Sleepy Hollow Real Estate Search

Sleepy Hollow 6+ Bedroom Properties for Sale

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Newest Sleepy Hollow 6+ Bedrooms Properties for Sale

$699,999
6 Beds 3 Baths 1030767 MLS
Welcome to 8 Fairway Drive in Port Jefferson Station, a beautifully renovated high-ranch offering the space, flexibility, and modern finishes today’s buyers are searching for. Completely transformed in 2023 with additional recent upgrades, this exceptional home features six spacious bedrooms, three full bathrooms, and a true mother-daughter configuration with proper permits perfect for a multi-generational living, or anyone seeking additional private living space. From the moment you enter, you are welcomed by a bright and inviting open concept design featuring hardwood floors, high ceilings, elegant wainscoting, and beautiful trim work throughout. The spacious living room is centered around a built-in electric fireplace, creating a warm and comfortable setting for relaxing or entertaining. The stunning HGTV-inspired eat-in kitchen is designed to impress, featuring a large center breakfast island with a built-in sink, quartz countertops, soft-closing cabinetry, stainless steel appliances, and plenty of workspace and storage. The open layout flows seamlessly into the living and dining areas, making this the perfect home for hosting holidays, gatherings, and everyday family life. Sliding glass doors lead directly to an oversized deck overlooking a huge private backyard, creating the perfect indoor-outdoor flow for barbecues, gatherings, entertaining guests, or simply relaxing in your own outdoor oasis. The upper level features an open living room, dining room, and kitchen combination, along with two generously sized bedrooms and a spacious primary bedroom connected to a beautifully updated Jack-and-Jill bathroom. The lower level offers an additional living area, three spacious bedrooms, and two full bathrooms, providing exceptional versatility and privacy. All six bedrooms are generously proportioned, and all three bathrooms have been tastefully updated. Additional features include central air conditioning, electric heat, gleaming hardwood floors, in-ground sprinklers in both the front and back yards, and quality finishes throughout, making this home as functional as it is beautiful. Ideally situated near the best of the North Shore, the home is approximately 10 minutes from Port Jefferson Village, where you can enjoy waterfront dining, local boutiques, coffee shops, parks, seasonal festivals, live entertainment, and beautiful harbor views. The Port Jefferson Ferry is also nearby, offering convenient service across Long Island Sound to Bridgeport, Connecticut—perfect for day trips, weekend getaways, or an alternative route to New England. Commuters will appreciate being only minutes from the Port Jefferson Long Island Rail Road station, providing convenient service into New York City. Manhattan is approximately 60 miles away, with train travel generally ranging from about 1 hour and 40 minutes to 2 hours depending on the schedule. The home is also conveniently located approximately 15–20 minutes from Stony Brook University and Stony Brook University Hospital, making it an ideal location for medical professionals, university employees, students, and families alike. Major roadways are easily accessible, with the Long Island Expressway approximately 15–20 minutes away, the Northern State Parkway approximately 25–30 minutes away, and the Southern State Parkway approximately 30–35 minutes away, providing convenient travel throughout Long Island and beyond. Offering modern luxury, exceptional craftsmanship, an incredibly versatile floor plan, and an unbeatable location close to shopping, dining, transportation, healthcare, education, and the waterfront lifestyle of Port Jefferson Village, this home truly checks every box. If you’ve been searching for your forever home, this is it. Completely move-in ready with absolutely nothing to do but bring your bags and start making memories at 8 Fairway Drive.

8 Fairway Drive, Port Jefferson Station

$799,995
17 Beds 4 Baths 1029585 MLS
Beyond the stone walls and winding roads of the legendary Beaverkill Valley lies a rare opportunity to become the next steward of one of the Catskills’ historic estates. Built in 1880 and set on 93 private acres across two tax parcels, this remarkable property borders thousands of acres of protected New York State land, offering an exceptional combination of privacy, natural beauty, and outdoor recreation. Encompassing nearly 6,800 square feet with 17 bedrooms and 4 bathrooms, the residence is rich in character and ready for a thoughtful restoration to its former grandeur. The grounds include a picturesque pond, three-car garage, and vintage tennis court, creating the foundation for an extraordinary family compound, sporting estate, or multigenerational getaway. Spend your days exploring the surrounding wilderness, casting a line on legendary Catskill trout streams, or simply enjoying the peace that only a property of this scale can provide. Located just minutes from Livingston Manor’s acclaimed restaurants, breweries, boutiques, and year-round cultural attractions, the estate offers the perfect balance of seclusion and convenience. Prospective purchasers may explore eligibility for membership in the exclusive Beaverkill Mountain Club, subject to the Club’s approval. Opportunities to acquire an estate of this size, history, and setting are increasingly rare. More than a home, this is a chance to preserve a remarkable piece of Beaverkill Valley history while creating a legacy property to be enjoyed for generations to come.

109 Mary Smith Hill Road, Livingston Manor

$2,495,000
6 Beds 4 Baths 1030573 MLS
Welcome to an extraordinary residence where timeless elegance meets modern sophistication. Perfectly positioned in one of Dix Hills' most prestigious neighborhoods, this impeccably reimagined and spacious 6-bedroom, 4-bathroom estate has been completely renovated with uncompromising attention to detail, offering the ultimate turnkey luxury lifestyle. Thoughtfully rebuilt from the inside out, the home features all-new electrical and plumbing systems, a 200-amp electrical service, brand new CAC units and exceptional craftsmanship throughout. Rich custom millwork, intricate crown moldings, and designer finishes elevate every space, creating an atmosphere of refined elegance. At the heart of the home is a spectacular chef's kitchen, designed to impress with premium finishes, custom cabinetry, luxury appliances, and an effortless flow for both everyday living and grand entertaining. Beautiful hardwood flooring extends throughout the home, leading to spacious living areas centered around a classic wood-burning fireplace that adds warmth and timeless charm. The fully finished basement provides exceptional flexibility, perfect for a fitness studio, recreation lounge or executive office. The attached garage showcases a professionally finished epoxy floor, delivering a sleek, showroom-quality appearance. Outside, the meticulously maintained and professionally landscaped grounds create an inviting setting for outdoor entertaining, relaxation, and year-round enjoyment. From its flawless renovations to its luxurious finishes and exceptional attention to detail, this home is a rare offering that seamlessly blends elegance, comfort, and modern convenience.

5 Hemingway Drive, Dix Hills

$1,649,000
6 Beds 5 Baths 1030467 MLS
**BRAND-NEW DETACHED 2-FAMILY IN GLENDALE** **Double Duplex Layout | Finished Basement | Private Parking** A standout opportunity in Glendale! This fully detached, brand new two-family home offers a beautiful brick facade, a smart double duplex layout, modern finishes throughout, and private parking for multiple cars. Set on an approximate 2,971 sq. ft. lot with approximately 2,448 sq. ft. of living space, this three-story property delivers the space, comfort, and flexibility today’s buyers are looking for. The home features two spacious duplex apartments, each designed across two levels: **Lower Duplex:** 3 bedrooms and 2 full bathrooms **Upper Duplex:** 3 bedrooms and 2.5 bathrooms The finished basement adds even more usable space, featuring a separate entrance, high ceilings, windows, a full bathroom, laundry hookup, and a brand-new washer and dryer. Everything is new from top to bottom, including the mechanical systems, kitchens, bathrooms, flooring, lighting, appliances, and finishes. Interior highlights include hardwood floors, recessed lighting, stainless steel appliances, granite countertops, split A/C units throughout, and beautifully finished modern bathrooms, including dual vanities in select baths. Exterior features include fenced front and rear yards, private parking for several vehicles, and a detached home setting on a tree-lined Glendale block. Conveniently located near Myrtle Avenue shopping, Atlas Park, public transportation, schools, and major highways. A rare chance to own brand-new construction with space, parking, modern design, and a highly functional two-family layout in Glendale. A truly SPECIAL opportunity in Glendale, don’t miss the chance to make this brand-new two-family home yours!

7036 70th Street, Glendale

$1,395,000
9 Beds 5 Baths 1030380 MLS
3 UNITS. Introducing a newly constructed attached three-unit property located in the highly desirable Van Nest section of the Bronx. Built with modern living and long-term value in mind, this impressive residence delivers a rare opportunity for both end-users and investors seeking a turnkey asset with strong income-producing potential. Thoughtfully designed with contemporary finishes, spacious interiors, and updated building systems, this property offers the perfect blend of comfort, functionality, and investment appeal. The residence features a total of 9 generously sized bedrooms and 5 beautifully finished bathrooms spread across three well-planned units. Each residence offers an open-concept layout that seamlessly connects the living and dining areas, creating an inviting atmosphere ideal for everyday living and entertaining. The kitchens are designed with style and practicality in mind, showcasing quality cabinetry, sleek countertop surfaces, modern fixtures, and ample storage space. Natural light flows throughout the property, enhancing the clean modern aesthetic and creating bright, welcoming interiors. The bedrooms are comfortably proportioned with substantial closet space, while the bathrooms are finished with contemporary materials and tasteful design elements that complement the overall sophistication of the home. Constructed with modern efficiency standards, the property includes updated mechanical systems, energy-efficient components, central heating and cooling, and in-unit laundry hookups where applicable. Every detail has been carefully considered to provide convenience, durability, and low-maintenance ownership for years to come. Perfectly positioned in Van Nest, the property offers easy access to major highways, public transportation, shopping centers, local restaurants, parks, schools, and neighborhood conveniences. Its strategic location makes commuting throughout the Bronx and into Manhattan both practical and efficient. This exceptional opportunity is ideal for a purchaser looking to occupy one residence while benefiting from rental income generated by the additional units. It also presents a strong option for investors seeking a newly built income-producing property with minimal upfront maintenance requirements and substantial earning potential. Estimated rental income for each three-bedroom residence ranges from approximately $3,500 to $3,850 per month, creating a potential gross monthly income between $10,500 and $11,550. Annual gross income projections can exceed $138,000, making this a compelling addition to any real estate portfolio. In addition to the sale, our team also provides full rental and tenant-placement services after closing, offering a seamless transition from acquisition to income generation. We help position your investment for immediate cash flow and long-term success.

508 VAN NEST, Bronx

$1,329,000
6 Beds 5 Baths 1030304 MLS
Whether you're seeking a sophisticated primary residence with supplemental income or a valuable addition to your investment portfolio, this remarkable property offers the perfect blend of luxury, flexibility, and long-term value. This custom built brand new construction two family will captivate you from the moment you arrive with its warm & welcoming energy. Ideal for buyers looking for space, plus income generating rental property to assist with mortgage payments. Welcome to 135-26 219 Street! A newly renovated two family spanning 6 bedrooms, 5 full baths! Sitting on 50x100 lot featuring a wide private driveway and garage! Perfect opportunity for buyers with large vehicles. Offering two 3 bedroom 2 bath units over a high ceiling full finished basement with both interior and exterior access. Both units enjoy modern, open concept living/dining areas which provide great space for entertaining. Beautiful chefs granite kitchens equipped with floor to ceiling custom cabinetry, adorned with a full fleet of stainless steel appliances and equipped with island for bar stool seating. Well proportioned bedrooms with ample closet space. The primary suite is your private escape. Featuring a private en suite with spa like finishes. Down the hall a additional fully tiled bathroom is adorned with state of the art wall & floor tiles and shared between the additional bedrooms. The high ceiling full finished basement can be used as the perfect in-law suite, media den, guest quarters or additional recreational space. Prime Springfield Gardens location. Just off Merrick Blvd, Springfield Blvd, Francis Lewis Blvd, Belt Parkway. Quick easy access to JFK airport, schools, shopping centers, restaurants, cafes, parks and many other vibrant neighborhood amenities.

13526 219th Street, Laurelton

$1,395,000
9 Beds 5 Baths 1030340 MLS
3 UNITS. Introducing a newly constructed attached three-unit property located in the highly desirable Van Nest section of the Bronx. Built with modern living and long-term value in mind, this impressive residence delivers a rare opportunity for both end-users and investors seeking a turnkey asset with strong income-producing potential. Thoughtfully designed with contemporary finishes, spacious interiors, and updated building systems, this property offers the perfect blend of comfort, functionality, and investment appeal. The residence features a total of 9 generously sized bedrooms and 5 beautifully finished bathrooms spread across three well-planned units. Each residence offers an open-concept layout that seamlessly connects the living and dining areas, creating an inviting atmosphere ideal for everyday living and entertaining. The kitchens are designed with style and practicality in mind, showcasing quality cabinetry, sleek countertop surfaces, modern fixtures, and ample storage space. Natural light flows throughout the property, enhancing the clean modern aesthetic and creating bright, welcoming interiors. The bedrooms are comfortably proportioned with substantial closet space, while the bathrooms are finished with contemporary materials and tasteful design elements that complement the overall sophistication of the home. Constructed with modern efficiency standards, the property includes updated mechanical systems, energy-efficient components, central heating and cooling, and in-unit laundry hookups where applicable. Every detail has been carefully considered to provide convenience, durability, and low-maintenance ownership for years to come. Perfectly positioned in Van Nest, the property offers easy access to major highways, public transportation, shopping centers, local restaurants, parks, schools, and neighborhood conveniences. Its strategic location makes commuting throughout the Bronx and into Manhattan both practical and efficient. This exceptional opportunity is ideal for a purchaser looking to occupy one residence while benefiting from rental income generated by the additional units. It also presents a strong option for investors seeking a newly built income-producing property with minimal upfront maintenance requirements and substantial earning potential. Estimated rental income for each three-bedroom residence ranges from approximately $3,500 to $3,850 per month, creating a potential gross monthly income between $10,500 and $11,550. Annual gross income projections can exceed $138,000, making this a compelling addition to any real estate portfolio. In addition to the sale, our team also provides full rental and tenant-placement services after closing, offering a seamless transition from acquisition to income generation. We help position your investment for immediate cash flow and long-term success.

506 VAN NEST, Bronx

$1,159,000
8 Beds 5 Baths 1030271 MLS
SOLID LEGAL 3-FAMILY BRICK HOME – With a PRIVATE DRIVEWAY - EXCEPTIONAL INVESTMENT OPPORTUNITY BONUS OPPORTUNITY FOR INVESTORS: An exceptional opportunity to expand your portfolio: TWO ADDITIONAL LEGAL 3-FAMILY PROPERTIES ARE AVAILABLE OFF-MARKET ON THE SAME BLOCK. One of these properties can be DELIVERED FULLY VACANT AT CLOSING, creating a rare chance to acquire multiple income-producing properties in the same location. Additional details are available upon request. PROPERTY OVERVIEW: Don't miss this opportunity to own a LEGAL 3-FAMILY, FULLY BRICK PROPERTY in the desirable Hunts Point neighborhood of the Bronx. Built in 2004, this well-maintained building offers approximately 3,224 square feet of living space across three stories, plus an unfinished basement, and includes a PRIVATE DRIVEWAY. With paying tenants already in place and ONE OF THE 3-BEDROOM APARTMENTS WILL BE DELIVERED VACANT AT CLOSING., this property is ideal for both investors seeking immediate rental income and owner-occupants looking to offset their mortgage with rental revenue. The property is currently generating OVER $10,000 PER MONTH IN RENTAL INCOME. APARTMENT BREAKDOWN: THIRD FLOOR: *Spacious 3-bedroom, 2-bath apartment *Primary bedroom with private bath and walk-in closet *Currently rented for $3,600 per month SECOND FLOOR: *Spacious 3-bedroom, 2-bath apartment *Primary bedroom with private bath and walk-in closet *Currently rented for $3,700 per month FIRST FLOOR: *2-bedroom, 1-bath apartment *Currently rented for $2,850 per month BASEMENT: The unfinished basement features a large open layout with a SEPARATE ENTRANCE. Buyers should verify any future use with the appropriate municipal authorities, as any conversion or rental would be subject to applicable permits and approvals. PROPERTY FEATURES • FULLY BRICK CONSTRUCTION • Built in 2004 • Building size: 20.67' x 52' • Approximately 1,074 square feet per floor • Approximately 3,224 total square feet • Hardwood floors throughout • THREE ELECTRIC METERS • THREE GAS METERS • PRIVATE DRIVEWAY • Well-maintained and move-in ready PRIME LOCATION: Conveniently located at 625 Coster Street, Bronx, NY, with easy access to the Bruckner Expressway, Bronx River Parkway, local bus routes, and the 6 train. The property is also close to schools, shopping, restaurants, cafés, parks, and other neighborhood amenities. Whether you're looking to expand your investment portfolio or purchase a primary residence with strong rental income potential, this LEGAL 3-FAMILY PROPERTY offers outstanding value in a sought-after Bronx location. SCHEDULE YOUR PRIVATE SHOWING TODAY. OPPORTUNITIES LIKE THIS ARE RARE.

625 Coster Street, Bronx

$2,399,000
6 Beds 4 Baths 1027951 MLS
MONTEBELLO PINES ESTATE! One-in-a-million opportunity! A magnificent paver driveway leads to one of the most stunning stucco homes you will ever see, offering extraordinary curb appeal and timeless elegance. Welcome home to a grand two-story entryway that sets the tone for this spectacular residence with an exceptional floor plan. A beautiful study with custom built-ins is perfectly situated off the entry, while the elegant formal living room flows seamlessly into the oversized dining room, creating the ideal setting for entertaining. The gourmet eat-in kitchen features quartz countertops, a center island, radiant heated floors, two sinks, two ovens, a Wolf double oven, Sub-Zero refrigerator, Bosch appliances, and high-end finishes throughout. Just off the living room, the breathtaking great room showcases soaring ceilings, radiant heated floors, dramatic floor-to-ceiling windows that flood the home with natural light, and access to a one-of-a-kind deck overlooking the spectacular property. A convenient mudroom leads to the impressive three-car garage with beautiful barn doors. The driveway and pavers were completed in 2021. Upstairs, the luxurious primary suite boasts a tray ceiling, a stunning spa-like bathroom, phenomenal closet space, and an incredible bonus room that can be used as a sitting room, home office, gym, or whatever best suits your lifestyle. Three additional spacious bedrooms with hardwood floors and a beautifully updated full bathroom complete the upper level. The walkout lower level is exceptional, featuring a huge family room, a bedroom, two additional versatile rooms ideal for offices, hobbies, or guests, a gym with radiant heated floors, and a central dehumidification system. Step outside to your own private oasis, complete with a gorgeous gunite pool, spa, and waterfall, surrounded by an elegant granite patio and lush, mature landscaping that creates unmatched privacy. The pool features a brand-new cover (2026), is separately fenced for added safety, and the backyard is also fully fenced. Additional highlights include a water softener, whole-house water filtration system, a 25-zone irrigation system to maintain the meticulously landscaped grounds, Z-Wave automated programmable lighting, and motion sensors for enhanced convenience, security, and smart-home living. This is more than a home—it's an extraordinary lifestyle opportunity that truly won't last. Homes of this caliber, combining impeccable craftsmanship, exceptional amenities, cutting-edge technology, and one of Montebello Pines' most prestigious settings, rarely become available. This is a once-in-a-lifetime opportunity to own a truly unforgettable estate where luxury, comfort, and sophistication come together in perfect harmony.

8 Lety Lane, Suffern

$1,250,000
6 Beds 3 Baths 1030126 MLS
Welcome to 1241 Putnam Avenue, a distinguished brick two-family residence located on one of Bushwick's beautiful tree-lined blocks. Rich in original character and timeless appeal, this exceptional home showcases decorative fireplaces, elegant mantels, and charming architectural details that reflect Brooklyn's classic craftsmanship. This versatile property is currently configured with three floors of living space, offering exceptional flexibility. The garden level features a spacious one-bedroom layout with a bright living room, an eat-in kitchen, a full bathroom, generous closet space, a separate laundry room, and direct access to a large private backyard—perfect for outdoor entertaining, gardening, or relaxing. The parlor level offers soaring ceilings, abundant natural light, two spacious bedrooms, a welcoming living room, a full bathroom, and an updated kitchen with a contemporary feel. The top floor features three generously sized bedrooms, a bright living room, a separate dining room, and a full bathroom, providing ample space for extended family, and guests. As a legal two-family home, 1241 Putnam Avenue presents a unique opportunity for homeowners and investors alike. Buyers may also wish to explore the potential for reconfiguring the layout to suit their individual needs. Ideally situated in the heart of Bushwick, you'll enjoy convenient access to the J, Z, and L subway lines, multiple bus routes, Citi Bike stations, neighborhood cafes, acclaimed restaurants, boutique shopping, parks, and Bushwick's renowned art scene and vibrant nightlife.

1241 Putnam Avenue, Brooklyn

$900,000
7 Beds 4 Baths 1029597 MLS
Private Hudson Valley Retreat on 9.6 Wooded Acres Featuring Two Charming Homes and Exceptional Income Potential Tucked away along a peaceful country road in the heart of Clinton, this remarkable Hudson Valley retreat offers a rare combination of privacy, natural beauty, modern infrastructure, and investment opportunity. Set on 9.6 secluded wooded acres with potential subdivision possibilities, this unique estate features two separate residences, each with its own well, septic system, electric service, and oil tank, creating endless possibilities for multi-generational living, rental income, weekend escapes, or future development. Surrounded by pristine forest and abundant wildlife, this tranquil sanctuary feels worlds away from the everyday. Enjoy the sights and sounds of nature from every direction, where deer wander through the woods, wild turkeys roam freely, foxes make occasional appearances, turtles can be spotted throughout the property, and owls hoot from the trees at dusk. The setting is exceptionally quiet and serene, offering the ultimate Hudson Valley lifestyle immersed in nature. The charming circa-1924 farmhouse serves as the property's centerpiece, blending timeless character with significant recent improvements. The main residence features beautiful natural cherry hardwood floors, soaring cathedral ceilings, spacious sun-filled living areas, and 2 cozy fireplaces that creates a warm and inviting atmosphere year-round. The second residence, a thoughtfully converted stable barn, offers a distinctive open-concept design filled with character and flexibility. Perfect for guests, extended family, a home office, artist's retreat, or additional rental income, this separate dwelling enhances the property's versatility and appeal. A detached two-car garage provides ample storage, workshop space, or future expansion opportunities. Multiple outdoor areas invite relaxation, entertaining, and appreciation of the surrounding natural landscape, including a deck overlooking the peaceful wooded setting. Adding to the property's value, both homes are currently occupied by long-term tenants and generate approximately $6,000 per month in rental income. Tenants pay all utilities, providing an attractive income stream for investors while preserving future owner-occupancy options. Ideally situated near the Taconic State Parkway and conveniently located between the highly sought-after villages of Rhinebeck and Millbrook, residents enjoy easy access to renowned vineyards, hiking trails, parks, farm markets, antique shops, charming cafe's, and some of the Hudson Valley's most celebrated dining destinations.

10-12 Woodlea Road, Salt Point

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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.