Living In Tarrytown, New York: A Real Estate and Lifestyle Experience

Tarrytown, New York—Old World Charm Less than an Hour from Midtown Manhattan

History of Tarrytown, New York

It is no wonder the Hudson River School of art was famed for its romanticized paintings of pastoral America. The Hudson River Valley was the ideal—and idealized—setting for depicting discovery, exploration, and settlement, three themes that epitomized 19th-century America. And Tarrytown, New York, a village in Greenburgh on the east bank of the Hudson River, epitomizes a modern version of a pastoral lifestyle less than an hour from Midtown Manhattan.

Natural beauty is not Tarrytown’s only claim to fame, though it likely is what attracted history makers there. Washington Irving set his novel The Legend of Sleepy Hollow in Tarrytown. John D. Rockefeller was among the first of a wave of wealthy New Yorkers to discover Tarrytown; he built an elaborate mansion, Kykuit, in the village in 1902. Cab Calloway, the jazz singer and bandleader, lived in Tarrytown during his later years. Sylvia Nasar, most famous as the Pulitzer Prize-winning author of A Beautiful Mind, the biography of the economics Nobelist John Forbes Nash, Jr., lives in Tarrytown.

Much of history is not romantic, but in history resides humanity. The Underground Railroad, the secret routes and safehouses used by African-American slaves making their way to freedom, ran through Tarrytown during the American Civil War (1861–1865). Oral history claims more than 30,000 people fled slavery via the Underground Railroad.

Like most of the villages either side of the Hudson River north of Manhattan, Tarrytown was settled in the 17th century by Dutch farmers, fur trappers, and fishermen on land procured from Native Americans. There are two versions of how the village received its name. Irving’s account in the opening paragraphs of The Legend of Sleepy Hollow credits housewives of an adjacent county who accused their husbands of tarrying in the village on market days. The more sober and literal Dutch called the area Terve Town, meaning Wheat Town, which was mispronounced as Tarry Town.

Getting to Tarrytown

The village of Tarrytown is about 25 miles from Midtown Manhattan. It is easily accessed by car via Interstate 287. The Metro-North Railroad provides commuter service to Grand Central Station from the Tarrytown station, also a main stop on the Hudson Line to and from Manhattan.

What to Do and See in Tarrytown

Most of the sights to see in Tarrytown are steeped in its settlement history. By the early 1900s there were more than 65 mansions in the village, earning it the title Millionaire’s Colony. According to the Tarrytown historian William C. Gross, it was considered the wealthiest town of its size anywhere in the world at the time.

The Carrollcliff, a Tudor-style castle built in 1897 by General Howard Carroll on 64 acres on the highest point in Tarrytown, still stands and is today the restaurant Equus. Hillcrest, an estate built in 1882 by Captain William Casey, was purchased by Samuel Clemens (Mark Twain) in 1904, who lived there for two years. The old mansion was demolished and the new grander Halleston estate was built on the site in 1915. It was renamed Tappan Hill in 1941 and is now a rentable reception venue. Not least is the Queen Anne-style Tarrytown Music Hall, built in 1885, the oldest continually operating theater in Westchester County.

Sunnyside is Washington Irving’s Gothic estate, originally built as a farmhouse in 1835, and occupied by four subsequent generations of the Irving family until 1945. It was purchased by John D. Rockefeller (of Kykuit and oil fame) for historic preservation and has been a museum since 1947. The Gothic Revival mansion Lyndhurst was built in 1838 and is now the home of the National Trust for Historic Preservation and open to the public.

If you would rather be outdoors than in, there is Pierson Park, with majestic views of the Hudson River and new Mario Cuomo Bridge (formerly the Tappan Zee) and live music in the amphitheater in the summer. The park connects to the Scenic Hudson River Walk. Two other parks offer great experiences for nature lovers: Patriot’s Park in the village and site of numerous Revolutionary War battlefields and, today, a Saturday farmer’s market; and Kingsland Point Park on the Hudson River, with access to the grounds of the old Tarrytown lighthouse.

Where to Shop and Dine in Tarrytown

Ona is a cornucopia of collectibles on Main Street, or, if flavored vinegars and olive oils are calling, visit Pure Mountain Olive Oil on North Broadway. Bella’s Boutique is also on North Broadway. On South Broadway, stop in Pretty Funny Vintage if you’re feeling pretty or funny or curious for all kinds of curios. A Nu Toy Store is on Main Street, Hank’s Alley for the kids is on Kaldenberg Place, and the New York Book Department is on Central Avenue, which sells, well, take a guess.

Hungry? If it’s fine dining you’re after, try The Twisted Oak, Cellar 49, Ruth’s Chris Steak House, or the Equus in the Tudor castle formerly called Carrollcliff. Moderately priced, ethnic, and locally-sourced restaurants abound, as do bistros, bars, breakfast places and more, all in the village center on and around Main Street.

Tarrytown School Districts

The Union Free School District of the Tarrytowns oversees 2,800 students in grades K–12 in five public schools. Sleepy Hollow High School, the public high school for grades 9–12, has about 850 students and, according to Niche, the US education research firm, it was rated A+ in 2019. Sperling’s Best Places to Live, calculated by the researcher Bert Sperling,and Neighborhood Scout, cite average US expenditure per student as $12,383, with schools in Tarrytown averaging an expenditure per student of $22,917, with 13 pupils per teacher.

Pocantico Hills Central School District oversees one school with 316 students in grades pre-K– 8 in Tarrytown. There also are nine private schools: six for Pre-K students, a Montessori school, as well as a primary parochial school for grades K–8, and the Hackley School for students in grades K–12.

Where to Live in Tarrytown

Education expenditures are higher in Tarrytown compared to national averages, as is the cost of living (by 84 percent). The median home price is $630,000, with 37 percent of home listings in the $586,000–880,000 range. Nearly 9 percent of homes on the market are listed for $1.2 million or above. The most expensive neighborhoods in Tarrytown include the area around South Broadway and Tarryhill Road just outside the village center, and the village center itself.

As to be expected in Hudson River towns and villages, the residential architectural styles pay homage to their history through the symmetry of early colonial styles featuring decorative and columned entryways or the steeply pitched gabled roofs of Tudor Revival styles, alongside homes with the clean lines and smart features of modern design.