My Account

Dashboard

Login using...

Siesta Key Real Estate

Siesta Key real estate

This gorgeous island off the coast of Sarasota, Florida is a captivating 8-mile long barrier island known as Siesta Key. 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 cottage, a luxury condo, or a single-family home on the beach or on a canal, you will find a wide variety of offerings here.  Learn more about Siesta Key.

Siesta Key Homes - Siesta Key Condos

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
Map Save this Search
Sort listings by:Price, High to Low

230 N Casey Key Rd, Osprey, FL - $14,750,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,009 SQFT
View details More Photos Save

Extremely Rare, One-of-a-kind 8.8 Acres Gulf To Bay, Secluded, Pristine, Private Executive Compound. Start Your Designs On This Fresh Canvas And See Your Dreamscape Come Alive! Design And Build Or Use The Existing Structures To Improve On. Located...

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

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 6,312 SQFT
View details More Photos Save

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...

Photo of Listing #A4104031

4011 Shell Rd, Sarasota, FL - $7,990,000

Residential, Single Family Home
  • 5 Beds
  • 9 Baths
  • 9,202 SQFT
View details More Photos Save

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 #A4113770

8448 Sanderling Rd, Sarasota, FL - $7,950,000

Residential, Single Family Home
  • 4 Beds
  • 4 Baths
  • 5,215 SQFT
View details More Photos Save

Welcome Home To Your Beachfront Masterpiece Where Your Spirit Of Freedom And Creativity Comes Alive! This “infinity House” Is Framed By Powdery Sand Beaches, Turquoise Blue Warm Gulf Waters, Breezes, & Tropical Gardens. So Called Because Panoram...

Photo of Listing #A4116794

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

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 8,158 SQFT
View details More Photos Save

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...

8306 Sanderling Rd, Sarasota, FL - $7,450,000

Residential, Single Family Home
  • 7 Beds
  • 6 Baths
  • 5,000 SQFT
View details More Photos Save

Experience Tropical Tranquility On A Spectacular Scale From This Sanderling Beachfront Estate, Poised On Almost Two Acres With 201 Ft. Of Pristine Walking Beach. With The Gulf Of Mexico On One Side And Heron Lagoon On The Other, The Property Is C...

4317 Midnight Pass Rd, Sarasota, FL - $6,500,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 7,121 SQFT
View details More Photos Save

Deeded Beach Access, Direct Coconut Bayou View And Boat Dock. Roof Top 2500 Sq Ft Deck With Incredible Views Of Downtown, Siesta Key And Gulf. Walk To Out Of Door Academy. Award Winning Contemporary Siesta Key Waterfront Residence. Architect Mark ...

Photo of Listing #A4111289

8585 Midnight Pass Rd, Sarasota, FL - $5,950,000

Residential, Single Family Home
  • 4 Beds
  • 7 Baths
  • 5,727 SQFT
View details More Photos Save

The Long, Winding Paver Drive Meanders Through The Walls Of Brick And Gated Entry Under Giant Oaks, Past The Pond And Rose Garden To A Manse Right Out Of The Pages Of "traditional Home". Set On Over 1.5 Bay Front Acres, This 4 Br M.l. Collingwood ...

Photo of Listing #A3996493

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

Land, Single Family Use
View details More Photos Save

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...

7722 Sanderling Rd, Sarasota, FL - $5,700,000

Residential, Single Family Home
  • 2 Beds
  • 3 Baths
  • 2,580 SQFT
View details More Photos Save

Extraordinarily Rare And Breathtakingly Beautiful, This Direct Beachfront Site Encompasses Over An Acre, With 201 Ft. On The Gulf Of Mexico. The Magnificent Tropical Setting Offers 14,875 Sq. Ft. Of Buildable Area, Making It One Of The Only Gulf-f...

7722 Sanderling Rd, Sarasota, FL - $5,700,000

Land, Single Family Use
View details More Photos Save

Extraordinarily Rare And Breathtakingly Beautiful, This Direct Beachfront Site Encompasses Over An Acre, With 201 Ft. On The Gulf Of Mexico. The Magnificent Tropical Setting Offers 14,875 Sq. Ft. Of Buildable Area, Making It One Of The Only Gulf-f...

145 Beach Rd, Sarasota, FL - $5,500,000

Residential, Single Family Home
  • 6 Beds
  • 6 Baths
  • 3,240 SQFT
View details More Photos Save

Rare “gulf Front Property" Siesta Key Compound. Over 23,000 Square Feet Of Land! (168 Beach Road; 145 Beach Road; 146 Avenida Veneccia) This Property Is Comprised Of 3 Separate Parcels That Are Combined, Including A Full “gulf Front” Vacant Beach...

Siesta Key

The name says it all. Who wouldn't want to live on an island called Siesta Key? One of several barrier islands off of the Sarasota mainland, Siesta Key offers casual island living at its best. With the Sarasota Bay on the east and the Gulf of Mexico on the west, the key is famous for its sugar-white beaches. Voted the Best Beach in America in 2011, Siesta has always been a favorite destination for tourists and locals alike. Whether you prefer the action of water sports or a more sedate day on the beach with a favorite book, there are plenty of spaces on Siesta Key for all types. 

The Siesta Key Village is a favorite spot for dining and nightlife, with everything from casual seafood restaurants to fine dining.  With a slightly more relaxed atmosphere than Longboat Key further to the north, residents and visitors alike flock to Siesta Key for the beaches and the casual Siesta Village nightlife, where you can always find people strolling between restaurants, cafes, pubs, and ice cream parlors. The entire island is about 8 miles long, and it includes numerous communities, dining and nightlife establishments, shops, and parks.

Siesta Key has long been an attraction to those who love a casual, beach-lover lifestyle. Siesta Key is home to an eclectic mix of residents and includes everything from exclusive waterfront penthouses and estates, to secluded neighborhood enclaves, to vacation town-homes and villas, and even historic cottages and bungalows. If friendly, island living is an attractive option for you, Siesta Key is a great place to live

As early as 1513, European cartographers designated Siesta Key on maps as “Sarasota Key.” 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 Boulevard 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 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 Depressions 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 is a major vacation spot, attracting as many as 350,000 visitors annually.

Siesta Key, Florida Map

Siesta Key Resources


Did you find your dream home? If not, please fill out the form below.
We'll do the search and send you all the homes available that match your criteria.

* Indicates a Required Field.

Your Contact Information
Property Information
Moving Details

Back to Top

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 August 28th, 2015 at 2:18am EDT.