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 Hudson River in Westchester County. Famous for its enchanting landscapes and rich literary heritage, Sleepy Hollow offers a unique blend of small-town warmth and vibrant community life. With its lush parks, scenic river views, and a plethora of outdoor activities, this idyllic locale is perfect for families, professionals, and anyone seeking a tranquil escape from the hustle and bustle of city life.

Sleepy Hollow is perhaps best known as the setting for Washington Irving's classic tale, "The Legend of Sleepy Hollow." The village's historical roots are evident in its well-preserved architecture and landmarks, such as the Old Dutch Church and the Sleepy Hollow Cemetery, where Irving himself is laid to rest. Beyond its fascinating history, the community is lively, with seasonal events, farmers' markets, and cultural festivals that bring residents together.

For those looking to call Sleepy Hollow home, the real estate market offers a diverse array of homes for sale. Whether you’re searching for a charming colonial, a modern townhouse, or a spacious family home, Sleepy Hollow has something to suit every taste and budget. With excellent schools, convenient transportation options, and a strong sense of community, it's no wonder that more people are choosing to make this enchanting village their home. Discover your dream property in Sleepy Hollow today and experience the perfect blend of history, nature, and 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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