Sleepy Hollow Real Estate Search

Sleepy Hollow 4 Bedroom Properties for Sale

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Newest Sleepy Hollow 4 Bedroom Properties for Sale

$1,259,999
4 Beds 3 Baths 1040601 MLS
Experience refined living in this beautifully updated and impeccably maintained 4-bedroom, 3-bath Split, perfectly situated in the highly sought-after Jericho School District. Designed with timeless elegance and modern comfort in mind, this exceptional residence offers an impressive blend of sophisticated finishes, quality craftsmanship, and thoughtful upgrades throughout. The inviting first floor features a gracious living room, elegant formal dining room, and a stunning updated eat-in kitchen enhanced by skylights that bathe the space in natural light. Rich hardwood floors, recessed lighting, and Andersen windows create a warm yet luxurious ambiance throughout the home. Designed for effortless everyday living, the home offers 2-zone central air conditioning, a 200-amp electrical service, and a 3-year-old boiler for exceptional comfort and efficiency. The finished basement provides versatile additional living space, perfect for entertaining, a media room, home office, or recreation area. Significant recent improvements include a 2019 roof, solar panels, fresh designer paint, new flooring, and beautifully updated bathrooms, allowing you to move right in with complete peace of mind. Step outside to your own private backyard retreat, where sliding glass doors lead to a spectacular in-ground swimming pool—the perfect setting for summer entertaining, relaxing weekends, and creating unforgettable memories. Complemented by an in-ground sprinkler system, attached one-car garage, steel beam construction, and exceptional outdoor space, this home truly offers resort-style living at home. Ideally located just minutes from premier shopping, parks, restaurants, transportation, and all local conveniences, this exceptional residence combines luxury, location, and lifestyle in one remarkable offering. A rare opportunity to own a move-in-ready home in the prestigious Jericho School District.

49 Village Drive, Jericho

$1,375,000
4 Beds 3 Baths 1047921 MLS
Welcome to this beautiful 4-bedroom, 2.5-bath Victorian, lovingly maintained by its original owners and showcasing true pride of ownership throughout. A charming front porch and inviting curb appeal welcome you into a spacious two-story foyer featuring natural hardwood floors. The elegant formal dining room and sitting room each feature French doors, creating beautiful spaces for entertaining or relaxing. The antique-white eat-in kitchen offers granite countertops, a center island, and an open-concept design flowing seamlessly into the family room, complete with a stunning marble gas fireplace. A first-floor office with its own private entrance provides the perfect space for working from home. Upstairs, the spacious primary suite features a walk-in closet thoughtfully outfitted with a washer and dryer for added convenience. The luxurious primary bath includes a Jacuzzi tub, separate shower, double vanity, and linen closet. Three additional generously sized bedrooms and a guest bath complete the second floor. The full basement offers high ceilings and an abundance of versatile living and storage space, including a secluded media room, recreational area, closets, and ample storage. Extending the living space beautifully, the all-season room provides the perfect transition to the private backyard. Step outside to enjoy a kidney-shaped heated pool, expansive paved patio, and multiple leisure areas designed for relaxing and entertaining.

7 Ona Avenue, Dix Hills

$749,000
4 Beds 3 Baths 1048211 MLS
Privately set on 2.4 picturesque acres in the Town of Newburgh, this distinctive Tuscan-inspired residence offers a rare sense of arrival—where graceful architecture, and beautiful natural surroundings come together to create an inviting Hudson Valley escape. Offering 4 bedrooms and 3 full bathrooms, the home blends timeless character with thoughtful updates and a seamless connection to the landscape. Sun-filled living spaces, rich hardwood floors, and a striking central staircase create an elegant first impression. The inviting living room features a beautiful working fireplace, while the spacious eat-in kitchen is appointed with granite countertops, stainless steel appliances, and direct access to a deck to enjoy morning coffee or host dinner parties. A versatile first-floor guest bedroom or bonus room, complemented by an adjacent full bathroom, offers exceptional flexibility for guests, a home office, or additional living space. Upstairs, the private upper-level terrace provides another peaceful vantage point from which to enjoy the surrounding landscape. The full walk-out basement provides abundant storage, a plug-in sauna, and exciting potential for future use. Recent improvements include a new roof and furnace, fresh interior and exterior paint, and a recoated and sealed driveway. Ideally situated just minutes from the Newburgh–Beacon Bridge and Metro-North, the property offers easy access to the Hudson Valley’s renowned dining, wineries, hiking trails, shopping, and year-round recreation. A rare combination of privacy, architectural character, and modern convenience, this distinctive residence is a beautiful place to call home.

5 Harvey Way, Newburgh

$799,000
4 Beds 3 Baths 1041929 MLS
Welcome to 16 Dogwood Drive, a spacious four-bedroom, 2.5-bath Colonial nestled in the incorporated Village of the Branch. Set on a beautiful .60-acre lot, this home offers a classic Colonial layout, generous living spaces, and wonderful potential to make it truly your own. The main level features a welcoming living room with a wood-burning fireplace, formal dining room, eat-in kitchen, den, and convenient half bath. The spacious layout provides comfortable areas for both everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms with ample closet space, including a primary bedroom with an en-suite full bath, along with an additional full hall bath. The primary bathroom has also been tastefully updated. Thoughtful improvements throughout the home include beautiful wood floors, vinyl siding, a newer cesspool, in-ground sprinkler system, and updated walls with new insulation in most living areas. The inner bedroom walls have also been soundproofed, providing added privacy and peace throughout the home. A full unfinished basement and one-car garage offer plenty of storage and the potential for future living or recreational space. Step outside to your own private backyard oasis, surrounded by mature Leyland cypress that create a peaceful and secluded setting. An in-ground pool and expansive paver-stone patio provide the perfect backdrop for summer relaxation, outdoor entertaining, and making lasting memories. Conveniently located between Smithtown and St. James, this home is close to shopping, restaurants, parks, recreation, and everyday amenities. With its classic Colonial charm, spacious rooms, established landscaping, and numerous updates, 16 Dogwood Drive is the perfect canvas to create the home you’ve always imagined personalized to reflect your own style, vision, and way of living!

16 Dogwood Drive, Smithtown

$6,250,000
4 Beds 5 Baths 1048059 MLS
Built in 2023 and set on 1.15 landscaped acres in Flower Hill, 105 Woodhill Lane pairs classic Colonial architecture with the thoughtful appointments of a custom luxury residence. Located within the Port Washington School District, this Manhasset home offers elegant entertaining spaces, two primary suites, and beautifully designed outdoor living. A circular driveway, manicured grounds, and welcoming front porch establish a gracious sense of arrival. Inside, hardwood floors, detailed millwork, and impressive ceiling heights define the interiors. A formal living room with coffered ceilings complements the dramatic two-story formal dining room. At the heart of the home, the chef’s kitchen features an oversized center island, premium stainless steel appliances, abundant cabinetry, and generous space for gathering. The adjoining family room is anchored by a gas fireplace, while a sweeping spiral staircase creates a striking architectural focal point. French doors open to a covered bluestone porch and patio, extending the living spaces outdoors. A sitting room, powder room, and oversized two-car garage with extra-high ceilings complete the main level. Upstairs, two primary suites offer exceptional flexibility. One features a walk-in closet and private en-suite bath. The more expansive retreat showcases soaring ceilings, a private sitting area with a gas fireplace, spacious dual closets, and a spa-inspired bath with a double vanity, dedicated makeup vanity, soaking tub, private water closet, and steam shower. Two additional bedrooms, another full bath, and a separate laundry room complete this level. The laundry area includes a specialized garment-care machine for refreshing and preparing clothing, while six integrated central vacuum systems serve the home. The finished lower level, with its own outside entrance, provides additional space for recreation and guests, including full bath, spacious living area, additional rooms, and ample storage. Outdoors, an expansive paver patio creates an inviting setting for dining and entertaining, framed by landscaped grounds and an in-ground vinyl pool and spa with a waterfall. Convenient to shopping, dining, transportation, and Americana Manhasset, 105 Woodhill Lane brings together recent construction, distinctive architectural detail, and the space to enjoy a refined indoor-outdoor lifestyle.

105 Woodhill Lane, Manhasset

$575,000
4 Beds 2 Baths 1046928 MLS
Get ready to fall in love with the wonderful vibe of this spacious raised ranch, perfectly set on 1.1+/- acres in the desirable Tillson area. With an inground pool, private yard, screened porch, expansive decking, and an absolutely amazing barn, this is a property designed for living, entertaining, creating, and enjoying everything the Hudson Valley has to offer. Inside, the home offers an abundance of space and flexibility, making it an ideal choice for those looking for room to spread out or a multigenerational living arrangement. The main level features a huge, light filled dining room, an eat in kitchen, and a welcoming living room centered around a beautiful wood burning stone fireplace. Three comfortable bedrooms complete the main level, along with a wonderful screened in porch overlooking the private yard, creating the perfect spot for morning coffee, summer dinners, or simply enjoying the peaceful setting. The lower level expands the possibilities even further with a generous family room featuring a woodstove, laundry room, bedroom, bathroom, and an incredible pool room complete with its own shower and sauna. Whether you envision a private guest suite, recreation area, home office, hobby space, or multigenerational living, there is room here to make it your own. And then there is the BARN! A true dream for the collector, woodworker, hobbyist, car enthusiast, entertainer, or anyone who has always wanted an amazing space of their own. Complete with a loft, carport, dedicated car service area, and plenty of room for projects, storage, gatherings, or perhaps the ultimate Hudson Valley barn party, this is a rare and exciting extra that takes the property to another level. Step outside and enjoy the inground pool, private grounds, multiple outdoor living spaces, and the freedom that comes with over an acre of property. All this in a fantastic location close to the funky and fabulous Village of Rosendale, Kingston, and New Paltz. Restaurants, shopping, hiking, biking, apple picking, fairs, festivals, art, music, and plenty of Hudson Valley adventure are all close by. It is the kind of location that lets you enjoy the best of the area while coming home to your own private retreat. Come for the space, stay for the lifestyle, and fall in love with the possibilities!

105 Orchard Street, Tillson

$339,000
4 Beds 2 Baths 1045165 MLS
Character, flexibility, and location come together beautifully in this spacious Kingston home! Set in the heart of the vibrant Midtown Arts District, this four bedroom, two full bath home offers an adaptable floor plan with plenty of room to live, work, create, and entertain. The main level features a generous living room with hardwood flooring and a charming faux mantel, creating a warm and inviting gathering space. A first floor bedroom with its own attached full bath offers wonderful flexibility for guests, a home office, or convenient one level living. The dining room flows into a kitchen filled with personality, complete with funky built in cupboards that add character and storage. Just beyond, a screened in back porch provides the perfect spot for morning coffee, evening conversations, or enjoying the outdoors bug free. Upstairs, three large bedrooms provide abundant space, including one bedroom with a connected office area and access to another full bath. Whether you need dedicated work space, a creative studio, guest accommodations, or simply room to spread out, this home offers options. The front porch adds privacy and valuable outdoor living space, while the fenced backyard creates a wonderful setting for gardening, play, pets, or summer gatherings. Practical updates include an on demand generator and new central air, adding comfort and peace of mind. And then there is the location! Become part of Kingston's MAD District, the Midtown Arts District, surrounded by creativity, galleries, restaurants, coffee shops, and the energy that makes this part of Kingston so appealing. The nearby Rail Trail offers opportunities for walking and biking, while Village Coffee, the new Metro Building and its innovative community of ideas, and countless other local destinations are all close at hand. A home with character, flexibility, outdoor space, and a location that puts you right in the middle of Kingston's creative scene. Come discover all that this special property has to offer!

144 Henry Street, Kingston

$1,599,000
4 Beds 5 Baths 1047480 MLS
Welcome to 206 Beverly Road - Meticulously rebuilt and expanded, this 4 bedroom, 4.5 bath home sitting on 1.2 Acres blends exceptional craftsmanship with modern luxury. A grand entry with soaring ceilings and beautiful 5-inch custom oak flooring creates an immediate sense of warmth and openness. The thoughtfully designed layout offers outstanding living space, with the first-floor den, living room, and dining area flowing seamlessly into the kitchen—the true heart of the home. Designed for both function and style, the chef’s kitchen features an oversized center island, custom cabinetry and lighting, premium Thermador appliances, a Sub-Zero wine fridge, a large custom pantry, and a butler’s serving station. Upstairs, you’ll find all four bedrooms, including a spacious primary suite with a spa-like bathroom, radiant flooring, and a custom walk-in closet. An additional en-suite bedroom, two more bedrooms, a custom full bath, and a designer laundry room complete the second level. The large, detached garage with additional loft space, a full basement (955 sq ft) with OSE, and a full-size attic (825 sq ft) provide abundant additional space to tailor to your needs. Built with meticulous attention to detail, this home also includes a whole-house Generac gas generator, all-new electrical, plumbing, roofing, an EV car charger, and energy-efficient features including a Navian combo boiler, Andersen 400 Series windows, and spray-foam insulation. A must-see for discerning buyers who appreciate quality craftsmanship, luxury amenities, and an oversized property.

206 Beverly Road, Huntington Sta

$1,189,000
4 Beds 4 Baths 1037307 MLS
Tucked into a private setting in Croton-on-Hudson, 133 Scenic Drive West is the kind of home that makes everyday life feel a little more like a getaway. With 4,000 square feet of living space, four bedrooms, 3.5 bathrooms, and a backyard designed for entertaining, this home offers plenty of room to spread out, gather, and enjoy both indoors and out. Inside, the main level is defined by 9-foot ceilings, hardwood floors, and a layout that flows easily from one space to the next. The living room features a gas fireplace and large windows, while the eat-in kitchen area is lined with sliding glass doors that bring in natural light and create a seamless connection to the outdoors. The doors open directly to the upper Trex deck, making it easy to step outside for morning coffee, dinner, or an afternoon overlooking the backyard and pool. A separate formal dining area provides additional space for entertaining and gathering. Upstairs, the spacious primary suite feels like its own retreat, complete with a large walk-in closet and private en-suite bath. Three additional bedrooms and a well-appointed hall bath offer flexibility for family, guests, home offices, or whatever the next owner needs. Conveniently located second-floor laundry adds ease and functionality to everyday living. The fully finished walk-out lower level adds another dimension to the home, with generous additional living space and sliding glass doors leading directly to the lower deck and backyard. Whether used as a family room, recreation space, home gym, guest area, or a combination of all four, it extends the home’s living space while maintaining a direct connection to the outdoors. And then there’s the backyard. Fully fenced and surrounded by mature greenery, the property feels remarkably private. The heated in-ground pool is the centerpiece, complemented by multiple outdoor living areas, including the upper Trex deck, lower covered Trex deck, and patio space. It’s a backyard designed just as well for quiet summer afternoons as it is for entertaining a crowd. Located near some of Croton-on-Hudson’s most loved features — trails, parks, kayaking, riverfront recreation, and the Croton-Harmon Metro-North station, with express service to Grand Central in approximately 50 minutes — this home offers an ideal balance of privacy and convenience. With nearby access to The Croton Dam and the Hudson River, 133 Scenic Drive West keeps you close to the outdoor lifestyle Croton is known for while still feeling tucked away. It’s the best of Croton living: spacious, private, connected, and surrounded by some of Westchester’s most beautiful natural destinations.

133 Scenic Drive W, Croton-On-Hudson

$2,795,000
4 Beds 7 Baths 1048047 MLS
Sunny Ridge. Brewster’s most extraordinary offering. Set behind iron gates up a long winding drive, this estate will thrill you. Perched on a peaceful cul-de-sac street in a highly sought-after location on the Southeast/North Salem border - just 60 miles from NYC and 4 miles to the Metro North train station. Set on over 15 acres with commanding panoramic views and a profound sense of privacy - your closest neighbors are the horses at the abutting farm. The 8,000+ sq. ft main residence offers a level of craftsmanship that simply doesn’t exist at this price point. As you step inside the entry foyer, the exquisite architectural details are immediately apparent - custom millwork, detailed moldings, elegant archways, tray ceilings, and gleaming hardwood floors. The focal point is an incredible floating staircase - providing access to three magnificent levels of luxury living. There is a formal living room with soaring 20+ foot ceilings, six fireplaces, a massive fully equipped chef’s kitchen, a fully finished 2200+ sq. ft lower level with custom wet bar, movie theater, gym, wine cellar, and two french door walkouts to covered patios. Multiple offices for working from home. Cozy den with french doors out to wrap-around mahogany deck, covered porch, and outdoor kitchen with patio. Gorgeous formal dining room - ideal for dinner parties and entertaining. Upstairs, there is an expansive primary bedroom suite with sitting area, balcony, spa-like bath, and dual walk in closets. Down the hall, there are three additional en-suite bedrooms with walk-in closets and a laundry room. There is an attached heated 4 car garage, as well as a custom-built 4,000 sq.ft carriage barn, which provides garage space for an additional 12 cars. The carriage barn also offers a world of possibilities as a guest house, art/music studio, and more. Sunny Ridge is a rare and compelling opportunity for the discerning buyer seeking a private, resort-caliber estate within easy reach of Manhattan.

16 Reynwood Drive, Brewster

$695,000
4 Beds 2 Baths 1047901 MLS
Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$1,325,000
4 Beds 4 Baths 1046553 MLS
Welcome to this exceptional residence where timeless elegance, thoughtful design, and impeccable craftsmanship come together on a peaceful, park-like property. Meticulously maintained and presented in exquisite condition, this stunning home offers a versatile floor plan designed to accommodate today's lifestyle with ease. The heart of the home is the custom gourmet kitchen, beautifully appointed with high-end appliances, a built-in wine refrigerator, abundant cabinetry, and generous workspace for both everyday living and entertaining. Rich hardwood floors, custom millwork, detailed moldings, and built-in cabinetry showcase the quality and attention to detail found throughout. Spacious and inviting living areas are enhanced by two gas fireplaces, creating warm and comfortable gathering spaces. The luxurious primary suite serves as a private retreat, featuring custom walk-in closets and a spa-like atmosphere. Three additional bedrooms provide ample space for family and guests, while exceptional storage solutions can be found throughout the home. The walk-out lower level offers tremendous flexibility with a fully equipped in law set up with an eat-in kitchen, living room, bedroom, full bath, and cedar-lined closets—ideal for extended family, guests, or multi-generational living. Outdoor living is equally impressive. Set amidst serene, professionally landscaped grounds, the property features a heated pool, expansive Trex deck, stone patio, and electric awning, creating the perfect setting for relaxation and entertaining. Updated mechanicals provide peace of mind and reflect the pride of ownership evident throughout this remarkable home. A rare offering that combines luxury, comfort, and functionality in a truly picturesque setting. Note that Lower Level is included in total square footage.

50 Wixon Pond Road, Mahopac

$2,150,000
4 Beds 3 Baths 1047922 MLS
Welcome to this exceptional, completely renovated four-bedroom, three-bathroom residence, privately nestled on a quiet cul-de-sac in the heart of East Quogue. Thoughtfully designed and beautifully appointed, this turn-key home seamlessly blends sophisticated modern living with the relaxed elegance of the Hamptons. An inviting open-concept layout is complemented by oversized glass windows, filling the home with natural light and offering beautiful views of the private, professionally landscaped grounds. At the heart of the home is a state-of-the-art chef’s kitchen, featuring premium Viking appliances, custom finishes, and an effortless flow into the living and entertaining spaces. Designed for both everyday living and sophisticated entertaining, the kitchen is as functional as it is beautiful. The home’s exceptional amenities continue outdoors with a fully equipped chef’s outdoor kitchen, creating the perfect setting for summer entertaining, al fresco dining, and relaxed Hamptons living. The beautifully landscaped private yard provides a serene backdrop for gatherings, recreation, and quiet afternoons at home. A thoughtfully designed private laundry suite adds convenience and functionality, while a dedicated pet room with direct access to the outdoors is an exceptional and rare feature for today’s discerning homeowner. Four spacious bedrooms and three beautifully renovated bathrooms provide comfortable accommodations for family and guests, while the home’s private cul-de-sac location offers a peaceful sense of seclusion without sacrificing convenience. Ideally situated in the heart of East Quogue, this home is moments from the area’s beautiful ocean and bay beaches, local shops, restaurants, and all that the Hamptons has to offer. Enjoy easy access to neighboring Quogue, Westhampton, and the best of the East End.

5 Deerland Drive, E. Quogue

$654,900
4 Beds 3 Baths 1028846 MLS
Welcome to this impeccably maintained 4 bedroom, 2.5 bath Colonial, gracefully situated on 2.1 acres of beautifully landscaped, level grounds that offer exceptional privacy and timeless curb appeal. Boasting over 2500 square feet of thoughtfully designed living space, this distinguished residence seamlessly blends classic elegance with modern comfort. The spacious primary suite features a generous walk-in closet and a beautifully appointed ensuite bath. A versatile study provides the perfect space for a home office, library, or guest room. The inviting family room is highlighted by a stunning propane fireplace, creating a warm and welcoming gathering space. The beautifully appointed kitchen boasts rich cherry wood cabinetry, a well-positioned center island, a large pantry, a spacious breakfast room, stylish lighting, and easy access to the formal dining room with another gorgeous propane fireplace. A cozy living room offers additional space for relaxation and entertaining. Quality craftmanship is evident throughout with gorgeous inlaid hardwood floors, elegant wood and crown moldings, and beautifully updated modern bathrooms. Additional highlights include a newer roof, a newer high-efficiency propane heating system with the added benefit of an auxiliary boiler heating system, two propane fireplaces, a spacious two-car attached garage, an extra one-car barn garage, and a full unfinished basement offering lots of space for storage. Step outside the home and discover your own private oasis. Surrounded by mature woods, this property offers exceptional privacy and the perfect setting for outdoor entertaining. Create your ideal gathering space by adding your own patio table, chairs, and outdoor bar, then cool off in the well-maintained newer above-ground pool featuring a spacious deck for relaxing and soaking up the sun. The expansive yard provides plenty of room for nearly any outdoor sport, party, or recreational activity. This remarkable property presents a rare opportunity to enjoy refined country living while remaining conveniently close to schools, shopping and major highways. It is ideal for anyone looking to enjoy the peaceful Hudson Valley Lifestyle.

2810 County Route 1, Port Jervis

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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.