Sleepy Hollow Homes for Sale

Welcome to Sleepy Hollow, New York—a picturesque village nestled in the heart of Westchester County, known for its rich history, stunning river views, and vibrant community spirit. Just a short drive from the bustling streets of New York City, Sleepy Hollow offers a serene escape while still providing easy access to urban amenities. This charming village is steeped in folklore, famously associated with Washington Irving's “The Legend of Sleepy Hollow,” and boasts a unique blend of historical charm and modern living.

As you explore the homes for sale in Sleepy Hollow, you’ll discover a diverse array of properties that cater to various lifestyles and preferences. From beautifully restored historic homes that echo the village's storied past to contemporary residences that boast modern amenities, there is something for everyone. Many properties offer stunning views of the Hudson River and the surrounding natural beauty, making it a perfect spot for nature lovers and outdoor enthusiasts.

The community is known for its welcoming atmosphere, with local events, farmers' markets, and cultural festivities that bring residents together. Families will appreciate the excellent schools and parks, while professionals will enjoy the convenient commuting options to New York City.

Whether you’re seeking a quaint cottage, a spacious family home, or a luxurious property with panoramic views, Sleepy Hollow has it all. Discover your dream home in this enchanting village and become a part of a community that celebrates its rich heritage while looking forward to a bright future. Come visit Sleepy Hollow—where history meets home!

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

$1,300,000

4 Beds ⋅ 4 Baths ⋅ 1040148 MLS

Welcome to 254 Farrington Avenue, where water views, flexible living space, and the character of Sleepy Hollow come together in a setting that feels tucked away while keeping you close to everything. Set just steps from the water, the home enjoys beautiful views right from the front of the property and offers a lifestyle that’s increasingly difficult to find in Westchester. Inside, the home offers 4 bedrooms, 3 full bathrooms and 1 half bathroom, with a layout designed to provide plenty of room to live, work, entertain, and unwind. Natural light fills the living spaces, while the home’s combination of original character and thoughtful improvements creates a warm, comfortable feel throughout. The kitchen flows naturally into the home’s gathering spaces and out toward the outdoor areas, creating an easy setup for everyday living and entertaining. Upstairs, the bedroom spaces provide privacy and flexibility, while the primary suite creates its own retreat. Outside, enjoy your own private space while having the waterfront practically at your doorstep. Morning walks by the water, evenings outside, and picturesque views become part of everyday life here. Located within the desirable Philipse Manor section of Sleepy Hollow, 254 Farrington offers convenient access to Metro North, the villages of Sleepy Hollow and Tarrytown, restaurants, shops, parks, and everything the Rivertowns have to offer. Come experience 254 Farrington Avenue and discover what makes this location and this home so special.

254 Farrington Avenue, 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.