Favorite Dwellings - Siesta Key

It wouldn't be a week in real estate if we didn't receive calls and inquires or preformed home searches for property on Siesta Key. A little bit of something for everybody, this barrier island is loved by many and world famous for its incredible, top ranking beaches. From luxury to laid back, siesta key is the place to be and it's an area the DWELL Team knows well. After years of helping buyers and sellers fulfill their real estate needs in the 34242, we've visited nearly every community and have a few we enjoy a little more than all the rest . Which ones you ask? Here are a few of our agents' sharing their favorite communities within Siesta Key.

James Tassell, PLLC


Located mid key you will find one of my favorite beachside condo communities on Siesta Key called Casarina. This hidden community off of Midnight Pass Road is made up of a single high rise building with a total of 89 units, which range in size from 1,382 to 2,542 square feet. What makes this community special? Firstly, the drive into the community feels like you are entering into a tropical oasis set well back off of the main road. Now if you are looking for a community where a large percentage of the units have a view of the turquoise blue gulf water and daily sunsets in a lower density community, then Casarina should be on your list. There is plenty of guest parking which isn’t always the case with Siesta Key condo communities. Residents have either an assigned garage parking space or a carport. One look at the spacious pool and spa area will make you feel like you are at a top rated hotel but without the crowds. For your convenience there is a cabana, rest rooms, and showers by the pool. Follow the paver pathway to make your way to the community outdoor grilling area with ample space for residents to sit and enjoy lunch or dinner. Of course what beachside community isn’t complete without its own sunset boardwalk leading you down onto the white soft powder of Siesta Key beach. There is an oversized clubhouse, which is often filled with bridge players and over looks a large pond with a fountain adding to the tranquility of the community. When you are ready to be more active you can take advantage of the fitness center and tennis courts. The community’s central location on the key means you can be in the village or on the south end of the key in minutes for happy hour or dinner. I suggest taking advantage of one of the free (tips welcome) transportation services on Siesta Key. Two of the more common condo questions ‘are pets allowed?’ and ‘what is the rental policy?’. Casarina allows owners to have one pet up to 25lbs. Owners may rent their condo five times a year with a one-month minimum lease period required. Prices range from the high $500Ks up into the millions. Don’t be surprise if there is only one or two units on the market at one time. Owners don’t like to sell too often.

Cathy Loeppke, PLLC

Sanderling Club

Who doesn’t love a great story?….As someone who loves history, art, and stories of bygone eras, Sanderling Club has held my intrigue for many years. In this timeless community is a timeless story with the original characters, living a generation or two before us, longing for the same things as many of us….peace, tranquility, and to commune in nature. The lead in this story was a man of great vision, Elbridge S. Boyd, who dreamed of a gulf front community with reverence for preserving the ecology while creating an esthetic quality unmatched along the Southwest Florida gulf coast. It was soon after world war II, when many were seeking a respite from the stresses and deep losses of war, that Boyd formed a company, Siesta Properties, Inc., to begin developing uninhabited, jungle-like coastal land surrounding a lagoon about a mile south of the South Siesta Key bridge (Stickney Pt. Rd) . Between 1946 and 1958, 67 “three-month” beach homes were built for “northerners” to enjoy a quiet and relaxed “barefoot on the beach” lifestyle during Sarasota’s balmy, winter months. These water front homes were built in phases on beach front lots of 150’, or on the lagoon (now known as Heron Lagoon) and along dredged canals connected to the lagoon. Later, the housing development expanded across the street on the bay side with a private, sheltered 15 boat marina.

Beginning in 1952, 25 gulf front cabanas were built for resident’s use (with roof lines bent to resemble waves) by the renowned architect, Paul Rudolph. Next, Rudolph built the Clubhouse with similar design features. They remain on the National Register of Historic Places. As the number of property owners increased, it became necessary to create a Homeowners Association and add some recreational amenities for residents. The community features the marina on the bay side. On the gulf side are 3 tennis courts, a playground structure and the gulf front Clubhouse with large patio, grilling area and unrivaled gulf and sunset views. Today, you’ll find luxury homes built in more recent years that replaced some original cottages. Sanderling Club, discreetly tucked in an Old Florida setting off Midnight Pass Rd, is known as an exclusive, private membership, guard-gated residential community of homes currently ranging in price between $1.2 million and $12 million. If you make this sanctuary your home, you’ll live among the Herons, Egrets, Gulls, Terns, Sanderlings, Sandpipers, and other native birds who came long before you…and you can help write the rest of the story.

Jason Wood 

Gulf and Bay Club

Luxurious, elegant and impeccably landscaped.  Gulf & Bay is perfectly positioned on a 32 acre community with many resort style amenities not found in any other community on Siesta Key.  This 392 unit community all face two large well manicured pond with fountains and lavish gardens with bridged walking trails. If you like to stroll the white quartz sand of Siesta Key, you have 800 feet of private beach area with lounge chairs all within a short stroll to the public beach. No need to drive anywhere as you are walkable to Siesta Key's north village area.

Gulf & Bay has two clubhouses, 8 tennis courts with pickle ball, racquetball and basketball just to name a few.  Don't want to be on the beach, you have 3 heated pools to choose from.  Grill out with friends under the tiki covered gas grills and picnic tables that front the manicured lakes.  There is also 24 guarded gate access for added security and exclusiveness not to mention the state-of-the-art video and FOB access elevators and beach front gates.  This community has thought of everything down to the electric charging station for your electric vehicles. 

Each condo unit has long views of the Gulf of Mexico and the lavish gardens not to mention sunsets that have made Siesta Key one of the best places in Florida to enjoy the end of the day with the beverage of your choice.  Siesta Key is a golf cart legal island and carts can be rented or a free ride can be arranged to get around the island at your convenience. 

Shopping, restaurants, bars and nightly entertainment will keep you entertained beyond expectations.  Gulf & Bay has everything you would come to expect of a true luxury community and Siesta Key has the rest.  It is a phenomenal community and my favorite to showcase on Siesta Key.

Ready to make your waterfront dreams come true with a great property on Siesta Key? Contact us at 941.822.0708 or [email protected], we're here and happy to assist.

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