The apple didn't fall far from the tree as far as the former president's namesake, Donald Trump Jr, is concerned. Donald Jr has made quite a name for himself as a businessman, author and former television competition judge. Don Jr has been fortunate, over the years, to call some stunning places home and enjoy the perks – and suffered the scandals – that come with the Trump name. Click or scroll to take a look at his luxury pads, including his current Florida mega-mansion.
Donald and the late Ivana Trump welcomed Trump Jr into the world on New Year’s Eve in 1977, while they were living at their coveted Olympic Tower condo in Manhattan. A couple of years later, the family moved to another prestigious address, the ultra-high-end 800 Fifth Avenue. At the time, the Trump name was making a frequent appearance in New York’s tabloids, given Trump Sr had proposed the world’s largest housing complex and according to The Guardian, managed to pull off a huge tax break for his first project, amongst other things.
While his parents were busy building the world (in)famous Trump brand, Don Jr was reportedly left in the care of nannies and Ivana’s Czech parents, Milos and Maria Zelnicek. Milos, an electrician and an avid outdoorsman, served as a role model to the young Trump. Don Jr grew up spending summers camping, fishing, hunting and learning the Czech language from his grandfather at his home in a town near Prague.
While the Olympic Tower condo was Don Jr's first home, two years later, the young family moved to the upscale 800 Fifth Avenue address, where Ivanka was born in 1981. A year later, Donald and Ivana bought their trophy weekend mansion in affluent Greenwich, Connecticut, where the children spent many happy days. With the birth of Eric in 1984, the growing family moved into the iconic glitzy Trump Tower on Fifth Avenue. In 1985, Trump scored another big real estate coup, purchasing the now infamous Mar-a-Lago resort in Palm Beach, Florida.
Don Jr's very first home in the 52-story Olympic Tower redefined luxury living when it was first built in 1975. Offering sweeping views of Central Park, Rockefeller Center, and a side-by-side alignment with the Empire State Building, the mixed-use skyscraper comes with the expected luxe amenities, including a full-time doorman, concierge and a live-in super. Its minimalist black-glass facade and prime Fifth Avenue location make its 229 condos a desirable “starter home” for any wannabe New York socialite, with a price tag starting at $2.6 million.
A couple of years after Don Jr was born, the Trumps moved to the even more coveted Upper East Side to 800 Fifth Avenue. One of New York's most high-end and desirable residential buildings, 800 Fifth Avenue' 229 luxurious units, spread across 33 stories, come with the usual billionaire-worthy amenities. It was also the place where Trump Jr welcomed younger sibling Ivanka in 1981.
With their growing family, the Trumps bought their first expansive weekend home for a cool $4 million in 1982 in affluent Greenwich, Connecticut. The six-acre and eight-bedroom mansion estate boasts of indoor and outdoor pools, a putting green, tennis courts, a guest house and staff apartments, and often formed the backdrop to many a happy time for the Trump children.
This image truly captures Trump Sr's persona and tastes, with the Georgian mansion displaying twin staircases, gold leaf wallpaper, extravagant murals and enormous crystal chandeliers. The 19,773-square-foot waterside property is emblematic of Trump's flashy style, according to The Wall Street Journal, and is in stark contrast to Don Jr's preferred modern contemporary interior tastes. Ivana was awarded the house in their divorce, who reportedly went on to sell it for $15 million to financier Robert Steinberg and his wife Suzanne.
Life as a Trump in America, where Don Jr was accompanied by bodyguards and surrounded by ritzy interiors, was a stark contrast to his low-key summer vacations near Prague with his grandfather. Soon after Eric was born in 1984, the family moved into a triplex penthouse apartment that was later extended to make a reportedly huge 10,996 square foot space at Trump's flagship property – the 58-story controversial Trump Tower on Fifth Avenue. With interiors dripping in 24-karat gold in typical Trump style, the property remains one of the family homes. However, Don Jr wasn't able to call this home for long as he was whisked off to boarding school at the age of 12 alongside Eric, following his parents' divorce. He then went to The Hill School in Pottstown, Pennsylvania.
In 1985, when Don Jr was seven, Trump Sr finally snapped up his current residence, Mar-a-Lago, in Palm Beach, Florida, after many attempts at a purchase, for a bargain $8 million. Apart from being the family's private residence, in the early 1990s, Mar-a-Lago was transformed into a members' club by Trump Sr. The historic Spanish-Moorish-style palace, originally built in 1927, also formed the backdrop to many a family Easter, Christmas and according to Business Insider, was also the venue for Don Jr and now ex-wife Vanessa Trump's wedding on November 12, 2005.
After the divorce, Ivana Trump was living her best life. Putting her money to good use, she acquired an idyllic, nine-bedroom ocean-front Palm Beach estate of her own – Concha Marina – which was conceptualized by architect Addison Mizner for himself in 1921. While the children spent time at Mar-a-Lago and Trump Tower, this was considered their primary residence (when they weren't at boarding school) until they flew the nest, as Ivana had been granted sole custody. She later sold the estate for $16.6 million in 2014.
When Trump Sr bought the opulent 230-acre Westchester Seven Springs estate in 1995 for $7.5 million, the aim was to transform it into a golf club. But Forbes reported that nearly two decades later, no greens had been built. Instead, the property had become a lavish (if isolated) family retreat, which was particularly fortunate for Trump's brood, especially during their childhood. And what a family retreat it is, with the 50,000-square-foot mansion boasting three swimming pools, a carriage house and 15 bedrooms, all surrounded by 230-acres of land.
Like his father, Don Jr went to the University of Pennsylvania's Wharton School of Finance and had the full college experience – even garnering a reputation as a big partier, according to Business Insider. However, after graduation, he did not immediately follow in his father's footsteps, opting instead to reportedly move to Aspen to fish, hunt and work as a bartender while living in a truck. It was during this period, in February of the year after his graduation, that his partying ways caught up with him and he was arrested for public intoxication during a Mardi Gras party in New Orleans. The Guardian reported he spent half a day in jail. He then opted to return from the metaphorical wilderness to New York in 2001, joining the Trump Organization.
He quickly moved up the ranks in his father's firm and three years later, snapped up his own Trump property for $990,000. The two-bedroom unit in the Trump Place condo tower on Manhattan's Upper West Side overlooked the Hudson River. Not a bad starter home! Donald Jr is reported to have earned his current estimated net worth of $300 million as Executive Vice President at his father's company. Unlike his father, he had kept a relatively low profile, but that has changed since he became a key member of his father's 2016 presidential campaign, speaking at political rallies and even the Republican National Convention.
While he was making his TV debut, co-starring on The Apprentice and judging several of his father's Miss USA pageants, his personal life was taking shape. He was said to have stopped drinking in 2003, and proposed to his then-girlfriend, model and pasta sauce heiress, Vanessa Haydon, soon after; his father had introduced the couple. In one of his first public missteps, Don Jr reportedly got his $100,000 ring for free in exchange for asking Vanessa's hand in marriage outside the jeweler's New Jersey store in front of the media.
Due to his own growing family and embarrassing reports stating that he was ousted from the condo's board in 2006 for neglectful management, Trump Jr sold his first home in 2010 to Brazilian model, Isabeli Fontana, for $1.8 million. The spacious monochrome apartment was recently put on the market again for $2.5 million and sold in 2021 for $2.4 million.
Donald Jr sold his Trump Place condo a year prior to buying two apartments in a non-Trump building known as The Sovereign in Sutton Place in 2009. According to StreetEasy, 12B was bought for $1.5 million and 12C for $1.125 million and reportedly assumed to have been combined to create a four-bedroom home for his growing family.
Donald Jr added a third apartment to his holdings in 2014 for $1.6 million, giving him approximately a total of 6,000 square feet of space, according to Mansion Global. The uber-fancy The Sovereign, on the Upper East Side, was designed by Emery Roth & Sons and is one of the most well-known post-war co-ops in New York. In addition to the luxury amenities that come as standard, according to the listing, the condo tower is notable for its elegant foyer, a mid-century modern masterpiece adorned with 1950s chandeliers built by Italian architect Carlo Scarpa.
After 13 years of marriage, Don Jr and Vanessa confirmed their split in March 2018, and divorce in a joint statement in 2019, a year after she reportedly inherited an estimated $62 million from her father's interest in Rao's Homemade pasta sauce. According to The Guardian, Vanessa was rumoured to have dated her assigned Secret Service agent shortly after, while Don Jr was romantically linked to former Fox News personality, Kimberly Guilfoyle, in April 2018. Although there are no images of his extended home, the unit next door that sold in 2015 for $2.5 million, gives you an idea as to how it might have looked.
Donald Trump Jr's now-fiancée, Kimberly Guilfoyle, was first introduced by mutual friends back in 2007 when she was reportedly one half of a liberal power couple. After the end of their previous respective relationships and three months after Vanessa filed for divorce, the two were quick to make their relationship Instagram official in June 2018. Kimberley even went on to join Donald Trump’s reelection campaign as a senior adviser about a year later. The Conservative power couple soon shacked up, buying their first home together – a $4.5 million Hamptons retreat – in 2019.
Their stunning 9,200-square-foot Hamptons home is part of the Bridgehampton gated neighborhood. The seven-bedroom, eight-full and three-half bathroom retreat sits on nearly four acres of the private gated community. With a double-height living room, two separate dining areas, a large farmhouse-style kitchen with an island and a screened patio overlooking the pool, the space is more than equipped to deal with Trump Jr's five children when they visit.
The grey-sided traditional mansion with a wooded deck also has a heated pool and spa with a waterfall, waterfront access to a 25-acre pond and a games room with a billiards table that opens out to the acres of manicured grounds. No wonder the couple made it their sanctuary during the COVID-19 lockdown.
The grand master suite of the house has its own seating area and private deck overlooking the entire property. Located on the first floor, the high ceilings, light colour scheme and abundance of windows make the space seem even larger. And as for the six other bedrooms, each comes with a spacious ensuite, providing privacy for all.
Following Trump Sr's defeat in the 2020 presidential election, Donald Jr and his fiancée, along with the rest of the Trump family, located to Florida in January last year. The state is not only red but a stronghold for Trumpism. The couple sold their lockdown home in March 2021 for $8.1 million, almost double what they paid for it, at a time when the Hamptons real-estate market was booming as a result of the pandemic.
The pair struck a $9.7 million agreement with Sheri B. Nelson, the ex-wife of former New York Yankees pitcher Jeff Nelson, to acquire their current home. An 11,300-square-foot estate, located in the Admiral's Cove neighborhood – an affluent and super-secure golfing and boating enclave in Jupiter – their love-nest is about a 20-minute drive from Mar-a-Lago in Palm Beach. However, not everyone was thrilled to call the couple neighbors.
The estate in Jupiter also happens to be where ex-wife Vanessa stays with their five children and includes a nearby Trump-branded golf course, Trump National Golf Club Jupiter. The six-bedroom, 11-bathroom mansion spans a massive 11,270 square feet and comes with a 1.18-acre lot. But even with all that land and privacy, The Daily Mail reported that as many as 30 neighbors are said to have written to the Admiral's Cove property owner's association to express their displeasure with Trump Jr's move to their neighborhood.
The deal went through the same month the pair sold their Hamptons property and seemed to have got their Florida mansion for a bargain, as according to the New York Post, the home was originally listed for an eye-watering $19.9 million back in 2017. But, after three years on and off the market and a $10 million price decrease, the mansion was ultimately sold to Trump Jr and Kimberly, who recently reportedly confessed that she already feels married to him.
A stark contrast to his father's glitzy tastes, listing images reveal that the property recently went through a makeover to include “new clean-white contemporary finishes”. The floor-to-ceiling arched windows and highly designed veranda make for picture-postcard views of the waterfront patio and the manicured backyard that houses a pool and a lush garden wall.
The open-plan space has plenty of indulgent features, including multiple fireplaces, glass walls, an elevator, an outdoor summer kitchen, a gym with a massage room and even a wood-paneled office. Located on the lower level, the master bedroom features a fireplace with a tray ceiling and contains an ensuite bathroom with dual vanities, a whirlpool and a separate shower. Residents also have access to the luxe amenities available at the Admiral's Cove club, such as golf, tennis and a spa.
The Daily Mail had initially reported that the pair got engaged quietly on Don Jr's birthday and New Year's Eve in 2020, however, Kimberly officially confirmed it on Instagram, just after Valentine’s Day 2022. The Trump family seem to be making Florida their new base, with Donald Sr and Melania formally moving to Mar-a-Lago, Eric and Lara Trump snapping up a $3.2 million Palm Beach mansion, Ivanka and Jared buying their Miami ‘Billionaire Bunker’, and even Tiffany joining the bandwagon with her own Miami home.
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