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 May 30, 2023
89
Listed
88
Avg. DOM
$1,227.35
Avg. $ / Sq.Ft.
$3,200,000
Med. List Price
89 Properties
Page 1 of 8
$32,500,000
Neighborhood: Fidder Bayou
6
Beds
6F31/2
Baths
9,754
Sq.Ft.
2022
Year Built
169
Days on Site
A4554778
MLS
Pre-Construction. To be built. This breathtaking estate brings the tranquility of the South Pacific to your own private beach on stunning Siesta Key. The home, being built by BCB Homes out of Naples,...
$22,000,000
Neighborhood: Siesta Key
4
Beds
4F21/2
Baths
8,138
Sq.Ft.
2016
Year Built
133
Days on Site
A4555451
MLS
Discover your very own island paradise on world-famous Siesta Key. Located on the north end of Siesta Key, this awe-inspiring estate was brilliantly created to deliver the perfect balance between...
$16,800,000
Neighborhood: Sanderling Club
6
Beds
7F11/2
Baths
10,624
Sq.Ft.
1986
Year Built
196
Days on Site
A4552224
MLS
Start living your dream island lifestyle in the ultimate beachfront paradise on Siesta Key. This private resort-like compound rests on over 4-acres between the tranquil blue Gulf of Mexico waters and...
$15,950,000
Neighborhood: Point Crisp Add
6
Beds
8F11/2
Baths
7,162
Sq.Ft.
2001
Year Built
48
Days on Site
A4565492
MLS
Siesta Key coastal home where superlatives are a way of life: 1.2 acres on a peninsula. 360-degree bay views. 546 feet of waterfront on Little Sarasota Bay. Water views from every room (including the...
$14,000,000
Neighborhood: Sanderling Club
2
Beds
3
Baths
2,580
Sq.Ft.
1983
Year Built
97
Days on Site
U8190545
MLS
Welcome to Casa Playa Privada Siesta, a waterfront masterpiece located in one of the most coveted Siesta Key gated
communities, the Sanderling Club.
A Gulf of Mexico beachfront gem with a...
$10,000,000
Neighborhood: Siesta Key
5
Beds
3F21/2
Baths
7,636
Sq.Ft.
1994
Year Built
196
Days on Site
A4552060
MLS
AS SEEN ON MANSION GLOBAL!! A one-of-a-kind estate situated on one of the most desirable streets on Bay Island at the north end of Siesta Key. The Freeling Drive Peninsula is sited on one of...
$9,995,000
Neighborhood: Siesta Properties Inc
4
Beds
4F21/2
Baths
4,799
Sq.Ft.
1987
Year Built
93
Days on Site
A4562212
MLS
Life at this gorgeously updated, Siesta Key beach home is a one-of-a-kind experience! Set among lush, Florida-friendly greenery directly overlooking the coastal landscape of the Gulf of Mexico, this...
$9,995,000
Neighborhood: Hidden Harbor Add
5
Beds
5F11/2
Baths
7,506
Sq.Ft.
2002
Year Built
61
Days on Site
A4565141
MLS
Experience the epitome of waterfront living at 1250 Hidden Harbor Way, Siesta Key, FL, a custom-built sanctuary where coast elegance meets timeless serenity. Nestled on a private, peninsula lot, the...
$9,790,000
Neighborhood: Siesta Key
2
Beds
2F21/2
Baths
4,750
Sq.Ft.
1996
Year Built
125
Days on Site
A4558393
MLS
The ultimate in beachfront living - introducing an exceedingly rare, single-family home offering on the white-sand beaches of world-famous Siesta Key. Enjoy daily walks, warm, gentle Gulf breezes and...
$9,000,000
Neighborhood: Sanderling Club
3
Beds
4F11/2
Baths
3,674
Sq.Ft.
1989
Year Built
80
Days on Site
A4562963
MLS
Presiding over sensational views of the Gulf of Mexico behind the private gates of the Sanderling Club, this beachfront property has few equals when it comes to tranquility, privacy and the rarity of...
$8,950,000
Neighborhood: Cocoanut Bayou
5
Beds
5F11/2
Baths
6,455
Sq.Ft.
2009
Year Built
80
Days on Site
A4560721
MLS
PRICE IMPROVEMENT! ONE of a KIND! A stunningly beautiful custom home in the very best of locations in coveted Cedar Park Circle on north Siesta Key. A short walk or bike ride to famed Siesta Beach...
$7,995,000
Neighborhood: Bay Island Shores
4
Beds
5F11/2
Baths
6,827
Sq.Ft.
1997
Year Built
168
Days on Site
A4554867
MLS
Welcome to Casa della Fontana, a stunning waterfront retreat nestled in the heart of the highly coveted Siesta Key in Florida. This Mediterranean-style masterpiece boasts expansive bay views and is...

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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