Sleepy Hollow Real Estate Search

Sleepy Hollow Properties between $900,000 and $1,000,000 for Sale

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Newest Sleepy Hollow Properties between $900,000 and $1,000,000 for Sale

$999,999
5 Beds 3 Baths 1028064 MLS
Welcome to your forever home, where privacy, space, and community come together in one of Tappan's most sought-after locations. Nestled at the end of a private road and situated on an impressive 0.77-acre lot, this exceptional five-bedroom, three-full-bath Colonial offers the perfect blend of peaceful living and everyday convenience. With no homes directly behind you, you'll enjoy a level of privacy that is increasingly difficult to find, while still being just minutes from everything that makes Tappan such a desirable place to call home. From the moment you arrive, you'll be captivated by the inviting wraparound rocking chair porch the perfect place to enjoy your morning coffee, unwind after a long day, or gather with family and friends while taking in the peaceful surroundings. Step inside and discover a home designed . Offering generous living spaces, five spacious bedrooms, three full bathrooms, and a beautifully finished basement, there is room for everyone to spread out, work from home, entertain, and create memories for years to come. The heart of the home flows effortlessly to the backyard, where a two-tier deck extends your living space outdoors. Whether you're hosting summer barbecues, celebrating birthdays, or simply enjoying a quiet evening overlooking your private backyard, this outdoor retreat was made for entertaining and everyday enjoyment. The expansive property offers endless possibilities for play, gardening, a future pool, or simply enjoying the serenity of having no rear neighbors. Located in the charming hamlet of Tappan, this home offers more than just beautiful living space—it provides an incredible lifestyle. Known for its strong sense of community, neighborhood events, parks, local restaurants, and welcoming atmosphere, Tappan continues to be one of Rockland County's most desirable places to live. you will appreciate the highly regarded schools, nearby recreational facilities, and convenient access to major highways, making commuting to New York City, New Jersey, and Westchester both simple and convenient. Homes offering this combination of privacy, nearly three-quarters of an acre, five bedrooms, three full baths, a finished basement, wraparound porch, expansive outdoor entertaining space, and an unbeatable location** are truly rare. If you've been searching for a home where your family can grow, entertain, and build lasting memories, this is the opportunity you've been waiting for. **Welcome home to Tappan.

4 Hauser Terrace, Tappan

$965,000
7 Beds 3 Baths 1029229 MLS
Experience exceptional value and flexibility in this remarkable two-family residence, offering over 3,000 square feet in one of Bayonne’s most desirable neighborhoods in a park-like setting. This spacious two-family home features a total of seven bedrooms and three bathrooms allowing for endless possibilities for your ever expanding needs. Pass by the beautifully landscaped front garden to access the welcoming entrances from the tranquil front veranda. The updated first-floor two-bedroom unit features hardwood floors and craftsman-style charm which seamlessly connects the foyer, living room and formal dining room. The fantastic layout of this home allows flow from the formal dining room into the recently renovated eat-in kitchen, which includes a pantry for added storage. Two nice-sized bedrooms and a well-designed bathroom complete this wonderful and charming first-floor unit. The extremely spacious second floor unit consists of five bedrooms and two full bathrooms across two levels including a separate space for a private office or bedroom.  Enjoy an outdoor oasis in the rear garden, perfect for relaxing and entertaining. Situated on a quiet, tree-lined street near parks, local shops, and transit options including the 34th St Light Rail. Do not miss the rare opportunity to own a two-family gem in this well sought after neighborhood. Off-street parking is available for up to 4 vehicles. Schedule your showing today- rare opportunities like this do not last.

99 W 37th Street, Other

$938,000
3 Beds 2 Baths 1029076 MLS
Nestled in a quiet, R2-A zoned pocket of Flushing, this beautifully maintained 1960 detached ranch perfectly blends classic comfort with exceptional functionality. The sun-drenched 996 sq ft main floor features pristine hardwood floors throughout, a bright living space, three comfortable bedrooms, and a full bathroom. For extra storage, a convenient pull-down ladder grants quick access to a fully finished attic. The home’s usable space expands with a massive 936 sq ft fully finished basement with a private entrance, bringing the total footprint to 1,932 sq ft. This flexible lower level adapts to long-term guests or premium entertaining, complete with a full bath, wet bar hospitality area, custom bar, and laundry room. Unrivaled structural and mechanical updates offer years of worry-free ownership. The home boasts a brand-new roof (2023), a new water heater (2025), and five ductless units for zoned climate control. Cozy radiator heating keeps winters warm, while professional French drains ensure the lower level stays bone-dry. Outside, a long private driveway leads to a detached 1-car garage. Your sanctuary is protected by a commercial-grade security network. Upgrades include a wall-mounted 6-camera CCTV system with a 2TB hard drive (expandable by 2 cameras), keyless front entry, anti-pick locks, and Door Armor reinforced entryways. Window security bars are also intelligently designed with thoughtfully engineered emergency exits from the bedrooms. Move-in ready and built to last, this Flushing gem is a rare find.

4724 168th Street, Flushing

$925,000
3 Beds 2 Baths 1027975 MLS
ATTENTION WORK-AT -HOME PROFESSIONALS AND THOSE SEEKING MOTHER DAUGHTER SET UP! Discover a true Pleasantville unicorn — a charming 1930’s single family home with legal commercial ground floor space offering rare flexibility, unbeatable walkability, and the kind of village convenience buyers dream about. Perfectly situated just 0.2 miles to the Pleasantville Metro-North Station, 0.4 miles to Bedford Road School, and 0.3 miles to both the Middle and High Schools, this home delivers effortless access to every part of town. Shops, dining, parks, the Farmers Market, and the Jacob Burns Film Center are all moments away, with easy ON/OFF access to the Saw Mill River Parkway for seamless commuting. County Tax classification code is R-02, the ground-floor unit is a standout feature — ideal as a professional home office (light business permitted) or as a 750 sq ft above ground living space. Previously used as a real estate office, it now functions as a comfortable residential space with endless potential with private entrance and second egress. . The main 3-bedroom apartment offers classic warmth and modern convenience, featuring a chef’s stove, EI kitchen w. SGD onto patio, formal dining room, sun room and living room. The second floor offers f primary bedroom, and two additional secondary bedrooms . The home has been fairly well maintained and is ready for you to personalize and make your own. This home offers off-street parking for at least three vehicles. With flexible zoning, walk-to-everything convenience, and timeless 1930’s character, 4 Depew Street is a one-of-a-kind Pleasantville opportunity. Zoning allows for 6 foot signage that is visible from Saw Mill River Parkway. .

4 Depew Street, Pleasantville

$975,000
4 Beds 2 Baths 1025708 MLS
Welcome to 22 Milburn Rd. This stunning, four-bedroom, two full baths, split-level home is move-in-ready, with over 2,220 square feet of living space, and is located in the award-winning Three Village School District. This home offers a perfect blend of comfort, style, and modern upgrades. Featuring a brand-new roof and new exterior siding, it boasts exceptional curb appeal. Inside, the entire top floor is adorned with gleaming hardwood floors, extending through the dining room, living room, kitchen, and all four bedrooms, complemented by elegant crown moulding. The kitchen is a chef’s dream with new Bosch appliances, a gas stove, and Kraftmaid custom bathroom cabinets. Additional highlights include baseboard heating, two wall-mounted A/C units, a natural gas burner, and a new electric panel with warranty. The home also offers tile flooring in the den, laminate in the basement, and wood-like porcelain tile in the laundry room and garage. Enjoy peace of mind with ADT Home Security, plantation shutters, and custom Hunter Douglas wood blinds and custom Norman Woodlore Plantation Shutters. Outdoor living is elevated with a brand-new stone-reinforced pool and new electrical box for the 22x44 heated salt-water pool, three sheds, plus a new garage door and new downstairs windows. A brand new Bosch heating and cooling system.. The beautifully landscaped "park-like" grounds include meticulously maintained trees, shrubs, species plantings, gardens, and a manicured lawn. The in-ground pool is conveniently centered on the property so that the owners can utilize the abundant acreage which extends beyond the pool. Three sheds can house pool accessories and garden tools, bicycles, and more. This home has proximity to shopping, dining, cultural venues (Staller Center), educational institutions (SUNY), hospitals, Renaissance Technologies, golf courses, tennis courts, public pools and beaches, easy access to mass transit, Port Jefferson Ferry, close to parkways and expressways, nearby houses of worship, and low taxes.

22 Milburn Road, South Setauket

$975,000
4 Beds 3 Baths 1026664 MLS
Nestled on a picturesque road in the heart of South Salem, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect balance of privacy, comfort, and convenience. Lovingly cared for by only its second owner, this exceptional home has been thoughtfully updated over the years while maintaining its warmth and charm. Set amid mature woodlands, the hilltop retreat offers a peaceful backdrop with exceptional privacy while remaining just minutes from everything you need. Designed for both everyday living and entertaining, the light-filled interior features a spacious, flowing layout with oversized windows that fill the home with natural light. The inviting living room is anchored by a cozy fireplace, creating the perfect gathering space, while the generous living areas seamlessly connect to an expansive oversized deck for effortless indoor-outdoor living. Whether hosting friends and family or enjoying a quiet morning surrounded by nature, the outdoor spaces are equally inviting. As the day winds down, unwind on the charming front porch and take in spectacular sunset views. Numerous improvements have been made throughout the years, including a beautifully renovated spa-inspired primary bathroom, an updated first-floor full bathroom, significant mechanical upgrades and many other thoughtful enhancements that provide peace of mind for years to come. The versatile lower level, currently configured as a recording studio, offers endless possibilities and can easily be transformed into a home office, recreation room, fitness studio, playroom, or creative space to fit your lifestyle. Ideally located just minutes from the charming hamlets of South Salem, Ridgefield and Katonah, you'll enjoy convenient access to boutique shopping, award-winning restaurants, wellness studios, parks, golf courses, hiking trails, and year-round recreation. Commuters will appreciate the nearby Katonah Metro-North Station with direct service to Grand Central Terminal, as well as easy access to I-684, I-84, and the Saw Mill River Parkway. Westchester County Airport is approximately 30 minutes away, making business and leisure travel effortless. The home is also conveniently located near highly regarded public schools. Whether you're seeking peaceful country living, an easy commute, or convenient access to vibrant town centers, this exceptional South Salem home offers the best of Westchester County living in one of its most desirable locations.

1 Sabbathday Hill Road, South Salem

$949,000
4 Beds 3 Baths 1026993 MLS
Circa 1921, this charming and thoughtfully updated 4-bedroom, 2.5-bath residence beautifully blends historic character with modern comfort. Lovingly maintained and improved throughout, this exceptional home offers a spacious and versatile layout designed for today's lifestyle. Inside, you'll find a warm and inviting floor plan featuring a stunning wood-burning stone fireplace, original pine floors throughout much of the home that add warmth and timeless character, an updated kitchen with granite countertops and newer appliances, beautifully renovated bathrooms, a convenient first-floor laundry/mud room, and an oversized Andersen sliding glass door overlooking the expansive backyard. A second staircase provides easy access to the primary bedroom while adding to the home's unique character and functionality. Numerous updates and improvements provide peace of mind, including a newer boiler, updated mechanicals, 200-amp electric service, smart thermostats, a central vacuum system, and thoughtful upgrades throughout. The basement and generous attic space offer additional storage and flexibility. Outside, enjoy a beautifully landscaped property designed for entertaining and relaxation. The backyard features a saltwater in-ground pool with new coping and a new filter, a new paver patio, in-ground sprinklers with a private well water irrigation system, and plenty of room for gatherings, recreation, and outdoor enjoyment. A huge detached two-car garage with new windows, equipped with an electric car charging station, provides ample parking and storage, along with a newly finished climate-controlled bonus room-perfect for a hobby space, studio, gym, workshop, home office, or private retreat. Combining timeless charm, modern updates, and exceptional outdoor living, this rare property offers the opportunity to own a piece of history with all the conveniences of today. Perfectly situated in the heart of Riverhead, this home offers the best of East End living. Enjoy easy access to downtown waterfront, local dining, shops, entertainment, and year-round events, while being just minutes from farms, vineyards, beaches, golf courses, and everything the East End has to offer.

312 Riverside Drive, Riverhead

$998,000
7 Beds 4 Baths 1027815 MLS
Welcome to an extraordinary custom-built Colonial situated on an exceptionally rare full-acre property, offering an unmatched combination of space, versatility, and lifestyle. Whether you're searching for your forever home, a multi-generational living opportunity, or the perfect property for a business owner, tradesperson, or outdoor enthusiast, this one-of-a-kind residence presents an opportunity rarely found in today's market. From the moment you arrive, you'll appreciate the impressive 200-foot private driveway leading to an expansive parking area accommodating 20+ vehicles, in addition to the attached 1.5 car garage. There's ample room for work trucks, trailers, RVs, campers, boats, and recreational vehicles—making this an exceptional property for contractors, hobbyists, collectors, or anyone who values freedom and flexibility. The thoughtfully designed layout offers generous living space throughout. The first level features three spacious bedrooms, a full bath, direct garage access, and a separate rear entrance—ideal for extended family or a possible mother-daughter configuration with proper permits. Adding even more value is the home's full-footprint oversized basement with 8-foot ceilings and a separate exterior entrance with poured concrete stairs. This expansive lower level provides exceptional storage and endless possibilities for a home theater, gym, recreation room, workshop, office, or additional living space (with proper approvals). The upper level is the heart of the home. Soaring cathedral ceilings enhance the living room, dining room, and kitchen, while skylights and oversized windows flood the space with natural light. The spacious primary suite offers an oversized en-suite bath and abundant closet space, including walk-in closets. Step outside into your own private backyard oasis featuring a spectacular oversized in-ground pool surrounded by nearly 1,500 square feet of premium, like-new paver patio, creating a true country club setting for entertaining or everyday relaxation. A charming wooden gazebo offers endless possibilities as a future pool cabana, outdoor kitchen, entertainment pavilion, or cozy gathering space with an outdoor fireplace. Beyond the pool, the sprawling lawn provides room for virtually every outdoor activity imaginable. Located within the award-winning Longwood Central School District, you'll enjoy outstanding educational opportunities, youth sports leagues, beautiful parks, and an active community. Conveniently close to shopping, dining, major roadways, beaches, and everyday conveniences, this home offers the perfect balance of privacy, accessibility, and exceptional quality of life. Properties offering this much land, parking, recreational space, and versatility are extraordinarily rare. Whether you're envisioning your forever home, accommodating multiple generations, operating a home-based business, or simply enjoying room to grow, this property delivers possibilities few homes can match. Rare. Spacious. Versatile. One of a Kind. A truly exceptional opportunity to own one of the area's most distinctive properties, where extraordinary indoor living, resort-style outdoor amenities, an oversized basement with incredible potential, and an unbeatable location come together to create the lifestyle you've been dreaming of.

241 Middle Island Road, Medford

$950,000
4 Beds 2 Baths 1027547 MLS
Welcome to your Dream home on a Huge .49 Acre of Level land. Resort Style Backyard with your own Private Swimming Pool- A BEAUTIFUL 4-bedrooms, DEN- (POSSIBLE 5th BEDROOM) 2 Full Bathrooms - This home offers perfectly blend timeless elegance, everyday comfort, and is a one of a kind - Well-maintained ranch-style residence, perfectly situated in a peaceful and highly desirable neighborhood . Offering the ease of one-level living with no interior steps, this exceptional home combines comfort, elegance, and functionality throughout. Designed with an open and inviting flow, the home features a spacious living room highlighted by a charming fireplace, a Huge formal dining room ideal for entertaining, and a beautifully updated eat-in kitchen appointed with granite countertops, stainless steel appliances, and ample cabinetry. The private primary suite offers a spacious retreat with 2 Spacious Walk-IN Closets complete with its own full bath, while three additional generously sized bedrooms and a Nicely, Updated Full Hall Jacuzzi bath. This Home offers plenty of room for family and Guests! Enjoy gathering in the warm and inviting Den or step outside to your own private backyard oasis—perfect for relaxing, outdoor dining, and entertaining. Well- maintained and move-in ready, this home offers the perfect blend of style, comfort, and convenience. Ideally located close to shopping, dining, parks, transportation, and all that the area has to offer, this is a rare opportunity to own a truly special home in a prime location. A must-see property that showcases pride of ownership throughout.

208 Woodhampton Drive, White Plains

$959,000
3 Beds 2 Baths 1027230 MLS
Just under two hours from New York City, a truly extraordinary country estate awaits in the picturesque foothills just outside Ellenville. Privately tucked away this one-of-a-kind contemporary residence is surrounded by a tranquil pond, a flowing creek, and 28 acres of pristine natural beauty, offering an exceptional retreat where architecture and landscape exist in perfect harmony. Arrive via your private road and discover an enchanting estate complete with a substantial outbuilding, charming gazebo, fenced garden, meticulously maintained wood fencing, and your own pond, complete with dock and fountain. Distinctive sloping stucco arches frame a gracious covered porch, creating a dramatic introduction to the home's remarkable interior through one of the many custom metal door handles. Designed and handcrafted by a German master cabinetmaker and his wife, this custom residence is a celebration of artistry and craftsmanship. Soaring ceilings, hand-hewn timber beams, sculptural arched doorways, and smooth stucco walls create an architectural aesthetic that is both timeless and unexpected. The spectacular 20-foot floor-to-ceiling fireplace, adorned with shimmering inlaid fool's gold, serves as the home's unforgettable centerpiece. The thoughtfully designed floor plan offers a luxurious main-level primary suite complete with a spa-inspired soaking tub and serene views of the surrounding landscape. Upstairs, an inviting entertaining loft features a custom bar, an overlook into the living room below, an additional bedroom, and a full bath. Every window frames peaceful views of nature, seamlessly connecting the home's exceptional interiors with its breathtaking setting. Completing the estate is an expansive outbuilding with ample space for a prized automobile collection, workshop, or extensive storage. Or perhaps use some of the cleared acreage to bring horses home and convert the pole barn into an equestrian facility. Ride out and condition your horses on your peaceful and private 28 acres. Both the residence and outbuilding were enhanced with durable standing-seam metal roofs in 2020, ensuring lasting quality while complementing the property's distinctive architectural character. Please note the exterior tastefully peppered with antlers, a nod to the properties unique rural character. A rare offering where exceptional design, privacy, and natural beauty converge, this remarkable estate delivers an unparalleled Hudson Valley lifestyle. Schedule your private showing today.

118 Bennett Road, Napanoch

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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.