A scenic and historic village with haunting allure on the Hudson River
Sitting on the Hudson River, just above the Mario Cuomo Bridge, the village of Sleepy Hollow keeps 11,000 residents. But while this is a small community in many respects, there’s plenty of open space to roam across. Go northeast, and there are nature preserves. Go southwest, and there are waterfront promenades. Residents also find connection to a world of adventure through historic locations, regular events, walkable retail strips and a rail station on the Hudson Line. “We have close proximity to New York City with trains, but we’re in the country,” says Phyllis Lerner, a local resident and realtor with Corcoran Legends Realty.
Formerly a Dutch mill town, today the local economy is sustained by small businesses and tourism. Fall brings the most tourists, thanks to the town being synonymous with Washington Irving’s 1820 ghost story, “The Legend of Sleepy Hollow.” Roughly 30,000 people showed up for a street fair in October 2024. The town is also frequently chosen by television and movie crews as a site for filming.
Sleepy Hollow New York is home to the legendary tale of The Headless Horseman.
Sleepy Hollow sits at the foot of the Mario Cuomo Bridge which crosses the Hudson River connecting Westchester County to Rockland County.
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Victorian charm mixed with luxury waterfront condos
Much of the town features a gridded layout. On the south side, streets feed into Beekman Avenue, one of the downtown drags. The north side is bounded by nature preserves and Broadway Avenue, the town’s other main thoroughfare. It’s not uncommon to see homes built from 1850s to 1900. Victorian-era charm is a strong suit for Sleepy Hollow. Closer to the downtown core, yards are substituted for sidewalks. There’s an assortment of homes, some with sharp gabled roofs and others that are flat-topped, rectangular and more like rowhouses. The northern part of town feels more classically suburban with ranch-style homes on grassy lots with mature shade trees. Luxury waterfront condo developments are the newcomers, like The Edge on Hudson, built at a former General Motors complex. “Development on the riverfront keeps expanding,” says Lerner. “It will be a whole world once it’s done.” The median price is $700,000, more than the national median.
The Edge-on-Hudson offers stunning views and luxury living and a wonderful community in Sleepy Hollow.
Homes in Sleepy Hollow vary from flat roof styling to pitch roof colonials.
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Union Free School District earns an A
Residents are served by the Union Free School District of the Tarrytowns, which scores an A rating from Niche. Over 2,500 students are in attendance overall, and there’s an 11-to-1 student-teacher ratio. In recognition of the town’s literary fame, the mascot for Sleepy Hollow High is the Headless Horseman – the central figure in Irving’s tale.
Sleepy Hollow Middle School and High School share the same campus.
The Horsemen is the mascot of Sleepy Hollow's school district.
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State parks and historic haunts to wander through
Rockefeller State Park Preserve is a popular place for birders and hikers, thanks to its extensive wooded trails and designation by the Audubon Society as an Important Bird Area. But there are more traditional parks closer to downtown, like Douglas Park, where the annual egg hunt and Haunted Hayride are held in spring and fall, respectively. There’s also a playground and a walking trail. Ball fields and athletic courts are found at Devries Park. For waterfront excursions, Kingsland Point Park is the site of the Tarrytown Lighthouse and a promenade. Historic places to wander include Old Dutch Church, Phillipsburg Manor and Sleepy Hollow Cemetery, where Irving, Andrew Carnegie, Walter Chrysler and William Rockefeller are buried.
All around Sleepy Hollow the town will remind you of its haunting folklore.
The Rockefeller Preserve is a wide open green space that is perfect for long walks and bird photography.
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Shopping and dining along Beekman Avenue and in Tarrytown
Beekman Avenue is a reliable strip when it comes to dining. Plenty of pizza places, Mexican spots and modern pubs line the way. Beekman extends to the river, where more conveniences are going in. “Right now, they’re building a supermarket,” says Lerner. The much-needed grocery store, part of the DeCicco & Sons chain, is expected to open in early 2025. There’s a farmers market in Patriot Park every Saturday from May to October. But further inland, Beekman intersects with Broadway, which leads south to downtown Tarrytown. Destination restaurants include Goosefeather, which serves Chinese fusion cuisine in an 1840s mansion. Mint is where diners can sample gourmet Moroccan dishes alongside a market full of Mediterranean goods. A mile further south along Broadway leads to the Harvest Field Market grocery store.
Sleepy Hollow Bookshop is a great local bookstore which organizes events in Sleepy Hollow.
The Bridge View Tavern in Sleepy Hollow offers a local beer menu and hearty American cuisine.
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Commuter rail stations and a county airport
There are commuter rail stations in Sleepy Hollow and Tarrytown, both served by the Hudson Line, which gets to New York City in about an hour. Or drivers can take the Saw Mill River Parkway to the Henry Hudson Parkway for a commute with riverside views. Westchester County Airport, about 30 minutes away, is the closest place to catch a flight. Westchester County is also served by the Bee Line System, so residents can take a bus to other cities in the county like White Plains.
Low property crimes compared to statewide trends
Sleepy Hollow is often called out for awards as one of the safest towns in New York. In 2024, it attained the state’s lowest property crime rate, with only six of these crimes reported. There was only one violent crime reported.
Written By
Paul Spencer
Photography Contributed By
Stephen Mihalchik
Video By
Edward Pokoj
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an experienced agent in this area.
GreatSchools:
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On average, homes in Sleepy Hollow, NY sell after 87 days on the market compared to the national average of 49 days. The median sale price for homes in Sleepy Hollow, NY over the last 12 months is $1,325,000, up 62% from the median home sale price over the previous 12 months.
Nestled on a picturesque, tree-lined corner lot in the desirable Philipse Manor neighborhood, this classic Colonial offers timeless charm and modern convenience. Enjoy the ease of a first-floor bedroom with full bath, ideal for guests or flexible living. Located just a short stroll from the Philipse Manor Metro-North station, you’re only 40 minutes from NYC—perfect for commuters who crave
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting.Our uncompromising commitment to
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting.Our uncompromising commitment to
Welcome to NorthLight, Sleepy Hollow?s premier residences at Edge-on-Hudson. Between a lighthouse and a legend, this brand-new luxury apartment community boasts modern conveniences with the small town Hudson River charm. Choose from a selection of studio, one-bedroom or two-bedroom apartment homes with some apartment homes including dens. Entertain poolside or on the lush roof deck and pent house
Amazing place Huge living room . Must see your new home in the heart of Sleepy Hollow. This inviting 4-bedroom, 2-bathroom house offers a bright extremely large living Room Dining room , eat in kitchen . Each bedroom is spacious and comfortable, with updated bathrooms adding a touch of style. Enjoy a private backyard for relaxation and entertaining. Conveniently located near local amenities and
Emerson is your gateway to Edge-on-Hudson, New York’s premier waterfront community. These thoughtfully designed one- and two-bedroom apartment homes feature a polished industrial aesthetic, spacious floor plans, and smart home appliances and technology. Luxury amenity options include a rooftop deck with breathtaking views of the Hudson, state-of-the-art fitness center, elevated communal spaces,
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