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 September 28, 2022
51
Listed
85
Avg. DOM
$1,135.17
Avg. $ / Sq.Ft.
$3,695,000
Med. List Price
51 Properties
Page 1 of 5
$16,995,000
Neighborhood: Siesta Rev Of
5
Beds
5F21/2
Baths
8,964
Sq.Ft.
2022
Year Built
115
Days on Site
A4537883
MLS
Under Construction. Pre-Construction. To be built. A very special opportunity for a unique owner. 4136 Higel is now under construction. It has been nearly one year in the making and this...
$12,600,000
Neighborhood: Bay Island Rep 01
5
Beds
4F21/2
Baths
7,487
Sq.Ft.
140
Days on Site
A4534680
MLS
Under Construction. Experience the majestic, private waterfront setting of this dazzling residence on Siesta Key with an approximate completion date of December 2022. Boasting 128' of water frontage...
$9,000,000
Neighborhood: Sanderling Club
2
Beds
3
Baths
2,580
Sq.Ft.
1983
Year Built
209
Days on Site
A4527041
MLS
Welcome to one of Southwest Florida's most incredible and rare pieces of beach front property. This striking Siesta Key home offers 203 linear feet of PRIVATE GULF FRONT BEACH with direct gentle...
$8,999,000
Neighborhood: Siesta Beach
5
Beds
6F21/2
Baths
7,566
Sq.Ft.
2007
Year Built
157
Days on Site
A4531700
MLS
Enjoy panoramic views of sunrise, sunset, and star gazing from your private waterfront oasis on the fashionable north end of Siesta Key. This exquisitely designed island-style home is the perfect...
$7,750,000
Neighborhood: Cocoanut Bayou
4
Beds
4F11/2
Baths
8,571
Sq.Ft.
2008
Year Built
104
Days on Site
A4539090
MLS
Live the life of a 17th-century Palladian Villa in the south of France in this Siesta Key waterfront masterpiece. This custom-built waterfront home on Cocoanut Bayou has 120 feet of waterfront...
$7,635,000
Neighborhood: Sarasota Beach
8
Beds
8F11/2
Baths
3,811
Sq.Ft.
2019
Year Built
182
Days on Site
A4529768
MLS
This giant 8 bedroom 8.5 bathroom home, offers over 4600 square feet of living and multiple balconies on all levels, a Roof-Top Deck, and an outdoor dining area just off the living room area. Of the...
$6,900,000
Neighborhood: Mira Mar Beach
7
Beds
7F11/2
Baths
3,600
Sq.Ft.
2023
Year Built
8
Days on Site
A4547903
MLS
Under Construction. The construction start date is Mid October 2022, with completion estimated Fall of 2023. This is both an amazing and rare opportunity to own a luxury second home or luxury rental...
4
Beds
4
Baths
2,827
Sq.Ft.
1959
Year Built
134
Days on Site
A4535443
MLS
Very Private! Gated entry to Blind Pass Road. Advantages. Can build another large house onproperty,or lot can be split and sold.
Rentals allowed. Large sund3eck overlooking Gulf. Dock n...
$6,500,000
Neighborhood: Bay Island/Siesta Key
5
Beds
5F21/2
Baths
4,985
Sq.Ft.
2023
Year Built
28
Days on Site
A4546740
MLS
Pre-Construction. To be built. A dream home built by well-respected Voigt Brothers Construction on 95 ft of water frontage. Great boating waters on Hanson Bayou with easy access and no bridges to the...
$6,475,000
Neighborhood: Sarasota Beach
8
Beds
6F11/2
Baths
4,094
Sq.Ft.
2017
Year Built
182
Days on Site
A4529764
MLS
This massive income-producing property on Siesta Key is finally for sale! Backed with years of rental history and a five-star rating by renters this property is an incredible opportunity. This giant...
$6,000,000
Neighborhood: Bay Island Shores Unit 1
4
Beds
4F21/2
Baths
6,395
Sq.Ft.
2006
Year Built
75
Days on Site
A4542278
MLS
This stunning north Siesta Key estate on sailboat water offers deep-water dockage and multiple lifts for serious boaters. Experience the magnificence of this impressive, private harbor-front...
$5,999,990
Neighborhood: Siesta Key
6
Beds
6
Baths
4,248
Sq.Ft.
2003
Year Built
70
Days on Site
A4542849
MLS
Welcome to one of the best beach homes on world-famous Siesta Key. This exquisite multi-family vacation home is situated perfectly with grand views of the Gulf of Mexico and the Siesta Key public...

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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