Sleepy Hollow Homes for Sale

Welcome to Sleepy Hollow, New York—a charming village steeped in history and natural beauty, nestled along the scenic banks of the Hudson River in Westchester County. Famous for its connection to Washington Irving's "The Legend of Sleepy Hollow," this picturesque community offers a unique blend of small-town charm and modern conveniences. With its lush parks, serene waterfront views, and vibrant local culture, Sleepy Hollow is an idyllic place to call home.

As you explore the homes for sale in Sleepy Hollow, you'll discover a diverse array of architectural styles that reflect the area’s rich heritage. From quaint colonial homes to contemporary residences, there’s something for everyone in this enchanting village. Many properties boast stunning river views, spacious yards, and easy access to local amenities, making it an ideal choice for families, professionals, and retirees alike.

The community is well-equipped with top-rated schools, delightful shops, and a variety of dining options, ensuring that residents enjoy a high quality of life. Outdoor enthusiasts will appreciate the numerous parks and hiking trails, including the nearby Rockefeller State Park Preserve, which offers miles of scenic pathways.

Whether you’re looking for a cozy cottage or a sprawling family home, Sleepy Hollow’s real estate market has a wealth of opportunities waiting for you. Embrace the charm of this historic village and discover your dream home in Sleepy Hollow today—where history meets modern living!

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.