You don’t have to travel to Newport to wander through grand historic estates, elaborate gardens and homes once occupied by some of America’s wealthiest and most influential families.
Westchester County has its own remarkable collection.
From the Rockefeller family’s hilltop estate overlooking the Hudson River to a Gothic Revival mansion that looks as though it belongs in the English countryside, some of the area’s most beautiful properties provide a glimpse into an era when prominent New York families escaped the city for sprawling country estates.
Many of these properties have been preserved, and several can still be toured today.
Here are some of the most beautiful historic estates in Westchester County.
Kykuit, The Rockefeller Estate – Pocantico Hills
Few names are as closely connected to American wealth and industry as Rockefeller, and one of the family’s most important homes sits right here in Westchester.
Kykuit, whose name comes from the Dutch word for “lookout,” sits high above the Hudson River in Pocantico Hills. The imposing estate was home to four generations of the Rockefeller family, beginning with Standard Oil founder John D. Rockefeller.
The Classical Revival mansion was completed in the early 20th century and became the centerpiece of the family’s vast Westchester property.
Yet the house itself is only part of Kykuit’s appeal.
Terraced gardens, fountains, sculptures and sweeping views toward the Hudson create the feeling of a European country estate. The property also became home to an impressive collection of 20th-century art associated with former New York Governor and U.S. Vice President Nelson Rockefeller.
Works by artists including Pablo Picasso, Henry Moore and Alexander Calder have been displayed throughout the house and grounds.
For decades, visitors have been able to tour portions of Kykuit through guided visits.
Important for 2026: Kykuit tours are currently on hiatus as the visitor experience is being reworked. Public tours are expected to return with a new format in 2027, so this is one Westchester treasure to put on the future-visit list.
Location: Pocantico Hills/Sleepy Hollow
Lyndhurst Mansion – Tarrytown
Drive along Broadway in Tarrytown and hidden beyond the gates is one of America’s most extraordinary Gothic Revival homes.
Lyndhurst Mansion was designed in 1838 by prominent architect Alexander Jackson Davis. With pointed arches, towers, dramatic rooflines and a picturesque setting overlooking the Hudson, it looks more like something encountered on a European country drive than a home just miles outside New York City.
The estate was owned over the years by three prominent families—the Pauldings, Merritts and Goulds.
Its best-known owner was railroad magnate Jay Gould, who purchased Lyndhurst in 1880 after initially using it as a summer retreat from New York City.
Unlike many historic houses assembled later as museums, Lyndhurst retains an extensive collection of furnishings and decorative objects connected to the families who actually lived there.
The surrounding landscape is just as important to the experience. The estate encompasses sweeping lawns, mature trees and Hudson River views, along with historic outbuildings and gardens.
Today, Lyndhurst is a National Trust Historic Site and offers mansion tours as well as access to its grounds. Seasonal events held on the estate make it particularly beautiful around the holidays.
Location: 635 South Broadway, Tarrytown
The Armour-Stiner Octagon House – Irvington
There is nothing else quite like the Armour-Stiner Octagon House.
Rising above its landscaped grounds in Irvington, the eight-sided Victorian mansion is immediately recognizable by its enormous domed roof.
The home began as an octagonal residence built around 1859–1860 for financier Paul J. Armour. It was later dramatically expanded by tea importer Joseph Stiner, who transformed it into the exuberant structure seen today.
Its design was inspired by the 19th-century fascination with octagonal houses, but the Armour-Stiner property takes the concept to an entirely different level.
The restored interiors are equally striking, filled with elaborate Victorian details, rich colors, period furnishings and decorative flourishes.
Unlike some historic properties that feel frozen behind velvet ropes, the Octagon House has the atmosphere of stepping directly into an eccentric and exceptionally glamorous Victorian residence.
The National Historic Landmark is open for guided tours on select days.
Location: 45 West Clinton Avenue, Irvington
Untermyer Gardens – Yonkers
The mansion that once stood at the center of Samuel Untermyer’s estate may no longer be the star, but its extraordinary gardens have survived—and have once again become one of Westchester’s great showplaces.
Attorney Samuel Untermyer purchased the former Greystone estate in 1899 and spent decades creating elaborate gardens overlooking the Hudson.
At its height, the estate encompassed approximately 150 acres, employed dozens of gardeners and was supported by an astonishing 60 greenhouses.
The gardens became so celebrated that tens of thousands of people could visit during major displays.
Today, approximately 43 acres remain as Untermyer Park and Gardens, and extensive restoration has returned much of the landscape to its former grandeur.
The centerpiece is the spectacular Walled Garden, inspired by ancient Indo-Persian garden design. Visitors encounter reflecting pools, mosaics, classical architecture and long sightlines that make the space feel worlds away from Yonkers.
Then there is the romantic Temple of Love, built into dramatic rockwork above waterfalls, along with the Vista overlooking the Hudson and Palisades.
For anyone interested in photography, architecture or gardens, Untermyer is easily one of Westchester’s most visually impressive destinations.
Even better: admission to the gardens is free.
Location: 945 North Broadway, Yonkers
The Rosen House at Caramoor – Katonah
Caramoor feels less like a traditional Westchester mansion and more like a Mediterranean villa transported to the countryside of Katonah.
The estate was created by Walter and Lucie Rosen, a cultured New York couple with a passion for music, art and travel.
Their home, now known as the Rosen House, incorporates architectural elements and decorative arts inspired by Europe and Asia. Rooms are filled with antiques, artwork and architectural pieces the Rosens collected during their travels.
The house surrounds a Spanish Courtyard, one of the property’s most enchanting spaces.
But music ultimately became Caramoor’s defining legacy.
What began with intimate performances at the Rosens’ country home eventually developed into the renowned Caramoor music program. Today, classical, jazz, roots and other musical performances continue to bring audiences to the estate.
Visitors can explore the historic house and grounds, while the gardens make Caramoor particularly beautiful during warmer months.
For a quintessential Westchester afternoon, it’s difficult to beat wandering the gardens before attending an outdoor concert.
Location: 149 Girdle Ridge Road, Katonah
Jay Estate – Rye
One of Westchester’s most historically significant estates sits surprisingly close to the bustle of Boston Post Road in Rye.
The Jay Estate was the childhood home of Founding Father and first Chief Justice of the United States John Jay.
Today, the 23-acre property overlooks Long Island Sound and preserves a landscape with thousands of years of human history.
Its architectural centerpiece is the stately 1838 Jay Mansion, built by John Jay’s son Peter Augustus Jay on the footprint of the family’s earlier home.
The Greek Revival mansion is distinguished by its enormous classical columns and graceful proportions. Parts of the earlier family home were actually reused in its construction.
The surrounding property includes meadows, gardens, orchards and views toward Long Island Sound.
The history here is also more complicated than a simple story of a Founding Father. Interpretation at the estate explores the Indigenous history of the land as well as the stories of enslaved and free people who lived and worked there.
The estate grounds remain open to visitors, but the 1838 mansion is closed during 2026 for restoration. The gardens are open on designated days during the season.
Location: 210 Boston Post Road, Rye
Merestead – Bedford
Set amid approximately 130 acres in Bedford, Merestead represents a slightly later chapter in Westchester’s grand country-estate era.
The Georgian Revival mansion was completed in the early 20th century as the country home of William Sloane and his wife, Anne Vanderbilt Sloane.
Yes—that Vanderbilt.
Anne was a granddaughter of William Henry Vanderbilt, connecting the property to one of America’s most famous Gilded Age dynasties.
The estate’s name combines the words “Mere” and “Stead,” reflecting family connections.
The imposing mansion sits within a landscape of woods, fields and gardens. Today the property is part of the Westchester County Parks system, and walking trails provide a way to experience the surrounding estate even when access to the mansion itself is limited.
Merestead is considerably less famous than Kykuit or Lyndhurst, which is part of its appeal. It feels like one of northern Westchester’s hidden remnants of the era when wealthy New York families created expansive country retreats beyond Manhattan.
Location: Byram Lake Road, Bedford
John Jay Homestead – Katonah
Westchester actually has two important properties associated with John Jay.
After retiring from public life, Jay moved to his farm in Katonah, where the John Jay Homestead became his family residence.
The house and surrounding property offer a very different experience from the grandeur of later Gilded Age estates. Rather than overwhelming visitors with opulence, the Homestead provides a glimpse into the life of one of America’s Founding Fathers and the agricultural landscape of early Westchester.
The property eventually expanded to hundreds of acres and remained in the Jay family for generations.
Today, the historic site includes the main house, gardens, barns and surrounding landscape.
It’s particularly beautiful in fall, when the historic buildings and rolling property are surrounded by autumn foliage.
Location: 400 Jay Street, Katonah
Sunnyside – Tarrytown
Few Westchester homes are as romantic as Sunnyside, the former home of The Legend of Sleepy Hollow author Washington Irving.
Irving purchased a modest property along the Hudson River in the 1830s and transformed it into the whimsical home seen today.
Its architecture incorporates Dutch Colonial influences, Gothic details and a distinctive tower, with vines climbing across portions of the façade.
The result looks almost like a cottage from one of Irving’s stories.
The setting adds considerably to its charm. Sunnyside sits along the Hudson surrounded by a picturesque landscape that Irving himself helped shape.
Considering his connection to The Legend of Sleepy Hollow, visiting Sunnyside during Westchester’s fall season feels especially appropriate.
Location: West Sunnyside Lane, Tarrytown
A Remarkable Legacy Hidden Throughout Westchester
What makes Westchester’s historic estates so fascinating isn’t simply their size or beauty.
Together, they tell the story of several different versions of Westchester.
There is the colonial Westchester of John Jay and Washington Irving’s romantic Hudson Valley. There is the Gilded Age world of Jay Gould and Samuel Untermyer. There are the enormous fortunes represented by names like Rockefeller and Vanderbilt. And there are patrons such as Walter and Lucie Rosen who transformed their country estate into a lasting center for music and culture.
Many of these properties were built because wealthy and influential New Yorkers wanted exactly what attracts people to Westchester today: beautiful landscapes, more space and an escape from the intensity of New York City without being terribly far away.
More than a century later, we get to enjoy what they left behind.
For Westchester residents, perhaps the most surprising part is just how many of these extraordinary places are sitting practically in our own backyard.