1127 Westway Drive, Lido Shores

Owners: Kenneth and Carrie Cox | 2016 rank: No. 1 | Value in 2016: $16,857,400, an increase of $894,900

Owned by pharmaceutical executive Carrie Cox (she’s been named one of the most powerful women in business six times by Fortune magazine), and her husband, Kenneth, a developer, the home is on five acres along New Pass in Lido Shores. The Coxes purchased it in 2003 for $11 million, and then gutted it to build a 19,658-square-foot home (7,151 square feet under air) with four bedrooms, seven bathrooms and a pool. The home has a history of well-known owners. Prominent Sarasota developer Joe Penner and his wife, Grace, built the home in 1989; later it was purchased by the late food magnate Daniel Kane.

2309 Casey Key Road, Nokomis

Owners: Fritz Faulhaber and Ping Pan Faulhaber trusts, Ma Ling trustee | 2016 rank: No. 2 | Value in 2016: $16,539,000, an increase of $1,006,500

The late Fritz Faulhaber and his 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 is headquartered. They purchased the Gulf-to-bay property for $2.06 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.

2209 Casey Key Road, Nokomis

Owners: Walter and Marilyn Kreiseder | 2016 rank: No. 4 | Value in 2016: $15,652,400, an increase of $1,227,200

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 $3.95 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 boat dock. 

1253 Hillview Drive, Sarasota

Owners: Bridgeview Land Trust, David and Lisa Grain | New on the list

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 in Sarasota, 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 (12,255-square-foot living area), 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 SATs, college trips and enrichment programs.  

1420 Bay Point Drive, Sarasota

Owner: Katherine Ebbeson | 2016 rank: No. 6 | Value in 2016: $13,339,200, an increase of $2,686,900 

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

4449 Bay Shore Road, Sarasota

Owners: James and Maryann Armour | 2016 rank: No. 3 | Value in 2016: $15,772,300, an increase of $147,200

This 21,192-square-foot Parisian-inspired home overlooking Sarasota Bay is owned by James and Maryann Armour. He’s the former CEO 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 Amours are supporters of the Fine Arts Society of Sarasota and Selby Gardens.

845 Longboat Club Road, Longboat Key

Owners: Mike and Michele McKee | 2016 rank: No. 5 | Value in 2016: $14,471,300, an increase of $534,900

Regent Court, inside the gates of the Longboat Key Club, is one of Sarasota’s most exclusive residential enclaves. This property, described as a modern Venetian palace, is owned by Mike and Michele McKee, who bought the property in 1998 for $2.15 million. The couple moved here after selling their manufacturing company in the Midwest. At 35,200 square feet (17,714 living area), the residence has six bedrooms, eight baths and a pool. Details include a grand salon, hand-painted ceilings, stone columns, Palladian windows and a sun-drenched atrium.

132 N. Washington Drive, St. Armands

Owners: Jeffrey and Mary Penny Vinik | New on the list

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 developing the $3 billion mixed-used Water Street Tampa project and is an investor in ventures from skin care to radiation protection gear for soldiers to video game headsets, according to the Tampa Bay Times.

1309 Vista Drive, Sarasota

Owner: Cynthia Kaye Wilson | New on the list

This home, also in Harbor Acres, is owned by Cynthia Kaye Wilson, formerly Cynthia Garrison, who had been married to the late Sheridan Garrison, a founder of the national trucking company American Freightways, which sold for $1.2 billion to FedEx Corp. in 2005. Wilson purchased the property in 2005 and eventually demolished the existing home to build an elegant two-story West Indies-style home situated on open bayfront. The home is 12,025 square feet (8,452 under air), four bedrooms, four full bathrooms, two half baths, and a pool.

825 Longboat Club Road, Longboat Key

Owner: P & W Charters LLC | 2016 rank: No. 9 | Value in 2016: $12,720,600, a decrease of $429,000

This Regent Court home is owned by P & W Charters, LLC, which shows ownership by British businessman William Archer and his wife Shirley. Archer, who regularly makes the lists of the U.K.’s richest, founded retailer Focus DIY—a home and garden store—with a partner in 1987. The business was sold by Archer and his partner for £650 million before it collapsed. The Longboat Key property was purchased for $12.5 million—a record at the time—in 2011. It is a two-story, six-bedroom, seven-bathroom (includes two half baths) home of 23,045 square feet (12,095 square feet of living area).