sunset And The Stars At Ni...

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9209 Midnight Pass Rd # 5, Sarasota $749,000

  • 3 Beds
  • 3.0 Baths
  • 1,632 SqFt

Sailboat Water With Deep Water Private Boat Dock. This Is The Lifestyle You Have Been Dreaming About. Three Decks, All With Unbelievable Views. Watch The Dolphin And Manatees Swim By, Fish Off Your Dock, Kayak, Canoe Or Hop On Your Boat For Dinner Along ...

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1240 Dolphin Bay Way # 303, Sarasota $739,000

  • 2 Beds
  • 2.0 Baths
  • 1,915 SqFt

Dolphin Bay Condo Located On Beautiful Siesta Key, Home Of "world Famous Siesta Key Beach" Which Holds The Esteemed Honor Of Being Named The #1 Beach In America. Built In 1998, This Condo Feels More Like A Home With Its High Ceilings And Open Living Space. ...

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1225 Whitehall Pl, Sarasota $1,195,000

  • 4 Beds
  • 5.0 Baths
  • 2,874 SqFt
  • 0.37 Acres

Discover A Stunning Mediterranean Style Home With Our Video Tour At Http:// And Experience The Siesta Key Lifestyle. Home Is A True Mariners Dream, Waterfront & Ready For Large Yachts Including Sailboats. This Get...

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1259 Southport Dr, Sarasota $2,495,000

  • 3 Beds
  • 4.0 Baths
  • 3,195 SqFt
  • 0.37 Acres

Custom Designed And Built By N.c. Ferguson Construction, Inc. This Stunning Contemporary Waterfront Home Is Situated On The Highly Sought After Canopied Road Of South Port Drive. Walking Into This Custom Designed Home You Are Greeted With Floor To Ceiling G...

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6703 Midnight Pass Rd # 213, Sarasota $399,000

  • 2 Beds
  • 2.0 Baths
  • 964 SqFt

This Condo Has Been Reborn.. A Beautiful Place To Call Home. Fully Furnished And So Warm And Inviting.. Brand New Water Heater, Electrical And Plumbing.. You Have To See This.. What A Masterpiece Just Minutes To The Number 1 Beach In The Usa.. Siesta K...

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5760 Midnight Pass Rd # D303, Sarasota $849,000

  • 2 Beds
  • 2.0 Baths
  • 1,361 SqFt

Owners Are Very Motivated, All Written Offers Will Be Considered!!! Welcome To Gulf & Bay Club Situated Directly On Siesta Key Beach, Rated The Top Beach In America By Trip Advisor. This Beautiful 2 Bedroom (and A Bonus Room With Bunk Beds), 2 Bath Unit Has...

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120 Whispering Sands Dr # V-20, Sarasota $464,900

  • 3 Beds
  • 2.0 Baths
  • 1,567 SqFt

Best Villa Location In Whispering Sands; So Close To The Private Beach. This Spacious Home Is Filled With Natural Sunlight And Has A Private Garden Area Out Back. Add To That, 3 Bedrooms Or 2 And An Office, 2-car Attached Garage And All Of The Social Amenit...

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Reviews for Siesta Key Real Estate

5 Based on 3 Ratings
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Recent Ratings & Reviews

Beth Lancaster, Visitor



#1 reason to live on Siesta - The Country's #1 Beach with it's perfect white quartz sand. #2 reason - you can drag out your old hula hoop and those pots and pans you want to replace and report to the beach's Famous Drum Circle to join the dance and performance. A celebration of our magnificent sunsets every Sunday as twilight approaches. Just when you think you've seen it all... kick off your shoes, grab your tambourine and delight in yet another perfect day. See you there :)

Cathy Loeppke, Visitor



Most often, when clients talk about Siesta Key they are envisioning Siesta Key Public Beach or Crescent Beach. However, as my local buyers found, there are some fabulous properties at the south end of Siesta Key on or near Turtle Beach! They recently purchased a beachfront condo at Fisherman’s Cove and can walk out their back door onto the beach, view sunsets over the Gulf of Mexico from their enclosed lanai, and dock a boat on the opposite side of their building with access to the ICW. They got all of this at a price significantly less than they would have paid for less features a mile up the road.

Marc Rasmussen, Resident

Siesta Key has one of the nicest beaches you will ever find. There is a good diversity of homes and condos available at various price ranges. It is a very relaxed island with an "Old Florida" feel. Some view Siesta Key not as pretentious as Longboat Key and Lido Key.


Some don't like the casualness of Siesta Key. They might feel like it is not "sophisticated" enough. Some people dislike the inconsistency of real estate. You might find a dumpy home in need of replacing next to a gorgeous waterfront.


If you enjoy the beach lifestyle and like a relaxed atmosphere you should explore the homes and condos of Siesta Key.

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Five Things You Should Know about Siesta Key

 Siesta Key beach has won the best beach in the U.S. by Dr. Beach.

 There are plenty of home and condo options on Siesta Key.

 The sand on Siesta Key beach is 99% quartz which prevents it from getting too hot.

 Siesta Key offers many condos that allow short term renting. 

Has more of a bohemian & laid back feel than Longboat Key & Lido Key. 

Homes For Sale on Siesta Key, Florida

Bay Island  Blind Pass 
Bayou Louise  Cocoanut Bayou 
Gulfmead Estates  Harmony 
Hidden Harbor Mangroves 
Mira Mar  Point of Rocks  
Point Crisp Riegels Landing 
Roberts Point  Sanderling Club 
Sara Sands  Siesta Bayside 
Siesta Cove  Siesta Key Beach 
Siesta Isles  Solymar 
Sandy Hook   

When people in Florida want to know the meaning of true paradise, they head to Siesta Key. Home to nearly 24,000 residents, it is known for its exquisite white sandy beaches that are renowned for staying cool to the touch. The 8-mile long barrier island, containing an eclectic mix of retirees, summer vacationers and families, is rapidly becoming just as well known for its beautiful, luxurious condos and seemingly endless options for entertainment, shopping, and dining. Having seen an increase in development within the past decade, Siesta Key has a number of excellent neighborhoods that offer something for everyone.

Bay Island

A great place to raise a family, Bay Island is composed of 169 single-family homes. Ranging from 800 square-foot bungalows to palatial homes of more than 8,000 square feet, Bay Island homes offer stunning views of both Sarasota Bay as well as the city skyline. Considered some of the best homes in Sarasota, they offer residents living along Flamingo Drive, Hamilton Avenue, Freeling Drive and others beautifully landscaped yards containing plenty of tropical trees and exotic plants.


Just as the name implies, this neighborhood offers residents a peaceful and beautiful setting from which to enjoy those summer evenings. Whether you're living on Treasure Boat Way, Primrose Path, or Featherbed Lane, Harmony offers affordable homes that suit many different lifestyles. A popular area for retirees, it's also well-suited for families or others on the fast track to success. Located in a true paradise, Harmony is not only a destination, but a way of life here as well.

Gulfmead Estates

A small neighborhood on the north end of Siesta Key, these waterfront homes offer beautiful views and overlook Lido Key, Bird Key, and downtown Sarasota. What makes these homes so popular with many residents is the easy access to and from Siesta Key. For those wanting to spend a day on the beach, it's as simple as taking a short bike ride to Siesta Key Beach or Shell Beach. Offering a wide variety of homes to fit almost any budget, Gulfmead Estates is a great neighborhood for those looking to settle down or simply enjoy a great vacation getaway.

Hidden Harbor

A charming neighborhood of 36 homes, Hidden Harbor is located on the east side of the island and features tropical landscaping and cobblestone streets. Considered to have some of the most unique and enchanting homes in Siesta Key, they range in size from 2,500-7,000 square feet.

Whether you want a larger neighborhood or a more secluded one in which to call home, Siesta Key neighborhoods offer that and so much more. If it is a taste of paradise you're seeking, consider the wonderful neighborhoods of Siesta Key.

Siesta Key Condos

Siesta Key condos are very popular among buyers. Here you can find a smaller and more affordable condominium that's within a short walk to the beach, a luxurious new penthouse overlooking the dazzling beach front, or something spectacular in the middle. There are plenty of developments to choose from in the Siesta Key condo market. Follow the links below to view all of the Siesta Key condos currently for sale.

Please see our Siesta Key condos page for more information 

Condos on the Beach   Condos on the Bay   Across Street From Siesta Beach
 Aloha Kai  Anchorage  Beach Villas
 Beachaven  Bay Oaks  Beach Way
 Casa Blanca  Bay Tree  Crescent Royale
 Casarina  Boca Siesta  La Siesta
 Crescent  Dolphin Bay Our House at Beach 
 Crescent Arms  Excelsior  Sunset Royale
 Crystal Sands  Gulf & Bay Bayside  Tivoli by the Sea
 El Presidente  Hamilton Club Terrace East 
 Excelsior  Harbor Towers  
 Fishermans Cove  Harbour Towne Newer Condos
 Fishermans Haven  Island Reef  Beach Villas
 Gulf & Bay Club  Marina Del Sol Crescent
Horizons West Mariners Inlet  Dolphin Bay
 House of the Sun  Midnight Cove  Hyatt
 Hyatt  Moorings  Seagrove
 Island House  Peppertree  
 Island Reef  Pointe  Short Term Rental Condos
 Jamaica Royale  Polynesian Gardens  Aloha Kai
 Midnight Cove  Provincial Gardens  Beachaven
Palm Bay Club  Sandy Cove  Casa Blanca
Peppertree  Sea Breeze  Crescent Royale
Sea Shell  Sea Club  Crescent Arms
Seagrove  Siesta Harbor  Crystal Sands
 Siesta Dunes  Somerset Cay  El Presidente
Siesta Gulf View  Summer Cove  Horizons West
Sarasota Surf & Racquet  Turtle Bay  Hyatt
The Terrace  Windward Passage  Island House
Tiffany Sands    Jamaica Royale
Tortuga    Palm Bay Club
Whispering Sands    Sarasota Surf & Racquet


The Siesta Key Lifestyle 

Have you ever dreamed about living within a short walk of one of America's top beaches? If so, relocating to Siesta Key can make that dream a reality.

Siesta Beach was ranked by National Geographic as one of the top family beaches in the country. it was also named by USA Today as a Readers Choice for America's best beach. You won't find rowdy spring breakers here. The pristine sand is an oasis of relaxation. Living in Siesta Key makes the beach a part of everyday life. There is no such thing as planning a "weekend beach trip",because it is a given you'll be spending a couple of hours on the beach every Saturday and Sunday. You can even hit the beach after work and catch a couple hours of sun. It's also a great time to take in the stunning sunset over the Gulf of Mexico with your significant other.

One of the best parts about Siesta Key is you can experience all the perks of a tropical vacation without leaving home. There are several quality fishing charters throughout the Key. These friendly local sailors are more than willing to induct you into the fishing culture that is tied to the area. If you are more of an adventurous type, then you will be happy to know Siesta Key has Parasailing, kayaking, and jet skiing. You don't have to worry about owning a boat or a jet ski, as there's a good chance you'll make quick friends with someone who owns both.

Siesta Key is also filled with dozens of shops. The shops range from your typical tourist beach shop, to high-end boutiques that would impress any fashionista. There are a few shops that sell obscure items, and these funky shops are what gives Siesta Key its flavor.

If you still need convincing on the quality of the Siesta Key lifestyle, then all you have to do is make a reservation at one of the restaurants. The Village Cafe is a perfect place to grab some breakfast as you watch the sunrise. It has been in business since 1995 and is a favorite among locals. After breakfast, stop by Captain Curt's Crab & Oyster Bar for a seafood feast. 

To sum it up nicely, the Siesta Key lifestyle is filled with beach relaxation, any activity involving the water, and delicious seafood.

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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 July 1st, 2015 at 10:42am EDT.