Siesta Key Homes for Sale


If you are looking to have it all in your vacation or retirement properties, Siesta Key, Florida homes are the choice for you. Here you'll find great weather, exclusive waterfront access, breathtaking estates and a relaxed lifestyle.

Situated just along Sarasota Bay as one of Sarasota, Florida's barrier islands, Siesta Key boasts an award-winning beach and engaging island activities. But you still get the best of both worlds, as you're just a short drive to the outstanding cultural venues, restaurants and shopping of Sarasota.

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Siesta Key Homes | Siesta Key Condos

Siesta Key Homes October 23, 2021
35
Listed
117
Avg. DOM
$787.14
Avg. $ / Sq.Ft.
$1,799,000
Med. List Price
35 Properties
Page 1 of 3
$17,900,000
Subdivision: Sanderling Club
6
Beds
6F21/2
Baths
9,096
Sq.Ft.
2010
Year Built
87
Days on Site
C7446517
MLS
Live your best life now in this amazing, rarely available beachfront residence on Siesta Key. Tucked privately behind the gates of the exclusive Sanderling Club, this modern beachfront home better...
$14,000,000
Subdivision: Sanderling Club Siesta Properties Inc
6
Beds
7F11/2
Baths
10,624
Sq.Ft.
1986
Year Built
439
Days on Site
A4474535
MLS
Relax, escape, and unwind from everyday life in the ultimate beachfront paradise on Siesta Key. Offering one of the area's most coveted lifestyles, this private resort-like compound rests on over 4...
$7,995,000
Subdivision: Siesta Key
6
Beds
6F11/2
Baths
6,553
Sq.Ft.
1987
Year Built
214
Days on Site
A4494487
MLS
Escape to your very own private island paradise on world-famous Siesta Key. Majestically poised along the shimmering waters of the Intracoastal Waterway sits this masterfully redesigned and...
$6,975,000
Subdivision: Siesta Key
4
Beds
4F11/2
Baths
6,044
Sq.Ft.
2004
Year Built
207
Days on Site
A4495995
MLS
One or more photo(s) has been virtually staged. One of the best locations in Sarasota on the coveted north end of Siesta Key, this Gulf-front estate has it all. Enjoy endless views of the Gulf of...
$5,999,000
Subdivision: Roberts Point 2
4
Beds
6F11/2
Baths
5,673
Sq.Ft.
1953
Year Built
20
Days on Site
A4514198
MLS
Experience views of shimmering turquoise water and tropical shores from this estate-size property with existing residence plus neighboring vacant lot on north Siesta Key. Boasting over 300' of water...
$4,990,000
Subdivision: Siesta Key
3
Beds
3F11/2
Baths
4,000
Sq.Ft.
2019
Year Built
106
Days on Site
A4505753
MLS
Enjoy waterfront living at its best in this beautiful 2019 custom-built home by Jonas Yoder Homes located on a private street on the north end of world-famous Siesta Key. This impressive residence is...
$4,900,000
Subdivision: Siestas Bayside Waterside East
5
Beds
4F11/2
Baths
6,326
Sq.Ft.
2008
Year Built
141
Days on Site
A4503179
MLS
Absolutely Stunning British West Indies style home, located on Siesta Key with the #1 voted Beach in the USA. Waterfront property on the Grand Canal for easy access to the Sarasota Bay. Large family...
$4,740,000
Subdivision: Sanderling Club
7
Beds
7
Baths
6,697
Sq.Ft.
1953
Year Built
673
Days on Site
A4454402
MLS
Enjoy 270 feet of unobstructed Gulf Views from this exclusive Sanderling Club estate on 2 acres of lush landscaping and endless possibilities! Welcome to this stunning, private & spacious estate with...
$4,100,000
Subdivision: Roberts Point 2
4
Beds
4F11/2
Baths
5,673
Sq.Ft.
1953
Year Built
20
Days on Site
A4514141
MLS
Experience views of shimmering turquoise water and tropical shores from this estate-size property on north Siesta Key. Boasting over 300' of water frontage, the homesite is poised to make the most of...
$3,995,000
Subdivision: Tortoise Estates
5
Beds
5F11/2
Baths
7,343
Sq.Ft.
1984
Year Built
107
Days on Site
O5957435
MLS
Nestled on the desirable quiet south end of Siesta Key, you will find your Happy Place! Walk into the front door of this newly remodeled home and your eyes are drawn to the beautiful curved staircase...
$3,485,000
Subdivision: Siesta Key
4
Beds
3F11/2
Baths
7,060
Sq.Ft.
1985
Year Built
121
Days on Site
A4504130
MLS
Ready to reimagine your lifestyle? Located on a quiet street on the north end of world-famous Siesta Key, this waterfront residence is just what you have been waiting for. The location is perfect for...
$3,450,000
Subdivision: Spice Bay
3
Beds
3F21/2
Baths
3,422
Sq.Ft.
2022
Year Built
323
Days on Site
A4484976
MLS
Pre-Construction. To be built. Pre-Construction, to be built. Take advantage of this ready to build opportunity in a boutique gated waterfront community on world-famous Siesta Key. Spice Bay, home to...

Why Choose Siesta Key Real Estate?

Often touted by travel magazines and internet sites, Siesta Key is home to the 2011 #1 Beach in USA. The first image that comes to mind of this barrier island would be the white-sand beaches for which this area is so well known. Pitch your beach umbrella, dig your toes in the sand, and take in the ocean views as the sun passes over the calm waters of the Gulf. The sense of relaxation extends right into Siesta Key Village, where sandals are seen more often than oxfords or pumps. Just a few blocks long, the Village is the meeting place for you and your neighbors – a casual hangout of open-air cafes and eclectic shops.

Lifeguard stand - Siesta Key BeachRelaxation is only part of the picture on Siesta Key. Boating along the intracoastal waterway and canals takes you through mangrove forests that make you feel as if you’re embarking on a unique tropical adventure. Parasailing, jet skiing and kayaking are favorite ocean-going pastimes, while on-shore residents enjoy biking, nature trails, as well as tennis. On the nearby mainland, you'll find some of the best and most exclusive golf on the Gulf Coast.

Siesta Key, Florida homes for sale run the gamut with architectural styles to suit every taste. You might opt for an existing residence, like a beachfront bungalow or cottage, on which you can stamp your own sense of decorating style. Or investigate the luxurious gated estates that boast unforgettable bay views, private pools and docking, and a host of other amenities designed for the discerning homeowner.

Location/Weather

Any discussion of Siesta Key, Florida homes must include the area’s desirable location. Situated between Roberts Bay and the Gulf of Mexico, this barrier island is connected to the mainland by north and south bridges providing easy access to downtown Sarasota and the mainland. Siesta Key is easily accessible to the Gulf region’s main attractions and activities. The Key is served by two major airports within a 15-mile radius. Major sports venues in Tampa are  about an hour away, and Orlando's Disney World is just a bit farther, yet and easy drive.

The weather in Siesta Key is typical of the Gulf Coast – a pleasant surprise for transplanted Northerners, who will experience a winter with average temperatures in the 60s instead of sub-zero. Summer heralds a more tropical kind of heat, which makes the waterfront lifestyle that much more enjoyable.

Things to Do on Siesta Key

Annual Sandsculpting Competition on Siesta KeyYou don’t need to search for fun on the Key, with choices that include beaches, boating and the “cradle of golf” that is Sarasota. Championship courses, on the mainland, like the Bobby Jones Golf Club, for instance, are steeped in golfing history. Off the links, you’ll find attractions for family and guests in Siesta Key’s tennis, volleyball, picnicking, street performances and even tropical bird watching along the groves. Some of the more popular annual events on the Key are becoming family vacation traditions:

  • Annual Crystal Classic Master Sandsculpting Competition
  • Annual Lightup the Village and Holiday Open House
  • Siesta Key Craft Festival
  • Valentine Stroll
  • Annual Easter Egg Hunt & Games
  • Siesta Fiesta

By night, take advantage of Sarasota’s amazing selection of casual and upscale restaurants, clubs and theaters, all within a short drive.

Discover Siesta Key

For outstanding, exclusive listings and a deep knowledge of the area, contact our expert REALTOR team which is ready to show you the best island properties. You'll find Siesta Key homes for sale on the Gulf, Sarasota Bay, the intracoastal and canals as well as inland. Architectural styles vary from old Florida ranch style to contemporary and Mediterranean. Look to our comprehensive, confidential services to handle every detail of your transaction to ensure a pleasant relocation to this wonderful little “strip of paradise” right on the Gulf of Mexico.

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