Sleepy Hollow Real Estate Search

Sleepy Hollow Properties for Sale

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Sleepy Hollow Properties for Sale

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Newest Sleepy Hollow Properties for Sale

$976,000
4 Beds 3 Baths 1049730 MLS
Tucked behind stately stone entrance pillars and a sweeping drive, this extraordinary center hall colonial offers more than 4,500 square feet of impeccably maintained living space, all set amid professionally landscaped grounds designed for both elegant entertaining and everyday enjoyment. From the moment you arrive, the pride of ownership is unmistakable—from the manicured lawns and irrigation system servicing both front and rear yards to the timeless architectural design and exceptional attention to detail throughout. Step through the front door into a stunning two-story foyer highlighted by extensive custom millwork, raised panel wainscoting, decorative columns, hardwood flooring, and a grand staircase that immediately showcases the home's quality construction and refined character. Designed with both functionality and sophistication in mind, the main level offers an exceptional blend of formal and casual living spaces. The private office provides an ideal work-from-home setting, while a separate library offers the perfect retreat for reading, studying, or quiet conversation. The formal dining room is beautifully appointed for holiday gatherings and special occasions. At the heart of the home is a spectacular chef's kitchen featuring custom cabinetry, granite countertops, center island seating, stainless steel appliances, and generous workspace. The kitchen flows effortlessly into the sun-filled breakfast area and expansive family room, creating an open-concept living space perfect for modern lifestyles. Rich hardwood floors, coffered ceilings, oversized windows, custom trim details, and a stunning stone fireplace create a warm and inviting atmosphere where guests naturally gather. Upstairs, the spacious primary suite serves as a private sanctuary. Cathedral ceilings create an airy sense of space and the alcove offers the perfect spot for reading, relaxing, or simply enjoying peaceful views of the surrounding property. Additional generously sized bedrooms provide comfort and flexibility for guests . The finished walkout lower level expands the home's living space even further, offering endless possibilities for recreation, fitness, hobbies, entertaining, or multi-generational living needs. While the interior is exceptional, the true magic of this property unfolds outdoors. Step onto the expansive Trex deck, complete with a beautiful arbor-covered sitting area overlooking what can only be described as a private resort. The heated in-ground pool is surrounded by elegant paver patios and lush gardens bursting with color throughout the season. A tranquil waterfall and water feature provide the soothing sounds of nature, while the custom outdoor fireplace creates the perfect gathering place on cool evenings. A timber-frame pavilion offers welcome shade for summer entertaining and outdoor dining. The charming pool house, complete with air conditioning and hand-painted decorative details, elevates the experience even further, providing a comfortable retreat for guests and poolside gatherings. Additional outbuildings, extensive hardscaping, mature landscaping, and open views of the surrounding countryside create a setting that feels both private and peaceful. This remarkable property offers a rare combination of luxury, comfort, craftsmanship, and outdoor living—all meticulously maintained and thoughtfully designed to create a lifestyle that is as beautiful as it is unforgettable.

161 Bergen Circle, Slate Hill

$749,000
2 Beds 2 Baths 1046469 MLS
Timeless and charming this 1925 Yonkers Home sits on a little over 1/3 of an acre of beautifully landscape property with amazing curb appeal and a HUGE amount of property for your outdoor enjoyment!!!!!. It also features an oversized separate 2 car garage w/attic space above for tons of extra storage and sits on the corner of Brewster Avenue and Mile Square, Road . this incredibly well maintained charming Home was officially configured as a 2 bedroom 2 bath home but it’s flexible layout lives as a 3 bedroom residence offering additional space for a bedroom/office/guest room/den. It also features beautiful stone work, solid mahogany entrance doors and oak flooring throughout most of the house. This is a unique and timeless opportunity to own a little bit of old with the modern conveniences of Town water and sewer. endless opportunities " there is an extra property lot attached to this property which could possibly allow for expansion of this house or an additional building lot, but you would have to check it out with the building department to confirm if it would be possible. It also Features a very spacious EIK and living room and an additional Lg bonus room currently being used as a master bedroom. Roof is only 12 years old!!! ONLY 19 MILES FROM NYC!!! Close to schools, shopping, and right near cross county parkway, 87 thruway, and the sprain parkway. "Between the Garage/Driveway and off street there is enough parking for 11 cars great for entertaining".

83 Brewster Avenue, Yonkers

$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

$1,049,000
3 Beds 2 Baths 1042543 MLS
Welcome to Pelham Bay! This legal two family home features a spacious two bedroom unit on the first floor with a large living room, kitchen, dining area, and bonus room with a door leading to the deck. The second floor has its own separate entrance and features a one bedroom unit, making this a great opportunity for homeowners with rental income to help offset expenses. The home is situated on a large, fenced-in, lot with plenty of off street parking, including an oversized two car garage and a long private driveway that can accommodate up to eight cars. The listed square footage does not include approximately 1,248 square feet of finished walk out basement space with a separate entrance, providing excellent flexibility and potential for an in law suite, additional living space, or entertainment area. With a little TLC, you can turn this property into your dream home. This is a great opportunity for homeowners, investors, or extended family living. For those looking to expand, the property is zoned R4A, which may offer an opportunity to add onto the existing home, providing significant potential to customize and increase the home's living space. The home will be delivered vacant. Conveniently located near major highways, the 6 train, express bus service to NYC, and the Q50 bus to Flushing, Queens, as well as shops, parks, restaurants, and other local amenities. Taxes do not reflect the NYS STAR school tax exemption.

1559 Hollywood Avenue, Bronx

$849,000
4 Beds 3 Baths 1049887 MLS
Completely re-built in 2009: of the 1962 structure, one small closet wall, garage and (partial) original basement was kept. An additional foundation was added to create what is now, the current home! The home and property are exceptional. From quiet mornings on the welcoming front porch to relaxed evenings on the rear patio, this is a home designed to be enjoyed. Warm, inviting and thoughtfully remodeled, it blends timeless Colonial character with the comfort, convenience and modern features today’s buyers appreciate. The home is in move right in condition, the location is mid-block, not backing, siding or fronting any busy roads, yet conveniently located to allow easy access in and out of the community. Step inside through the dramatic cathedral entrance foyer, where generous room sizes, hardwood floors throughout and a gracious, flowing layout immediately set the tone. The formal living room or parlor offers a versatile setting for welcoming guests, reading, relaxing, studying or creating an elegant home office. At the heart of the home is the spacious eat-in kitchen, beautifully appointed with granite countertops, Energy Star appliances, gas cooking and a convenient butler’s service area—perfect for casual meals, holiday gatherings and effortless entertaining. A gas burning fireplace adds warmth and character to the inviting living spaces, while the conveniently located first-floor laundry and mudroom with separate outside entrance that also provides access to the basement brings everyday practicality to the home’s thoughtful design. The upper level features four generously sized bedrooms, included, the Primary with a luxurious en-suite, abundant closet space and the storage every home needs. The partially finished basement provides even more room to enjoy, with flexible space for recreation, hobbies, fitness, guests or additional work-from-home needs, additional basement space makes room for whatever your heart desires. A separate side entrance via the mudroom/laundry area allows for convenient access to the basement. The majority of the home was re-built/renovated in 2009. The home features but is not limited to the following; Andersen 400 Series windows, 200-amp electrical service and a French drain system surrounding the home—valuable improvements that enhance comfort, efficiency and peace of mind. Outside, the beautifully maintained and rear fenced property creates a wonderful private setting for relaxing, entertaining, gardening and enjoying the seasons. The front porch, rear patio and attractive grounds extend the living experience well beyond the interior. Ideally located minutes to Bay Shore’s vibrant Main Street, exceptional dining, cafes, shopping, the Great South Bay waterfront, Fire Island ferries, parks, beaches, the Long Island Railroad and major roadways, this home offers an appealing combination of neighborhood charm and everyday convenience. First time offered and an unbelievable value—this exceptional, beautifully designed Colonial is ready to welcome its next owner. Move right in, settle in and make it yours. First showing - full weekend, allowing all that are truly serious and interested to visit and envision yourself in this home.

1456 Pine Acres Boulevard, Bay Shore

$6,900,000
5 Beds 5 Baths 1004680 MLS
Just three homes from the Atlantic Ocean and located within the desirable Beach Hampton community, this fully renovated beach cottage offers private beach access and an exceptional coastal lifestyle. Originally built in 1950 and completely reimagined in 2019, the residence encompasses approximately 3,100+/- square feet across three levels. The home features 5 bedrooms and 4.5 baths, thoughtfully designed to accommodate both everyday living and entertaining. Renovations included the addition of a second-floor primary suite, two guest bedrooms with a shared bath, a first-floor ensuite bedroom, and a legal lower-level ensuite bedroom accompanied by a spacious full gym. An open-concept layout highlights a well-appointed kitchen with stainless steel appliances, flowing seamlessly into inviting living and gathering spaces enhanced by hardwood flooring, two fireplaces, and abundant natural light. Additional amenities include a private guest suite, gym, laundry area, alarm system, forced-air heating and cooling with three zones, central air conditioning, propane fuel, and attached garage access from the finished lower level. Outside, the 0.23+/- acre property is designed for effortless summer enjoyment with a heated 19 x11 resistance swim gunite pool, patio, outdoor shower, irrigation system, grill tied to the gas line, cedar shake siding, cedar roof, and a full-house generator. A particularly notable feature of this coveted location, the property is situated outside of a flood zone. Combining modern upgrades, beach rights, and a prime location just moments from the shoreline, this turnkey offering presents a rare opportunity in one of the Hamptons' most sought-after waterfront communities.

74 Hampton Lane, Amagansett

$1,495,000
3 Beds 2 Baths 1029901 MLS
A peaceful contemporary retreat surrounded by nature, this unique home offers an exceptional blend of privacy, comfort, and convenience. Dramatic floor-to-ceiling windows in the living room, dining room, and office capture beautiful wooded views of the Leatherstocking Trail while filling the home with an abundance of natural light. The spacious deck provides the perfect outdoor setting for entertaining, relaxing, or simply enjoying the tranquil surroundings. Tucked away on a private cul-de-sac and set on approximately one-third of an acre, this home offers a quiet, country-like setting while remaining conveniently connected to the neighborhood and surrounding amenities. Inside, you’ll find soaring cathedral ceilings, hardwood floors, central air, and a modern eat-in kitchen featuring a Bosch dishwasher (2025), Vinotemp 28-bottle wine refrigerator (2025), and LG refrigerator (2023). The inviting living room is highlighted by a striking stone fireplace, creating a warm and welcoming focal point. An attached two-car garage provides added convenience and storage. Enjoy the best of both worlds with a tranquil, nature-filled setting just 35 minutes from Manhattan. The train station and major parkways are less than a mile away, making commuting and travel exceptionally convenient. The finished basement offers an additional 288 square feet of living space, not included in the stated square footage. Additional features and improvements include: Oil heat with an above-ground oil tank, Upgraded electrical system and main subpanels (2026), New pitched roof (2026), 1 Flat roof replaced in 2022, Gutters replaced in 2023, Extended sprinkler system servicing the front and back yards. Replaced exterior stairs and walkway pavers (2023), Replaced stair railing to wrought iron. Step and pathway lighting installed in 2023. STAR tax exemption: $937.12 not included in taxes.

4 Leatherstocking Lane, Mamaroneck

$5,750,000
3 Beds 5 Baths 1048050 MLS
Set within an exclusive gated community along the LI Sound, this extraordinary 6,000+ sq. ft. Mediterranean-style waterfront residence offers a rare combination of architectural elegance, exceptional craftsmanship, expansive living spaces, and an unparalleled waterfront lifestyle. Set on nearly one acre, the stucco-and-stone home enjoys beautiful water views and access to a private community beach. From the moment you enter, the quality, scale, and craftsmanship are immediately apparent. Venetian plaster walls, custom woodwork, and White Oak trim, moldings, and doors are featured throughout. A dramatic two-story entrance with a grand staircase creates an impressive introduction to the residence. The nearly 4,000 sq. ft first level is designed for sophisticated entertaining and everyday living, with soaring cathedral ceilings and generously proportioned rooms. Water views can be enjoyed from the living room, dining room, kitchen, family room, primary suite and bedrooms. The elegant living room features a striking coffered ceiling and water views, while the formal dining room provides an impressive setting for entertaining. At the heart of the home is a beautifully designed open-concept chef's kitchen, family room, and breakfast nook, all oriented toward the water. The kitchen features designer appliances, a combination of granite and wood countertops, and an oversized center island with storage and wine refrigerator. The adjoining family room features a wood-burning fireplace and numerous sliding glass doors that open to the expansive deck, creating a seamless connection between the interior and spectacular waterfront setting. The oversized deck overlooks the Long Island Sound and private community beach and features a gas grill, perfect for entertaining, outdoor dining, or relaxing while taking in the views. The luxurious primary bedroom suite is a private retreat with high ceilings, gas fireplace and magnificent waterfront sunrise views. The spa-like marble primary bath features a walk-in shower, dual sinks, and a freestanding soaking tub. An oversized custom outfitted his-and-hers walk-in closet provides exceptional storage and organization. A handsome mahogany office offers a sophisticated private workspace, while the spacious laundry room provides extensive storage and functionality. Upstairs, two large bedrooms offer generous accommodations, complemented by two full bathrooms and one half bath. A substantial bonus room provides tremendous flexibility and can be configured as an additional family room, media room, home gym, playroom, bedrooms, or private retreat. The upper level continues the home's generous proportions while taking advantage of the property's beautiful water views. Adding to the home's comfort, radiant heat extends throughout the residence as well as the 3-car garage, providing warmth underfoot and comfort during the colder months. Outside, the expansive deck serves as an extension of the home's living and entertaining spaces, overlooking the Long Island Sound and private community beach. A rare offering in one of Westchester's most desirable waterfront settings, this exceptional Mediterranean residence combines timeless architecture, exquisite craftsmanship, extraordinary scale, and a private Long Island Sound lifestyle near restaurants, yacht clubs, shopping and parks.

14 Brittany Lane, New Rochelle

$719,000
3 Beds 2 Baths 1050347 MLS
WHERE TIMELESS CHARM MEETS EXCEPTIONAL OPPORTUNITY. Discover the warmth, character, and enduring appeal of this beautifully maintained Colonial, ideally situated in one of Smithtown’s most desirable neighborhoods. Rich hardwood floors, an inviting fireplace, and flowing floor plan create an atmosphere that feels instantly like home. Offering three spacious bedrooms and one-and-a-half baths, this residence features a gracious living room with fireplace, Dining room, and eat-in Kitchen. The partially finished basement provides abundant storage while offering potential for additional living space. Step outside and experience a setting that feels straight from the pages of a storybook. Meandering stone pathways weave through mature landscaped gardens, leading to an expansive fenced backyard that invites summer gatherings, outdoor celebrations, or simply peaceful evenings surrounded by nature. Perfectly positioned on a quiet residential street, this exceptional home offers the tranquility buyers seek while remaining just minutes from the Long Island Expressway, Northern State Parkway, shopping, dining, and all that the Town of Smithtown has to offer—including its renowned parks, beaches, and recreational amenities. Whether you’re searching for your forever home or a rare opportunity in one of Long Island’s most sought-after communities, this residence offers the perfect blend of charm, comfort, location, and future potential.

20 Brook Lane, Smithtown

$359,999
1 Beds 1 Baths 1050327 MLS
Welcome to 10 Smithtown Boulevard, Unit 6A, a beautifully redesigned main-level residence offering elevated co-op living in the highly sought-after Smithtown School District. Completely transformed with modern finishes and thoughtful design, this home combines the comfort of a high-end residence with the value of co-op ownership. Sunlit interiors, seamless flow, and quality craftsmanship create a space that feels both sophisticated and inviting. A Rare and Highly Valuable Feature of this home is the fully enclosed and secure 300-square-foot private storage space located directly beneath the unit, offering exceptional convenience and flexibility rarely found in co-op living. The designer kitchen features custom cabinetry, sleek finishes, generous storage, and a spacious dining area perfect for everyday living or entertaining. The spa-inspired bathroom showcases clean lines and elegant modern details. The king-sized primary suite is exceptionally spacious for a one-bedroom and offers abundant closet space. A versatile flex area provides the ideal setting for a home office or quiet retreat. Light oak hardwood floors run throughout the home, complemented by crown molding, modern lighting, and a soft neutral palette that enhances the bright, airy feel. Additional features include: • Assigned parking for two vehicles Immaculate and move-in ready, this home presents a rare opportunity in one of Smithtown’s most desirable communities. One of a kind. A true step above.

10 Smithtown Boulevard Unit #6A, Smithtown

$799,990
3 Beds 2 Baths 1050166 MLS
Welcome to this beautifully maintained back-to-back split located in one of Massapequa Park's most desirable neighborhoods. Located within the highly regarded Massapequa School District, this exceptional home offers the perfect combination of comfort, space, and convenience. Enjoy an easy walk to the LIRR train station, local shopping, restaurants, parks, and everything that makes this vibrant community so desirable. Pride of ownership is evident throughout this thoughtfully updated home. The showpiece is the spectacular great room, renovated within the last decade, featuring custom built-in woodwork and benches, an elegant gas fireplace with a stunning exotic wood mantel, abundant natural light from oversized windows, and generous walk-in closets. A beautifully renovated half bath completes this impressive living space, making it ideal for entertaining or everyday family living. Additional highlights include: Recently renovated sunroom offering the perfect space to relax year-round Central air conditioning In-ground sprinkler system Spacious rear deck overlooking the expansive yard Large backyard offers substantial green space—ideal for pets, outdoor entertaining, or future enhancements Attached garage and ample storage Well-maintained interior with a functional multi-level layout designed for today's lifestyle Offering approximately 1,647 square feet of living space, 3 bedrooms, 1.5l bathrooms, a finished basement, attached garage, and situated on a generous 7,200-square-foot lot, this home provides the space and flexibility today's buyers are looking for. Rarely does a home combine this level of care, thoughtful updates, oversized property, and unbeatable location. Whether you're hosting family gatherings in the spectacular great room, enjoying quiet mornings in the sunroom, or taking advantage of the easy commute and nearby amenities, 244 Ocean Avenue is a wonderful place to call home and the perfect setting to create lasting memories.

244 Ocean Avenue, Massapequa Park

$599,999
3 Beds 2 Baths 1045639 MLS
Incredible opportunity to own a magnificent circa-1900 Victorian that has been thoughtfully cared for and beautifully updated, ideally situated in the Village of Lindenhurst on an oversized lot in a prime mid-block location. Exceptional curb appeal begins with mature, meticulously maintained landscaping, vinyl siding accented by cedar-impression siding, a brick front porch with PVC railings, a charming covered portico, and an original vintage front door with glass detail. A paving-stone walkway leads to the entrance, while the long, oversized blacktop driveway with Belgian block borders and apron extends to a detached one-car garage equipped with electricity and provides abundant additional parking. The backyard offers multiple areas for outdoor enjoyment, perfect for entertaining and taking in the seasons. Step inside to an inviting entry foyer showcasing gleaming original hardwood floors, beautiful vintage millwork and custom moldings surrounding many of the doors and windows, and a stunning original staircase that reflects the home’s timeless Victorian character. The spacious formal living room is filled with natural light and features beautiful moldings and a ceiling fan. At the heart of the home is the chef’s kitchen featuring light maple cabinetry, a large breakfast bar with granite countertops, stainless steel appliances, abundant cabinet and counter space, a tile backsplash, recessed lighting, gas cooking, a refrigerator with water and ice dispenser, and a full-glass door providing direct access to the backyard. The first floor also features an enormous bedroom with gleaming hardwood floors and a ceiling fan, along with a beautifully appointed full bath featuring a glass-enclosed stand-up shower and custom tilework. Upstairs are two additional generously sized bedrooms with hardwood floors and ceiling fans, a second full bath with a tub and shower, and a convenient laundry space with washer, dryer, and additional cabinetry. Most of the interior has been freshly painted, and Andersen windows add to the home’s many desirable features. A full unfinished basement provides additional storage and houses the gas hot water heater and Peerless boiler with Riello burner. A rare opportunity to enjoy the character, vintage millwork, and craftsmanship of a classic Victorian combined with thoughtful updates, generous indoor and outdoor living space, and a fantastic Village of Lindenhurst location, within walking distance to the LIRR train station and numerous restaurants.

16 Grove Street, Lindenhurst

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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.