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

$949,000

3 Beds ⋅ 1 Baths ⋅ 1041980 MLS

Nestled in the heart of Pocantico Hills Hamlet, this special three bedroom home offers a truly magical setting, with direct access to the enchanting Rockefeller trails. Step outside and enjoy miles of trails perfect for walking, strollers, running, and exploring natue - right from your own backyard. Everyday life is wonderfully convenient, too. The Pocantico Hills School, swimming pool, and recreation facilities are just five minutes away. The school serves children from Pre-K for 3 & 4 year olds through eighth grade, with a choice of high schools in nearby Briarcliff Manor, Pleasantville, and Sleepy Hollow. The community’s recreation amenities include an Olympic-size swimming pool, baby pool, new pickleball courts, tennis courts, and basketball courts, along with summer camp programs for children. And then there is the setting itself. Life here has a distinctly storybook quality: hear the clip-clop of horses passing by, listen for the bells of the historic Union Church, and look across the yard to the breathtaking Chagall stained-glass windows glowing within the church. Enjoy the best of nearby Tarrytown, Sleepy Hollow, Briarcliff Manor, and Pleasantville, with easy access to wonderful parks, restaurants, shops, and everyday amenities, as well as all major parkways. Peaceful, connected to nature, rich in history - and wonderfully close to everything. This is a truly special place to call home. Don't miss it!

540 Bedford Road, Sleepy Hollow

$935,000

3 Beds ⋅ 2 Baths ⋅ 1019682 MLS

Nestled in the highly sought-after Sleepy Hollow Manor neighborhood, this charming 3-bedroom ranch offers easy one-level living in a picturesque setting. Filled with natural light, the home features spacious living and dining areas, hardwood floors, and a welcoming living room anchored by a wood-burning fireplace, creating a warm and inviting gathering space. A standout feature is the all season sunroom, providing the perfect space to relax, entertain, or work from home. From the sunroom, step out onto the expansive deck overlooking the front property, an ideal spot for morning coffee, outdoor dining, or simply taking in the peaceful surroundings. The property is enhanced by mature trees, lush gardens, and an abundance of colorful plantings that provide year-round beauty and exceptional curb appeal. The backyard offers a private retreat with thoughtfully curated landscaping, while the front gardens create a welcoming first impression. An unfinished basement provides generous storage space and future potential for hobby, workshop, or organizational needs. Located just moments from the Philipse Manor train station, Hudson River parks, trails, and the vibrant shops and restaurants of downtown Sleepy Hollow and Tarrytown, this home combines suburban charm with exceptional convenience.

5 Lakeview Avenue, Sleepy Hollow

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