Sleepy Hollow Real Estate

3 Beds ⋅ 1 Baths ⋅ 1041980 MLS

Nestled in the heart of Pocantico Hills Hamlet, this special threebedroom 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 nature— right from your own backyard. Everyday life is wonderfully convenient, too. The Pocantico Hills School, swimming pool, and recreation facilities are just a five minute walk 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, Pleasantville, and Sleepy Hollow.The community’s recreation amenities include an Olympic-size swimming 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

$1,540,000

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. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #PH501, 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. Additional Information: Amenities:Storage,

4 Lighthouse Landing Unit #302, 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

$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

$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

Sleepy Hollow Real Estate

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