Sleepy Hollow Homes with Driveway Parking features

Welcome to Sleepy Hollow, New York – a picturesque village nestled in the heart of Westchester County, where history meets modern charm. Known for its stunning riverside views and rich literary heritage, Sleepy Hollow is not just a place to live; it's a lifestyle. With its iconic landmarks like the Old Dutch Church and the breathtaking landscapes along the Hudson River, this enchanting community offers residents a unique blend of tranquility and vibrancy.

Sleepy Hollow is also home to a variety of beautiful homes, many of which feature convenient driveway parking. Imagine coming home to your charming abode, where you can easily park your vehicle right outside your door. This feature is particularly valuable in a community like Sleepy Hollow, where the serene streets invite leisurely strolls and outdoor exploration. Driveway parking not only adds convenience to your daily routine but also enhances the overall appeal of your property.

Whether you’re looking for a cozy cottage, a spacious family home, or a modern townhouse, Sleepy Hollow has something for everyone. Residents enjoy easy access to local parks, quaint shops, and delightful eateries, all while being just a short commute from the bustling city of New York.

Experience the perfect balance of suburban serenity and urban accessibility in Sleepy Hollow. With homes that offer the added benefit of driveway parking, you can embrace the charm of this historic village while enjoying the comforts of modern living. Come discover your dream home in Sleepy Hollow, where every day feels like a story waiting to be told!

Newest Sleepy Hollow Homes with Driveway Parking features

$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

$1,195,000

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

$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

$1,299,000

2 Beds ⋅ 3 Baths ⋅ 971802 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

$1,850,000

4 Beds ⋅ 5 Baths ⋅ 971740 MLS

Please send pof or pre app to phyllis before showing...Beautiful 4-bedroom, 3 full and 2 half bath townhome at Brownstone- Edge on Hudson, perfectly positioned to capture breathtaking river views and the iconic Mario Cuomo Bridge. This exceptional home showcases top-notch craftsmanship in the heart of Sleepy Hollow along the Hudson River. Designed for today’s modern lifestyle, it features an open floor plan, high ceilings, oversized windows, and rich hardwood floors throughout. The first level offers a flexible bedroom or home office with a full bath, a mudroom, and direct access to the two-car garage. On the second floor, natural light pours into the spacious dining area, gourmet kitchen is a chef's dream, complete with high-end appliances a walk-in pantry, and oversize center island. Living room, which features a gas fireplace, custom built-ins, and access to a private terrace. A powder room completes this level. Upstairs, the primary suite offers a walk-in closet and a luxurious en-suite bath. Two additional bedrooms, hall bath and laundry . The top level is designed for entertaining, featuring a large recreation room with a half bath, wine fridge, ice maker, and projector with screen. Step outside to a loft-style area with a counter, sink, and dishwasher, leading to a spacious deck with stunning river and bridge views. Enjoy a vibrant waterfront lifestyle with a scenic river walk and the nearby upscale DeCicco & Sons gourmet market, offering a specialty deli, fresh baked goods, a bar, and a large outdoor patio. Convenient jitney service to Tarrytown and easy access to Metro-North provide a seamless commute to Manhattan. This exceptional location combines the charm of picturesque villages, historic landmarks, and expansive green space with modern convenience. Don’t miss this one!

203 Palisades Boulevard, Sleepy Hollow

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.