Dream Homes

The 10 Most Expensive Homes in Sarasota

What all 10 share are prime waterfront locations and lots of square footage.

By Susan Burns, Cooper Levey-Baker, and Kim Doleatto October 20, 2023

Compared to Buckingham Palace, valued at $4.9 billion, or the priciest home in the U.S., dubbed “The One” in Bel Air, Los Angeles, which fetched $126 million at auction last year, the Sarasota-Manatee luxury home market remains humble, even while it recently introduced its most costly listing yet, at just under $34 million. (Just last year, that peak was $25 million.)

To put together this list of our area’s most expensive homes, we used property appraiser records from Sarasota and Manatee counties to find the area’s 10 most highly valued single-family homes. Last year, all 10 were located in Sarasota County. This year, a Manatee County home on Longboat Key cracked the list. Still, what surprised us—given all the new wealth pouring into the region and the reams of new, high-end construction—is how stable the top 10 list remains, even as we update the list annually. Nine of the 10 homes from 2019 still rank in the top 10 and are still owned by the same people. Something else to note? The jumps in home values over the course of just one year (one is up by almost 33 percent) highlight the fact that Sarasota and Manatee county luxury living is in high demand. Let's also offer a special shoutout to Ohana on Longboat Key, which was valued at $19 million and change, but did not qualify as a single-family home.

Let's get to it. Here's the list.

6910 Point of Rocks Road, Sarasota.

No. 10: $18,381,600

6910 Point of Rocks Road, Sarasota

Owners: Gary and Elizabeth Kompothecras

Value in 2022: $16,339,800

Gary and Elizabeth Kompothecras bought land on Siesta Key in 2003 for $2.3 million and built this 13,562-square-foot home by 2010. The founder of the 1-800-ASK-GARY referral service and a former chiropractor, Gary says it took seven years since there were “a lot of change orders and waiting on materials like imported silks and limestone.” The seven-bedroom, seven-bathroom home includes a sauna, hot tubs, a bowling alley, a steam room, a wine cellar, a theater and private beach access. The multi-storied, columned mansion was modeled after William Vanderbilt’s Marble House in Newport, Rhode Island, which was designed by architect Richard Morris Hunt in 1892. That home reflected the taste of Vanderbilt’s wife, Alma, who was educated in France and developed a fondness for its art and culture. In fact, it was that mansion that started the Beaux-Arts craze in Newport.

Locally, the Kompothecras home is one of the most famous houses in town, thanks to its starring role on the MTV reality show Siesta Key, which originally followed the couple’s son Alex and his cohort. “I get a lot of knocks on the door from people wanting a tour,” Gary says. The property underwent a recent remodel and cost the couple roughly $5 to $6 million. Already, they’ve added torches out front, “like Mount Olympus,” Gary says.

6021 Gulf of Mexico Drive, Longboat Key.

No. 9: $18,532,969

6021 Gulf of Mexico Drive, Longboat Key

Owners: Lisa Peters and John Lueken

Value in 2022: $12,484,805

The only Manatee County home to make our top 10 list, it made headlines when it sold in 2020, breaking the sale record at the time at $13 million plus $100 in an all-cash deal, making it the highest residential real estate sale ever recorded in Sarasota, Manatee and Charlotte counties.

The 7,000-plus-square-foot, four-bedroom home at 6021 Gulf of Mexico Drive has numerous luxury amenities and is set on a walking beach, which was very important to the buyers, says Kim Ogilvie of Michael Saunders & Company, who represented them.

Ogilvie was also the realtor with the previous record-breaking sale, a Gulf-front estate on Westway Drive in Lido Shores that sold in 2006 for $13 million. When her Longboat Key clients discovered that, they were happy to offer the additional $100 to the total price. “I’m happy to break my own record,” Ogilvie told us at the time.

Due to a confidentiality agreement with the buyers, she couldn't reveal anything about the couple, except that they wanted a beachfront location, privacy and proximity to amenities like the restaurants that have popped up on north Longboat Key.

857 Longboat Club Road, Longboat Key.

No. 8: $19,310,500 

857 Longboat Club Road, Longboat Key

Owners: Pleasant Real Estate LLC, MaryAnn Mathile 

Value in 2022: $17,997,400

Built in 2008, this 15,954-square-foot home has six bedrooms, 12 bathrooms and a pool. Purchased in 2000 by the late Clayton Lee Mathile and his wife, MaryAnn, they transferred the deed to Pleasant Real Estate in 2003. After leaving his job as an accountant at the Campbell Soup Company, Mathile, originally from Ohio, bought the Iams pet food company in 1982 and built it into a powerhouse, then sold it to Proctor & Gamble in 1999 for $2.3 billion, placing him on the Forbes billionaire list. MaryAnn received an honorary doctor of humanities degree from Saint Mary’s College in 2006, and she and her husband gifted the school $9 million in 2011. Founded in 1989, The Mathile Family Foundation has granted more than $230 million to nonprofits that help children and families. Clayton also founded Aileron, a nonprofit focused on helping businesses thrive, and authored self-help books focused on how to win big in business. He passed away in August 2023 at the age of 82.

4449 Bay Shore Road, Sarasota.

No. 7: $21,010,700

4449 Bay Shore Road, Sarasota

Owners: James and Maryann Armour 

Value in 2022: $19,809,700

This massive, 21,192-square-foot Parisian-inspired home overlooking Sarasota Bay is owned by James and Maryann Armour. He’s the former chief executive officer and chairman of AM General, LLC of South Bend, Indiana, a defense contractor that makes Humvees and Hummer SUVs. The Armours purchased the unfinished home for $19 million in 2008 from financier Howard Jacobs. After years of controversy and lawsuits over the existing home’s defects, the Amours ended up investing $14 million in renovating it. The three-story, Beaux-Arts-style home has 10 bedrooms, 17 bathrooms and a pool. The address is also listed as the headquarters for their nonprofit, the James and Maryann Family Foundation, which supports the Fine Arts Society of Sarasota, The Van Wezel Foundation and Marie Selby Botanical Gardens, to name a few.

845 Longboat Club Road, Longboat Key.

No. 6: $21,276,700 

845 Longboat Club Road, Longboat Key

Owner: 845 LBCR Land Trust, James and Laura Rogers 

Value in 2022: $19,831,800

Serenissima, Italian for “most serene,” made headlines in 2017 when it went on the market for $26.5 million, making it Sarasota’s most expensive single-family listing ever. The price later dropped to nearly $19.8 million and fetched $16.5 million when it eventually sold in 2020, tying it with a Casey Key home for the most expensive residential sale in Sarasota County. The home is a grand Venetian-inspired estate in the Longboat Key Club’s Regent Court neighborhood and has nearly 20,000 square feet of living space, including six bedrooms, six full baths and two half-baths, and generous outdoor terraces with water views. Among its many custom details are a gilded birdcage elevator and hand-painted murals on the dining room ceiling.

The address is the home base for the James and Laura Rogers Foundation, a nonprofit that has donated to arts and youth development nonprofits in Tennessee. The couple started the foundation in 2011. “They’re the nicest down-to-earth people,” said Rich Polese, a founding agent with Compass who represented the two in the transaction. “They decided they wanted to explore properties in Florida, looked at the east coast and weren’t impressed, and then came over to the west coast. The first time they ever came to Longboat was when I met them, and they absolutely fell in love with it.”

1253 Hillview Drive, Sarasota.

No. 5: $22,198,100 

1253 Hillview Drive, Sarasota

Owners: Bridgeview Land Trust, David and Lisa Grain

Value in 2022: $20,964,300

Investment executive David Grain and his wife, Dr. Lisa Butler Grain, own this property in Harbor Acres, one of the hottest neighborhoods in town. Grain was a Wall Street investment banker and then an executive in the telecommunications industry before he launched his own private investment firm, Grain Management. Once owned by Dow Jones Co. billionaire heiress and New College of Florida supporter Jane Bancroft Cook, the home was bequeathed to New College and sold at auction for $3.9 million. The property sat empty for years before the Grains purchased it in 2006 for $6.5 million. In 2018, they built a 28,182-square-foot, four-bedroom mansion. Tapped for leadership on many state and federal councils, including being appointed to a U.S. Department of Homeland Security council by President Barack Obama, David Grain is also the founder of a college prep program that has helped hundreds of local African American and Hispanic students with their SATs, college trips and enrichment programs.

2309 Casey Key Road, Nokomis.

No. 4: $22,345,000 

2309 Casey Key Road, Nokomis

Owner: Ping Faulhaber

Value in 2022: $21,463,400

The late Fritz Faulhaber and his engineer wife, Ping, liked the friendliness of Sarasota and the education at Pine View, so they moved their young family to Casey Key from Clearwater, where The Faulhaber Group companies are headquartered. They purchased this Gulf-to-bay property for just over $2 million in 1998, built a 19,674-square-foot, Spanish-style home in 2007 and later created an award-winning 1.2-acre pagoda garden. The Faulhabers also created the Suncoast Science Center/Faulhaber Fab Lab in Sarasota to inspire young people to enter careers in science. Ping is the executive director, and, last year, was elected to the Gulf Coast Community Foundation’s board of directors for a three-year, four-month term.

1420 Bay Point Drive, Sarasota.

No. 3: $22,410,100

1420 Bay Point Drive, Sarasota

Owner: Katherine Ebbeson

Value in 2022: $22,102,500

Former Congresswoman and Florida Secretary of State Katherine Ebbeson (née Harris) built this 16,016-square-foot bayfront home in desirable Bay Point Park in 2012. The architecture follows the Beaux-Arts style, based on Paris’ Hotel Biron, which was constructed in 1730. The house has six bedrooms, 11 baths, a pool, a boathouse and a dock. Now out of politics (she certified the Florida recount in the controversial 2000 presidential election), Ebbeson—the granddaughter of citrus and cattle magnate Ben Hill Griffin, for whom the University of Florida’s football stadium is named—married Texas banker Richard Ware in 2017; the couple splits their time between Sarasota and Amarillo, Texas.

2209 Casey Key Road, Nokomis.

No. 2: $22,438,100 

2209 Casey Key Road, Nokomis

Owners: Walter and Marilyn Kreiseder

Value in 2022: $20,318,800

Inventor and plastics mogul Walter Kreiseder and his wife, Marilyn, own this Casey Key Mediterranean mansion. Walter, who holds numerous patents, was a former owner of injection molder Courtesy Corp. in Illinois. Purchased in 1999 for nearly $4 million, the original home, designed by Ralph Twitchell of the Sarasota School, was razed to make way for a 14,898-square-foot home with four bedrooms, eight bathrooms, a beach cabana and a boat dock. During the build, it was rumored to be Oprah’s new abode. The gossip garnered the site unwanted attention and drop-ins from wannabe paparazzi until someone erected a hand-drawn sign that read, “Not Oprah’s.” Builder Michael Walker, president of Michael K. Walker Associates in Sarasota, who led the project, says he isn’t sure how the rumor got picked up, but says an elongated letter “O” cutout shape in the privacy wall may have been the culprit—it even had tour buses stopping to gawk.

132 N. Washington Drive, Sarasota.

No. 1: $23,031,600 

132 N. Washington Drive, Sarasota

Owners: Jeffrey and Mary Penny Vinik

Value in 2022: $21,281,600

Hedge fund legend and Tampa Bay Lightning owner Jeffrey Vinik and his wife, Mary Penny, own this showstopping mega-mansion on St. Armands Key. One of the largest homes in Sarasota, it was reportedly nicknamed by neighbors the S.S. Magellan for its cruise ship proportions and for the $500 billion Magellan Fund Vinik managed in the ’90s. Vinik bought two existing mansions and razed them to build this stark-white, ultramodern complex of 24,040 square feet (16,245 indoors). The home includes eight bedrooms, eight full bathrooms, five half baths and a swimming pool on Sarasota Bay with a view of the Ringling Bridge. Vinik is also an investor in ventures from skincare to radiation protection gear for soldiers and video game headsets, according to The Tampa Bay Times. 

This summer, Vinik sold his share of Strategic Property Partners, the real estate company behind the 56-acre Water Street Tampa development, a $2 billion project. He's also selling a minority interest in the Tampa Bay Lightings to Arctos Sports Partners for $1.4 billion. He was instrumental in turning around the team after he had purchased it for $170 million in 2010 when it was losing millions and ranked at the bottom of the NHL for attendance and revenue. Although this home may be the area's most expensive, its price point is paltry next to the $63.8 million Aspen mansion Vinik bought in August.

Filed under
Show Comments