Sleepy Hollow Real Estate

Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, New York—a charming village steeped in history and natural beauty, nestled along the picturesque Hudson River in Westchester County. Known for its captivating landscapes and rich cultural heritage, Sleepy Hollow is a hidden gem that offers a unique blend of small-town charm and modern amenities.

This enchanting village is perhaps best known as the setting of Washington Irving's classic tale, "The Legend of Sleepy Hollow." Visitors and residents alike can explore the iconic sites associated with the story, including the historic Sleepy Hollow Cemetery and the majestic Philipsburg Manor. The area is perfect for those who appreciate both literature and history, with numerous events and festivals celebrating its storied past.

Nature enthusiasts will find plenty to love in Sleepy Hollow. The village boasts stunning river views, lush parks, and scenic hiking trails. The nearby Rockefeller State Park Preserve offers over 1,000 acres of protected land, ideal for hiking, biking, and enjoying the tranquility of the great outdoors.

Culinary delights await at local eateries, where you can savor everything from farm-to-table fare to international cuisine, all within a friendly, welcoming atmosphere. With a strong sense of community, Sleepy Hollow hosts various events throughout the year, fostering connections among residents and visitors alike.

With its rich history, breathtaking scenery, and vibrant community spirit, Sleepy Hollow is more than just a place to live—it's a lifestyle. Whether you’re seeking a peaceful retreat or an active community, this enchanting village invites you to make it your home.

Newest Listings in Sleepy Hollow

102 Legend Drive Unit #303, Sleepy Hollow
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 1063497 MLS
Elevated Living at Edge-on-Hudson! Discover an exceptional blend of contemporary design, effortless comfort, and extraordinary outdoor living at 102 Legend Drive, Unit 303. One of a total of 17 Condominium Lofts completed in 2022, this beautifully appointed corner two-bedroom, two-bath duplex residence offers an expansive open-concept layout filled with natural light, elegant finishes, and thoughtfully designed spaces for both everyday living and entertaining, a private roof terrace, and one of the few indoor parking spaces. Oversized black-framed windows create a striking architectural backdrop, while rich hardwood floors add warmth and sophistication. The beautifully designed open kitchen features crisp white cabinetry, stainless steel appliances, and an oversized island with seating for four. The adjoining dining and living areas flow seamlessly together, creating an inviting atmosphere for intimate gatherings or larger celebrations. A private balcony extends the living space outdoors. The primary suite offers a peaceful retreat with two walk-in closets and a spacious bath featuring a double vanity and glass-enclosed shower. The sun-flooded and versatile second bedroom at the opposite end of the living space offers privacy and works great as a bedroom, guest room or office. A full hallway bath as well as in-unit laundry completes the main level. Upstairs, a sun-filled loft-style office or bonus room opens directly onto the home's spectacular private rooftop terrace. This extraordinary outdoor oasis offers abundant space for dining, lounging, and entertaining beneath the open sky. Imagine summer dinners under the pergola, evenings gathered around the fire table, or simply enjoying a quiet morning coffee in your own private retreat. Additional highlights include one of the few and highly coveted private indoor garage spaces and access to beautifully designed community amenities, including a fitness center and residents' lounge. Set within Edge-on-Hudson, Sleepy Hollow's exciting Hudson River waterfront neighborhood, this distinctive residence combines the charm of the historic Hudson Valley with a sophisticated, contemporary lifestyle. Enjoy proximity to waterfront recreation, local restaurants, shopping, and the many attractions of Sleepy Hollow, Tarrytown, and the other nearby "Rivertowns." A remarkable opportunity to enjoy modern luxury, exceptional private outdoor space, and the best of Hudson Valley living.

102 Legend Drive Unit #303, Sleepy Hollow
364 Legend Drive Unit #108, Sleepy Hollow
$2,125,000
3 Beds ⋅ 5 Baths ⋅ 936219 MLS
Luxury townhomes on the edge of the Hudson River. One Kingsland at Edge-on-Hudson offers a unique collection of thoughtfully designed townhomes, nestled along the Hudson River in Sleepy Hollow. With a deep commitment to quality and the detailed essentials of modern living, Sun Homes offers a unique chance to live within easy access to nature, community, culture, and home – all in one day. Three-to-five-bedroom townhomes, ranging in size from 2,955 SF to 4,140, all feature elevators, fireplaces and an exquisite quality of materials, craftsmanship, and design. Natural hardwood flooring, private outdoor spaces, and soaring ceilings create inviting spaces. Set within the award-winning community of Edge-on-Hudson, the One Kingsland neighborhood is ideally located highlighting park and river views, a private Clubhouse, Pool & Gym and just a few short minutes from two Metro-North Stations and a new DeCicco & Sons market.

364 Legend Drive Unit #108, Sleepy Hollow
315 Hollows Pass Unit #42, Sleepy Hollow
$2,450,000
3 Beds ⋅ 5 Baths ⋅ 936770 MLS
Luxury townhomes on the edge of the Hudson River. One Kingsland at Edge-on-Hudson offers a unique collection of thoughtfully designed townhomes, nestled along the Hudson River in Sleepy Hollow. With a deep commitment to quality and the detailed essentials of modern living, Sun Homes offers a unique chance to live within easy access to nature, community, culture, and home – all in one day. Three-to-five-bedroom townhomes, ranging in size from 2,955 SF to 4,140, all feature elevators, fireplaces and an exquisite quality of materials, craftsmanship, and design. Natural hardwood flooring, private outdoor spaces, and soaring ceilings create inviting spaces. Set within the award-winning community of Edge-on-Hudson, the One Kingsland neighborhood is ideally located highlighting park and river views, a private Clubhouse, Pool & Gym and just a few short minutes from two Metro-North Stations and a new DeCicco & Sons market.

315 Hollows Pass Unit #42, 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 (vacant). 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 (425 SqFt) with separate laundry, and direct access to a 1-car garage. The second floor unit is vacant. 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 in the photos - this apartment can be seen in person)

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
212 Beekman Avenue, Sleepy Hollow
$995,000
5 Beds ⋅ 2 Baths ⋅ 818602 MLS
Welcome to 212 Beekman Avenue, a versatile multi-family property with commercial zoning, offering endless possibilities in Sleepy Hollow. This unique property features two distinct apartments and is ideal for investors or those seeking a flexible living space. The ground floor apartment has 2 bedrooms, 1 bath. The first floor apartment is a duplex with 3 bedrooms and 1 bath, catering to a variety of lifestyle needs. Enjoy the comfort of central air conditioning throughout the property, ensuring a pleasant atmosphere during any season. There is a large back yard and an outbuilding in the back of the property for storage. The commercial zoning adds an extra layer of opportunity, allowing for potential business ventures or mixed-use possibilities. With its prime location on Beekman Avenue, 212 offers both convenience and potential. Whether you're looking to invest, live, or work, this property is a must-see. Explore the opportunities today and imagine the future that awaits!

212 Beekman Avenue, 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
4 Lighthouse Landing Unit #PH501, Sleepy Hollow
$1,540,000
2 Beds ⋅ 3 Baths ⋅ 1042876 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. New Construction.

4 Lighthouse Landing Unit #PH501, Sleepy Hollow
4 Lighthouse Landing Unit #302, Sleepy Hollow
$1,780,000
2 Beds ⋅ 3 Baths ⋅ 1042873 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. New Construction.

4 Lighthouse Landing Unit #302, Sleepy Hollow
4 Lighthouse Landing Unit #305, Sleepy Hollow
$1,840,000
2 Beds ⋅ 3 Baths ⋅ 1027122 MLS
The Daymark brings luxury waterfront condominium living to the banks of the Hudson River in Sleepy Hollow, New York. Envisioned by architecture firm COOKFOX, The Daymark offers modern day comforts while harnessing the breathtaking beauty of its surroundings. Interior materials have been chosen to reflect the organic tones and textures of its waterfront setting. Our uncompromising commitment to quality extends into each uniquely designed residence with spacious open floor plans and crafted, quality materials. Fully-equipped kitchens offer state-of-the-art integrated appliances while bathrooms offer a private oasis clad in marble with floating tubs. The Daymark lifestyle extends beyond each residence with indoor/outdoor amenities including lobby with concierge, fitness center with yoga studio and swimming pool with stunning views. The indoor and outdoor amenity spaces have been thoughtfully curated to support life, work and a passion for healthy, balanced living. New Construction.

4 Lighthouse Landing Unit #305, 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.

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