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$2,695,000
4 Beds ⋅ 4 Baths ⋅ 906140 MLS
ARCHITECTURAL MILLWORK... COFFERED CEILING... RAISED MOLDINGS....DESIGNER BATHS... CUSTOM KITCHEN WITH 10 FT ISLAND .... STAINLESS APPLIANCES ...QUARTZ COUNTERTOPS ...SUN ROOM OFF KITCHEN....HARDWOOD FLOORING... ALL NEW ANDERSEN BLACK FRAME WINDOWS ...HARDIE PLANK SIDING TOTAL RENOVATION JUST COMPLETED SHOWS LIKE A MODEL

19 MICHAELS Lane, Old Brookville
$2,499,999
5 Beds ⋅ 4 Baths ⋅ 1019434 MLS
This extraordinary Old Brookville estate at 19 Pheasant Hill Lane, featured in Architectural Digest, is a rare Georgian inspired residence that embodies timeless architecture, exceptional craftsmanship, and refined design. Perfectly positioned on two flat, private acres along one of Old Brookville’s most peaceful and coveted streets, this 5 bedroom, 3.5 bath home offers elevated living within the award winning North Shore School District. A charming circular driveway welcomes you to the stately facade, where grand Georgian columns create an unforgettable first impression. Beyond the marble foyer, the home unfolds with elegant living spaces rich in character and architectural detail. Luxurious marble bathrooms, custom designer lighting throughout, and a spectacular all glass cupola that fills the home with natural light showcase the remarkable quality and craftsmanship found in every room. Designed for today's lifestyle, the thoughtfully planned layout includes a first-floor bedroom, ideal for guests, extended family, or a private home office. Every space reflects warmth, sophistication, and timeless appeal, creating a home that is both inviting and impressive. The fully finished lower level is an entertainer's dream unlike any other. Featuring an expansive restaurant style bar, a custom built nightclub inspired entertainment venue complete with a DJ booth, dance floor, and generous gathering areas, this one of a kind space is perfectly suited for hosting unforgettable celebrations and private events. Outside, the sprawling two acre property offers endless possibilities to create your own resort style backyard oasis. With ample room for a luxurious pool, spa, outdoor kitchen, tennis or pickleball court, and beautifully landscaped gardens, the grounds provide the perfect canvas for exceptional outdoor living. Ideally located just minutes from the charming villages, fine dining, boutique shopping, renowned country clubs, parks, and Long Island Rail Road stations, this exceptional residence offers the perfect balance of privacy, convenience, and prestige. A truly remarkable Architectural Digest featured estate where timeless elegance, extraordinary entertaining, and the coveted Old Brookville lifestyle come together in one exceptional offering.

19 Pheasant Hill Lane, 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
$21,500,000
10 Beds ⋅ 10 Baths ⋅ 1010319 MLS
Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 33+ 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, four 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 Pound Hollow Road, 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
$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
$4,399,000
5 Beds ⋅ 8 Baths ⋅ 987442 MLS
Set within the rarefied landscape of Old Brookville, this striking Mid-Century Modern residence is a study in architectural drama and refined design. Celebrated in Luxe Interiors + Design at the time of its transformation, the home reflects the visionary collaboration between its owners and the acclaimed firm Garcia/Maldonado, Inc.. The result is a masterwork where every line, material, and proportion has been considered with uncompromising precision. A rich palette of exotic woods—mahogany, oak, and birch—anchors the interiors with warmth and texture, while the architecture itself unfolds with quiet grandeur. The great room is nothing short of breathtaking: a soaring vaulted ceiling, commanding fireplace, and an expansive wall of glass dissolve the boundary between indoors and out, flooding the space with natural light and framing the surrounding landscape as living art. An elegant dining room overlooks the property and is the perfect venue for entertaining. At the heart of the home, the kitchen is both generous and inviting—designed for gathering and everyday luxury—with a substantial center island, sunlit breakfast room, and seamless connection to an open den. A separate media room, complete with a built-in bar and sliding doors, offers the flexibility for both intimate evenings and vibrant entertaining. The first-floor primary suite is a private sanctuary, opening directly to the grounds and featuring its own fireplace. A dramatic staircase leads to a secluded study—an architectural moment that elevates both function and form. The suite is further enhanced by a bespoke fitted closet room and a spa-like bath, exquisitely detailed in teak wood to evoke a sense of serenity, complete with dual vanities, a soaking tub, and a separate glass-enclosed shower. Upstairs, three oversized ensuite bedrooms, each with their own bath are complemented by an open lounge, creating a natural gathering space bathed in light. The lower level extends the lifestyle with a recreation room, additional den, and dedicated gym. Set across three exquisitely landscaped acres, the property evokes a private country club experience: a newly crafted Ipe deck, sparkling in-ground pool, Har-tru tennis court, and cabana complete this exceptional offering—where architecture and setting exist in perfect harmony.

93 Hoaglands Lane, Old Brookville
$6,850,000
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
$3,899,000
6 Beds ⋅ 5 Baths ⋅ 957864 MLS
Nestled in the heart of Old Brookville, this private oasis offers the perfect blend of luxury, tranquility, and modern living. Set on a sprawling, flat 3.2 -acre lot within the prestigious North Shore School District, this property feels like your own year-round retreat. As you approach via the picturesque private driveway, you're greeted by lush, mature landscaping that ensures complete seclusion. The property boasts a sparkling gunite saltwater pool with a chic pool house, a clay tennis court, and plenty of open space to enjoy outdoor living at its finest. Step inside this contemporary gem, and you'll find a thoughtfully designed floor plan that caters to comfort and style. The main level features a stunning primary ensuite with its own private deck—your perfect sanctuary for morning coffee or evening relaxation. The home has been meticulously updated with hardy plank siding, new windows, a modern A/C system, and a hot water heater. Simply move in and make it your own! Whether you're lounging by the pool, hosting friends on the tennis court, or unwinding in your serene retreat, this home truly offers a vacation lifestyle all year long. Don’t miss your chance to experience the ultimate in privacy and luxury living.

91 Hoaglands Lane, 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
$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.