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

$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

Start Your Search

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.