Browse All Glen Head NY Properties with Pool for Sale

Welcome to 22 Evans Drive, an exceptional residence set on over two acres in the prestigious Village of Brookville. Offering approximately 6,750 square feet of living space, this impressive home combines grand proportions, timeless elegance, and exceptional privacy. Designed for both sophisticated entertaining and comfortable everyday living, the home features expansive living areas, abundant natural light, generously sized bedrooms, and a seamless flow throughout. The beautifully landscaped property provides a peaceful, private setting with plenty of space for outdoor entertaining and relaxation. Located within the highly regarded Jericho School District and surrounded by some of Long Island’s most distinguished estates, this remarkable Brookville property offers a rare combination of space, privacy, and convenience—just minutes from shopping, dining, major roadways, and the LIRR. A truly special opportunity to own an impressive estate in one of Long Island’s most desirable communities.

22 Evans Drive, Glen Head

$799,999

3 Beds ⋅ 2 Baths ⋅ 1041833 MLS

THE "ULTIMATE" GLEN HEAD OPPORTUNITY — HARBOR VIEW, IN-GROUND POOL & TREMENDOUS POTENTIAL — OFFERED AT JUST $799,000 Located in the desirable Harbor View section of Glen Head, within the Hamlet of Oyster Bay, this expanded Cape offers an exceptional opportunity for buyers looking to renovate, customize, and create a home that reflects their own vision. Situated on an approximately 7,035-square-foot lot, the property offers a compelling combination of location, outdoor living, privacy, and future potential. The interior is ready for updating and renovation, providing the perfect canvas for a buyer to re imagine the space and make it their own. The backyard is a true highlight and is designed for entertaining, featuring a fenced-in backyard featuring an in-ground swimming pool with a Salt water conversion system , expansive patio areas, an enclosed/covered porch overlooking the pool, and a separate gazebo ideal for outdoor dining, entertainment, relaxing, and enjoying the warmer months. Conveniently located near the LIRR, shopping, restaurants, and everyday amenities, and situated within the highly regarded North Shore School District. North Shore Senior High School was recently ranked No. 2 among Nassau County’s Top 10 High Schools in the ranking provided. With its sought-after Harbor View location, generous lot size, impressive outdoor amenities, and substantial renovation potential, this property presents an exciting opportunity to create something truly special in Glen Head. Pool -Property -Potential & Location Offered at just $799,000. Come see the possibilities this Harbor View home has to offer. The home is being sold as-is and offers an excellent opportunity for updating, expansion, customization. The kitchen ,Baths and interior finishes are dated and ready for renovation,while the property offers tremendous potential to create a home that suits your style and needs. Whether you’re an end user, investor, or contractor, this is a unique opportunity to unlock the full potential of the home and property. BRING YOUR VISION and make 2 Ruth Place your own.

2 RUTH Place, Glen Head

$789,000

5 Beds ⋅ 2 Baths ⋅ 1040374 MLS

This double dormered Cape Cod features a living room, formal dining room, a kitchen, a den, two bedrooms and a full bath on the main floor and three bedrooms including the primary bedroom ( full with primary bedroom is huge and could easily be divided into two separate bedrooms ) and a bath on the second floor. There is a full basement, a one car garage that is not in good shape, an in-ground pool that needs to be repaired or replaced, hardwood floors, tile floors, a newer main roof, all gas cooking and Heating and a very quiet location that is walk to most things. This house needs a lot of work but is a diamond in the rough.

1 Glen Cove Drive, Glen Head

$2,775,000

4 Beds ⋅ 4 Baths ⋅ 1025463 MLS

Nestled on two private acres, this stunning 4-bedroom, 3.5-bath ranch combines timeless comfort with resort-style living, featuring over 3,100 square feet, an in-ground pool, and beautifully designed indoor-outdoor spaces, all within the acclaimed North Shore School District.

153 Brookville Lane, Glen Head

$3,950,000

5 Beds ⋅ 8 Baths ⋅ 1010610 MLS

Welcome to 8 High Meadow Ct, a stunning classic all brick Colonial spanning 6000sqft of luxury set on a magnificent serene Old Brookville cul de-sac. This 5 bedroom Gem is rich with architectural details, exquisite millwork and designer finishes. A Gracious two-story Foyer introduces expansive principle rooms including Living Room/Fireplace, Formal Dining room, Den/Fireplace and Library/Office /Fireplace for effortless grand entertaining or more intimate gatherings Custom Cabinetry surrounds the fabulous Chef's dream Kitchen for endless storage with separate spacious Breakfast room overlooking pool setting. The primary bedroom is a lavish retreat with sun-lit sitting room, fireplace, wardrobe dressing area and luxurious spa bath occupying the prime position of the 2nd floor . Two spacious bedrooms with shared bath and wrap around hallway leading to 4th en-suite bedroom complete the 2nd floor. Lower level is partially finished with playrooms, storage closets, large cedar closet and 1/2 bath. Step outside to brick-walled patio with built-in BBQ and multiple bluestone patios and walkways lined with vibrant gardens leading to the sparkling gunite heated pool with jacuzzi waterfall, Surrounded by lush landscaping, a covered patio with ceiling heaters opens to the very spacious Guest/Pool House with living room, full kitchen , full bath, laundry room and dressing room for a year round retreat. 3 car garage. 2 magnificent private acres, Locust Valley SD. By Appointment

8 High Meadow Court, Glen Head

$2,995,000

3 Beds ⋅ 3 Baths ⋅ 1003540 MLS

Built new in 2017 with the highest of standards on an ultra-private 1 acre property in Glen Head. This one level 3 bedroom ranch luxury home offers quality finishes, exceptional craftsmanship and a comfortable floor plan. The main living area is an open concept eat-in-kitchen to a great room with fireplace and formal dining. A separate den with beautiful paneled walls is to the front of the house. Custom millwork, high ceilings and wide plank hardwood floors throughout. Natural gas and full radiant heat. The custom kitchen is equipped with Wolf and Sub-Zero appliances, quality cabinetry, marble countertops, centre island and premium details. Spacious primary bedroom suite with lux primary bathroom. Lots of closets and storage. Full basement with outdoor entrance, complete with gym, office and recreational room, cedar closet and more. Outdoor living is equally impressive with a covered heated lanai, bluestone patio, heated gunite swimming pool, pavilion/pool house, outdoor shower, and lush professional mature landscaping creating a true private retreat. Additional highlights include James Hardie siding, real stone veneer, alarm and camera system, sprinkler system, epoxy-finished 2-car garage, and two hidden storage sheds. A rare North Shore offering combining privacy, luxury and resort-style living. North Shore School District, Glen Head Elementary and quick access to local towns and shops, golf and tennis clubs, beaches and more.

379 Frost Pond Road, Glen Head

$2,699,000

5 Beds ⋅ 4 Baths ⋅ 989507 MLS

Welcome to this exceptional home located in Brookville Village, within Jericho School District. Perfectly situated in a peaceful and quiet neighborhood, this property offers both comfort and convenience. Close to schools, making daily routines effortless; Easy access to major highways for a smooth commute; Minutes from shopping, dining, and everyday essentials; New attic insulation for improved energy efficiency; Brand new roof for long-term peace of mind; Newly installed 22 kW whole-house generator; Chimney recently repointed with new lining; Recently redone gunite pool – perfect for relaxation and entertaining; Spacious outdoor area ideal for gatherings and activities; This home combines modern upgrades with a tranquil setting, offering a rare opportunity to own this move-in ready gem!

14 Ormond Park Road, Glen Head

$2,699,900

5 Beds ⋅ 4 Baths ⋅ 974758 MLS

Stunning Old Brookville Estate on 2 Acres with Pool & Outdoor Oasis Welcome to this exquisite 5-bedroom, 4-bathroom home nestled on 2 acres of beautifully landscaped property in the prestigious area of Old Brookville. This elegant residence offers the perfect blend of luxury, comfort, and privacy. Step inside to discover spacious living areas filled with natural light, including a grand living room with a cozy fireplace, a formal dining room, and a gourmet kitchen. The primary suite is a private retreat, complete with a spa-like en-suite bathroom. The fully finished basement is an entertainer’s dream, featuring a custom bar and ample space for gatherings. Outdoors, enjoy a serene backyard paradise with an in-ground pool, a charming gazebo, and a spacious patio—perfect for relaxing or entertaining. This exceptional property offers a rare opportunity to own a piece of paradise in one of Long Island’s most desirable locations. Don’t miss out on this remarkable home!

Glen Head

$2,099,000

4 Beds ⋅ 3 Baths ⋅ 920526 MLS

Exceptional Custom-Built Colonial in the Heart of Glen Head Don’t miss this rare opportunity to own a truly one-of-a-kind custom-built home in the desirable Glen Head community. Thoughtfully designed and built with no expense spared, this residence is a masterpiece of quality craftsmanship, luxury finishes, and modern functionality — far beyond basic or “just to code.” Step into a grand center hall colonial featuring a dramatic entry foyer, stunning custom white oak flooring, and intricate moldings throughout. The expansive open-concept layout flows seamlessly into a gourmet chef’s eat-in kitchen, complete with a massive 2” quartz island, top-of-the-line GE Cafe appliances, LED lighting, and custom cabinetry — ideal for everyday living and entertaining. Unmatched Construction & Features: Radiant heat throughout all levels, including the basement, Superior 2"x6" framing and steel beam construction, 10' ceilings on lower level, 9' on main and 8' upstairs, One-foot-thick foundation for durability and insulation. All principal rooms are generously sized, filled with natural light, and designed for both comfort and elegance. Outside, enjoy your private backyard oasis with a beautiful in-ground pool featuring a smart filtration system and automated retractable cover, plus a sleek outdoor kitchenette area — perfect for relaxing and entertaining year-round. All perfectly situated on over a quarter-acre of manicured property in a prime location. This home is a rare gem offering the perfect blend of timeless design and cutting-edge construction.

9 Hill Drive, Glen Head

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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.

Glen Head Homes with Pool

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