Half Hollow Hills Homes with Pool

Welcome to the enchanting Half Hollow Hills School District, an exceptional educational hub nestled in the heart of Suffolk County, New York. Renowned for its commitment to academic excellence, this district boasts a diverse array of programs and resources designed to nurture the talents and aspirations of every student. With highly qualified teachers and a robust curriculum, students are encouraged to explore their interests, excel in their studies, and develop into well-rounded individuals.

Half Hollow Hills is not just about education; it's a vibrant community that emphasizes the importance of family and connection. Residents enjoy a plethora of recreational activities, including parks, sports facilities, and local events that foster a sense of belonging and camaraderie. The district is home to several top-rated schools, making it an ideal location for families seeking a supportive environment for their children’s growth.

For those looking to settle in this picturesque area, you'll find an array of stunning homes, many of which come with the added luxury of private pools. Imagine basking in the sun by your very own oasis, perfect for family gatherings, summer barbecues, or simply unwinding after a long day. These homes not only offer comfort and style but also provide a unique lifestyle that enhances the joy of living in Half Hollow Hills.

With its exceptional schools, beautiful neighborhoods, and inviting homes with pools, Half Hollow Hills is a place where families can thrive and create lasting memories. Come discover the charm and opportunities that await you in this remarkable community!

Newest Half Hollow Hills Homes with Pool

$849,999

3 Beds ⋅ 3 Baths ⋅ 1031057 MLS

A 3-bedroom, 2.5-bath Expanded Ranch in Dix Hills, with living space spread across a spacious main level and a full basement. The main level features a formal living room and dining area with hardwood floors. The kitchen includes oak cabinetry, tile backsplash, granite counters, a center island with a breakfast bar, and an overhead skylight. A massive family room extension with vaulted ceilings and skylights connects to a convenient powder room. Three bedrooms round out this level, including a primary suite with a private full bath. Outside, a paver patio, in-ground swimming pool, and fully fenced yard create a private outdoor oasis. Close to major highways, shopping, and zoned for Half Hollow Hills schools.

51 Longworth Avenue, Dix Hills

$5,999,999

6 Beds ⋅ 9 Baths ⋅ 1031747 MLS

Poised behind private gates atop one of Long Island's highest elevations, this extraordinary all-brick manor estate is a masterwork of timeless architecture and uncompromising luxury. Encompassing six lavish bedroom suites, six full baths, and three elegant powder rooms, the residence is surrounded by picturesque English gardens and acres of lush parkland, offering an unrivaled sense of serenity, privacy, and grandeur. Bordering an extensive network of scenic hiking and horseback riding trails, the estate offers a seamless connection to nature, creating an exceptional setting for outdoor recreation and equestrian pursuits. A true trophy estate, this one-of-a-kind property boasts its own FAA-recognized private helipad, providing the rare privilege of effortless helicopter access to Manhattan, the Hamptons, and beyond—transforming travel into an experience of unparalleled convenience. Every inch of this magnificent residence reflects exceptional craftsmanship and meticulous attention to detail. Rich custom millwork, exotic quarter-sawn hardwood floors, and imported marble finishes create an atmosphere of refined elegance, while state-of-the-art geothermal heating and cooling, radiant heated floors throughout, and advanced energy-efficient systems provide modern comfort without compromise. Designed for both everyday luxury and grand-scale entertaining, the estate features a spectacular gourmet eat-in chef's kitchen, an opulent primary suite worthy of a five-star resort, expansive guest or extended-family accommodations, four stately fireplaces, intricate bespoke ornamental ironwork, a comprehensive security system, and a heated driveway. The resort-inspired grounds are nothing short of extraordinary, showcasing a heated saltwater swimming pool and spa enhanced by cascading waterfalls, creating a private oasis of relaxation. Inside, an exceptional array of amenities awaits, including a starlit home theater, indoor squash court, full basketball court, professional-grade fitness center, game room, workshop, and beautifully appointed guest quarters. A residence of this caliber is exceptionally rare—where architectural excellence, cutting-edge innovation, and world-class amenities converge to create one of Long Island's most distinguished private estates. Additional Features: Energy-efficient insulated doors, elegant formal living and dining rooms, exquisite marble baths, generously appointed guest quarters, abundant storage and utility spaces, and an uncompromising commitment to craftsmanship, luxury, and enduring quality. This remarkable estate offers an unparalleled lifestyle where privacy, prestige, and sophisticated living exist in perfect harmony, presenting a once-in-a-generation opportunity to own one of Long Island's most iconic legacy properties.

18 Gwynne Road, Melville

$2,450,000

5 Beds ⋅ 4 Baths ⋅ 1029677 MLS

Dix Hills Stunner! Set On a Beautifully Landscaped Acre, This Spectacular 5 Bedroom 4 Bath Expanded Colonial Offers The Perfect Blend Of Luxury, Comfort And Timeless Elegance. Thoughtfully Designed Throughout Featuring A Dramatic Two-Story Grand Entry Foyer, Vaulted Ceilings, First Floor Guest Quarters, Custom Chef's Kitchen And A State-Of-The-Art Media Room. Luxury Finishes And Premium Upgrades Throughout Include Rich Hardwood Flooring, Custom Mouldings, Radiant Heat Flooring, Remote Controlled Hunter Douglas Blinds, A Whole House Generator, Advanced Air Purification And Whole-House Water Filtration Systems. Designed For Both Everyday Living And Unforgettable Entertaining, This Exceptional Home Features A Heated 24x44 Saltwater Pool, An Impressive Outdoor Cabana And Professionally Designed Landscape Lighting That Beautifully Illuminates Both The Front And Rear Grounds. Every Detail Has Been Thoughtfully Curated To Create An Exceptional Home Both Inside And Out. This One-Of-A-Kind Private Retreat Is The Perfect Place To Call Home. Conveniently Located Close To Highways, Schools, Parks & Shops

1 Winston Court, Dix Hills

$1,425,000

4 Beds ⋅ 3 Baths ⋅ 1028257 MLS

Set on 1.25 private acres in Melville, this expansive ranch offers a rare combination of space, flexibility, and lifestyle in the coveted Half Hollow Hills School District. Featuring 4 bedrooms and a seamless indoor outdoor flow, the home is perfectly suited for everyday living and comfortable entertaining. The resort style backyard is surrounded by mature landscaping and features an inground salt water pool, creating a peaceful and private setting ideal for relaxation and outdoor enjoyment. A tremendous lower level with 9 foot ceilings and the full footprint of the home offers endless possibilities for recreational space, a gym, media room, guest area, or additional amenities tailored to your needs. With separate access and a versatile layout, the home may be well suited for a private office, guest suite, or flexible living arrangement. Conveniently located near major highways, shopping, dining, parks, and community amenities, this property combines privacy, accessibility, and outstanding value in one of Melville’s most sought after locations. Low taxes complete this incredible opportunity.

54 Dix Woods Drive, Melville

$1,600,000

5 Beds ⋅ 4 Baths ⋅ 1016292 MLS

Welcome to this well-maintained Center Hall Colonial situated on just over one private, level acre in Dix Hills. Offering more than 3,500 square feet of interior living space, this spacious home features 5 bedrooms, 3.5 bathrooms, a full finished basement, a 2-car garage, and an extended driveway. Enjoy a private backyard setting perfect for relaxing and outdoor entertaining. Designed for comfortable living, this home offers generously sized rooms, newer hardwood flooring throughout the first and second levels, and an open-concept flow between the custom kitchen and inviting den. The kitchen, renovated in 2017, features wood cabinetry, granite countertops, a center island with custom exhaust hood, double ovens, and access to the backyard deck. The den features a wood-burning fireplace, creating a warm and comfortable space for everyday enjoyment or gatherings while maintaining an open connection to the kitchen and main living areas. The outdoor living space offers a fully fenced, private backyard with mature landscaping, a spacious deck, and a propane-heated gunite in-ground pool with a marble dust finish completed in 2022—ideal for enjoying summer days. The second level features a spacious primary suite with a walk-in closet and an updated en-suite bath (2020) offering radiant heated flooring, a whirlpool tub with temperature control, and quality finishes. Four additional bedrooms and a full hall bath complete the upper level. The full finished basement provides additional recreation space, a full bathroom, and abundant storage. Additional updates include a new roof (2025), gas conversion and heating system (2024), Andersen windows (2024), gutters with leaf protection system, 200-amp electrical service, generator hookup, and an 8-zone irrigation system (not represented). Cesspool pumped in 2020. A wonderful opportunity to own a spacious, well-maintained home in Dix Hills offering privacy, generous living space, and desirable outdoor amenities. Conveniently located near shopping, restaurants, parks, public transportation, and major highways and parkways for easy access to surrounding areas and commuting destinations.

17 Calumet Drive, Dix Hills

$995,000

5 Beds ⋅ 3 Baths ⋅ 1027204 MLS

Welcome to 2 Fairhaven Drive, Wheatley Heights, an exceptional colonial style home located in the highly sought-after Half Hollow Hills School District, offering luxury living, outstanding energy efficiency, and an incredible indoor-outdoor lifestyle. The exterior of this beautifully maintained 2 level home showcases outstanding curb appeal with manicured landscaping, water features, and a welcoming presence. The beautiful and private backyard offers an in-ground swimming pool, a basketball 1/2 court, a custom wood-burning fire pit seating, creating the perfect setting for entertaining or relaxing with family and friends. The home's owned solar panels, combined with its Pearl Energy Certification and enhanced attic, wall, and basement insulation, contribute to remarkably low electric costs and exceptional year-round efficiency and savings. Coupled with its very low property taxes, the new roof & new windows, this home offers tremendous long-term value. In addition, the home’s reverse osmosis water filtration system provides added convenience and peace of mind. The 1st floor offers a spacious and inviting eat-in kitchen with abundant cabinetry & generous counter space. Adjacent to the kitchen is the oversized family room complete with a wood-burning fireplace that can warm the entire home and sliders to the back yard. Hardwood floors flow throughout the home. The spacious living room features a beautiful coffered ceiling and offers sliding door access to backyard patio. The formal dining room and a beautifully updated 1/2 bath complete the 1st level of this home. The second level features 5 generously sized bedrooms w/ hardwood flooring throughout. The spacious primary suite offers privacy and luxury with its spa-like bathroom and oversized custom California-style walk-in closet. The finished lower level adds incredible versatility and lifestyle appeal, offering a home gym, an elegant wine cellar, and a relaxing sauna, creating the ultimate in-home wellness experience. Ideally situated close to shopping, dining, parks, and major transportation routes, this exceptional property offers the rare opportunity to enjoy luxury amenities, energy efficiency, and a convenient location all within one of the area's most desirable school districts.

2 Fairhaven Drive, Wheatley Heights

$1,699,000

6 Beds ⋅ 6 Baths ⋅ 1002859 MLS

Nestled on a quiet cul-de-sac in one of Melville's most desirable neighborhoods, 26 Tamara Court is a custom-expanded residence offering exceptional space, comfort, and resort-style living. A dramatic 2-story foyer, soaring ceilings, and an open floor plan create an impressive setting for both everyday living and entertaining. Offering 6 generously sized bedrooms, a private first-floor home office, and a 3-car garage, the home also features elegant formal living and dining rooms, a spacious great room with a fireplace, and a finished lower level complete with a home theater, recreation area, and half bath. The oversized primary suite offers a spacious en-suite bath and generous closet space. The spacious, well-appointed kitchen features granite countertops and an impressive collection of premium appliances, including a Bertazzoni gas range with six burners, Full Size Sub zero Fridge & Full Size Subzero Freezer,an integrated grill, a large oven and secondary oven, a separate full-size wall oven, and an additional two-burner electric cooktop, offering exceptional flexibility for everyday cooking and entertaining. The backyard is the true showpiece of the property—a private resort-style retreat designed for entertaining and enjoying the outdoors. Highlights include a recently marble-dusted gunite pool, a renovated tennis court, newly reconstructed retaining walls, and an outdoor kitchen featuring two built-in BBQ grills, a two-burner cooktop, and generous patio space for dining, relaxing, and hosting guests. Combining impressive scale, outstanding amenities, and an exceptional cul-de-sac location, 26 Tamara Court presents a rare opportunity to own a truly special home in the heart of Melville.

26 Tamara Court, Melville

$1,499,000

6 Beds ⋅ 5 Baths ⋅ 1022708 MLS

Introducing 8 Penn Dr- Welcome to an exceptional luxury residence featuring an ADU with a private entrance in the heart of Dix Hills, where refined design meets effortless living. This expansive 6-bedroom, 5-bathroom home offers a rare blend of scale, sophistication, and versatility—perfectly suited for multigenerational living or those seeking elevated space to live and entertain. Set on beautifully landscaped grounds, the home showcases grand, sun-drenched interiors with oversized windows that flood each space with natural light. The thoughtfully designed layout features expansive living and dining areas, ideal for both intimate gatherings and large-scale entertaining. At the heart of the home is a gourmet chef’s kitchen, complete with modern appliances, sleek finishes, and ample space to create and gather. The primary suite serves as a true private retreat, offering generous proportions and a spa-like ensuite bath designed for comfort and relaxation. Every detail has been curated to enhance both style and functionality, while the outdoor spaces provide a seamless extension of the home’s living experience. A 2-car garage along with 4 additional parking spaces ensures convenience for residents and guests alike. A rare offering in a prime Dix Hills location, this home delivers luxury, flexibility, and timeless appeal.

8 Penn Drive, Dix Hills

$1,195,000

4 Beds ⋅ 2 Baths ⋅ 1026605 MLS

Tucked mid-block on a quiet, tree-lined street in the coveted Half Hollow Hills School District, this beautifully maintained four-bedroom, two-bath residence offers a rare opportunity to enjoy privacy, space, and effortless living on a flat, just shy of one-acre property. Lovingly cared for, the home offers a wonderful blend of timeless character and some meaningful updates, including beautifully renovated bathrooms, an inviting eat-in kitchen, and a spacious two-car garage. Recent improvements—including the roof, siding, Azek trim, fencing, and pool filter and pump, brand-new washing machine—provide both style and peace of mind. Beyond the home’s welcoming interior lies a backyard designed for making memories. The sparkling in-ground pool serves as the centerpiece of an expansive, level property with endless possibilities. Whether you envision summer entertaining, a future pickleball or tennis court, a sports field, or simply room to roam, this exceptional setting offers the flexibility to create the lifestyle you’ve always imagined. The lower level provides an abundance of space, offering remarkable versatility for recreation, fitness, hobbies, media, or whatever best complements your lifestyle. Perfectly positioned in one of Dix Hills’ most sought-after neighborhoods, this exceptional property combines timeless appeal, meaningful updates, and an extraordinary setting—offering the space to live, entertain, and grow for years to come. A rare offering where location, lifestyle, land, and value come together—this exceptional opportunity is one you won’t want to miss.

18 Millet Street, Dix Hills

$1,995,000

6 Beds ⋅ 4 Baths ⋅ 1025383 MLS

Set on a beautifully landscaped, level acre in the Half Hollow Hills School District, 76 Wildwood Drive is a stately 3,803-square-foot Colonial offering an exceptional combination of architectural presence, refined interiors and resort-style outdoor living. An impressive stucco façade framed by grand double columns creates a distinguished arrival, while magnificent eight-foot cherrywood and leaded-glass double entry doors introduce a home designed for both elegant entertaining and comfortable everyday living. Inside, a gracious entry foyer opens to formal living and dining rooms appointed with rich oak flooring, crown molding and abundant natural light from Andersen architectural windows. The thoughtfully designed six-bedroom layout includes two versatile first-floor bedrooms or offices and a full bath, providing ideal accommodations for guests, extended family or working from home. The inviting family room is centered around a fireplace, while cathedral and tray ceilings, chandeliers, Hunter Douglas window treatments and quality Masonite doors add character and sophistication throughout. At the heart of the home is an extraordinary chef’s kitchen showcasing the craftsmanship of custom Snaidero Italian cabinetry, granite countertops, a glass-tile backsplash and a generous center island. An exceptional collection of professional-grade appliances includes a Sub-Zero triple-compartment refrigerator and freezer, separate Sub-Zero ice maker, Thermador six-burner gas cooktop with island hood, GE Café French-door double wall ovens, Thermador warming drawer, Bosch dishwasher and Ca’Lefort wine cooler. A double sink, additional prep and bar sink, pantry, wet bar and dry bar make the space exceptionally well suited for entertaining on any scale. The second level is highlighted by a spacious primary suite featuring two walk-in closets and a beautifully renovated private bath featuring a wide standup shower with bench, double vanity, premium finishes and radiant heated flooring. Three additional bedrooms and another renovated full bath complete the upper level. In total, the home offers three full and one half baths, all newly renovated with contemporary materials, timeless design and frameless glass enclosures. A remarkable 560-square-foot recreation room with soaring 10-foot ceilings and dramatic walls of glass provides a sun-filled setting for entertaining, fitness, recreation or relaxation. The newly renovated, partially finished basement offers additional flexible living space, along with a dedicated laundry and utility area. Outdoors, the private, fenced grounds create a true backyard retreat, centered around an impressive 40,000-gallon saltwater swimming pool and expansive patio. Additional features include a 2.5-car garage, three-zone central air conditioning, four-zone heating, radiant bathroom floors, natural gas, exterior motion lighting and a comprehensive SimpliSafe security system. With its commanding architecture, beautifully renovated interiors, extraordinary kitchen, flexible living spaces and exceptional one-acre setting, 76 Wildwood Drive presents a rare opportunity to enjoy sophisticated living in the heart of Dix Hills.

76 Wildwood Drive, Dix Hills

$1,050,000

5 Beds ⋅ 3 Baths ⋅ 1024922 MLS

Endless possibilities await in this spacious 5-bedroom, 2.5-bath home! Offering an expansive floor plan with remarkably large rooms throughout, this home provides the space and flexibility today’s buyers are looking for. Hardwood floors add warmth and character, while the basement offers additional storage. Step outside and enjoy the in-ground saltwater pool featuring a new liner and new saltwater system installed in 2024,creating the perfect setting for relaxing or entertaining. Additional highlights include natural gas cooking, an in-ground sprinkler system, and the potential for an accessory apartment with proper permits. Whether you’re looking to create your dream home or invest in a property with exceptional potential, this is an opportunity you won’t want to miss.

12 Princeton Drive, Dix Hills

$825,000

4 Beds ⋅ 3 Baths ⋅ 1024796 MLS

Location, Location, Location - Beautifully Maintained Expanded Ranch Located in the Highly Sought Area of Dix Hills. This 4 Bedroom, 2.5 Bathroom Home Features: Living Room, Formal Dining Room, Eat-in Kitchen, Den with Masonry Fireplace and French Doors Leading Out to Oversized Patio – which is Perfect for Entertaining, Enclosed Backyard Boasts Privacy and In-ground Pool. Home's Additional Amenities Boasts: 200 Amp Electric, Hardwood Flooring, Marble Flooring, Full, Finished Basement with Outside Entrance, Attached 1-Car Garage, Multi-Car Driveway, In-ground Sprinklers. Recent Updates: BRAND NEW ROOF, Pool Liner (2024). Ideally Located - Close to Area Parks and Pool, Schools, Shopping and More. Award Winning Half Hollow Hills School District and True Taxes are $12,676. This Home is Just Waiting for the Right Buyer to Start Creating Their Lifetime Memories, So Come and Make it Your Own! Will Not Last Long – So Call Today to Schedule an Appointment for Your Private Viewing.

10 Arcadia Drive, Dix Hills

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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.