Sleepy Hollow Real Estate

Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, NY – a picturesque village nestled along the banks of the Hudson River in Westchester County. Rich in history and natural beauty, Sleepy Hollow offers a unique blend of charming small-town vibes and modern conveniences, making it a perfect place to call home.

Famous for its connection to Washington Irving’s legendary tale, “The Legend of Sleepy Hollow,” this enchanting neighborhood is steeped in lore. As you stroll through its tree-lined streets, you'll encounter beautifully preserved historic homes, many dating back to the 18th and 19th centuries. The village is also home to the iconic Sleepy Hollow Cemetery, where visitors can pay their respects to Irving himself, along with other notable figures.

Nature enthusiasts will appreciate the abundant outdoor activities available in Sleepy Hollow. The scenic waterfront parks, such as the stunning Kingsland Point Park and the expansive Sleepy Hollow State Park, offer picturesque hiking trails, picnic spots, and breathtaking views of the Hudson River. The nearby Rockefeller State Park Preserve is a haven for walkers, cyclists, and horseback riders, with its miles of serene trails amidst lush landscapes.

Families in Sleepy Hollow benefit from a tight-knit community atmosphere and access to top-rated schools, making it an ideal place for raising children. Local shops, cafes, and restaurants provide a delightful array of dining and shopping options, ensuring that residents have everything they need within reach.

With its rich history, vibrant community, and stunning natural surroundings, Sleepy Hollow is more than just a place to live – it’s a lifestyle waiting to be embraced. Discover the charm of Sleepy Hollow today!

Newest Listings in Sleepy Hollow

7 Holland Avenue, Sleepy Hollow
$1,250,000
5 Beds ⋅ 4 Baths ⋅ 1060733 MLS
Tucked away in the highly sought-after Webber Park neighborhood of historic Sleepy Hollow, this 3-family home offers an exceptional opportunity for an Owner-occupant looking to live in one unit, while offsetting their mortgage and property taxes with rental income from the other two units. The largest unit is a 3-bed / 1.5-bath / 1,450 SqFt Duplex on the West-side and is available for immediate move-in. In addition, this "owners" unit has an interior staircase from the main-level to a large, unfinished basement (425 SqFt, which is in addition to the stated square footage) with full ceiling height, laundry, and direct access to a 2-car garage. On the East-side, are two 1-bed / 1-bath units. The first-floor unit has an interior staircase to a second large, unfinished basement with laundry, and direct access to a 1-car garage. This near-to-all location offers many benefits with a neighborhood park (Douglas Park), easy access to the Old Croton Aqueduct Trail and The Rockefeller State Park Preserve, a short walk into the heart of the Village where you will find shops, restaurants, and the transformative Edge-on-Hudson waterfront park/community. For commuters, enjoy a scenic stroll to the Philipse Manor train station (39-minute express trains from Grand Central). If you enjoy street fairs, cultural festivals, live jazz, rich history, local legends, and one of the country’s most celebrated Halloween destinations, you will love calling Sleepy Hollow home! Stated taxes are before the STAR savings of $1,591 for those who owner-occupy/qualify. (NOTE: there are no interior photos of the 1-bed first floor occupied unit, which is of similar condition to the other two units shown.)

7 Holland Avenue, Sleepy Hollow

40 Andrews Lane, Sleepy Hollow
$999,000
2 Beds ⋅ 4 Baths ⋅ 1021377 MLS
Welcome home to Sunset Villas on Andrews Lane, an exclusive new community of just nine luxury townhomes perfectly situated in the Village of Sleepy Hollow. Enjoy no HOA fees for the first 6 months. This beautifully designed four-level residence offers modern luxury, exceptional living space, and thoughtful finishes throughout. The entry level features an oversized foyer with ceramic tile flooring, a powder room, and direct access to an oversized one-car garage. The main level showcases a designer kitchen with quartzite countertops, stainless-steel appliances, abundant storage, and generous workspace. Step outside to the deck, ideal for al fresco dining and entertaining. The adjoining living room features a fireplace, recessed lighting, crown molding, and a warm, inviting atmosphere. Hardwood floors continue throughout the second, third, and fourth levels. The third floor offers two en-suite bedrooms, including a spacious primary suite with double closets. The fourth-floor family/guest room features a full bath, walk-in closet, and access to a private rooftop terrace, an incredible setting for relaxing, entertaining, and taking in the sunset. Located directly across from Barnhart Park and playground, Sunset Villas offers easy access to scenic river views, dining, shopping, and all that Sleepy Hollow has to offer. Modern luxury, flexible living space, and an exceptional location await. Some photos and the attached video depict the staged model unit.

40 Andrews Lane, Sleepy Hollow

11 River Street Unit #107, Sleepy Hollow
$2,100,000
2 Beds ⋅ 2 Baths ⋅ 1055772 MLS
Exceptional Waterfront Living at River House This spectacular two-bedroom, two-full-bath residence represents a rare opportunity to experience waterfront living at its finest. Located directly along the Hudson River, this exceptional home combines breathtaking river views, walls of windows, and an extraordinary private terrace of nearly 900 square feet, creating an indoor-outdoor living experience rarely available in the Rivertowns. From sunrise through sunset, the Hudson River becomes the backdrop to everyday life. Expansive windows flood the residence with natural light while showcasing sweeping panoramic views of the Hudson River, the Manhattan skyline, and the iconic Mario Cuomo Bridge. The oversized private terrace provides an exceptional setting for morning coffee, outdoor dining, entertaining, or simply enjoying the ever-changing beauty of the river, skyline, and surrounding landscape. The thoughtfully designed two-bedroom, two-full-bath layout offers both comfort and versatility, with generous living spaces equally suited to relaxed everyday living or sophisticated entertaining. The seamless connection between the interior and outdoor spaces makes this residence truly distinctive. Additional highlights include two assigned indoor parking spaces, each with dedicated private EV charging, along with the convenience of a fitness center, pool, and concierge service. Beyond the residence, an exceptional waterfront lifestyle awaits. Enjoy immediate access to the Hudson River promenade and RiverWalk, with scenic pathways, green space, waterfront recreation, and some of the area's most sought-after dining and entertainment. The Farmer & the Fish, RiverMarket Bar & Kitchen, and DeCicco's are all within walking distance, along with Tarrytown's restaurants, shops, Music Hall Theatre, and the Tarrytown and Washington Irving Boat Clubs. For commuters, the Tarrytown Metro-North station is within walking distance, providing a seamless connection to Manhattan. A rare combination of space, natural light, extraordinary outdoor living, stunning Manhattan and Mario Cuomo Bridge views, direct Hudson River frontage, resort-style amenities, and walkable convenience, this residence offers a lifestyle that is exceptionally difficult to duplicate.

11 River Street Unit #107, Sleepy Hollow

323 Palisades Boulevard, Sleepy Hollow
$1,800,000
3 Beds ⋅ 5 Baths ⋅ 1053361 MLS
A rare opportunity to own an exceptional four-level end-unit residence at coveted Edge-on-Hudson in Sleepy Hollow. Offering 3 bedrooms plus a beautifully appointed corner office, 2 full and 3 half baths, and a large two-car garage, this sophisticated home combines custom design, abundant natural light and exceptional indoor-outdoor living. The first level welcomes you with a beautiful corner office surrounded by windows and finished with custom floor-to-ceiling cabinetry and built-ins—an elegant and inspiring space for working from home, a library or private retreat. A spacious mudroom with custom built-ins provides exceptional organization and convenience, while the large two-car garage offers direct access and abundant storage. The second level is the heart of the home, with an expansive open floor plan designed for entertaining. The custom gourmet kitchen features a striking navy island and custom hood, a six-burner gas cooktop and generous workspace. The kitchen flows seamlessly into a large dining area and spacious living room, anchored by a gas fireplace that creates a warm and inviting gathering space. The third level is devoted to private living, offering three bedrooms including a generous primary suite with a large walk-in closet. Beautiful wood floors continue throughout the bedrooms, while a conveniently located dedicated laundry room with full-size washer and dryer on pedestals adds effortless practicality. The fourth level delivers an extraordinary lifestyle experience with a spacious family room, half bath and an inviting indoor-outdoor entertaining environment. Designed for relaxed gatherings, this level opens to areas for indoor-outdoor dining including a built-in outdoor barbecue & refrigerator, garden-style sitting and outdoor entertaining, creating a private retreat above it all. As a coveted end unit, the home is surrounded by an exceptional number of windows, allowing every level to be beautifully bathed in sunlight. High ceilings, rich dark hardwood floors and privacy-coated windows and doors add to the home’s sense of sophistication, comfort and privacy. With four distinct levels thoughtfully designed for living, working, entertaining and relaxing, this is far more than a townhome—it is a luxury residence with the scale, privacy and versatility of a single-family home, within the exceptional Edge-on-Hudson community on The Hudson River. Walk to shopping, restaurants, park and train station. The association also provides shuttle to train station.

323 Palisades Boulevard, Sleepy Hollow

201 Horseman Boulevard Unit #101, Sleepy Hollow
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 1049806 MLS
Welcome to Horseman Boulevard. Just 25 miles north of NYC, Sleepy Hollow offers luxury living at its best in The Edge-on-Hudson, a modern, walkable riverfront community overlooking the Hudson River. This stunning corner unit features high ceilings and walls of glass that fill the space with natural light. Your private French doors off the living area open to a huge patio of 1,173 SF, perfect for outdoor dining and hosting large gatherings. Any chef would enjoy this open concept kitchen with high-end stainless-steel appliances and granite countertops. The primary en-suite bedroom includes two custom walk-in closet areas and a spa-like bathroom, while the second bedroom offers a spacious closet and private bathroom. Additional upgrades throughout the home include: Kohler fixtures, custom wallcoverings, tile backsplash in the kitchen, upgraded primary bathroom shower tile walls, waterfall quartz countertop, Century cabinetry hardware and electrical lighting package. Enjoy a heated garage with private entry and driveway space for a 2nd car, plus a community room, fitness center and train shuttle. Enjoy the DeCicco & Sons gourmet market, featuring a coffee and wine bar right at your doorstep. Look forward to additional “coming soon” eateries and new high end shopping options for effortless, carefree living. Conveniently located nearby the Rockefeller Trails, historical sites, river walk promenade, dog park, pickleball courts, and plenty of cultural events like music festivals, Halloween celebrations, and Rivertown art festivals, this home perfectly blends suburban charm with urban convenience.

201 Horseman Boulevard Unit #101, 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.