Back in 1982 when he was still a Democrat, before he was a multi-billionaire and a brand name and reality television star and on his first marriage to Ivana, Donald Trump was a rising star in the New York City real estate world and shopping for his first trophy mansion. Politics aside, Trump is a success story that is hard to ignore. His fabulous homes that began with that first mansion in Connecticut is a big part of the GOP presidential candidate’s story. His former Greenwich home is for sale and recently reduced from $54 million to $45 million.

Trump’s collection of expensive and even a few historic homes rivals almost anyone else in the world.   His main residence is a posh three-level penthouse at Trump Tower on New York’s Fifth Avenue where he has lived and supervised his vast business operations since 1983. Also in the Gotham area, in 1996 Trump purchased a 60-room mansion in Bedford, New York with three pools and a bowling alley. He later bought Albemarle with a 23,000-square-foot home, vineyard and winery on 2,000 acres in Virginia for $12.7 million, a fraction of the original asking price of $100 million. It is now a B&B  known as Albemarle Estate at Trump Winery with daily room rates ranging from the upper $300s to $700s.  

In 2008, Trump expanded his home stockpile to the West Coast when he purchased a six bedroom, 10,400-square-foot home on Rodeo Drive in Beverly Hills. Trump’s #1 trophy home is still his Mar-A-Lago mansion and resort for the ultra wealthy in Palm Beach, Florida that he purchased in 1985 for $10 million. The 1920’s mansion with 62,000 square feet and over 100 rooms was originally built for Post Cereal heiress, Marjorie Merriweather Post.

Trump was only 35 when he and Ivana purchased his starter mansion, a 5.8-acre home on a peninsula in Greenwich for $4 million. Always a family-oriented business, Ivana was also remodeling the Plaza Hotel in Manhattan which Trump purchased in the early 1980s and she was able to incorporate many of the same materials in the decoration of their new home creating a residence dripping in gold leaf, elegant chandeliers and crown moldings. When they divorced in 1991, Ivana won the mansion in the property settlement. She sold the home in 1988 for $15 million and the mansion’s new owners immediately began a renovation to tone it down a bit adding tennis courts, indoor lap pool, sauna and a 4,000-square-foot addition with guest suites.

Originally built in 1939 for Robert Hillas, president of the Super Heater Company in New York City, the 19,773-square-foot Georgian Colonial main house and guest house have eight bedrooms, thirteen baths, a three-story rotunda foyer with double grand staircase, formal rooms and views of Long Island Sound. Also included in the sale is a home theater, putting green, multiple terraces and patios, tennis courts and three fully-equipped staff apartments.

Awaiting a new Greenwich billionaire resident, Donald Trump’s former Connecticut mansion with major additions, six waterfront acres and a private boat dock is on the market at $45 million. The listing agent is Tamar Lurie of Coldwell Banker in Greenwich, Connecticut.

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Image Credits: Photo from Weekly Real Estate Hot List Photos (TopTenRealEstate).