Old Brookville Homes with Pool

Old Brookville Homes with Pool

Welcome to Old Brookville, a hidden gem nestled in the heart of Nassau County, New York. This picturesque village is renowned for its sprawling estates, lush greenery, and serene ambiance, making it a coveted destination for those seeking a luxurious lifestyle in a tranquil setting. With its tree-lined streets and expansive properties, Old Brookville exudes an air of elegance that appeals to families and professionals alike.

One of the standout features of homes in Old Brookville is the abundance of properties equipped with stunning swimming pools. Imagine stepping into your own private oasis, where you can unwind on warm summer days, host unforgettable gatherings, or simply enjoy a peaceful afternoon under the sun. These homes not only boast exquisite architectural designs but also offer expansive outdoor spaces perfect for entertaining or relaxing with family.

Old Brookville is not just about beautiful homes; it also provides residents with a strong sense of community and access to top-rated schools, making it an ideal place to raise a family. The village is conveniently located near major highways, providing easy access to Manhattan and other nearby attractions, while still maintaining its peaceful, suburban charm.

For those who appreciate nature, the area is dotted with parks and recreational spaces, perfect for leisurely strolls or weekend picnics. With its perfect blend of luxury living, community spirit, and natural beauty, Old Brookville stands out as a premier destination for homebuyers looking for a serene yet sophisticated lifestyle. Come discover the allure of Old Brookville and find your dream home with a pool today!

Newest Old Brookville Homes with Pool

$5,250,000
6 Beds ⋅ 10 Baths ⋅ 1031994 MLS
Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

33 Chicken Valley Road, Old Brookville
$13,600,000
10 Beds ⋅ 10 Baths ⋅ 1034316 MLS
Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 15+ acre equestrian estate formally named 'Westward' presents a rare opportunity to acquire a significant piece of North Shore history. Privately nestled amid rolling pastures, mature woodlands, and formal gardens, the estate seamlessly blends timeless architectural elegance with an unparalleled country lifestyle just moments from New York City. Originally commissioned in 1924 for noted industrialist and financier Benjamin Brewster Jennings - President and Chairman of Socony-Mobil and a prominent figure in New York's financial and corporate circles - this Georgian Revival brick residence with a cascading slate roof was masterfully designed by renowned architect Walter B. Chambers. The estate's distinguished landscape plan was created by legendary landscape architect Ellen Biddle Shipman, whose formal gardens and thoughtfully designed grounds continue to define the property's enduring beauty. Approached by a long, tree-lined drive framed by classic stone walls, the stately residence commands a setting of exceptional privacy and serenity. Encompassing three full levels of living space, the home is distinguished by grand entertaining rooms, soaring proportions, multiple wood-burning fireplaces, graceful arched windows, leaded-glass details, and an abundance of natural light. A gracious entrance vestibule opens to a sweeping curved staircase, while expansive formal living and dining rooms provide an elegant backdrop for entertaining on any scale. The 10 bedroom, 9.5 bathroom primary residence also features a spacious eat-in kitchen, indoor spa pool, vast slate patios and an outdoor swimming pool with cabana set against picturesque grounds, providing an idyllic backdrop for outdoor enjoyment. For equestrian enthusiasts, the property offers a turnkey horse facility. The grounds include a well-maintained main barn, run-in sheds (equipped with stalls, water, and electricity), a hot walker, extensive paddocks, and open acreage ideal for riding and grazing. Additionally, this unmatched property includes charming gatehouse cottages, staff apartments, and multiple ancillary structures, most of which have been recently renovated, creating flexibility for guests, caretakers, or income-producing opportunities. Located within one of the North Shore's most prestigious and historically significant communities, the estate enjoys close proximity to Long Island Sound beaches, renowned equestrian facilities, and some of the region's finest private clubs and golf courses. Zoned within the esteemed North Shore Central School District. Rarely does a property of this caliber come to market - offering a remarkable combination of provenance, architectural distinction, equestrian amenities, acreage, and development potential. A legacy estate of exceptional character and enduring significance, representing the very essence of North Shore country living.

97 A Pound Hollow Road, Old Brookville
$5,999,999
7 Beds ⋅ 9 Baths ⋅ 1021590 MLS
Old Brookville | Welcome to 3 Valentine Farm Court, where timeless architecture, exceptional craftsmanship, and an unmatched collection of luxury amenities define one of the North Shore's most impressive private estates. Positioned behind double iron gates at the end of a secluded cul-de-sac, this stately brick center hall colonial is situated on more than three meticulously landscaped acres, combining remarkable privacy with an extraordinary level of recreation and entertaining amenities. The residence is introduced by a spectacular two-story domed foyer showcasing a sparkling chandelier, intricate hand-painted ceiling details, and extensive custom millwork carried throughout every level of the home. Formal and informal living spaces are thoughtfully arranged, including an expansive formal living room, richly appointed mahogany library, inviting family room with one of three wood-burning fireplaces, formal dining room, powder room, and a spacious first-floor en-suite bedroom with separate exterior access. The custom kitchen is appointed with premium gas appliances, custom cabinetry, a center island with seating, an adjoining breakfast area, and an expansive butler's pantry connecting directly to the formal dining room. Extending from the main level, an elevated terrace with a built-in outdoor kitchen overlooks the estate grounds and pool complex below. The second level features five bedroom suites, each with their own full bathroom. Occupying its own wing of the home, the primary suite includes a private balcony overlooking the property, separate sitting room, two oversized walk-in closets, and an expansive en-suite bathroom with dual vanities and a jetted soaking tub. Designed as an exceptional recreational and entertaining space, the lower level features a custom wet bar, expansive gathering areas, a fully equipped fitness center, additional bedroom and full bathroom, oversized laundry room, and a below-grade indoor sports court with min. 15-foot ceilings—a rarely available amenity in residential construction. The outdoor amenities are equally impressive. The resort-inspired grounds are centered around an oversized gunite swimming pool with an integrated spa and water features, surrounded by expansive patios and mature landscaping. A fully equipped pool house includes a full bathroom, laundry facilities, and an indoor kitchen with a built-in grill opening directly onto the pool terrace. Completing the estate is a full-size sports court configured for both tennis and basketball, along with an oversized three-car garage equipped with vehicle lifts offering additional space for the car enthusiast. Representing an exceptional combination of scale, craftsmanship, and amenities on more than three private acres, 3 Valentine Farm Court presents a rare opportunity within one of the North Shore's most distinguished settings.

3 Valentine Farm Court, Old Brookville
$4,795,999
11 Beds ⋅ 14 Baths ⋅ 1016829 MLS
A truly extraordinary opportunity to create one of Brookville's most distinguished private estates. Nestled on an expansive 15-acre parcel in the prestigious Village of Old Brookville, this remarkable property offers an unparalleled setting on one of the area's most coveted and desirable streets. Plans envision a magnificent 22,000-square-foot luxury residence thoughtfully designed to blend timeless elegance with modern sophistication. Surrounded by mature landscaping and serene natural beauty, the estate offers exceptional privacy while remaining conveniently located near renowned schools, country clubs, fine dining, and major transportation routes. A picturesque private pond serves as the centerpiece of the grounds, creating a tranquil and captivating backdrop for the future residence. The vast acreage presents limitless possibilities for world-class amenities, including formal gardens, resort-style outdoor living spaces, recreational facilities, and equestrian pursuits. Rarely does an offering of this caliber become available—a unique chance to build a legacy estate tailored to your vision in one of Long Island's most exclusive enclaves. An exceptional canvas upon which to create a truly iconic residence

1 Penny Pond Court, Old Brookville
$5,499,000
9 Beds ⋅ 8 Baths ⋅ 1005247 MLS
Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. Inside, the richly paneled foyer and wide pegged oak floors set the stage for exquisite architectural details, including a sweeping staircase and intricate custom millwork. The first floor offers a seamless blend of grandeur and comfort. The magnificent living room and banquet-sized dining room both feature elegant fireplaces, while the gourmet kitchen boasts a spacious center island and a bright breakfast room. A butler’s pantry adds convenience, and the library, adorned with built-in bookcases and a fireplace, offers a cozy retreat. Additional highlights include a sunroom, two en suite guest bedrooms, a first-floor washer/dryer, and a powder room. Oversized windows throughout the home provide breathtaking views of the lush grounds. The expansive primary suite is a private sanctuary, complete with a fireplace, spa-like bath, dressing area, and a large balcony overlooking the manicured gardens. This level also features four additional bedrooms with two Jack-and-Jill baths, two additional fireplaces, a gracious hall bath, a gym/bedroom, an office/bedroom, and a second-floor laundry room. The lower level offers an abundance of recreational space, including a playroom, arts and crafts area, and a full bath. The exquisitely landscaped grounds provide something for everyone, offering endless opportunities for relaxation and entertainment. The sunken gardens, originally designed by renowned landscape architect Robert Ludlow Fowler Jr., are a marvel to behold. They gracefully lead the way to a serene 20x50 saltwater gunite pool that is complemented by a spacious, elegant pool house. Sports enthusiasts will appreciate the lighted clay tennis court and a heated, enclosed outdoor structure, perfect for squash or basketball. Adding to the estate’s appeal, a charming three-bedroom, two-bath guest cottage provides comfortable accommodations, while a three-car heated garage with a separate workroom ensures ample space for vehicles and storage. This extraordinary estate is a timeless masterpiece inside and out, seamlessly blending historic charm with modern refinement.

8 Stonegate Lane, Old Brookville
$3,600,000
7 Beds ⋅ 6 Baths ⋅ 995929 MLS
Rosegate is an enchanting mini estate that harkens back to golden age of the North Shore of Long Island. This architectural gem has been thoughtfully expanded over the years into a stately 7-bedroom Colonial, set on 2.85 acres of lush, storybook grounds. Every inch of Rosegate exudes character and charm from its Ludowici style roof to its diamond trellis ivy covered walls. Step through the front entrance, and you’re greeted by exquisite hand-painted murals that set the tone for the artistry and elegance within. The sun-drenched living room and formal dining room, with their graceful proportions and classic design, provide an exceptional setting for entertaining, while timeless details like wood-pegged and parquet floors along with elegant archways elevate every space. For those seeking quiet retreat, the library leads to a cozy bedroom (or office) with a beamed ceiling and French doors that open to the serene pool area. A touch of convenience and sophistication, the home also features an elevator for easy access to the second-floor primary suite. A separate guest wing with three bedrooms and a full bath offers privacy and comfort for visitors. The outdoors are a masterpiece in their own right. The gated front garden with whitewashed brick sitting walls and specimen plantings is highlighted by a charming center fountain. The rear garden, with its sweeping lawn, showcases a sparkling Gunite pool surrounded by a bluestone patio—perfect for summer gatherings. A charming greenhouse by the 3 car garage completes this idyllic retreat. Steeped in history yet updated with modern comforts, Rosegate is more than a home—it’s a timeless escape that captures the heart and imagination.

285 Piping Rock Road, Locust Valley
$6,450,000
7 Beds ⋅ 10 Baths ⋅ 991638 MLS
Set behind private gates in the prestigious Estates at Greenfield, this stately brick Georgian Colonial is perfectly positioned on three + magnificently landscaped acres, offering an exceptional blend of timeless architecture and resort-style living. A gracious approach leads to a generous courtyard, creating a striking first impression and a true sense of arrival. Inside, a dramatic two-story center hall marble foyer showcases a sweeping wrought iron circular staircase and exquisite, detailed millwork that sets the tone for the home’s refined interiors. The formal living room is both elegant and inviting, complete with a custom built-in bar and hardwood floors while the generous dining room is perfectly suited for grand entertaining. A warm and inviting den with a fireplace sits just off the chef’s kitchen and sunlit breakfast nook, creating an ideal flow for everyday living. A richly appointed home office features its own fireplace, custom built-in shelving, and a convenient half bath. The first floor is further enhanced by a private ensuite bedroom, perfect for guests or extended family. The second level offers a luxurious primary en-suite retreat with a fireplace, a gracious sitting room, and multiple custom-fitted closets. The spa-like marble bathroom adds to the sense of indulgence. Four additional ensuite bedrooms provide comfort and privacy, while a fabulous bonus room offers flexibility as a second den, media lounge, or computer room. The lower level has been thoughtfully designed for recreation and relaxation, featuring a game room, media area, gym, and abundant storage. Outdoors, the property is truly extraordinary—lush, expansive, and beautifully curated with mature specimen trees that provide both privacy and natural beauty. Designed for both relaxation and recreation, the grounds include a sparkling pool and hot tub, a full-service cabana, and a fully equipped outdoor kitchen ideal for seamless entertaining. A sports court and playground complete this exceptional offering. The property is simply divine—an all-encompassing retreat in The Estates at Greenfield, where every amenity has been thoughtfully curated, offering a lifestyle so complete there is truly no reason to ever leave home.

6 Evergreen Way, Old Brookville
$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
$3,499,000
6 Beds ⋅ 9 Baths ⋅ 921399 MLS
Welcome to 12 Ridge Ct, located in the heart of Old Brookville in the Brookville Meadows. This is your window of opportunity to live in the Gold Coast on 3.4 acres of flat land. From the moment you turn on to the tree-lined street (White Gate Dr.) entering Brookville Meadows, you will feel the caliber of luxury you are about to enter. This home boasts over 7,800 sq feet, the open layout will give you endless possibilities. Enjoy your very own private elevator that goes to every level of the house. This estate offers 6 bedrooms, 7 full baths, and 2 half baths. Step inside and experience the grand scale of the first floor, where the expansive Great Room serves as the heart of the home. Featuring a striking two-sided fireplace, it seamlessly flows into a cozy Family Room, perfect for gatherings or quiet evenings. The Primary Suite occupies its own private wing on the main level with a guest powder room and offers a serene retreat, complete with a sitting area and fireplace, two full bathrooms, two full closets, and an adjoining bedroom with elegant French doors — ideal as a nursery, home office, or additional private suite. On the opposite wing, a private entrance leads to a sun-drenched, oversized Eat-In Kitchen, featuring Marvin windows that flood the space with natural light, Sub-Zero refrigerator, and two Bosh dishwashers. This space opens directly into a formal Dining Room, ideal for hosting. Nearby, you'll find a spacious Guest Ensuite, a convenient Laundry Room, and interior access to a 4-car garage. A hallway from the garage leads to both the backyard and the enormous, partially finished full basement — the full footprint of the home, offering endless potential. There are two full bathrooms with direct access to the pool. The second floor features three large bedrooms. Two share a Jack & Jill style full bathroom, while the third enjoys its own ensuite bath and a private balcony with stunning views of the backyard. An additional oversized bonus room offers incredible flexibility — ideal for a playroom, gym, media room, or extra bedroom. Step outside into your resort-style oasis. The beautifully renovated in-ground gunite pool is the centerpiece of this entertainer’s dream yard. A poolside kitchenette, a charming gazebo, and a pristine tennis court complete the scene — perfect for hosting, relaxing, or simply enjoying the peace and privacy of your own estate.

12 Ridge Court, Old Brookville
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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.