Sleepy Hollow Real Estate Search

Sleepy Hollow 5 Bedroom Properties for Sale

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Newest Sleepy Hollow 5 Bedroom Properties for Sale

$1,249,999
5 Beds 3 Baths 1041078 MLS
Welcome to this beautifully expanded split level home in the heart of Massapequa Park, ideally situated on a unique-shaped lot offering exceptional outdoor living. The home offers 5 bedrooms 2.5 baths, including a spacious primary suite with its own full bath. Completely renovated about 4 years ago the open floor plan creates a spacious, inviting flow throughout the main living areas, perfect for both everyday living and entertaining. The chef's kitchen features a large center island, granite countertops, stainless steel appliances, abundant cabinetry, and plenty of storage space. The formal dining room provides the perfect setting for gatherings and special occasions. The expanded living room offers a warm and comfortable living area highlighted by a striking gas fireplace with beautiful stone surround and also provides direct access to the backyard as does the main-floor den, making indoor-outdoor living effortlessly. Step outside to your private backyard oasis fully fenced featuring an in-ground pool, spacious deck, patio, and awning for convenient shade and coverage. The uniquely shaped lot provides character, privacy, and plenty of space to enjoy the outdoors. Conveniently located near parks, shopping, dining, LIRR, and everyday amenities, this home combines space, comfort, modern updates and exceptional outdoor living in a desirable Massapequa Park location. A wonderful opportunity to make this expansive and versatile home your own.

5 Renee Place, Massapequa Park

$6,495,000
5 Beds 6 Baths 1039871 MLS
Some homes simply command your attention. This is one of them. Perfectly positioned at the end of prestigious Jagger Lane, this extraordinary new construction offers over 5000 square feet of thoughtfully designed contemporary living, masterfully crafted to capture calming views of Moriches Bay while embracing the privacy of its natural surroundings & peaceful flora. Designed with both luxury and functionality in mind, the home's fluid floor plan begins on its entry level, where four spacious en-suite bedrooms provide exceptional comfort and privacy. The primary en-suite, situated on the southern side of the home, opens to its own balcony, where floor-to-ceiling glass sliders frame mesmerizing bay vistas. The three additional generously sized, en-suite guest bedrooms and dedicated laundry room complete this first of three levels. The top floor is nothing short of spectacular. Anchored by a designer chef's kitchen featuring premium appliances, double ovens, a speed oven, two dishwashers, a built-in espresso station, ice maker and expansive center and peninsula islands (with seating for 9), it’s space is created for effortless entertaining. A sun drenched south-facing office/bedroom offers sweeping bay views - an inspiring backdrop for work or quiet reflection. Adjacent is a handsome media room/den which shares a convenient full bathroom. The expansive dining and living rooms are nothing short of breathtaking — open, light-filled spaces that flow seamlessly through grand glass doors to the rear yard, blurring the line between indoor luxury and outdoor splendor. The outdoor living experience is equally exceptional. Resort-caliber amenities include a heated, salt water gunite pool with integrated spa and sun shelf, elegantly appointed lounging and entertaining areas, complete with a dedicated outdoor shower and bath — every detail curated for ease and indulgence. The 800 square foot lower level is as impressive as the floors above offering an abundance of storage and space along with direct access to the home's three-car garage, while a private elevator connects all floors with effortless ease ensuring convenience and accessibility. Designed with sustainability at its core, the home features a fully integrated solar panel system with an impressively low HERS energy rating, delivering exceptional efficiency and environmental responsibility. Offered fully furnished and impeccably appointed, this singular residence presents a rare opportunity to own a truly turnkey luxury retreat perched above the timeless beauty of Moriches Bay.

1A Jagger Lane, Westhampton

$899,995
5 Beds 4 Baths 1039943 MLS
Beautifully Renovated Five-Bedroom Home with Finished Basement Welcome to this beautifully updated five-bedroom, three-and-a-half-bath home, offering spacious living areas, modern finishes, and a versatile fully finished basement with a private entrance. Set on a half-acre property, this home features a private backyard that is ready for a pool. The property is completely fenced in with a new fence and includes an irrigation system, mature landscaping and plants, and a large driveway with ample space for multiple cars. Additional features include central air and much more. The main level features a beautifully remodeled kitchen with new appliances, granite countertops, and new flooring. The home offers hardwood floors throughout, a spacious living room with a cozy fireplace, a large dining room, and a convenient laundry area. The main house includes four bedrooms, two full bathrooms, and one half bathroom, providing plenty of space for comfortable living. The fully finished basement adds exceptional versatility, featuring two additional bedrooms and one full bathroom, along with its own private entrance. This space is ideal for extended family, guests, a home office, recreation, or additional living arrangements. Additional features include a one-car garage, generous living spaces, central air, and a well-designed layout that combines comfort and functionality. A great opportunity for those looking for a spacious, updated home with additional private living space, a large fenced-in property, and room to create the backyard of their dreams.

674 Flanders Road, Riverhead

$1,499,000
5 Beds 5 Baths 1040719 MLS
Goshen School District! Set at the end of a quiet cul-de-sac in the prestigious Farmingdale Heights neighborhood, this extraordinary custom-built residence offers an impressive combination of luxury, privacy, and exceptional indoor and outdoor living. From the moment you arrive, the professionally designed landscaping, expansive grounds, and striking architectural details set this home apart. With 5 bedrooms, 4.5 baths, and an abundance of thoughtfully designed living space, this home is built to impress while offering the comfort and privacy of a true retreat. A grand two-story foyer welcomes you with marble floors, an elegant staircase, crystal chandeliers, and dramatic floor-to-ceiling windows. Walnut-stained hardwood floors, soaring ceilings, designer lighting, crown moldings, tray ceilings, and vaulted ceilings add sophistication throughout the open floor plan. The impressive great room is the centerpiece of the home, featuring soaring two-story ceilings, walls of windows, and a custom stone fireplace with an Xtrordinair insert, updated for efficient supplemental heating. A striking catwalk-style balcony overlooks the great room, creating an impressive architectural focal point while connecting the upper-level living spaces. The gourmet kitchen is equally impressive, featuring a large center waterfall island, white Calacatta Harmony countertops and a matching Calacatta Harmony stone backsplash, solid brass features, premium stainless steel appliances, pantry, and direct access to the expansive Trex deck—perfect for entertaining and enjoying the surrounding grounds. The main level includes a private bedroom suite or home office with its own full bath, along with an additional powder room. Upstairs, the luxurious primary suite features a private sitting room, spa-like bathroom, and custom walk-in closet. An additional bedroom offers an ensuite bathroom, while two more bedrooms share a Jack-and-Jill bathroom. All bedrooms feature custom closets and large windows. Additional amenities include a Hydro-Air heating system, whole-house double water filtration system, owned solar panels offsetting approximately 89% of electric costs, a 3-car garage with EV Charger, and a walkout basement. The backyard transforms the property into a private outdoor oasis. A custom-built pool is surrounded by approximately 3,000 square feet of bluestone patio, natural rock walls, a six-foot privacy fence, and an impressive outdoor kitchen designed for entertaining. Professionally designed landscaping and an irrigation/sprinkler system create a beautifully maintained setting throughout the property while providing privacy and enhancing the home's exceptional curb appeal. A truly turnkey residence offering luxury, privacy, exceptional craftsmanship, and resort-like outdoor living in one of Goshen's most sought-after neighborhoods. High Quality Construction, Cement Board (Hardy-Plank) and Stucco Siding. The Solar panels are owned.

34 Woodcrest Lane, Goshen

$699,000
5 Beds 4 Baths 1041722 MLS
Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful, wooded setting. From the inviting covered front porch, step inside to spacious, light-filled rooms that blend comfort and elegance. Rich hardwood floors, soaring ceilings, abundant windows, and a beautiful stone fireplace create a warm and welcoming atmosphere. The heart of the home is the expansive open kitchen, featuring modern appliances, generous cabinetry, and plenty of counter space, making it ideal for everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, offering both open gathering spaces and cozy nooks. Five generously sized bedrooms provide flexibility and room for everyone. Enjoy the outdoors from the extensive decks overlooking the mature, wooded surroundings, complete with a charming koi pond that adds to the property's peaceful, natural setting. Whether enjoying morning coffee, entertaining guests, or simply unwinding, this outdoor space offers a tranquil retreat. Adding exceptional versatility, a separate approximately 800-square-foot building offers endless possibilities as an art studio, workshop, private office, creative space, or whatever best suits your needs. With its combination of generous living space, distinctive character, privacy, and flex outbuilding space, this property offers a truly special place to call home.

65 Oxford Springs Road, Chester

$699,000
5 Beds 3 Baths 1040487 MLS
Set on a beautiful private property in Mahopac, this impressive 5-bedroom, 3-bath residence offers over 3,000 square feet of thoughtfully designed living space, an inviting floor plan, and an exceptional backyard ideal for entertaining and everyday enjoyment. The main level features a bright and welcoming living room with fireplace, hardwood floors, and a generous bay window. The updated kitchen combines style and functionality with abundant cabinetry, granite countertops, stainless steel appliances, and a comfortable dining area. The adjoining dining room is a true focal point, showcasing soaring vaulted ceilings, exposed beams, skylights, and walls of windows overlooking the lush grounds, creating a wonderful sense of space while bringing the outdoors in. The flexible floor plan provides ample room for entertaining, working from home, and comfortable everyday living. The lower level offers exceptional versatility with a well-appointed in-law suite featuring its own living area, kitchenette, bedrooms, and full bath—ideal for extended family, guests, or multi-generational living. Outside, the property takes on a resort-like feel. The in-ground pool is surrounded by an expansive patio with ample space for lounging, dining, and entertaining, while the private, level yard provides plenty of room for recreation, gardening, and outdoor activities. Multiple gathering areas create a natural extension of the home's living space and make it easy to enjoy the property throughout the warmer months. Offering generous proportions, a flexible layout, quality updates, and an exceptional outdoor setting, this Mahopac residence delivers the perfect balance of comfort, privacy, and versatility.

41 Fenwood Road, Mahopac

$750,000
5 Beds 2 Baths 1039504 MLS
Welcome to this beautiful, well-maintained, detached 5-bedroom, 2-full-bathroom home located on a quiet dead-end street in the desirable Westchester Square neighborhood of the Bronx. Offering a versatile three-level layout, this home combines comfortable living with potential for future expansion and investment. The main living level features a fully updated kitchen with high-end cabinetry, granite countertops, stainless steel appliances, and a premium Sub-Zero refrigerator. Beautiful wood flooring extends throughout the main level, which also includes a recently renovated full bathroom. The second and third levels offer five bedrooms with new carpeting. For year-round comfort, the home is equipped with ductless mini-split systems for heating and cooling, complemented by a central oil heating system with individual zone thermostats. Outdoor features include a charming front sitting porch, rear deck, and a spacious private backyard, providing excellent space for entertaining and outdoor enjoyment. The front garden area may offer potential for conversion to a private driveway, subject to required municipal approvals. The flexible layout may also provide potential for conversion to a two-family configuration for rental income or multi-generational living, subject to all applicable permits and approvals. Conveniently located within walking distance of public transportation, shopping, schools, restaurants, and neighborhood amenities. The property is also situated near the planned East Bronx Metro-North station project, which is expected to bring future regional rail service to the area. A unique opportunity to own a detached home with modern updates, generous living space, outdoor amenities, and potential for future investment or customization. This is the house you've been waiting for. Come check it out and make it your home.

1521 Hone Avenue, Bronx

$1,780,000
5 Beds 3 Baths 1040739 MLS
Welcome to an exceptional residence where timeless Colonial architecture meets sophisticated modern living. Completely renovated from top to bottom and set on an oversized property in the heart of Mineola, this impressive five-bedroom, 2.5-bath Center Hall Colonial has been thoughtfully designed with an extraordinary level of attention to detail, quality, comfort, and technology. A gracious center hall leads to bright, elegant living spaces, including a formal living room with a dual-sided fireplace opening to a sun-filled den, a formal dining room and a private home office. The chef’s kitchen features quartz countertops, a porcelain backsplash, oversized sink, pantry and integrated LED lighting, and opens to an enclosed porch ideal for casual dining or entertaining. Upstairs are four generously sized bedrooms, including a serene primary suite, along with beautifully renovated baths and a fully built out primary closet with integrated LED lighting. Major updates include new plumbing, electrical and HVAC systems, central air, gas heat and cooking, updated water service and a new sprinkler system. Smart-home features include a wireless alarm and camera system, enhanced Wi-Fi, built-in multi-zone speakers, smart garage access and EV charger readiness. A full basement, walk-up attic and detached two-car garage with loft provide abundant storage and flexible space. A turnkey Mineola home offering exceptional space, modern updates and outstanding versatility.

220 Pomander Road, Mineola

$1,645,000
5 Beds 5 Baths 1041395 MLS
Welcome to this exceptional brick residence located in Hamilton Estates in the Town of Tuxedo, NY, where mountain views, privacy, and enduring craftsmanship define everyday living. Set on 1.6 acres at the end of a quiet cul-de-sac, this home offers approximately 6,200 square feet of finished living space, including a newly completed lower level designed for modern lifestyle needs. A circular driveway and timeless architectural lines create a confident first impression. Inside, oak flooring, solid 6-paned hardwood doors, and a solid mahogany front entry reflect quality throughout. Oversized Pella windows frame sweeping mountain views and bring in abundant natural light. The main level balances comfort and scale, offering open yet defined living spaces ideal for both daily life and entertaining. The kitchen features stainless appliances, custom cabinetry, generous prep space, and a dining area overlooking the yard — relaxed, functional, and welcoming. The owner’s suite serves as a private retreat with a spa-style bath, soaking tub, and separate shower. Three additional bedrooms provide flexibility for family or guests. A separate entrance leads to a fully equipped private apartment-suite with its own bedroom, living room, and kitchen — ideal for extended family, guests, or multi-generational living. The newly finished lower level significantly expands the home’s livability. Designed with entertaining in mind, it includes large open recreation areas, space for a pool table, a dedicated workout area, and a full bathroom. Fire egress windows were added during renovation, enhancing safety and natural light. Two oversized unfinished storage rooms, along with multiple additional closets, provide substantial storage rarely found in homes of this size. Outdoors, the setting is peaceful and private. The park-like property includes a 100-yard putting green, deck, and built-in grill for easy outdoor gatherings. The home abuts a wildlife easement, preserving both privacy and the natural beauty that makes the Town of Tuxedo so special. Additional features include steel I-beam construction with 10-inch foundation walls, a 350-foot drilled well producing approximately 50 gallons per minute, 17-zone irrigation system, full-house security, oil heat (above-ground tank), and a three-car attached garage. Located in the Town of Tuxedo in the Hudson Valley, Hamilton Estates offers a quiet residential setting with convenient access to major highways, commuter routes, and nearby amenities. A great opportunity to own a substantial luxury home in Hamilton Estates with meaningful square footage, structural integrity, and flexible living space.

17 Constitution Court, Tuxedo Park

$1,088,000
5 Beds 2 Baths 1038973 MLS
Discover an exceptional opportunity in the desirable West End of Floral Park Village! This beautifully maintained 5 Bedroom, 2 Bathroom Colonial combines classic character with an impressively spacious layout designed to accommodate a variety of lifestyles. Step inside to a bright and welcoming Living Room that flows into the Formal Dining Room, Kitchen, Powder Room, and expansive Breakfast Nook and Den, creating wonderful spaces for both comfortable everyday living and memorable gatherings. A rear door provides convenient access to the beautifully landscaped backyard, extending the living and entertaining space outdoors. Upstairs, five generously proportioned Bedrooms and a Full Hall Bathroom provide plenty of room to spread out, while the home's thoughtful layout offers wonderful flexibility as needs change over time. The Full Basement further expands the possibilities with multiple recreation and bonus areas, laundry, utilities, and abundant storage. Set on a beautifully landscaped 50' x 100' property, the home features a private backyard, long driveway, and the added convenience of a detached one-car garage. Living in Floral Park Village means enjoying an exceptional array of municipal and recreational amenities, including private police and sanitation services and a Recreation Center featuring an Olympic-size pool, tennis and pickleball courts, basketball and volleyball courts, baseball fields, hockey facilities, and more. Near shopping, dining, major roadways, and the LIRR with direct service to Grand Central, Penn Station, and Atlantic Terminal, this home is also located within highly regarded School District #22. Selling is "As Is". Offering exceptional space, versatility, and a sought-after West End location, make this your next move!

53 Larch Avenue, Floral Park

$969,000
5 Beds 3 Baths 1041250 MLS
Welcome to 130-49 232 Street! A newly renovated, turn key, move in ready cape nestled on a beautiful tree lined street of Laurelton. Sitting on a 50x100 lot, featuring a wide private driveway, garage, and tons of yard space to enjoy outdoor gatherings. As you enter the first floor you are greeted by the expansive, sun drenched, modern, open concept living/dining area which provides great space for entertaining. The beautiful chefs granite kitchen is equipped with floor to ceiling custom cabinetry and adorned with a full fleet of stainless steel appliances. 3 Spacious bedrooms on the first floor. Each bedroom is well proportioned and equipped with ample closet space. The second floor has an additional bedroom and full bath. This space is setup to function as the primary suite. Fully tiled bathroom adorned with state of the art wall & floor tiles. The high ceiling full finished basement has both interior and exterior access. Configured as 1 bedroom 1 bath unit, this space can be used as the perfect in-law suite, NYC ADU, guest quarters or additional recreational space. Renovations include brand new select wide oak wood flooring, recessed lighting, updated electrical, heating, plumbing and central air systems throughout. Prime Laurelton location. Conviently located with close proximity to major transportation which makes commuting a breeze. Just off Francis Lewis Blvd, Merrick Blvd, Laurelton Parkway, Belt Parkway, Cross Island Parkway, Southern State Parkway. Quick easy access to schools, shopping centers, restaurants, cafes, parks and many other vibrant neighborhood amenities.

13049 232nd Street, Laurelton

$1,099,988
5 Beds 4 Baths 1039816 MLS
Welcome to this spacious 3,800-square-foot Colonial home, featuring a versatile split-level layout with 5–6 bedrooms and 4 full bathrooms, offering plenty of room for an extended or growing family. The home features a possible mother-daughter setup with proper permits, providing flexibility for multigenerational living. Step through the large walk-in entry into a bright and welcoming interior filled with an abundance of natural light and impressive high ceilings. The first floor features 2 generous bedrooms, 2 large living rooms, 2 full bathrooms, a kitchenette, and a laundry room, along with an attached 3-car garage. The second floor offers a formal living room with a wood-burning fireplace and a possible private office, providing an elegant and flexible space for entertaining or working from home. The third floor showcases an additional dining room, a large eat-in kitchen, and 4 bedrooms, including a primary bedroom with a private full bathroom and its own deck. The home's flexible layout provides plenty of space to accommodate a variety of living arrangements. Additional highlights include hardwood floors, high ceilings, central air, an attic for extra storage, a covered porch, a back deck with a Jacuzzi, and a private driveway. Situated on a generous 19,602-square-foot lot, the property also features an updated roof (2019) and low taxes. This unique home offers exceptional space, versatility, and comfort, with plenty of room to make it your own.

23 Colonial Drive, Smithtown

$1,799,999
5 Beds 5 Baths 1007192 MLS
Welcome to an impressive new construction residence in the heart of Levittown, where contemporary design, generous proportions, and refined finishes come together on an oversized lot of nearly 12,000 sq. ft. Offering approximately 3,800 sq. ft. of living space, this thoughtfully crafted home delivers the space, style, and functionality sought for modern living. Step inside to a striking open-concept interior filled with natural light, featuring 9-foot-high ceilings throughout the property, oversized windows, decorative wall molding, and sophisticated architectural details. This home offers 5 spacious bedrooms and 5 beautifully appointed bathrooms, including a private main-level en-suite bedroom, ideal for guests or extended living. The centerpiece of the home is the designer chef’s kitchen, featuring gas cooking, premium Bosch stainless-steel appliances, custom cabinetry, an oversized waterfall quartz island, elegant finishes, and a hidden walk-in pantry. An effortless connection to the living and dining areas creates an impressive setting for both everyday living and entertaining. Upstairs, a spacious loft with sunset views adds another inviting living area. Four generously sized bedrooms feature custom closets, while the luxurious primary suite offers two oversized custom walk-in closets and a spa-inspired bathroom finished with carefully selected details. A conveniently located second-floor laundry room with a deep linen closet adds everyday practicality and valuable storage. The approximately 1,800 sq. ft. full basement features 9-foot ceilings, egress windows, and direct walk-out access to the yard, providing substantial additional space and flexibility. Outside, front and rear pavers, a fully fenced yard, and in-ground sprinklers complement the expansive property. The generous backyard provides plenty of room for outdoor entertaining, recreation, and the potential for a future pool. Ideally located near schools, shopping, dining, recreation, and community amenities, this distinctive Levittown residence combines new construction, impressive scale, contemporary style, and thoughtful functionality in one remarkable home. A rare opportunity to own a newly built residence designed to make an impression from the moment you arrive.

23 Harrow Lane, Levittown

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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.