Ever dreamt of living like a Gilded Age millionaire, even just for a day?
Grab your car keys because Long Island is packed with jaw-dropping mansions that’ll make you feel like you’ve stepped straight into an old-school movie set.
We’re talking giant estates with secret passageways, marble staircases, sprawling gardens, and maybe even a few peacocks strutting around.
Whether you’re into fancy architecture and epic gardens or just love snooping around grand old houses, this route is a must.
Ready to find out where the millionaires of the past kicked back?
Let’s hit the road—you’re gonna want to see these places for yourself.
1. Hempstead House & Castle Gould – Sands Point Preserve
Hempstead House and Castle Gould in Port Washington feature stone towers, grand staircases, and 216 acres of gardens, woodlands, and views of Long Island Sound.
Hempstead House is a 40-room mansion once owned by railroad tycoon Howard Gould.
Castle Gould, built to look like Ireland’s Kilkenny Castle, was originally meant to be the main house but ended up as stables and a carriage house instead.
You can wander the lush rose gardens and even spot filming locations from movies like Great Expectations and Malcolm X.
2. Westbury House – Old Westbury Gardens
Next up, say hello to Westbury House—a giant, red-brick Charles II-style mansion surrounded by some of the prettiest formal gardens you’ll ever see.
Built in 1906 for John S. Phipps, this 23-room house is packed with antique furniture, marble fireplaces, massive windows overlooking pools, and walled gardens.
You can stroll through the rose garden, snap pics by the grand staircase, or catch seasonal events like outdoor concerts and spooky Halloween nights.
(Westbury House normally closes in October and usually reopens in April.)
3. Coe Hall – Planting Fields Arboretum State Historic Park
Just when you think Long Island’s mansions can’t get grander, Coe Hall delivers with Tudor-style vibes and 409 acres of gardens, greenhouses, and giant beech trees.
Built in the 1920s by insurance mogul William Robertson Coe, this 65-room mansion has hand-carved woodwork, stained glass windows, and a built-in pipe organ.
After touring the mansion, you can wander through the Camellia Greenhouse, check out exotic plants in the Main Greenhouse, or picnic on the rolling lawns.
4. Chelsea Mansion – East Norwich
If you want to see something totally different, Chelsea Mansion in East Norwich mixes French and Chinese design.
It is located in a super photogenic spot, surrounded by over 500 acres of forest, ponds, and peaceful gardens.
Built in 1924 by Alexandra and Benjamin Moore, this unique mansion has its own moat and plenty of charm.
5. Sagamore Hill National Historic Site – Oyster Bay
You can’t do a Long Island mansion tour without stopping at Sagamore Hill—the primary home of President Theodore Roosevelt.
Nicknamed the “Summer White House,” this 23-room Victorian house showcases Roosevelt’s trophies and bookshelves stacked from floor to ceiling.
After checking out the mansion, you can hit the nature trails, wander down to the beach, or chill on the porch where Teddy himself used to sip coffee and talk politics.
6. Oheka Castle – Huntington
Get ready for some serious wow factor at Oheka Castle in Huntington, one of the largest private homes in the U.S.
Built in 1919 by financier Otto Kahn, this 109,000-square-foot French-style château comes complete with grand ballrooms, formal gardens, and a sweeping staircase.
You can even book a room and stay overnight, living like royalty for a night.
It’s been a filming spot for everything from classic films to Taylor Swift’s “Blank Space” video, so don’t be surprised if it feels more Hollywood than history class.
7. Vanderbilt Museum, Mansion & Planetarium – Centerport
Swing over to the Vanderbilt Museum, Mansion & Planetarium in Centerport—part mansion, part natural history museum, part stargazing hotspot.
This Spanish Revival estate was the summer home of William K. Vanderbilt II.
It’s packed with unique treasures, such as taxidermy animals, marine specimens, and a giant collection of model ships (the guy loved boats).
After roaming through the 24-room mansion, you can catch a show at the planetarium’s dome theater or peek through the observatory’s telescope.
8. Bayard Cutting Arboretum & Mansion – Great River
And if you’re craving one last dose of Gilded Age beauty, head to Bayard Cutting Arboretum & Mansion in Great River for a chill, nature-filled finale.
This cozy Tudor-style mansion, built in 1886 for railroad baron William Bayard Cutting, sits right on the Connetquot River.
It is surrounded by 691 acres of lawns, walking trails, and some seriously impressive trees (think towering firs and rare conifers).
Inside, you’ll find lovely wood-paneled rooms and fireplaces, and outside, you can wander the formal gardens or grab a treat at the Hidden Oak Café.
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