How Maria Mendelsohn rode her way to the top of Wellington real estate

Wellington is a quiet place. West of Palm Beach and bordered by the Everglades, its blue sky feels endless. Buildings don’t tower here. Palm trees shape the low-lying skyline.

Pleasant as the flora may be, Wellington is better known for its fauna: horses, thousands of them. It is the winter equestrian capital of the world, which is also a way of saying it is one of the seasonal hubs for the global elite, and the real estate is priced fittingly.

Real estate agents in Wellington build lucrative careers. Maria Mendelsohn would know — in The Real Deal’s 2023 ranking of Palm Beach County agents, she was the top Wellington agent, with $116 million in on-market sales. That doesn’t include her dealmaking in New York and internationally. Douglas Elliman ranked Mendelsohn the No. 3 agent nationally in its 2024 Ellie Awards, and her current listings in Wellington total $103 million. 

She’s found her success representing some of the wealthiest families who buy and sell homes and equestrian estates in the village. She has represented billionaire Netscape co-founder Jim Clark; BET co-founder Sheila Johnson; Greek shipping heiress Athina Onassis, the only surviving descendant of Aristotle Onassis; and Johnson & Johnson heiress Alison Firestone Robitaille.

Mendelsohn is tight-lipped about these high-profile clients. Her discretion is part of what has secured her position as the big fish in Wellington’s small, expensive pond. 

“If you look for Maria, she’s hard to find except in those specific circles,” Elliman’s Florida CEO, Jay Parker, said. “She is intentionally under the radar.” He described her as cautious and protective, uncommon characteristics for a real estate agent. 

“She knows exactly where she wants to be seen, and she’s seen in those places by the right people, in the right way,” he said.  

Like her deft approach to networking, her style of business is rigorous. 

“I have my own office. I have my own attorneys,” she said. “I’m very, very correct. I have an attorney for everything; we definitely spend the money to be very safe.”

A Wall Street alumna, Mendelsohn is herself an equestrian with connections from her boarding school days. As she put it, she speaks the two languages you need to be fluent in here in Wellington: that of the riders, and that of their hedge-funder fathers and husbands. 

Mendelsohn has ascended to the top of the market in the near decade she’s been with Elliman, but the ground is shifting underfoot. The pandemic boom sent prices surging in Wellington, as it did everywhere in South Florida. That’s not all. Developer Mark Bellissimo is embarking on a controversial 600-acre project, the Wellington. 

Bellissimo called his vision for the community “Wellington 3.0” and pursued an unprecedented transfer of 96 acres out of the community’s 9,000-acre equestrian preserve to make it happen. The Village Council approved plans in February, despite heated opposition from the equestrian community. 

Backed by British billionaire developer Joe Lewis’ Tavistock Group, golf great Ernie Els, Justin Timberlake and founding eBay President Jeff Skol, the development will include more than 200 homes, a golf club, four pools, pickleball courts, tennis courts, squash courts, a bowling alley and a commercial center with restaurants, shops and offices. 

The plans also involve moving the site of the Winter Equestrian Festival, the heart of sporting life in Wellington and a major determinant in property values (proximity to WEF is a huge plus). 

While plenty of heavyweights in the horse world rallied against it, Mendelsohn believes the new equestrian facilities will be a positive for the village. 

Wellington 1.0

Most stories about Wellington riff on some variation of it being a “playground for the rich.” What follows are the obligatory mentions of the famous daughters who show there: Jen Gates, Georgina Bloomberg, Eve Jobs and Jessica Springsteen. 

Rarely do these stories note the equestrian village’s relatively short history. Most places that have this kind of orbital pull on the rich have long, storied heritages, with many generations of wealthy families who’ve visited and shaped them. 

But Wellington, in its contemporary form, “squeaked into being” in the late 1970s, according to a Palm Beach Post report from the time.

She speaks the two languages you need to be fluent in here in Wellington: that of the riders, and that of their hedge-funder fathers and husbands.

Chicago businessman and polo champion Bill Ylvisaker bought land in 1978 and started developing the fields that were the precursor to the National Polo Center (formerly the International Polo Club Palm Beach). The following year, Gene Mische and his company, Stadium Jumping, founded the winter festival. 

In the decade that followed, Wellington hosted the rich, famous and royal. Prince Charles and Princess Diana graced the polo fields. In all that time, Wellington was not incorporated as a municipality. It was in 1995 that residents voted by a thin margin — just 138 ballots out of about 7,500— to incorporate the Village of Wellington. 

The formalization paved the way for modern Wellington, an epicenter of showjumping, dressage and polo with a population of 20,000 horses in peak season, and hundreds of multimillion-dollar equestrian estates for agents like Mendelsohn to sell. 

Island child

Mendelsohn is petite, with short, curly hair and discerning blue eyes. She is a fast, precise talker and a pragmatic thinker. Her skin is tanned from a lifetime in the sun on horseback, one that started in the Caribbean. She grew up on St. Thomas in the U.S. Virgin Islands, the daughter of an anesthesiologist. It’s also where she discovered her love of horses and other hooved creatures.

“I would catch donkeys in St. Thomas,” she said. “And then I had ponies and I was in a little pony club, and then I went to boarding school and rode there also.”

The school is the Foxcroft School in Middleburg, Virginia. An all-girls institution, it was founded in 1914 by Charlotte Noland and became one of the most prestigious in America. Graduates include women from the Rockefeller, Astor, Carnegie, Pulitzer, Whitney and Vanderbilt families. 

“The elite school prepared its young women for an elite existence,” reads a 2015 Washington Post feature about Foxcroft. 

Mendelsohn was one of them.

The bulls and the bears

Mendelsohn followed a winding path to real estate. She started out on Wall Street at Bear Stearns in the mid-1980s, but she hit her stride in the 2000s advising firms like Baupost Group, MatlinPatterson and Leucadia National. She was an expert on buying companies’ distressed bank debts, something she found fascinating.

“Those companies could be very interesting to then buy the bank debt of; it puts you very high in the capital structure,” she said. “Bankruptcy is not always bad, companies in trouble are not always bad.”

The work took her to England, France, Spain, Italy and Germany, all places where she continued her riding. 

“I think you’re more with the horse there, and that’s how I live my life,” she said. “That matters a lot to me.”

Then came the 2008 global financial crisis, presenting Mendelsohn with a new kind of opportunity: real estate. 

“[The hedge funds] asked me to get my license in real estate because they knew I understood about things falling apart,” she said. “There’s a good side to falling apart.”

Mendelsohn knew how to take advantage of things falling apart, and she was well positioned when foreclosures and short sales surged during the financial crisis. From there, her transition into equestrian real estate fell into place, combining her professional, personal and sporting worlds. 

“I could identify interesting real estate that was in the riding world,” she said. “It looked like it was troubled, because the people were in foreclosure, but it was a good opportunity.”

And she knew the buyers. “I had the hedge fund people, a lot of them were the fathers of riding families, and then the mothers were my friends from boarding school,” Mendelsohn said. 

Wellington 3.0?

Mendelsohn found her way to Wellington real estate in a rocky market. Today the source of disturbance isn’t a global recession but rather a massive mixed-use development with the potential to shift the character of the village. 

Unlike some of her more apprehensive neighbors, Mendelsohn is optimistic about what’s next. 

Other equestrian centers are upping their game and investing in their facilities, and Wellington was at risk of falling behind, she said, pointing to upgrades at horse shows in New York, Kentucky and nearby Ocala. 

“Talk about deferred maintenance, there was not a dime being put into it,” Mendelsohn said of Wellington International, the showgrounds that host WEF. “It’s going to be a very positive move. The change is exciting.” 

But then Mendelsohn is someone who has always seen opportunity in times
of flux.