Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, New York—a picturesque village nestled in the heart of Westchester County, renowned for its enchanting landscapes and rich history. With its charming small-town vibe and stunning riverside views, Sleepy Hollow offers a unique blend of modern living and historical significance.

Steeped in legend, Sleepy Hollow is famously linked to Washington Irving’s classic tale of “The Legend of Sleepy Hollow,” which brings a whimsical touch to this vibrant community. Residents and visitors alike can explore the iconic sites, including the Sleepy Hollow Cemetery, where Irving himself rests, and the historic Old Dutch Church, a beautiful example of colonial architecture.

Nature lovers will find solace in the lush parks and scenic trails that line the Hudson River, perfect for hiking, biking, or simply enjoying a leisurely stroll. The nearby Rockefeller State Park Preserve offers miles of trails and breathtaking views, making it an ideal spot for outdoor enthusiasts.

In addition to its natural beauty, Sleepy Hollow boasts a thriving arts scene and a variety of dining options, from cozy cafes to upscale restaurants. The village hosts numerous events throughout the year, fostering a strong sense of community and camaraderie among residents.

With its convenient location just 30 miles north of Manhattan, Sleepy Hollow provides easy access to urban amenities while maintaining the tranquility of suburban life. Whether you’re seeking a family-friendly neighborhood, a vibrant cultural scene, or simply a place to unwind, Sleepy Hollow is a hidden gem that invites you to call it home. Discover the charm of Sleepy Hollow today!

Newest Listings in Sleepy Hollow

$970,000

7 Beds ⋅ 4 Baths ⋅ 1030605 MLS

Centrally located in the historic Village of Sleepy Hollow, just one block from vibrant Beekman Avenue, this turnkey Two-Family home with numerous improvements and updates in recent years, offers an exceptional opportunity for owner-occupants and investors alike. Both units are uniquely large duplexes - 1,745 SF (4 bed, 2 full baths) and 1,650 SF (3 bed, 2 full baths) - each featuring a private deck, an eat-in kitchen, in-unit laundry, high ceilings, tall windows, and on-site parking. This property is ideally suited for those looking to live in one unit while offsetting their mortgage and property taxes with rental income, or investors looking to add to their rental portfolio. Within one mile you’ll find the Metro-North Tarrytown Station (36 minutes from NYC), the scenic Hudson River waterfront, marinas, restaurants, and the transformative Edge-on-Hudson development, DeCicco & Sons gourmet supermarket, and more. 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 this Fall. Stated taxes are before the STAR savings of $1,591 for those who owner-occupy.

9 Irving Place, 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. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #305, Sleepy Hollow

$479,500

4 Beds ⋅ 2 Baths ⋅ 1019741 MLS

Exceptional investment opportunity in the heart of Sleepy Hollow! This legal two-family property offers tremendous potential for investors, contractors, builders, or buyers seeking to restore a property in one of Westchester County's most desirable river communities. Being sold strictly **AS-IS**, the home requires substantial renovation and presents an ideal full rehabilitation project. Ideally situated just moments from the vibrant downtown, enjoy convenient access to the Metro-North train station, the Hudson River waterfront, parks, restaurants, shopping, and the scenic RiverWalk. The rear porch offers seasonal views toward the Governor Mario M. Cuomo Bridge, adding to the property's unique setting. Whether your vision is to renovate and hold as an income-producing asset or restore it for resale, this property offers an exceptional opportunity to create value in a location where renovated multifamily homes continue to see strong demand. Buyers are encouraged to perform their own due diligence regarding condition, zoning, permits, and future use.

10 Clinton Street, Sleepy Hollow

$1,195,000

1 Beds ⋅ 2 Baths ⋅ 1011963 MLS

Welcome to The Lofts at Edge-on-Hudson, where modern design meets vibrant waterfront living and a quick walk to the Metro North Train takes you right into Manhattan. This exceptional 1,178-square-foot duplex features a finished loft that can easily serve as a second bedroom, home office, or guest space, along with a private 300-square-foot rooftop deck complete with a covered pergola - an ideal setting for outdoor dining, entertaining, or simply relaxing. Inside, the open-concept floor plan is filled with natural light and enhanced by soaring 10-foot ceilings and wide-plank hardwood floors. The chef's kitchen is beautifully appointed with quartzite countertops, custom cabinetry, a full tile backsplash, stainless steel appliances, a professional-grade hood, and a peninsula with seating for four. The spacious primary suite offers a walk-in closet, while the luxurious bath features marble finishes and a mirrored vanity. Additional upgrades include custom closets, designer shades, and in-unit laundry. A private heated garage with EV charging capability and built-in storage, plus an additional driveway parking space, provide rare convenience. Residents enjoy access to premium amenities including a fitness center, owners' lounge, rooftop terrace, full-time superintendent, rentable storage, and Verizon FiOS included in the HOA. Located in Sleepy Hollow's award-winning Edge-on-Hudson waterfront community, residents are just moments from the RiverWalk promenade, parks, trails, DeCicco & Sons, waterfront restaurants, and Metro-North service to Grand Central. This is a rare opportunity to enjoy sophisticated loft-style living in one of Westchester's most exciting riverfront destinations.

102 Legend Drive Unit #301, Sleepy Hollow

$2,175,000

4 Beds ⋅ 5 Baths ⋅ 1010732 MLS

Introducing one of the most exceptional residences in the sought-after Edge-on-Hudson. This stunning Toll Brothers end-unit, the largest model in the community, has been extensively upgraded and professionally designed, offering a level of sophistication and customization rarely found in new construction. Walls of windows and glass doors bathe the home in natural light, creating bright, inviting spaces and seamless indoor-outdoor living. Thoughtfully curated by a professional interior designer, the residence showcases elevated finishes, custom details, and a refined aesthetic throughout. The spectacular rooftop retreat serves as a private oasis, featuring a covered outdoor living room with lounge seating and an expansive open-air terrace ideal for dining, entertaining, and relaxing. Equally impressive is the custom-finished two-car garage, designed to complement the home’s luxury lifestyle while providing exceptional functionality and storage. Combining the privacy and abundance of light afforded by a premier end location with extensive upgrades, designer finishes, and outstanding indoor and outdoor living spaces, this turnkey residence represents a rare opportunity within Westchester’s premier waterfront community. Conveniently located On the Hudson River, The Riverwalk, parks, restaurants, shopping, and Metro-North for an effortless short commute to Manhattan.

340 Horseman Boulevard, Sleepy Hollow

$1,249,500

2 Beds ⋅ 3 Baths ⋅ 1010826 MLS

Single-floor living at its finest at the Lofts at Edge-on-Hudson. This stunning 1,190 sq. ft. two-bedroom, two-ensuite layout with additional powder room (2.5 bath total) blends generous interior space with a private covered balcony. The open layout feels expansive and airy, enhanced by hardwood flooring, 10-foot ceilings and southern exposures that fill the home with natural light throughout the day. The kitchen features a refined palette of materials, including waterfall quartz island countertops, full-height custom cabinetry, complete tile backsplash, stainless steel appliances, and a professional-grade hood, creating a space that is as functional as it is elegant. Thoughtful upgrades continue throughout the home, including fully built-out walk-in closets, custom wallcoverings, Hunter Douglas automated shades, custom loft curtains, water filtration system, lighting upgrades, in-wall Sonos speakers, and in-unit laundry. The primary bath features full-height porcelain tile and natural blue stone flooring and the second bedroom ensuite features porcelain tile throughout. The energy efficient HVAC system features an Energy Recovery Ventilator (ERV) system, an advanced mechanical ventilation system that continuously replaces and filters the home's air with fresh air, improving interior air quality, lowering utility costs, and creating healthier living spaces. The covered balcony has been upgraded with maintenance free Teak wood composite decking and year round plantings, creating a polished outdoor retreat perfect for coffee at sunrise or effortless indoor–outdoor entertaining. Parking and storage are equally convenient with a private garage equipped with built-in storage plus additional parking available in a private lot. Residents of the Lofts enjoy access to a lounge, fitness center on the first floor, and rooftop terrace. Building has full-time super and storage closets available for rent on the first floor. Verizon FiOS is included in the HOA. Located within Edge-on-Hudson, Sleepy Hollow’s vibrant waterfront community just 25 miles north of Midtown Manhattan, the building is ideally positioned near the RiverWalk waterfront promenade, scenic trails, parks, and DeCicco & Sons gourmet market. Two Metro-North stations with express service to Grand Central are nearby, with shuttle pickup and drop-off directly at the building entrance. A rare opportunity to enjoy modern loft living with outdoor space in one of the Hudson River’s most exciting waterfront communities. Town and school taxes have been successfully grieved and reductions are in place for 2026.

100 Legend Drive Unit #206, Sleepy Hollow

$1,950,000

4 Beds ⋅ 5 Baths ⋅ 1005652 MLS

Experience the pinnacle of waterfront living in this extraordinary Park Model residence, the largest and most extensively customized townhome in the prestigious Edge-on-Hudson Brownstone collection. Perfectly positioned to capture sweeping Hudson River vistas and the glowing lights of the Mario M. Cuomo Bridge, this exceptional home transcends standard luxury through bespoke craftsmanship, designer finishes, and state-of-the-art infrastructure. The journey begins on the entry level with a sophisticated library-style study, or first-floor bedroom, featuring herringbone flooring and a hand-carved sandstone mantel on a decorative fireplace meticulously crafted by artisans in India. This level of thoughtful design continues throughout the residence, from the designer wallpapered “jewel box” powder rooms to the custom millwork, curated finishes, and three distinctive gas fireplaces that create warmth and character across multiple living spaces. At the heart of the home is a world-class chef’s kitchen designed for both everyday living and elegant entertaining. Anchored by an oversized waterfall concrete island, the space features furniture-quality custom cabinetry and a professional-grade appliance suite including Wolf, Sub-Zero, and Miele. The kitchen flows seamlessly into the expansive Great Room, where a stunning custom marble gas fireplace serves as a dramatic focal point, framed by elegant architectural detailing and abundant natural light. Upstairs, the primary suite offers a boutique-hotel-inspired sanctuary with dual walk-in closets and a spa-like bath featuring a freestanding soaking tub, and custom designer mirrors. Additional guest accommodations provide flexibility for family and visitors, while a dedicated laundry room conveniently located on the bedroom level offers exceptional everyday convenience. The top floor functions as a private retreat, an en-suite bedroom and bath, complete with its own gas fireplace. From here, French doors open onto a truly spectacular rooftop oasis with stunning river views designed for year-round entertaining. This remarkable outdoor living space features an automated louvered pergola, premium wood decking with integrated lighting, a built-in Alfresco outdoor kitchen, under counter refrigeration, and a gas fireplace for cooler evenings—all set against panoramic Hudson River views that create an unforgettable backdrop for dining, entertaining, or simply watching the sunset or fireworks. The lifestyle here is defined by effortless connection and exceptional convenience. Whether starting your morning on the scenic riverfront paths, picking up gourmet essentials at DeCicco & Sons, enjoying waterfront parks and green spaces, or taking the private shuttle to Metro-North for a seamless Manhattan commute, every amenity is at your doorstep. Residents also enjoy premier access to the Tarrytown Recreation Center, featuring a swimming pool, fitness center, tennis courts, and pickleball facilities. This is far more than a residence—it is a sophisticated waterfront sanctuary designed for those who refuse to compromise on quality, craftsmanship, lifestyle, or location.

207 Palisades Boulevard, Sleepy Hollow

$2,500,000

4 Beds ⋅ 5 Baths ⋅ 1007046 MLS

The Layout and First Impressions Living in this modern, four-level end-unit brownstone is an absolute dream. The home is completely flooded with natural light, which perfectly highlights the neutral color palette. No expenses were spared on upgrades, putting down top-tier Light Oak engineered hardwood throughout the entire home. When you enter on the ground floor, you walk into a functional space featuring a mudroom, direct access to the two-car garage, and a flexible bedroom that can be used as a home office. Main Living and Gourmet Kitchen Upstairs is the heart of the home—an open-layout living with high-end finishes. The kitchen is a true chef’s space with crisp white cabinetry, top of the line appliances, a massive center (extra thick) marble island, and endless counter space. In the living room, the absolute focal point is the floor-to-ceiling dark stone fireplace surround, which naturally draws people in for conversation. The dining room feels straight out of a design magazine, anchored by a glamorous, custom breakfront that always sets an elegant tone for dinner parties. Note: All four of the Bedrooms have ensuite bathrooms. The primary suite on the third floor is a personal sanctuary. It features two massive walk-in closets and a spectacular, tres chic spa bath with specifically chosen fixtures. The laundry room is conveniently located on this same floor, right next to the second bedroom. On the top floor, a built out a fully finished loft. It has a third bedroom that is perfect for guests or a second home office. It also features a 15-foot square den equipped with its own refrigerator, sink, & dishwasher creating a Wet Bar area—ideal for watching the game and/or entertaining in general. Best of all the rooftop terrace is where you can enjoy daytime sun or spend your evenings, taking in breathtaking views of the waterfront and the bridge. The partially covered terrace (which also allows you to have the option to escape the sun if/when desired) is equipped with a custom outdoor kitchen with a built-in grill. There is also a natural gas fireplace (which is a rare amenity sighting in these style brownstones) making it an incredible & unique spot for alfresco outdoor dining and hosting. The location itself is unbeatable. Just steps from the front door is the RiverWalk paths featuring gorgeous landscaping, benches, nighttime lighting, performance spaces, and Horan's Landing Park giving access to paddleboarding & Kayaking. Let's not leave out the Historic Lighthouse flanked by Kingsland Point Park. To make things even sweeter, the new DeCicco's market is just a stones throw away. Amazing list of extra amenities included: This "High-Tech" unit is equipped with automatic blackout shades throughout if/when desired. Actually...you will be able to control the thermostat, blinds, tv's, and speakers all from your smartphone (via: Control4 Ring, & MyQ programs/apps. It provides a quick 37-minute commute to Manhattan and sits steps from the historic, amenity-rich village of Sleepy Hollow & Tarrytown.

324 Horseman Boulevard, Sleepy Hollow

$1,500,000

5 Beds ⋅ 4 Baths ⋅ 1004633 MLS

Rare Sleepy Hollow 2-Family Double-Duplex with River & Bridge Views.....!! This opportunity in the heart of historic Sleepy Hollow has been impeccably maintained is perfect for smart investors or owner-occupants looking for financial flexibility. Both spacious units are incredibly clean and feature beautifully updated kitchens and bathrooms, allowing you to move right in. A finished lower walkout level with a separate entrance provides excellent bonus space. The property offers unmatched convenience with a massive driveway that parks over 10 cars, plus a large 5-car detached garage. Best of all, the property is commercially zoned including the separate (detached) building at the rear of the lot which can be utilized in many ways—ideal for a private office or retail business or just collect cars! Location is everything, and this home puts you in the center of it all. You are just steps away from the scenic waterfront, Old Croton Aqueduct, and Rockefeller Preserve trails. Walk to local schools, vibrant shops, and dining. Commuters will love the easy trek to the Metro-North train station. With ongoing village redevelopment boosting long-term value, this is an investment you do not want to miss. Having parking on Beekman Ave. is a premium.....and to state it again so you are clear...this (Double Lot) property hosts a total of 15 cars comfortably. 10 Cars in driveway and 5 cars in the garage. Come see for yourself.....

144 Beekman Avenue, Sleepy Hollow

$699,000

5 Beds ⋅ 2 Baths ⋅ 979061 MLS

Location, Location, Location...Own a Piece of New York's Halloween Capital - Sleepy Hollow! Located a few blocks from the Hudson River & all the Awesome sight's that make this Village Special: Historic Sleepy Hollow Cemetery & Old Dutch tours, Headless Horseman Bridge, Washington's Headless Horseman Statue & Haunted Orchards. Live here - a great investment & rent out the other unit, This desirable Multi-family home is the best place to Live...Imagine the possibilities. Was updated in past 20 years. Being sold As-is as - it needs some TLC! Unit#2 - Upper floor 2 Bedroom unit has partial River/Bridge views, Pull down Attic that is excellent storage: partial standup with Plywood board flooring & 2 windows. Unit#1 is the Main Unit with Hard-Wood Floors Main floor entry into Living Room, Den/Home Office, Primary Bedroom w/stairs to back yard & Full Bathroom. Then 1 flight down to Bedroom 2 & 3, with lots of closets (including Hall Cedar closet), Large Eat in Kitchen, Mud room with exit to Back Yard - with Hook up for a Washer/Dryer if desired. Come take a look & walk around the neighborhood - visit the shops, restaurants and Markets including the new Favorite: DeCicco & Sons Market. This is why Zip Code 10591 is So DESIRABLE!!! ***NOTE: NO OFF STREET PARKING - GARAGE IS NEIGHBORS NEXT DOOR!!!

34 Cedar Street, Sleepy Hollow

$999,999

2 Beds ⋅ 4 Baths ⋅ 997463 MLS

Welcome Home to Sunset Villas at Andrews Lane Sleepy Hollow, NY. From $899,999+ Discover Sunset Villas, an exclusive collection of nine luxury townhomes, perfectly nestled in the heart of the Village of Sleepy Hollow. Enjoy a limited-time advantage with no HOA fees for the first 6 months and step into a lifestyle that blends modern elegance with everyday convenience. This stunning (end unit) four-level residence offers a thoughtfully designed layout and elevated finishes throughout: Grand entry level featuring an oversized foyer with ceramic tile flooring, a convenient powder room, and access to a spacious one-car garage. A designer kitchen at the heart of the home, showcasing quartzite countertops, sleek cabinetry, and premium stainless-steel appliances—ideal for both everyday living and entertaining. Seamless indoor-outdoor living with a private deck, perfect for al fresco dining. A light-filled living room with fireplace, enhanced by recessed lighting and elegant crown molding. Beautiful hardwood flooring flows throughout the upper three levels, creating a warm and cohesive feel. The third level features a luxurious primary suite with double closets and a spa-like en-suite bath, along with a generously sized second bedroom with its own en-suite. The fourth level offers a versatile family or guest retreat, complete with a full bath, walk-in closet, and a private rooftop terrace—an extraordinary space to unwind, entertain, and take in breathtaking sunset views. Location matters—and this one delivers: Directly across from Barnhart Park & Playground. Moments from Hudson River views. Close to fine dining, boutique shops, and village charm. Easy access to major commuting routes. Modern luxury. Scenic surroundings. Effortless living. Sunset Villas is the perfect place to call home.

36 Andrews Lane, Sleepy Hollow

$999,999

2 Beds ⋅ 4 Baths ⋅ 997460 MLS

30 Andrews Lane, Sleepy Hollow

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