Sleepy Hollow Homes for Sale

Welcome to Sleepy Hollow, New York—a picturesque village steeped in history and charm, nestled along the banks of the majestic Hudson River. Located in Westchester County, this enchanting town is known for its stunning natural beauty, vibrant community, and rich cultural heritage, making it an ideal place to call home.

Sleepy Hollow is perhaps best known as the setting of Washington Irving's "The Legend of Sleepy Hollow," but its allure extends far beyond literary fame. Residents enjoy a serene lifestyle surrounded by lush landscapes, scenic parks, and breathtaking river views. The village boasts a variety of outdoor recreational opportunities, from hiking the trails of the nearby Rockefeller State Park Preserve to enjoying leisurely strolls along the waterfront.

For those considering making Sleepy Hollow their home, the real estate market offers an array of charming properties that cater to diverse tastes and lifestyles. Whether you are looking for a quaint historic home, a modern townhouse, or a spacious family residence, Sleepy Hollow has something for everyone. With homes for sale featuring unique architectural designs, ample outdoor space, and proximity to top-rated schools, this area is perfect for families, professionals, and retirees alike.

In addition to its stunning homes, Sleepy Hollow is conveniently located just a short drive or train ride away from New York City, providing easy access to urban amenities while maintaining a peaceful, small-town atmosphere. Discover the magic of Sleepy Hollow—where history, community, and natural beauty come together to create the perfect place to call home. Explore the homes for sale today and start your journey in this charming village!

Newest Sleepy Hollow Homes for Sale

$599,900

3 Beds ⋅ 2 Baths ⋅ 978945 MLS

Village charmer, completely renovated from top to bottom and truly move-in ready! This beautifully refreshed 2,200 sq ft home features freshly painted interiors, tiled bathrooms, and a bright, airy layout filled with natural light and an open floorplan. The stylish kitchen boasts sleek stainless steel appliances and quartz countertops; perfect for modern living. Enjoy the inviting front porch, convenient in-home laundry, and full finished basement with walk out. The private, fenced-in backyard with a lovely patio and storage shed creates the perfect setting for relaxing or entertaining, all just moments from everything the village has to offer!

30 Kendall Avenue, Sleepy Hollow

$12,000,000

5 Beds ⋅ 6 Baths ⋅ H6335041 MLS

Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central core is a great room with 20 foot ceilings and walls of glass facing the river. Equestrian facilities include a 14-stall stable, indoor and outdoor riding arenas, six fenced paddocks and two grooms's apartments. A manager's house, greenhouse, carriage barn and equipment garage are all well located to support the stable, main house and property. Direct trail access from the property is provided through north and south gates to the 55-mile carriage trail network of the 1,800 acre Rockefeller State Park. Winterburn Farm is an extremely rare opportunity offering a pristine architectural house amid a beautiful landscape of unparalleled privacy.

48 Raafenberg Road, Sleepy Hollow

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.