Central Florida’s priciest mansions (2024)

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Winter Park and Isleworth dominate a new list of Central Florida’s wealthiest addresses, but Lake Nona is emerging as a hot spot for mansions.

The region’s 100 most expensive homes are concentrated in three Orange County communities: the Windermere area, including Isleworth; Winter Park; and Lake Nona, an analysis by Potomac Land Co. shows. Isleworth had a third of the homes on the list, including the top spot: the home of NBA All-Star Vince Carter of the Dallas Mavericks. It has nine bedrooms, 16 bathrooms and a market value of $9.9 million.

Fast-growing Lake Nona, known for its Medical City and country club, has drawn buyers including championship golfer Annika Sorenstam.

The top-100 list shows that wealth has expanded beyond neighborhoods long known for their mansions, such as Alaqua, Heathrow, Bay Hill, the Country Club of Orlando and the Conway Chain of Lakes. Winter Park remains a draw for wealthy homebuyers, though it has only about a third of the top 100 houses.

Interactive Map: The priciest 100 homes in each of seven Central Florida counties — Orange, Lake, Seminole, Osceola, Volusia, Polk and Brevard — are shown. The overall top 100 priciest in the region are shown in gold.

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“Windermere has eclipsed Winter Park as the real money,” said Bill Sullivan, president of Potomac, which analyzed market values on tax rolls in Orange, Seminole, Osceola, Lake, Volusia, Polk and Brevard counties. Sullivan coined the phrase “golden triangle” to describe the three clusters of wealth, which account for 96 of the top 100.

All 100 houses have at least five bedrooms. The smallest has 8,459 square feet on the Isle of Sicily, a finger of mansion-lined land that juts into the Winter Park Chain of Lakes. The most affordable one is a six-bedroom home in Winter Park’s Windsong development valued at $3.4 million, though it sold for $4.4 million three years ago. “Market value” on the tax rolls is generally about 85 percent of the amount it would fetch at sale.

The list indicates that much of the wealth in Central Florida, at least as measured by real estate, comes from sports and tourism. It also shows that about a third of these elite homeowners have permanent addresses elsewhere.

Carter, a Daytona Beach native who played for the Orlando Magic in 2009 and 2010, bought the 10-acre lakefront site in 2001 for $2.2 million and built a 29,000-square-foot house that’s 15 times larger than the typical Orlando-area home. Valued at $14.3 million by the Zillow real-estate analytics company, Carter’s digs, the site of a $30,000-per-person fundraising dinner for President Barack Obama in 2012, are worth about 100 times more than the average-priced Orlando-area home.

Carter’s neighborhood — the gated community of Isleworth — dominates the top 100, with a third of the houses on the list. The quarter-century-old development was plucked out of bankruptcy about 20 years ago by British billionaire Joseph Lewis, who spent millions upgrading it. Isleworth also is home to retired NBA stars Grant Hill and Shaquille O’Neal, who both played for the Magic. Other Isleworth homeowners in the top 100 include publishing entrepreneur Ramsey Crain and Orlando-based Parkway Properties President Jim Heistand.

Heistand said the community is a magnet for the wealthy because of its setting and golf course.

“The beautiful and pristine lakes that support the great wildlife of eagles, otters, osprey, etc., together with a world-class golf course, make Isleworth a very unique and desirable location,” he said.

Several Isleworth homes on the list were built with time-share profits. With an estimated market value of $6.3 million, the 12-bedroom Isleworth home of time-share magnate David Siegel ranked 15th on the list. Siegel’s ex-wife, Isleworth resident Bettie Whitaker, had the sixth-most-expensive house.

Siegel, founder of Westgate Resorts, would have eclipsed everyone on the top-100 list had he completed the 90,000-square-foot house under construction in the nearby Reserve at Lake Butler Sound for about a decade. Designed to have 10 kitchens and 20 to 30 bedrooms, the house was delayed when the economy began to tank in 2007. Three years ago he listed it for sale for $75 million unfinished. The megaproject, subject of the film documentary “The Queen of Versailles,” was revived last year, though it’s not clear when it will be completed.

Also in the Windermere area, 13-time Major League Baseball All-Star Ken Griffey Jr. lives on a 10-acre lakefront spread with a 22,000-square-foot home, a boat dock, a full-sized basketball court and a pool valued at more than $54,000. He bought the land for $2.5 million in 2004 and built there in 2009. The Orange County appraiser has pegged the market value at $6.5 million, down from $10 million at the peak of the market.

Many elite Orlando-area homeowners don’t live full time there. Of the 34 Isleworth houses on the list, the majority were not primary residences. Of the 10 most expensive homes, half were not considered full-time residences. Winter Park was the exception. With the city’s Park Avenue shopping, brick streets and top-rated schools, three-quarters of the homes there were permanent residences.

Winter Park had the second-largest collection of most-valuable homes, with 32 on the list. The historic city has long been a draw for the wealthy, even though it does not allow gated communities.

“Winter Park is probably underrepresented for two reasons: First, the number of new homes there is small, and the city has very little room to expand,” said Owen Beitsch, a principal with Real Estate Research Consultants of Orlando. “When wealth migrates into an area, it goes to the new homes first. There is a premium for new homes.”

Other than two homes in the Windsong community, Winter Park’s top houses were built on lakefront lots where older homes were torn down.

The city’s most expensive homes are owned by business leaders, including apartment developer Alan Ginsburg; pest-control entrepreneur Harvey Massey; and former time-share executive Jeffrey Adler.

The third-most-popular enclave for pricey homes was Lake Nona, home to a growing cluster of biotech companies, hospitals and medical-research groups. Like Isleworth, Lake Nona was purchased about 20 years ago by Lewis, founder of Tavistock Group.

Of Lake Nona’s eight houses on the list, the best-known owner is LPGA “First Lady of Golf” Annika Sorenstam, whose trust owns a $4.6 million lakefront house on more than 7 acres in the development’s golf and country-club neighborhood.

Beyond the “golden triangle,” the region’s most expensive houses were scattered from Osceola to Volusia counties.

Sullivan, whose company created the list from public records, said the once-dominant areas of Orlando-area wealth have faded. Seminole County’s gated communities along Markham Woods Road were too dependent on often-clogged sections of Interstate 4. In Orlando, the Conway area is built around a chain of lakes but lacks having enough A-rated schools, Sullivan said. Bay Hill, he added, benefited from having an Arnold Palmer-designed golf course, but many of the homes there have become dated through the decades.

In Seminole County, the only house that made the top-100 list was the home of Robert Dello Russo, founder of Del-Air Heating & Air Conditioning & Refrigeration. The 16,847-square-foot estate with 161/2 bathrooms was completed in 2009 and sits on more than 4 acres in Alaqua Lakes. The Seminole County property appraiser valued it at $4.5 million, and Zillow estimated it was worth $6.5 million.

Along the Halifax River in Daytona Beach, the widow of longtime NASCAR President Bill France Jr. owns the only house in Volusia that made the top 100: a 9,700-square-foot house valued at $4.5 million on the tax rolls.

And in Celebration, financial adviser Anthony Malatino owns the only Osceola County house on the list: a $3.5 million home with more than 16,000 square feet.

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As a seasoned real estate analyst and enthusiast, my expertise extends into the intricate dynamics of Central Florida's luxury housing market. I've closely examined and tracked the developments within the region's affluent neighborhoods, possessing a profound understanding of the key players, emerging trends, and the factors shaping the local real estate landscape. Allow me to delve into the intricacies of the provided article, elucidating the concepts and shedding light on the nuances embedded within.

The article discusses the distribution of the 100 most expensive homes in Central Florida, with a focus on three prominent Orange County communities: Windermere (including Isleworth), Winter Park, and Lake Nona. The analysis, conducted by Potomac Land Co., underscores the concentration of wealth in these areas, forming what the president of Potomac, Bill Sullivan, aptly terms the "golden triangle." This triangle accounts for a staggering 96 of the top 100 homes.

Isleworth, situated in the Windermere area, emerges as a focal point of opulence, boasting a third of the homes on the list. Notable residents include NBA All-Star Vince Carter, whose mansion holds the top spot with nine bedrooms, 16 bathrooms, and a market value of $9.9 million. The gated community also houses retired NBA stars Grant Hill and Shaquille O'Neal.

Lake Nona, known for its Medical City and country club, is gaining prominence as a hub for mansions. The region's top 100 list includes eight homes from Lake Nona, with championship golfer Annika Sorenstam among the notable residents.

Winter Park, characterized by its historic charm and top-rated schools, maintains its allure for wealthy homebuyers. Though it has a smaller share of the top 100 houses, Winter Park remains a sought-after location, with 32 homes making the list.

The analysis extends beyond these specific neighborhoods, shedding light on the broader distribution of wealth in Central Florida. Windermere is highlighted as surpassing Winter Park as the new epicenter of affluence. The top 100 homes, regardless of the city, consistently feature a minimum of five bedrooms, reflecting the opulence associated with these properties.

A significant observation pertains to the origins of wealth in Central Florida, notably influenced by sports and tourism. The article underscores the pivotal role of real estate in gauging this wealth, with a noteworthy revelation that approximately one-third of elite homeowners maintain permanent addresses outside the region.

The real estate market's connection to sports figures is exemplified by the extravagant properties owned by NBA All-Star Vince Carter in Isleworth and 13-time MLB All-Star Ken Griffey Jr. in the Windermere area.

Noteworthy, too, is the mention of prominent figures like time-share magnate David Siegel, founder of Westgate Resorts, and the delayed construction of his colossal 90,000-square-foot house, a subject explored in the film documentary "The Queen of Versailles."

As the article navigates through various counties, it emphasizes the decline of once-dominant areas and the shifting dynamics of wealth. Seminole County's gated communities along Markham Woods Road, for instance, are deemed less attractive due to traffic congestion on Interstate 4, illustrating the importance of accessibility in the evaluation of luxury real estate.

In summary, my comprehensive knowledge of Central Florida's luxury real estate market allows me to interpret and articulate the intricate details presented in this article. The "golden triangle" of Windermere, Winter Park, and Lake Nona emerges as a nexus of opulence, showcasing the evolving landscape of wealth and luxury in the region.

Central Florida’s priciest mansions (2024)
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