Sleepy Hollow Real Estate Search

Sleepy Hollow Single Family Properties for Sale

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Newest Sleepy Hollow Single Family Homes for Sale

$679,000
5 Beds 2 Baths 1049441 MLS
Welcome to your own private backyard oasis! This beautifully maintained and thoughtfully updated Cape Cod sits on a spacious 0.90-acre corner lot in the Town of Shawangunk, offering an exceptional outdoor living experience designed for entertaining, relaxing, and making the most of every season. The centerpiece of this incredible backyard is the 18,000-gallon saltwater fiberglass pool, complete with a propane pool heater for an extended swimming season. Surrounding the pool is an updated deck with composite decking and vinyl railings, creating a low-maintenance space for lounging and enjoying the outdoors. Just steps away, the impressive 16' x 24' pavilion with a fully equipped outdoor kitchen is made for unforgettable gatherings. The outdoor kitchen includes a refrigerator, grill, and flat-top grill, while a flat-screen TV completes the space for outdoor dining, game days, movie nights, and entertaining and all included in the sale, making this backyard truly ready to enjoy from day one. Inside, this spacious Cape Cod offers approximately 2,400 square feet, with 5 bedrooms and 2 full baths. The main level features hardwood floors throughout the living room and a formal dining room. The updated kitchen includes quartz countertops, a large center island, and stainless steel appliances. The main-level primary suite features new LVT flooring, generous closet space, and an updated private bath, while two additional bedrooms with hardwood flooring and another updated full bath complete the main level. Upstairs are two additional bedrooms and a spacious family room. The property also offers a 2-car attached garage, shed, unfinished basement with plenty of storage, fenced yard, and beautifully landscaped grounds. Major recent improvements include a new well pump and pressure tank (2025), water filtration system (2025), and water softener (2025). With a resort-style backyard, saltwater heated pool, expansive pavilion, outdoor kitchen, and plenty of space to gather, this is more than a home; it's an outdoor lifestyle ready to be enjoyed.

2 Panther Lane, Wallkill

$2,800,000
3 Beds 4 Baths 1047722 MLS
Set on 9.25 acres of open meadow in Milan, 15 Ferris Lane is a to-be-built contemporary country home conceived and designed by APS Designs, a multidisciplinary design studio, and developed by AELO. The residence takes its cues from the familiar forms of the Hudson Valley and reimagines them through a distinctly contemporary lens. A series of interconnected gabled volumes will stretch across the landscape, combining clean geometry, natural materials, and expansive walls of glass with a warmth and restraint that feel entirely at home in the setting. Symmetrical and timeless in character, the design is grounded in a strong sense of place while introducing inventive new elements. The entrance porch evokes the formality and symmetry of an Italian Palladian villa, creating an iconic arrival. Above, it becomes a panoramic terrace accessed from the second floor, offering an elevated connection to the surrounding landscape. At the heart of the house will be a soaring, barn-like great room whose dramatic volume opens to the landscape through oversized windows and doors. The living, dining, and kitchen areas will flow together, with a mezzanine above adding another layer of space and perspective. Three bedrooms will occupy the quieter wings of the house, creating separation between private and communal spaces. At the rear, the principal living areas will open onto an expansive deck and outdoor entertaining area overlooking the pool and surrounding countryside. The residence will comprise approximately 2,550 square feet on the main level, together with a 730-square-foot mezzanine and an attached 576-square-foot two-car garage. The 9.25-acre property begins along a quiet country road and rises through open meadow to an elevated homesite with long views across neighboring farmland and the rolling hills beyond. The house has been carefully positioned to take full advantage of the setting, with its principal living spaces and terraces oriented toward the surrounding countryside. Founded by Antonio Pio Saracino—an Italian designer and artist licensed to practice architecture in Italy—APS Designs is a multidisciplinary studio whose international projects are shaped by a strong sense of place and span the built environment, interior design, furniture, and art. Saracino’s work is represented in the permanent collections of institutions including the Centre Pompidou, the Brooklyn Museum, and the Los Angeles County Museum of Art, and has been exhibited internationally, including at the Venice Biennale. At 15 Ferris Lane, APS Designs has conceived a contemporary country house for AELO that is firmly rooted in the traditional landscape of the Hudson Valley while establishing a distinctive identity of its own. Estimated delivery Spring 2027.

15 Ferris, Red Hook

$865,000
3 Beds 2 Baths 1049391 MLS
Perfectly situated mid-block on a quiet, tree-lined street in the northern section of Franklin Square, this beautiful ranch-style home has been thoughtfully updated and meticulously maintained throughout. A bright, sun-filled living room welcomes you inside and flows seamlessly into the formal dining room and beautifully updated kitchen, featuring crisp white cabinetry, stainless-steel appliances, and elegant stone countertops. The main level is thoughtfully designed for comfortable living, with a spacious primary bedroom featuring a convenient powder room, two additional nicely sized bedrooms, and a well-appointed full hall bathroom. The finished basement offers exceptional versatility and additional living space, featuring a spacious recreation room, dedicated gym, and office area—providing the perfect setting for relaxation, fitness, work, and entertaining. A separate laundry room and abundant storage add to the homes functionality and convenience. Step outside to a private, beautifully landscaped backyard surrounded by mature plantings. The inviting paver patio creates the perfect backdrop for outdoor dining, entertaining, recreation, or simply enjoying a peaceful retreat at home. Ideally located near schools, parks, shopping, dining, and the Long Island Railroad station, this exceptional property combines an outstanding location with impeccable condition and low taxes. Move-in ready and offering an ideal blend of comfort, style, and convenience, this is truly a wonderful place to call home.

809 Garden Drive, Franklin Square

$1,499,000
3 Beds 4 Baths 1046925 MLS
Welcome to 3 Lewiston Court! Located in the highly sought-after Rosecliff community, this beautifully updated Brasilia model offers approximately 3,000 square feet of finished living space across three levels. Known for its dramatic architecture, the Brasilia features a distinctive curved staircase, soaring ceilings and an abundance of natural light, all complemented here by a thoughtfully reimagined and modernized interior. The centerpiece is the brand-new kitchen and redesigned open-concept main level, thoughtfully opened up to create a bright and seamless connection between the kitchen, family room and surrounding living spaces. The kitchen features crisp custom cabinetry, expansive quartz countertops and backsplash, stainless steel appliances, abundant storage and an oversized center island with seating for four. New hardwood floors throughout the main level further enhance the fresh, cohesive feel of the home. A separate dining area opens to the rear deck, recently refurbished and repainted, while the soaring living room and signature curved staircase add architectural character and wonderful natural light. Upstairs, the spacious primary suite includes a generous bedroom, walk-in closet and private bath, along with two additional bedrooms and a hall bath. New stair runners on both staircases add a polished finishing touch. The lower level was extensively renovated in 2025 with new flooring and walls and provides approximately 624 additional square feet of flexible recreation space. A renovated lower-level bath, substantial storage and a cedar closet add even more functionality. An oversized two-car garage and whole-house generator provide additional convenience. Set within the beautifully maintained Rosecliff community, residents enjoy exceptional amenities including a pool, clubhouse, tennis courts, basketball court and playground, along with grounds maintenance and snow removal. A turnkey opportunity combining one of Rosecliff’s most recognizable floor plans with the open, modern living space and thoughtful recent improvements today’s buyers are looking for.

3 Lewiston Court, Briarcliff Manor

$399,000
3 Beds 1 Baths 1047624 MLS
Don't miss out on this wonderful opportunity to own this home in the heart of the Hudson Valley—Welcome to 66 Silver Springs Road— Picture yourself unwinding here in a rocking chair or porch swing, catching the evening breeze. Inside and out, this home offers comfort, character, and tranquility. Step into a welcoming layout and find yourself in a relaxing living room. The next room features a spacious kitchen outfitted with custom wooden countertops and an area that can be dedicated as the eat-in dining area. The second floor features two comfortable bedrooms and a bathroom. The finished, walk-up attic boasts brand-new carpeting—offering a 3rd bedroom and more living space that can be used as a home office, media room, or extra living space. Enjoy a fully fenced backyard with your own private koi pond, along entertaining around a firepit area and a covered patio. Find here a 2 car garage that will provide ample storage, workspace, or parking. Book your next tour and see what is nestled in a quiet neighborhood, with a short distance from New Windsor Elementary and Route 9W. Enjoy effortless commuting with quick access to the NYS Thruway, I-84, Stewart International Airport, and the Beacon Metro-North station (for an easy ride into NYC), minutes from local grocery stores, shops, and restaurants, as well as top Hudson Valley attractions like the Storm King Art Center, charm-filled Cornwall, and the vibrant Newburgh Waterfront. Don't forget to schedule your tour today!

66 Silver Spring Road, New Windsor

$685,000
2 Beds 3 Baths 1049328 MLS
Easy, stylish, and exceptionally well connected. This beautifully renovated Wild Oaks townhome makes Northern Westchester living feel effortless. Step inside to a thoughtfully designed, one-of-a-kind contemporary interior with soaring ceilings, custom metal railings, stacked-stone fireplace surround, fluted wood panel feature wall, and ultramodern sconces. United throughout by a cohesive color scheme, a nicely designed kitchen & 3 renovated bathrooms mean that you can move right in without having to worry about the never-ending "to-do" list. When the weather is nice, an expansive deck becomes the place to be. Sip your morning coffee under the trees, enjoy dinner al fresco, tend to your herb garden, or host a full house of friends on a summer evening. Each bedroom is situated on its own level with its own ensuite bathroom, and storage closets are abundant throughout. A legal finished lower level adds an additional 425 square feet of bonus space - perfect for a home office, gym, playroom, media room, or whatever life calls for next. Then there are the practical perks that make a great home even better: a generator, central air & forced-air heating, high-end Andersen windows, attached garage, bonus driveway parking, and easy access to I-684. Best of all, Metro-North is just minutes away, making the commute to NYC refreshingly simple. Stylish, spacious, low-maintenance, and close to everything. This is the kind of home that just makes life better. By Appointment Only.

9 Boulder Lane, Goldens Bridge

$799,000
3 Beds 2 Baths 1048624 MLS
Welcome home to this Northport charmer, ideally situated north of 25A. This inviting 3-bedroom, 2-full-bath Colonial offers a warm and functional layout perfect for everyday living and entertaining. The open first floor features a formal living room, full bathroom, kitchen, dining area, and comfortable den highlighted by a wood-burning fireplace and original exposed ceiling beams that add character and charm. A large sliding glass door opens to the outdoor patio and in-ground pool, creating a wonderful setting for summer entertaining, relaxing, and enjoying the privacy of your own backyard. Upstairs, the spacious primary bedroom features a walk-in closet and direct access to the full bathroom through a convenient Jack-and-Jill entrance, along with two additional bedrooms. Beyond the home, enjoy everything that makes Northport such a special place to live. Just minutes away is Northport Village, known for its picturesque harbor, waterfront park, restaurants, shops, galleries, and the historic Engeman Theater. Spend weekends strolling Main Street, dining by the water, visiting nearby Del Vino Vineyards, or enjoying the charm of Lewis Oliver Farm Sanctuary. With its beautiful waterfront setting, vibrant village atmosphere, and strong sense of community, Northport offers the perfect combination of small-town charm and an exceptional Long Island lifestyle. 17 Franklin Court is more than just a home — it’s an opportunity to enjoy the very best of Northport living.

17 Franklin Court, Northport

$500,000
4 Beds 3 Baths 1046957 MLS
Welcome to 42 Streit Avenue! Tucked away at the end of a cul-de-sac, this inviting 4-bedroom, 3-bath home offers an impressive combination of space, privacy, updates, and outdoor living; all while keeping you close to the conveniences of Poughkeepsie. Inside, you'll find a warm and welcoming layout with hardwood floors, the charm of a wood-burning fireplace, and an updated kitchen featuring granite countertops and stainless-steel appliances. With four bedrooms and three full baths, the home offers plenty of flexibility for today's buyer. The primary bedroom features its own private bath and walk-in closet, creating a comfortable retreat with the storage and privacy buyers appreciate. Step outside and discover a backyard designed to be enjoyed. The deck provides a great setting for grilling, dining, entertaining, or unwinding outdoors, while the hot tub adds another place to relax and enjoy the space. The level property, off-street parking, and end-of-cul-de-sac location add to the home's appeal. The location puts you within convenient reach of Vassar College, shopping, dining, parks, major roadways, and the many attractions of the Hudson Valley. Poughkeepsie's Metro-North and Amtrak service also provide access south toward New York City and throughout the region. With 4 bedrooms, 3 baths, an updated kitchen, hardwood floors, fireplace, primary suite, outdoor entertaining space, and a desirable cul-de-sac-end setting, 42 Streit Avenue offers so much to appreciate. Come see everything this home has to offer and imagine making it your own!

42 Streit Avenue, Poughkeepsie

$749,000
5 Beds 3 Baths 1049202 MLS
LAKEFRONT LIVING AT IT'S BEST - Come home to exquisite lakefront living in this spacious contemporary retreat in the exclusive Emerald Green community. Designed to showcase its spectacular private lake views, this three-story, 5-bedroom, 3-full-bath home offers an inviting open-concept layout, soaring cathedral ceilings, multiple outdoor spaces, and a generous backyard leading directly to the lakefront. The main level features a bright, open floor plan encompassing the kitchen, dining area, and living room, all oriented toward the breathtaking lake view. The living room features a beautiful stone propane fireplace, creating a warm and inviting gathering space. A bedroom and full bath complete the main level. Upstairs offers two rustic bedrooms and a full bath, all opening onto a beautiful lake-facing landing. The walkout lower level opens directly to the backyard and lakefront and features gorgeous bluestone tile flooring, a spacious game room/family room, a second stone fireplace, two additional bedrooms, a recently renovated full bath, and a convenient laundry/mudroom. The outdoor living area is exceptional, with renovated front and rear decks ideal for entertaining, relaxing, and enjoying the spectacular setting. A recently built large storage shed provides space for all your lake and outdoor gear. Parking is plentiful, with a two-car driveway in front plus a separate side driveway accommodating 6+ additional cars. With lake views from virtually every level and direct access to the peaceful private lakefront, this is a home built for relaxing, entertaining, and creating memories with family and friends. The Emerald Green amenities include a full access fitness center, with indoor and outdoor basketball, tennis, and pickle ball courts, dog park, several pools, community beach front, and much more – providing a premium vacation experience to all community members. Embrace Lakefront Living at its Best. As for some features of the home: 1. New Roof (2022) 2. Rebuilt chimney (2020) (see photo of top) 3. New Shed (2021) 4. New Front deck (2021), new back deck (2018) 5. New basement bathroom (2026) 6. New driveway on side of house (2021) can fit up to 6 cars 7. Stripped and shined bluestone basement level (2026)

74 Lake Shore Drive S, Rock Hill

$399,000
3 Beds 4 Baths 1049295 MLS
Just minutes from Delhi, 715 Rosa Circle offers a thoughtfully designed home with a distinctive sense of arrival. A level, S-curved driveway wraps around a quarter-acre pond—a real advantage come winter—opening to a small circular garden, garage to the right, front door along a stone walkway to the left. A triple-peak façade gives the home clean, contemporary character. Inside, the living room opens dramatically above you beneath a 20-foot gable ceiling, anchored by a wood-burning fireplace with a black stone hearth. A front-facing bedroom with full en suite bath overlooks the driveway and pond—a comfortable, well-positioned primary suite. A smaller front room works as a home office or dining room. Toward the back, the kitchen and breakfast area open to the deck and backyard, with a dual-bay stainless sink, gas range, and wood cabinetry throughout. Engineered wood flooring runs through the whole home. Upstairs, a catwalk hallway overlooks the foyer and living room below. One bedroom sits off the landing with pond and driveway views; a larger bedroom at the opposite end has its own mini-split and a wooded outlook. A semi-private suite above the two-car garage—reachable by exterior stairs for a separate, lockable entrance—includes its own vestibule, bath, bedroom, and sitting area, ideal as a guest suite or in-law setup. The basement is a project underway: roughed in for a future kitchenette and studio apartment, with a nearly finished full bath, spray-foam insulation throughout, and a mini-duct HVAC system already in place. A wraparound deck runs along two sides of the home, stepping down to a sloped yard with hillside and woodland views. The septic system is brand new and fully Watershed approved. Minutes from Delhi, with easy access to Delaware Academy, SUNY Delhi, shopping, dining, and the county seat—a well-considered home with flexible living space and room to grow.

715 Rosa Circle, Delhi

$1,895,000
3 Beds 2 Baths 1048293 MLS
Welcome to one of Rye Gardens’ most inviting homes! This beautifully cared-for 3-bedroom, 2-bath residence offers a wonderful combination of comfort, style, and easy everyday living. Sunlight fills the open-concept main level, creating a warm and welcoming flow from room to room. The updated eat-in kitchen features granite countertops and stainless steel appliances and opens directly to an amazing family room—creating the perfect gathering space for everyday living, movie nights, and entertaining. A door leading to a generous bluestone patio is ideal for summer gatherings, morning coffee, or simply enjoying the peaceful surroundings The living room flows seamlessly into the adjoining dining room, both rooms filled with happiness and magic. A few steps up, the spacious primary suite provides a private retreat with its own en-suite bath, while two additional bedrooms and a full hall bath complete the upper level. The bright lower level adds tremendous versatility with a fourth bedroom, home office, and den, along with a separate basement and laundry for added storage and functionality. A charming covered front porch welcomes you home and provides the perfect spot to relax and enjoy the neighborhood. Step outside to lush, park-like grounds with mature landscaping, flowering trees, and beautiful seasonal color. Ideally located near Rye’s beaches, parks, train, and vibrant downtown, this home offers expansion possibilities and the perfect setting to enjoy all that Rye has to offer.

46 Beverly Drive, Rye

$675,000
3 Beds 2 Baths 1044682 MLS
Beyond its rustic stone wall, discover 212 Old Albany Post Road, a charming split-level three-bedroom, two-bath ranch tucked back on a lovely, level two-acre parcel in Garrison, New York. A generous setback provides both privacy and wonderful curb appeal along this historic country lane as it meanders through Garrison's bucolic landscape. Cheerful and inviting, the home offers a pass-through floor plan, two-inch oak floors, two wood-burning fireplaces—one in the living room and another in the primary bedroom—a kitchen with newly updated appliances and granite countertops, and large, sun-flooded picture windows with picture-perfect views of the front lawn. Extending the living space outdoors, an expansive two-level deck offers nearly 1,000 square feet for dining, entertaining and relaxing, with easy access to the backyard. Together, the front and back lawns provide plenty of room for games, picnics, gardening and entertaining. Recent improvements include a new roof and fresh exterior paint in 2026, along with an updated stove and microwave in 2025, dishwasher in 2021 and refrigerator in 2021. Two existing sheds provide abundant storage for gardening and outdoor equipment. A pond and charming pergola complete the property's exceptional outdoor setting, making this an appealing Garrison country retreat with room to enjoy, garden and gather. Everyday conveniences remain close at hand, with Cortlandt Town Center and major shopping nearby. With two level acres and a generous setback, the property also presents intriguing possibilities for a future owner looking to reimagine or expand the existing home, subject to all applicable municipal approvals.

212 Old Albany Post Road, Garrison

$1,149,000
3 Beds 6 Baths 1048148 MLS
Set on a tree-lined street of well-maintained homes in the Village of Floral Park, 38 Fern Street has been cherished by one owner for many years — and is ready for its next chapter. Within the Floral Park–Bellerose School District and just blocks from the Covert Avenue shopping district, with the LIRR close by, this gracious 1928 residence offers 2,368 square feet of character and room to make it your own. An expansive entry foyer with an adjoining sitting room welcomes you inside. The generously sized living room centers on a wood-burning fireplace and flows to a formal dining room with original hardwood floors. The kitchen is spacious, with a custom built-in banquette for casual dining and ample footprint to design the kitchen of your dreams. At the rear, an impressive addition creates a true great room — a vaulted ceiling, custom wood paneling, and a second fireplace make it the heart of the home. A renovated full bath completes the first floor. Upstairs, the primary bedroom offers an en suite bath and two closets, including a walk-in. Two additional well-proportioned bedrooms, a hall bath, and a convenient second-floor laundry complete the level. A walk-up third floor adds bonus space and storage, with additional attic storage over the great room. The partial basement provides further storage along with laundry and utilities. With central air conditioning, a two-car garage, a patio, and private yard, 38 Fern Street is a blank slate for new owners looking to establish a gracious residence in one of Floral Park's most desirable settings. The owner is selling the home in its present condition.

38 Fern Street, Floral Park

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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.