Once used for the Kennedy family’s summertime respites, the 340-acre estate, known as Red Gate Farm, is epic. Before it meets the ocean, the pristine lawn and marsh is home to a lovely five-bedroom house, a boathouse, a hunting cabin original to the property, a storage unit, two garages, and a “fairy treehouse” that Jackie Kennedy had built for her grandchildren. Jackie and John F. Kennedy’s daughter, Caroline Kennedy, put the exquisite property up for sale in June, and no one has yet purchased the $65-million-dollar home.
Maybe you’ve heard of them? National football superstar Tom Brady and international supermodel Gisele Bundchen have been every Bostonian’s neighbor since the pair bought a parcel of Brookline land and built a custom home there in 2015. The sun-filled dwelling hit the market just last week, and is asking $39.5 million—superfans should jump on it now.
What’s better than a house filled with books? Nothing, for Pulitzer Prize-winning author Doris Kearns Goodwin and her late husband, presidential speechwriter Richard Goodwin. Beyond the grand mahogany library, there are built-in bookshelves in several of the home’s 16 rooms—and from couches to window seats, plenty of perches to enjoy them. If the myriad bookcases don’t clue you in, details such as checkerboard floors, a tea paper ceiling, and a spiral staircase that leads up to an observation tower also hint at the home’s distinguished history of ownership. The five-bedroom residence—a revamped farmhouse from the 1850s—sits on just under two beautifully landscaped acres, and could be yours for $1,985,000.
For those looking for privacy, but also a mansion, this place should do it for you. Surrounded by some seven tree-filled acres, the 26,623-square-foot house itself enjoys a generous buffer zone. The limestone museum-like manse boasts a palatial interior (note the sweeping staircase and soaring ceilings), stunning patio, and even a pond. Listed at $90 million when it first hit the market in 2016—then including 14 acres of property instead of the modest seven it now offers—the price dropped to $69 million a year ago, and is now on sale for just (!) $38 million, the Boston Business Journal reports. Football fans might be impressed that the Woodland Road manor is just down the street from the Brady/Bundchen homestead that hit the market, but sneakerheads will appreciate that the house’s current owner is none other than Reebok founder Paul Fireman.
Before he lived in the White House, Donald Trump lived in a simple white house. Stretching around nearly 20,000 square feet, the “yuge” oceanfront estate comprises an indoor and outdoor pool, a tennis court, a putting green, a home theater, and much more. Trump’s ex-wife Ivana sold the sprawling Greenwich home the couple once shared for $15 million in 1998, according to the Wall Street Journal. The Journal reports that the mansion was once listed for $54 million, then reduced to $45 million, before being taken off the market “just as Mr. Trump’s presidential campaign was heating up.” Now, the lesser-known white house is back at it, asking a discounted $38.5 million.
More infamous than famous, the dirt basement of this humble home once served as a graveyard for three of Whitey Bulger’s victims, whom he also killed in the house. Though a family has happily lived in the home since the ’80s, they’re now putting it up for $3.5 million. Seem steep? Consider the 5,000-square-foot lot as a development opportunity—the listing agent suggests tearing the place down and starting afresh. The plot is zoned for 10,00 square feet of living space, after all.
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