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Island Lifestyle and Architectural Gems on Sarasota’s Siesta Key

Sarasota’s Siesta Key

A contemporary waterfront home listed for sale in Siesta Key, Sarasota.

There’s no denying that Siesta Key is known far and wide for its beach.

“It’s a crescent-shaped, big, beautiful, wide beach, and the sand is 100% soft, pure white quartz,” said Jonathan Abrams, a broker with Michael Saunders & Company.

The island, or “the key” as it’s called by locals, has its own unique, laid-back island feel for people who visit as well as for locals, said Joel Schemmel of the Schemmel Group, the Sarasota affiliate of Sotheby’s International Realty.

“Every island in the area has a slightly different character, and on Siesta Key, it’s more casual and relaxed,” he said. “You really feel like you’re on an island, even though it’s logistically easy to get on and off the key” to take advantage of all that Sarasota has to offer.

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Siesta Key is a 3.5-square-mile barrier island off Florida’s southwest coast. Although the key is part of Sarasota, it is its own census-designated place with its own ZIP code, made up of four main areas: Siesta Key, Crescent and Turtle beaches, and Siesta Key Village. Siesta Key Beach runs along the southwestern edge of the island facing the Gulf of Mexico, and Roberts Bay separates the island from the rest of Sarasota, on the mainland to the northeast.

Two bridges, one at either end of the island, connect Siesta Key to the rest of Sarasota, on the mainland.

Price Range

The entry price for a single-family home in the luxury market, according to Mr. Abrams, is roughly $800,000, but the average sale price is $2.2 million.

“For true luxury homes, you’re looking at more like $2.5 million to $3 million,” he said.

Buyers can expect to find amenities such as pools, lanais, lush landscaping, and, for beachfront homes, pristine views of the water. Many older, fully restored and updated homes tend to have better views, while newer homes tend to be smaller and sit along the key’s inlets, said Brian Loebker, also a broker with Michael Saunders & Company.

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Prices and amenities are often lifestyle-driven, Mr. Schemmel said, citing examples such as proximity to the village and the beach, boating access, and docks and lifts. According to data from Mr. Schemmel, the average and median prices of single-family homes currently on the market are just under $1.76 million and $1.25 million, respectively, though prices can climb much higher.

“This year alone, Siesta Key has seen six closed sales over $5 million,” Mr. Loebker reported. The highest asking price of a home currently on the market is $12.9 million. That property sits on a three-acre beachfront compound and takes full advantage of more than 500 feet on the Gulf of Mexico.

For condos, the price of entry is roughly $300,000, Mr. Abrams said. The average listing price for luxury condos currently on the market is just under $811,000, according to Mr. Schemmel. At that price point, Mr. Loebker said, buyers could expect either an older building with water views in need of updating or a fully updated building with little to no view.

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Siesta Key Village

The high end neighborhood in Siesta Key is known far and wide for its beach.
Michael Saunders & Company

For a true high-end, waterfront condo, he said, buyers could expect asking prices as high as $3 million for 2,500 to 4,500 square feet. One 4,574-square-foot condo in the Oceane boutique luxury development, which has drawn considerable interest from buyers from the northeast and midwest U.S., is currently on the market, listed at $4.425 million.

Housing Stock

A wide range of architectural styles is represented on Siesta Key. For Mr. Schemmel, this diversity is one of the things that makes Siesta Key unique. “You can find everything from historic, 1950s to ’60s ranch and beach houses to ultra-modern homes,” he said. He and other brokers noted a preference for the clean lines, large windows and open layouts characteristic of more contemporary homes.

“The area is known for the Sarasota School of Architecture,” Mr. Schemmel said, “and that certainly has a following. Individual streets tend to take on their own character, though.” Mr. Abrams noted that homes designed by architects Paul Rudolph, Jack West, and Ralph Twitchell, all connected to the Sarasota School, can be found on Siesta Key.

There are few remaining development opportunities along the beachfront, which limits newer inventory. Single-family homes are more typical on the north and south ends of the key as well as the bayfront, whereas condos are concentrated on public beaches. There, they represent the vast majority of new development and fetch the highest prices.

More historic condo buildings generally offer typical amenities such as a pool and perhaps tennis courts, while newer developments commonly include pools, spas, cabanas, massage rooms, and fitness centers.

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What Makes it Unique

A relaxed, island lifestyle, privacy, and exceptional beaches make Siesta Key stand out among Florida’s many sought-after areas. “The atmosphere on Siesta Key is very casual,” Mr. Schemmel said. “It has a very casual, down-to-earth feeling.”

Siesta Key Village

Michael Saunders & Company

Luxury Amenities

Siesta Beach, the only major public beach on Siesta Key, is known for its soft, superfine quartz sand. It has also been named a top beach by the Travel Channel and AARP. The warm, calm, clear waters of the Gulf of Mexico and radiant Floridian sunshine make Siesta Key’s beaches a destination for buyers, locals as well as vacationers.

Siesta Key has its own village, with restaurants, such as The Cottage, which serves up seasonal, inventive, globally inspired cuisine; the mainstay Siesta Key Oyster Bar; and the Toasted Mango Café, frequented by locals and celebrities alike. Foxy Lady, a small boutique that features clothing from designers from around the world, is located in Siesta Key Village, where the Palm Beach-based designer brand Lilly Pulitzer also opened a new boutique earlier this month.

Siesta Key Village

Michael Saunders & Company

On the mainland, which is within 15 minutes of Siesta Key, the island’s residents can take advantage of all Sarasota has to offer, including Michael’s On East, an upscale, supper club-like anchor of Sarasota’s culinary scene, and Indigenous, a New American restaurant whose seasonal cuisine prominently features sustainable seafood.

Sarasota also has numerous cultural offerings, such as its own orchestra, opera and ballet, and the Sarasota Art Museum.

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The Sarasota-Bradenton International Airport is a 20-minute drive from Siesta Key. “The number of commercial flights is ever increasing,” Mr. Schemmel said, and the Venice Municipal Airport, two miles south of Sarasota, “is a very easy airport to use for private flights.”

The Siesta Key Marina and the Bayfront Marina, at the southern tip of the key, offer storage and lift services for those whose homes don’t include their own docks and lifts, and can accommodate boats and yachts up to 60 feet.

Many buyers seek out homes on Siesta Key because of Sarasota’s excellent schools, both public and private. In the school district of Sarasota County, the Pine View School, serving grades 2 through 12, is consistently ranked among the best schools in the country. In 2019, the U.S. News & World Report ranked it 15th among public high schools in the United States and first in Florida. The Out-of-Door Academy, a much sought-after private school, according to Mr. Loebker, serves students in kindergarten through 12 grade, and is located in Siesta Key.

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Who Lives There

“Siesta Key is known for its ‘quiet wealth,’” Mr. Loebker said, adding that although the area has long attracted older, well-to-do buyers, “it’s amazing to see the interest in the luxury market from younger people each year.”

He and Mr. Abrams concurred that many buyers, especially self-made entrepreneurs looking to relocate from the northeast and mid-atlantic regions of the U.S., have increasingly sought homes on Siesta Key.

Mr. Schemmel noted the same trends, pointing to the relatively lower property taxes in Florida.

He estimated that 60% of owners of single-family homes and 30% to 40% of condo owners live on Siesta Key year-round, and said that roughly 85% to 88% of buyers are American, while Canadians are best represented among buyers from outside the United States.

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The presence of the IMG Academy, an advanced multi-sport training and educational institution, whose alumni include the Williams sisters, Pete Sampras and Andre Agassi, also draws athletes from around the world.

“Siesta Key was known as a safe haven for celebrities going back to the 1950s and that culture has remained, but privacy is obviously very important,” Mr. Abrams said, explaining that the island affords all of its residents an easygoing, neighborly atmosphere, regardless of their high-profile status.

Several executives of Fortune 100 companies as well as high-profile members of the tech industry also reportedly own homes on Siesta Key.

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Notable Residents

Former Baltimore Orioles All-Star Brian Roberts reportedly is building a home on Siesta Key. Businessman Gary Kompothecras, the founder of the ASK-GARY medical and legal hotline, lives in a $12.6 million million mansion on the island with his wife, Elizabeth. Meanwhile, John Melk, co-founder of Blockbuster Video, built a six-bedroom home in Siesta Key in 2008, and sold it to socialites and businesspeople Jeff and Susan Jones, of JCI Jones Chemicals, for $10.3 million in 2008.


In 2017 and 2018, Siesta Key saw a transition toward a more balanced market between buyers and sellers, Mr. Schemmel said, and he expects this trend to continue, shifting toward a sellers’ market, based on inventory and value. The average price for a single-family home over the past 12 months is $1.4 million, with little change over the last year.

Siesta Key Village

Michael Saunders & Company

In terms of value, Mr. Schemmel pointed to the advantages of the market in Sarasota overall, relative to the markets of the northeast and other areas of Florida, such as West Palm Beach or Naples. Giving the example of a $7.5 million beachfront home on three acres with 300 feet of beach frontage, he said “you just can’t have that in Naples, but if you could, it would be $20 million. Homes there can cost as much as 30% to 40% more.”

Mr. Abrams noted the vast range of property types and prices, which attract buyers from all over the United States as well as from abroad. “Listings are on the market for three to four months, and 95% of offers are higher than list price,” he said. But, the number of days on the market has generally been increasing, especially for condos, which may offer opportunities for prospective buyers.

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