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$10,250,000
7 Beds ⋅ 12 Baths ⋅ 1050255 MLS
An extraordinary custom-built estate set within one of Old Brookville’s most prestigious gated communities, this magnificent residence offers an exceptional setting for grand-scale living and refined entertaining. The seven-bedroom, 12-bathroom home is complemented by an impressive eight-car garage and an array of resort-style amenities, including a luxurious pool house, swimming pool, hot tub, and private tennis and multi-sport court. A rare offering that seamlessly combines scale, privacy, and sophistication in one of Long Island’s most coveted enclaves. A grand entrance hall with soaring ceilings introduces the home’s elegant interiors. The main level features a chef’s eat-in kitchen, breakfast room, formal living room, formal dining room, family room, library, and lounge, providing an ideal balance of formal and informal living spaces. The second floor is anchored by a commanding primary suite with expansive his-and-her walk-in closets and separate his-and-her bathrooms. The remaining bedrooms are generously proportioned and each includes a private full bathroom. The finished basement extends the home’s exceptional amenities with a gym, spa, entertainment room, and lounge, creating a private retreat for wellness, recreation, and relaxation.An extraordinary custom-built estate set within one of Old Brookville’s most prestigious gated communities, this magnificent residence offers an exceptional setting for grand-scale living and refined entertaining. The seven-bedroom, 12-bathroom home is complemented by an impressive eight-car garage and an array of resort-style amenities, including a luxurious pool house, swimming pool, hot tub, and private tennis and multi-sport court. A rare offering that seamlessly combines scale, privacy, and sophistication in one of Long Island’s most coveted enclaves. A grand entrance hall with soaring ceilings introduces the home’s elegant interiors. The main level features a chef’s eat-in kitchen, breakfast room, formal living room, formal dining room, family room, library, and lounge, providing an ideal balance of formal and informal living spaces. The second floor is anchored by a commanding primary suite with expansive his-and-her walk-in closets and separate his-and-her bathrooms. The remaining bedrooms are generously proportioned and each includes a private full bathroom. The finished basement extends the home’s exceptional amenities with a gym, spa, entertainment room, and lounge, creating a private retreat for wellness, recreation, and relaxation.

18 Evergreen Way, Old Brookville
$1,449,000
4 Beds ⋅ 2 Baths ⋅ 1048833 MLS
Sea Cliff charm takes on a whole new meaning at “Herbert’s Hill,” a truly one-of-a-kind 4-bedroom, 2-bathroom Tudor with a remarkable artistic history. Built in 1912 by an artist, the home, formerly known as “The Artist Tudor”, still showcases the original owner and builder’s work throughout, including original murals, painted glass, and handcrafted architectural details. Rich walnut wood, exposed ceiling beams, archways, and other period details create a warm and captivating sense of character and eccentricity at every turn. The kitchen features a hand-painted tile backsplash which is a treat from the current artists and owners, while a second floor room with oversized windows offers an ideal setting for a home office, studio, or creative retreat. Downstairs, the “Beer Garden Cellar” is perhaps the home's most intriguing space, preserving the original artist's work with painted glass windows, timbered ceilings, and an angled brick fireplace featuring a Viking ship. It is a space that begs to be explored and offers a fascinating glimpse into the home's past. Outside, a wrap-around path winds through a peaceful garden oasis with a koi pond and waterfall. This is not simply a house, it is a piece of Sea Cliff history filled with artistry, craftsmanship, and unmistakable personality. A must walk through for those who appreciate originality and have the vision to thoughtfully maintain and preserve something truly special.

230 Littleworth Lane, Sea Cliff
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 1042500 MLS
Quintessential Colonial in the Heart of Sea Cliff Beautifully appointed, spacious, and thoughtfully updated, this classic Colonial offers an exceptional layout with incredible flow, abundant natural light, and generous living space throughout, all in one of Sea Cliff’s most desirable locations. From the moment you enter, soaring cathedral ceiling and skylights create a dramatic, light-filled foyer, complete with two closets and an immediate sense of space. The floor plan is truly one of the highlights of this home, you simply couldn’t ask for a better layout. The main level features gracious formal living and dining rooms, while the heart of the home is the chef’s kitchen, flowing naturally into a sun-filled breakfast area and spacious den. Beautiful glass doors open directly to the private backyard, patio, and built-in fire pit, creating the perfect indoor-outdoor connection for everyday living, entertaining, summer evenings, and crisp fall nights. Upstairs, the expansive primary suite is a true retreat with cathedral ceilings, skylights, a beautifully renovated primary bath, and generous closet space. Three additional bedrooms, a full bath, and conveniently located second-floor laundry complete this level. Abundant closet and storage space can be found throughout the entire home, something you truly appreciate once you live here. The fully CO’d finished lower level provides incredible additional living space with a wet bar, large bathroom, and plenty of room for a playroom, movie room, gym, home office, or whatever suits your lifestyle. A finished two-car garage adds even more convenience. With high ceilings, wonderful proportions, an exceptional floor plan, and effortless flow from one room to the next, this is truly the quintessential Sea Cliff Colonial. And the location is hard to beat, just moments from the village, shops, restaurants, parks, beaches, and everything that makes Sea Cliff such a special place to feel right at home.

60 Lafayette Avenue, Sea Cliff
$949,000
2 Beds ⋅ 4 Baths ⋅ 1048063 MLS
Welcome to this sun-drenched and stylish Glen Head fully-updated townhouse in the Fairway View development, perfectly positioned with ideal southern exposure that bathes the home in natural light all day long. Step into a dramatic entry foyer with soaring cathedral ceilings that flow seamlessly into an open-concept living area. Sleek black hardwood floors anchor the residence, creating a sophisticated backdrop for both daily living and effortless entertaining. The gourmet eat-in kitchen features timeless quartz countertops, a matching backsplash, an expansive island with abundant storage, and a dedicated laundry area with pantry space. Step through sliders from the main living space onto your private back deck—an idyllic setting for outdoor dining or peaceful morning coffee. Upstairs, the primary suite serves as a true sanctuary, complete with a generous closet system and a tranquil, Zen-inspired en-suite bathroom. A spacious second bedroom, an additional full bath, and a versatile den/office space with its own private upper-deck access offer endless flexibility for work or guests. The fully finished basement adds exceptional living space, featuring an open layout, a third full bathroom, and an egress window. Situated in the prestigious, award-winning North Shore School District, this home offers the ultimate blend of privacy and convenience—just minutes from top-rated schools, local dining, community amenities, Tappen Beach, and the Glen Head LIRR for a effortless commute.

40 Cedar Lane N Unit #40, Glen Head
$1,699,900
4 Beds ⋅ 3 Baths ⋅ 1039834 MLS
Experience Modern Living with Historic Charm. 4 Beds | 2.5 Baths | Meticulously Expanded & Rebuilt in 2017. Welcome to a stunning example of comfortable living nestled in the charming community of Sea Cliff. Originally built in 1898, this exquisite Colonial home has been meticulously expanded and completely rebuilt in 2017 by a builder ensuring top-quality materials, premium finishes, and meticulous craftsmanship throughout. Elegant & Intelligent Living Spaces: * Grand Welcome: A classic covered front porch leads into a spacious living space perfectly designed for today's lifestyle. * Chef's Heart: A modern kitchen equipped with state-of-the-art appliances and high-end finishes. * Smart Home Technology: Fully integrated SMART home automation paired with custom automated Hunter Douglas blinds. * Premium Finishes: Rich hardwood floors run seamlessly throughout the entire home. * Daily Convenience: A functional mudroom features custom built-ins alongside a stylish powder room. Your Second-Floor Sanctuary: * Primary Suite Oasis: A luxurious retreat featuring a spacious walk-in closet and a spa-like marble bathroom complete with radiant heat, a steam shower, and a separate soaker tub. * House Accommodations: Three additional bright bedrooms, a centrally located hall bath, and a dedicated upstairs laundry area. Bonus Spaces & Private Resort Grounds: * Finished Basement: Provides a dedicated play area for guests, plus abundant extra storage. * Oversized Property: A custom-made fence with a beautiful arbor completely surrounds the property, offering ample private outdoor space. * Outdoor Entertaining: Enjoy a private patio, custom landscaping, professional exterior lighting, and hassle-free in-ground sprinklers. * Ample Parking & EV Ready: A 2-car detached garage recently updated with sleek epoxy flooring and an electric car charger, plus room for 3–4 additional cars in the private driveway. The Sea Cliff Lifestyle: Perfectly located close to beautiful North Shore beaches and quaint village shops, this home offers the absolute best of Sea Cliff living. Enjoy the dual benefits of exceptionally low taxes and enrollment in the highly acclaimed North Shore School District.

18 20th Avenue, Sea Cliff
$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
$5,498,000
7 Beds ⋅ 8 Baths ⋅ 1009813 MLS
Nestled on approximately 5 landscaped acres in Old Brookville, this distinguished estate offers exceptional space, privacy, and classic Gold Coast character. The property includes a stately main residence, a separate 3-bedroom guest cottage, and a pool house, providing flexible living and entertaining opportunities. The main residence offers approximately 5,764 square feet of living space with 7 bedrooms, soaring ceilings, hardwood floors, and elegant French arched windows that bring abundant natural light throughout the home. Expansive interiors overlook manicured grounds, gardens, and open scenic views. Recently renovated bathrooms blend modern updates with timeless design, while generously sized living areas provide comfort and functionality. The beautifully maintained grounds showcase seasonal landscapes and mature plantings, creating a serene setting year-round. Accessed through a gated entrance and private drive, this exceptional estate presents a rare opportunity to own a significant property in the desirable Village of Old Brookville.

952 Cedar Swamp, Old Brookville
$699,000
3 Beds ⋅ 1 Baths ⋅ 1002991 MLS
Charming one-level ranch offering easy living and modern updates! This well-maintained home features three spacious bedrooms, a beautifully updated full bath, and a brand-new eat-in kitchen perfect for everyday living and entertaining. The inviting living room includes a door leading directly to the backyard, creating a seamless indoor-outdoor flow. Additional highlights include a versatile bonus room ideal for a home office, den, plus a one-car attached garage for convenience. Nestled on a quiet, tree-lined street with low taxes, this home is perfectly located close to downtown, beaches, shopping, and restaurants. A wonderful opportunity for comfortable and convenient living! North Shore School District with a Glen Cove address.

12 Ronan Road, Glen Cove
$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
$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
$3,299,888
6 Beds ⋅ 6 Baths ⋅ 977675 MLS
Welcome to a rare opportunity to own a fully renovated and extended estate—rebuilt from the studs up and reimagined for modern luxury in the heart of one of Long Island’s most coveted neighborhoods. Set on a beautifully manicured 2 acre lot, this 6-bedroom, 5.5-bathroom smart residence combines sophisticated design, premium finishes, and cutting-edge amenities, offering a seamless blend of elegance. Every inch of the home reflects quality and intention—from the radiant heated floors throughout the entire main level and every bathroom to the sleek, designer fixtures and finishes throughout. The gracious first floor features a private guest suite with a separate entrance, ideal for extended family and guests. The chef’s kitchen is the true centerpiece—a culinary dream outfitted with a massive center island, top-tier stainless steel appliances, including a 48” Bertazzoni induction range with double ovens, oversized refrigerator and freezer, dual dishwashers, custom cabinetry, beverage drawers, and thoughtful built-ins—all designed to inspire both intimate dinners and large-scale entertaining. The second floor is home to a luxurious primary suite with a spa-inspired en-suite bath, radiant heated floors, oversized closet, and tranquil views of the property. Three additional spacious bedrooms upstairs offer generous closets, and large windows that flood the rooms with natural light. With a dedicated second-floor laundry area, convenience meets everyday function for busy households. The fully finished basement features its own private exterior entrance and offers an abundance of versatile space, including a wine cellar, gym, recreation, full laundry room, and more— The home's brand-new exterior features include a new roof, striking black energy-efficient windows, and a large Trex deck that opens from the kitchen to your own private oasis complete with an in-ground pool. Every system has been updated—new electrical, plumbing, floors, HVAC, and insulation—ensuring true turnkey luxury living. This is more than a home—it's a statement. A rare offering of timeless craftsmanship and modern design in one of the most distinguished enclaves.

33 High Farms Road, 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
$5,490,000
6 Beds ⋅ 6 Baths ⋅ 845880 MLS
Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

89 Pound Hollow Road, Old Brookville

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.