The Great Gatsby turns 100 this year. The F. Scott Fitzgerald classic has made its way onto required reading lists in schools nationwide, been made into numerous films and inspired Halloween costumes long after the Roaring ’20s ended.
And for that, Long Island says, “You’re welcome.” Great Neck inspired the West Egg (where new money frequented), while Port Washington inspired the “old money” East Egg. People can still tour the Sands Point property in Port Washington, which Fitzgerald reportedly thought of while penning the novel. But the Gold Coast of Nassau County isn’t the only place with historic homes to explore.
While the East End may not have inspired the East Egg, the Hamptons and Shelter Island are home to many properties steeped in history. Some exude serious Gatsby vibes, while others embrace the more bucolic nature of the region.
Whatever you fancy, historical pedigree is alive and well at these five historic homes in the Hamptons and on Shelter Island.

Sylvester Manor Educational Farm, 80 N. Ferry Road, Shelter Island, 631-749-0626
Once the home of Triangle Trade sugar merchant Nathaniel Sylvester, this 240-acre property has a spot on the U.S. National Register of Historic Places. Sylvester Manor acknowledges its complicated — and sordid — history as a former sugar plantation worked by enslaved Africans and indentured Indigenous and European laborers. Today, it seeks to be a sight for good. While the manor home is closed and about to embark on a multi-million dollar renovation and creation of a dedicated history center, people can still explore the property, which is now a livestock and vegetable farm used for a CSA and popular farmstead. There are also trails people can walk with leashed dogs, science-based and musical camps and school break programs for kids and musical programming all summer long on the grounds.

Mulford Farmstead Museum, 10 James Lane, East Hampton, 631-324-6869
Another East End landmark listed on the National Register of Historic Places, Mulford Farm’s farmhouse, isn’t a relic. Instead, the building, initially built in 1680, possesses many of the same framing and wood beams as it did in 1750. Samuel “Fish Hook” Mulford, the first of many generations of Mulfords to own the property, had the barn built in 1721. It’s considered one of the state’s most unspoiled English-plan barn forms from the time — a genuine representation of how the earliest residents built structures that were integrated into daily life. The East Hampton Historical Society bought the Mulford Farmstead Museum, which also includes a recreated 18th-century garden, in 1948 and continues to operate it today. Guests can schedule a private visit by calling 631-324-6850, ext. 2, and are encouraged to check the event calendar for farmhouse hours. The property is accessible when the farmhouse is closed, and you can take a self-guided tour using an app.
Pollock-Krasner House and Study Center, 830 Springs Fireplace Road, East Hampton, 631-324-4929
Lovers of history and matters of the heart will relish an opportunity to explore the home once occupied by artists Jackson Pollock and his wife, Lee Krasner, a pair of lauded abstract expressionist painters. Inside, you’ll still find the furnishings and artifacts that were in the studio when Krasner died in 1984, some of which (like a hi-fi phonograph and jazz record collection) once belonged to Pollock. It also contains some of the couple’s early works. Exhibitions feature works from historical and modern-day artists. The Pollock-Krasner House, also on the National Register of Historic Places, is open seasonally on Thursdays through Sundays from May through October. Reservations are required, and SUNY and CUNY students and professors get in free.

Thomas and Mary Nimmo Moran Studio, 229 Main St., East Hampton, 631-324-6850
Before it was a magnet for celebrities, the distinct natural light made the Hamptons a haven for artists. Thomas Nimmo is credited with ushering in the Hamptons’ reputation as an artists’ colony when he built the first East Hampton studio in 1884. Guests can now visit the Queen-Anne-style cottage and see what Nimmo once saw. Schedule a private visit by phone at 631-324-6850, ext. 2, and check the event calendar for programming and hours, which can vary.
Montauk Manor, 236 Edgemere St., Montauk. 631-668-4400
This opulent spot perched on a hilltop on The End serves up those Gatsby vibes at every turn. Built in 1927, Montauk Manor’s lobby has sitting areas with furnishings from the time and dazzling chandeliers. There is also a restaurants, Monte’s at the Manor, a private health club, tennis courts and an outdoor area with panoramic bird’s eye views of Montauk below. People can live out their Daisy Buchanan dreams by spending the night in accommodations ranging from studios to three-bedroom condos.