Sleepy Hollow Homes for Sale

Welcome to Sleepy Hollow, New York—a charming village nestled along the picturesque banks of the Hudson River in Westchester County. Renowned for its rich history and enchanting landscapes, Sleepy Hollow offers a unique blend of small-town charm and modern amenities, making it an ideal destination for families, professionals, and anyone seeking a serene lifestyle.

Steeped in legend, Sleepy Hollow is famously known as the setting of Washington Irving's "The Legend of Sleepy Hollow." This captivating narrative adds a touch of whimsy to the village, and its historical significance is reflected in the well-preserved architecture and scenic parks that dot the landscape. Residents enjoy stunning riverfront views, lush greenery, and an array of outdoor activities, including hiking trails and waterfront parks.

The real estate market in Sleepy Hollow is as diverse as its community. Homes for sale range from charming historic houses with character to modern, spacious properties that cater to contemporary tastes. Whether you're seeking a quaint cottage or a luxurious family home, Sleepy Hollow offers a variety of options to suit your needs. The local real estate market is vibrant, with properties that often boast beautiful gardens, scenic views, and easy access to amenities.

Living in Sleepy Hollow means being part of a close-knit community that values tradition and progress. With excellent schools, delightful dining options, and a rich cultural scene, you’ll find everything you need right at your doorstep. Discover your dream home in this enchanting village and experience the magic of Sleepy Hollow for yourself!

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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