5 Gatsby-esque homes fit for the Roaring 2020s

These North Shore showstoppers bring us back to the Jazz Age

1 Swan Landing
1 Swan Landing

Imagine working from home in the Roaring Twenties. From 1922 to 1924, American novelist F. Scott Fitzgerald and international partygirl Zelda Fitzgerald did exactly that from their 5,000-square-foot home in Great Neck, Long Island.

It was on 6 Gateway Drive that Scott and Zelda hosted the debaucherous ragers that would come to define the Jazz Age, as immortalized in “The Great Gatsby.”

Scott didn’t get much writing done there –– and you’d be hard-pressed to find a writer who could. Two years of financial struggles, drunken antics and Zelda’s theatrics made it hard to stay focused, but it was great source material.

Here are five homes that remind us of the extravagant venues where the Fitzgeralds partied through the early 1920s, for anyone looking to do some “research” for the next great American novel.

Zelda’s Theatrics
$20 million | 7 BR, 9 BA | Mill Neck, NY

If you’ve ever felt the need to jump fully clothed into a water fountain, you’ll know how our girl Z felt when she famously did just that in Union Square. That was one of her tamer episodes, but it might have been smarter to do it some place like 315 Mill Hill Road. It’s got an in-ground pool, a stylish little cabana and, yes, a reflecting pond with a fountain. Chandeliers hang from almost every ceiling in this manse, save for the wood-paneled study and indoor theater. Unfurling from the top is the pièce de résistance: a spiral staircase –– but maybe don’t tell Zelda about that part.

Dance Yourself Clean
$6 million | 6 BR, 6 BA | Great Neck, NY

As the original flapper, Zelda foxtrotted and Charlestoned her way through the Roaring Twenties. 17 Lake Road would have been the perfect venue for her and Scott to cut a rug. Long stretches of glistening wood and tile throughout practically beg to be shimmied upon, while the intricate molding and gilded accents on the walls add to the regal vibe. Any home with space to dance needs enough space to breathe –– this one’s got a powder room, sauna and master bath for when it’s time to cool off –– no fountain though, unfortunately.

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Flop Era
$6 million | 13 BR, 10 BA | Glen Head, NY

After his play, “The Vegetable,” flopped, Francis Scott did what any sensible, cash-strapped and debt-saddled writer would: locked himself in an unheated room and spent his days cranking out content for local magazines. 174 Hegemans Lane, on the other hand, has seven fireplaces. This fully heated and centrally air-conditioned home has Gothic-style elements reminiscent of the home of fellow writer, drinking buddy and BFF Ring Lardner. Lardners’ place may have also been a party house for the Gold Coast glitterati, but this Glen Head mansion has a sprawling study with a cozy wood-panelled interior. With 7.1 acres of land to stretch your legs, it would have been the perfect venue for both house parties and writers’ retreats.


The 21st Amendment
$11.5 million | 21 BR, 14 BA | Mill Neck, NY

Did Scott ever make moonshine? Probably not, and he wouldn’t have had to if he lived at 385 Oyster Bay Road. This one was built in 1966, but the gold details and unapologetic opulence harken back to the Art Deco movement. You won’t find any bathtub gin in the master bath, only mirrors upon intricately framed mirrors and a blue-accented chandelier. A stage curtain-red movie theater and hot pink sitting area are just two places where he and Zelda could steal away from the crowd, chilled wine bottles from the cellar in hand –– or enjoy a nightcap by the fountain after a long day of short-story writing. Thank goodness for the 21st Amendment.


Jay Gatsby’s Dream
$45 million | 13 BR, 10 BA | Great Neck, NY

There would have been no better (or wetter) place to spend the steamy summer nights on the Gold Coast than 1 Swan Landing. In the spirit of never having to choose, this mansion boasts waterfront views, a deep water dock, an indoor pool, outdoor pool, fountain and wine cellar. People who read the book will tell you that it’s “really” about the emptiness of wealth, but if there’s anywhere Jay Gatsby could have lived his glitzy American dream, it would have been here.

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