What makes a property expensive in Sarasota? Size matters, of course, and so do luxurious amenities, from custom-designed wine rooms to lavish outdoor spas and kitchens. But there’s one key asset that each of the 20 highest-appraised homes in Sarasota County offers to its fortunate owners: glorious waterfront views. Every one of these (mostly) magnificent mansions enjoys a prime waterfront location. Sixteen look out at the Gulf of Mexico from the offshore keys, and four are perched on the mainland bayfront

Wealth tends to gravitate to wealth, and that’s true when it comes to residences as well. Fourteen of the homes, ranging in value from $8.4 million to $16.9 million, are grouped in three exclusive enclaves: Regent Court on Longboat Key, Westway Drive on Lido Key and Casey Key Road on Casey Key. Some have ties to Sarasota history, including one owned by descendants of one of our most prominent pioneers. And this isn’t the first time some have seized the spotlight. A number of the homes have appeared on the pages of our magazine, and a few have graced the cover.

After obtaining the homes’ appraised values and addresses from public records, we tracked down the owners, an effort that in some cases involved threading through a maze of LLCs and legal and financial representatives. These are people who could choose to live just about anywhere in the world, and we wanted to ask them what drew them to Sarasota, the history of their home, and what they enjoy about living here. Not everyone was willing to speak to us, but some were remarkably accessible and open.

Most of them moved here from the Northeast and the Midwest, time-honored feeder markets for Sarasota. Some are well known in our region for their philanthropy, board leadership and public service, while others keep deliberately low profiles. But even the most private must occasionally put up with gawkers who drive by or park their boats in front and stare. Some people go even farther. One owner told us a stranger knocked on his door one sunny morning and said he’d parked his car in the driveway and planned to spend the day enjoying the beach. “Just come and get me when you need me to move the car,” he told the owner.

No. 1

$16,857,400

1127 Westway Drive | Owners: Carrie and Kenneth Cox

The most expensive home in Sarasota sits on five acres on New Pass on Lido Key on Westway Drive, a street where several of Sarasota’s priciest homes are located. The original home on the site was built by the late wholesale food magnate and philanthropist Daniel Kane in 1991. Now owned by pharmaceutical executive Carrie Cox and her husband, Kenneth, a developer, the home and additional land were purchased in 2003 for $11 million. The Coxes gutted the home and built a 19,658-square-foot edifice (7,151 square feet under air) with four bedrooms, seven bathrooms and a pool hidden from view by a thick wall of trees and gates. Carrie Cox, who has been named one of the nation’s top female CEOs and was a global president at Schering-Plough, Merck & Company, is now the CEO of Humacyte, Inc., a small North Carolina-based biotech firm that creates soft tissue parts for regenerative medicine. (In 2009 Forbes reported she was the third-highest paid female CEO in the country, with a total 2009 compensation of $23 million.)

 No. 2

$16,539,000

2309 Casey Key Road |Owners: Fritz and Ping Faulhaber

A friend introduced engineers, philanthropists and world travelers Fritz and Ping Faulhaber to Sarasota more than 15 years ago when they were living in Clearwater, where MICROMO, one of The Faulhaber Group companies (the company has 1,500 employees and locations in 29 countries), is headquartered. Then parents of young children, they were attracted by Pine View, Sarasota’s school for the gifted, along with the beaches and friendly people. “We spent so much time in Sarasota we decided, ‘Let’s just move here,’” Ping says. 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 their award-winning 1.2-acre pagoda garden, which contains Chinese pavilions, a conservatory, rose garden and edible garden. The location on Casey Key suits them. “It’s private, quiet and still close to civilization,” Ping says.

Supporters of STEM education in Sarasota, the Faulhabers created the Suncoast Science/Faulhaber Fab Lab in 2015 to inspire young people to enter careers in science.

No. 3

$15,772,300

4449 Bay Shore Road | Owners: James and Maryann Armour

Mired in a six-year legal battle over construction defects, this 21,193-square-foot Parisian-inspired home is owned by native Tennesseans 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, located a little bit south of the John and Mable Ringling Museum, for $19 million in 2008 from financier Howard Jacobs, who was building the mansion for himself, according to the Sarasota Herald-Tribune. The Armours put another $14 million into renovating it and then 15 months later filed lawsuits against Jacobs and contractors for defects. The three-story, Beaux Arts-style home, which overlooks Sarasota Bay, has 10 bedrooms, 17 bathrooms and a pool.

No. 4

$15,652,400

2209 Casey Key Road | Owners: Walter and Marilyn Kreiseder

This stately Mediterranean mansion on Casey Key Road belongs to inventor and plastics mogul Walter Kreiseder and his wife Marilyn. Walter Kreiseder, 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. When it was under construction in 2002, rumors started that Oprah Winfrey was building the home, and people kept driving by and getting out of their cars to take photographs. Eventually someone scribbled “Not Oprah’s” near the home.

No. 5

$14,471,300

845 Longboat Club Road | Owners: Mike and Michele McKee

Located inside the gates of the Longboat Key Club on the Gulf of Mexico, this modern Venetian palace is the first of four homes on our list located in the exclusive enclave Regent Court, where a regal row of mansions overlooks the Gulf of Mexico. Owned by Mike and Michele McKee, the property was purchased in 1998 for $2.15 million. Michele McKee says the family discovered Longboat 35 years ago, when their sons were young. They moved here after selling their manufacturing company in the Midwest and purchased a series of condos on Longboat, which they love for its tranquil summers, small-town friendliness and many in-season activities.

They “stumbled upon the lot at Regent Court,” she says, and built this home, an homage to 15th-century Venetian Renaissance elegance. The 17,714-square-foot 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. The McKees—she’s a retired interior designer—were involved every step of the way. “At times there are four generations of family in the house,” says Michele. “We can’t imagine living anywhere else.”

No. 6

$13,339,200

1420 Bay Point Drive | Owner: Katherine Ebbeson

Former Congresswoman and Florida Secretary of State Katherine Harris Ebbeson (she certified the Florida recount in the controversial Bush/Gore presidential election of 2000) built this 16,016-square-foot bayfront home in Harbor Acres in 2012 with her late husband Anders after purchasing the property in 2003 for $3.8 million. She poured years of energy and research into the imposing Beaux Arts-style edifice, based on the Hotel Biron in Paris, which was built in 1730 and is now the home of the Rodin Museum. The house has six bedrooms, 11 baths, a pool, boat house and dock. Now out of politics, the community-minded Ebbeson—who is from an influential Florida family and is the granddaughter of citrus and cattle magnate Ben Hill Griffin—is the energy and organizer behind the Sarasota Bradenton Modern Pentathlon, and an investor in Healthy Earth, a sustainable food company based in Sarasota. (This home was also one of our “Most Beautiful.")

No. 7

$13,306,300

1360 N. Casey Key Road | Owner: 1350 LLC

Located on the north end of Casey Key, this Gulf-to-bay, 8.5-acre property is like no other on our list. It’s a reminder of what Casey Key used to be like, a beautiful seaside setting where nature rather than mansions dominated the landscape. The property holds five smallish homes, surrounded by trees and built between 1968 and 1993. It’s owned by the family of the late Karl Wamsler, the former CEO of a German chemical company. Wamsler died in June 2016. He was married to Bertha Honore Thorne, the great-granddaughter of Bertha Honore Palmer, the wealthy Chicago socialite who fell in love with Sarasota in the early years of the 20th century and at one time owned a third of Sarasota County.

Karl Wamsler’s wife was also the sister of billionaire Oakleigh Thorne, who ran a New York-based publishing company. Pauline Wamsler Joerger—Karl Wamsler and Bertha Honore Palmer’s daughter—now lives in Sarasota and has said that the compound was the site of many family get-togethers.

No. 8

$12,967,200

857 Longboat Club Road | Owner: Pleasant Real Estate LLC

The second Regent Court home on the list is a 15,954-square-foot home with six bedrooms, 12 bathrooms and a pool built in 2008. Purchased in 2003, the home was bought in 2000 by Clayton Lee Mathile and his wife Mary; they transferred the deed to Pleasant Real Estate in 2003. Mathile is a well-known businessman and philanthropist who built the Iams pet food company into a powerhouse and sold it to Proctor & Gamble for $2.3 billion. (He famously shared the proceeds with Iams’ 2,000 employees.) The Mathile family lives in Dayton but frequently visits their Longboat beach home.

No. 9

$12,720,600

825 Longboat Club Road | Owner: P & W Charters, LLC

According to property appraiser records, this home—also in Regent Court—is owned by P & W Charters, LLC, which has an address in Great Britain that 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. After various acquisitions, the business became the largest independent DIY retailer in the U.K. The chain, heavily leveraged, eventually collapsed, but not before Archer and his partners received more than £650 million after selling, according to The Sunday Times of London. Archer’s fortune has been estimated at £150 million. 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 home of 12,095 square feet.

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The home of Gary Kompothecras ("Ask Gary") and his wife Beth on Point of Rocks on Siesta Key.

No. 10

$12,613,900

6910 Point of Rocks road | Owners: Gary and Elizabeth Kompothecras

Gary Kompothecras, the founder of the ASK-GARY medical and legal hotline, left college in Tampa in 1983 to come to Sarasota to work as a stockbroker. In 1990 he left to go to chiropractor school in Atlanta but returned in 1995 and headed to Siesta Beach. “I always wanted to live near a beach,” he says. His wife, Beth, owns So Staged Events. Their first home was on a canal, unsafe for their two sons with autism because deed restrictions would not allow a high fence. Eventually they found a lot outside the city on Point of Rocks, which they bought for $2.3 million, and then built a 13,560-square-foot limestone home modeled after the Marble House in Newport, Rhode Island, built for William Vanderbilt. With seven bedrooms and eight bathrooms, the Kompothecras residence was designed for their six children, he says, and has a bowling alley, pool room and a yard with a high fence. He notes that people often wander onto the property and try to walk in the front door. “Maybe they think it’s a hotel,” he says.

No. 11

$9,713,000

1067 Westway Drive | Owners: Thomas and Paula McInerney

This secluded property, hidden from the street by trees, is set on the northern edge of North Lido Beach. The 7,400-square-foot, two-story home was built in 1996 and sold for $13 million a decade later to Thomas and Paula McInerney of Westport, Connecticut. After working in the world of private equity, the couple together founded Connecticut’s Bluff Point Associates with a portfolio concentrated in health care, information technology and wealth management. In addition to their main home, the McInerneys also own a pair of adjacent vacant properties to the south, together worth another $4.1 million.

No. 12

$9,554,300

1160 N. Casey Key Road, Osprey | Owners: Bob and Jayne Gunther

Now on the market for $14.5 million (reduced from $16.9 million), this 9,500-square-foot Gulf-to-bay extravaganza on the north end of Casey Key took six years to build, a dream project for Bob and Jayne Gunther. The couple wanted a U-shaped footprint around a grand, two-story outdoor living area with a Mediterranean Revival style reminiscent of legendary 1920s architect Addison Mizner. Among a host of other amenities, the house has a billiards room, nine-car garage and two bayside docks. Bob is the chairman and CEO of Highpoint Tower Technology, which grew out of a company he and his father, Frank, founded in 1967, when they built a TV and radio tower on family land on Staten Island. (Frank’s long career in radio technology included installing the transmitter-receiver in Amelia Earhart’s plane.) The company today owns a number of towers around the United States, with several sites in Southwest Florida. Just three years after completing their home, the Gunthers decided to downsize to something closer to 5,000 square feet.

No. 13

$9,542,800

1301 Dixie Lee Lane | Owner: Ariane Dart

Philanthropist Ariane Dart purchased this bayfront Landings property in 2006 for just over $1 million and in 2011 finished construction on a six-bedroom, 13,000-square-foot main home and a second 1,700-square-foot, two-bedroom house. Ariane’s husband, Bob Dart, is a scion of the Dart family, estimated as one of the world’s wealthiest by Bloomberg Businessweek, with a fortune built by manufacturing plastic and Styrofoam cups, plates and containers (including the iconic Solo cup). Ariane is a director and officer in the Dart Foundation, which in 2015 gave more than $2.3 million in grants to a number of nonprofits and schools. She’s also on the board of Forty Carrots Family Center and has played a leading role in its annual spring Firefly fund-raising gala. The couple also has a residence in the Cayman Islands.

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This classically designed home overlooks Big Pass on Siesta Key.

No. 14

$9,101,500

4300 Higel Ave. | Owners: Jeff and Susan Jones

Built in 2008 by John Melk, co-founder of Blockbuster Video, this six-bedroom, classically designed 8,600-square-foot home with direct access to a private crescent of white Siesta Key sand was sold to Jeff and Susan Jones for $10.3 million in 2014. (We’re told fashion designer Michael Kors considered buying it before deciding to build a home on Longboat Key.) The Joneses have remade much of the property, including replacing the lawn with XGrass synthetic turf, a project that included adding a regulation-size putting green to the front yard. “We were keen to do it when we saw that the product is really identical to the real stuff,” Jeff says. Jeff, the grandson of the founder of JCI Jones Chemicals, took over the company in 1993 and moved its headquarters to Sarasota five years later. The company provides water purification chemicals to municipal water authorities, pharmaceutical companies and manufacturers around the world, with outposts stretching from London to Tacoma. Susan, the company’s chief administrative officer, is active on Sarasota’s nonprofit circuit and often chairs major fund raisers.

No. 15

$9,008,900

835 Longboat Club Road | Owners: Vern and Sandy Buchanan

Vern and Sandy Buchanan built their 9,900-square-foot Mediterranean Revival manse in 1998, shortly after buying the beachfront Longboat Key lot for $1.8 million and becoming prominent on Sarasota’s social and political scene. Vern earned his fortune in Michigan by founding American Speedy Printing, a franchise print shop, while still in his 20s. He bought and ran automobile dealerships after moving to Florida and is involved in dozens of other businesses, including offshore reinsurance, aircraft leasing and a charter boat company. In 2006, he was elected to the United States Congress as a Republican. Now in his fifth term, he serves on the powerful House Ways and Means Committee. In 2015, he was ranked the ninth-wealthiest member of Congress, with a net worth of $49.9 million.

 No. 16

$8,634,300

1333 Westway Drive | Owner: Colleen Ofield

As the trustee for the Craig Ofield Florida Trust, named for her husband, Colleen Ofield purchased this 8,800-square-foot Lido Key home overlooking New Pass for $8.4 million in 2010, shortly after the original owners built the structure, which included a movie theater, wine bar and wine room, two swimming pools and a guest house. Craig is the president of Bulk Barn, Canada’s largest bulk food retailer, with 250-plus locations, and the son of the chain’s founder, Carl. Colleen is an executive vice president in the company, headquartered in Aurora, Ontario. The couple is known to shun the social spotlight, both at home and here in Sarasota.

No. 17

$8,435,700

8250 Sanderling Road | Owners: Bill Crouse and Elaine Eglberger

Designed in 2000 by Sarasota’s award-winning modernist Guy Peterson, this home was overhauled after being purchased by husband and wife Bill Crouse and Elaine Eglberger for $8.9 million in 2014. “We gutted it,” says Crouse, “and upgraded everything on the property, the exterior, the landscaping. New electrical, new lighting, plumbing, new air-conditioning, new roof. It’s basically brand-new.” He says the home makes an ideal showcase for their art collection, which includes a rare selection of Art Deco posters printed between the World Wars. Crouse spent his early career in advertising and has written a book, The Art Deco Poster, on the topic. He was also president of a medical equipment subsidiary of Johnson & Johnson and for the last 25 years has been engaged in a biotechnology venture capital firm. The two are supporters of Ringling College; they’ll show their posters to graphic design students during a visit scheduled for November.

 No. 18

$8,412,600 

1240 N. Casey Key Road | Owners: Ed and Betsy Cohen

“We’re very architecture-focused,” says Betsy Cohen. Indeed they are. Their Casey Key property holds two striking modern structures—by far the most architecturally significant on our list—each designed by an internationally famous architect. In 1981, Betsy and her husband Ed purchased an iconic 1957 Paul Rudolph-designed home and painstakingly restored it. Later they commissioned acclaimed New York architect and personal friend Toshiko Mori to design a guest house on an adjacent property and an addition to the main house. Mori’s plans fit seamlessly with the original design and the stunning bay-to-Gulf landscape, and a recent Harper-Collins book about beach houses around the world features the Cohen home and the guest cottage.

No. 19

$8,369,400

1157 Westway Drive | Owner: Ira Barsky

The former home of Joseph and Grace Penner, a prominent Sarasota couple in the 1980s, this 10-room contemporary-style Lido Shores house, built in 1974, is nestled into the curve of north Lido Key, with a swimming pool just steps away the Gulf of Mexico. In 1991, Ira Barsky and his wife Lee retired here from the Northeast, where he had been involved in finance and industrial companies. “Serendipity brought us here,” he says. Drawn to the Lido Shores area, they rented a house two doors away from their current home. Soon afterwards, he says, the Penner home became available and they purchased it. In 1999, Ira Barsky co-founded the Animal Rescue Coalition, bringing together leaders from local animal welfare organizations to help end the killing of the region’s adoptable dogs and cats. “It’s something I’m very proud of,” he says.

No. 20

$8,360,000 |  1011 Casey Key Road |Owner: Kenneth Rowe

In 1967, Kenneth Rowe founded IMP Group International in Halifax, Nova Scotia; he grew the company into a global power with divisions in the aerospace, aviation, health care and IT fields and a number of contracts with the Canadian military. Now 81, he continues to serve as executive chairman. He purchased his 2004-built, 10,300-square-foot south Casey Key residence for $7.6 million in 2011. The house, which overlooks the Gulf of Mexico, has six bedrooms, six bathrooms, four-and-a-half-baths and three fireplaces.

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