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$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
$2,199,999
6 Beds ⋅ 4 Baths ⋅ 959191 MLS
Sprawling Brick Expanded Ranch in Prestigious Old Brookville! Welcome to this impressive custom-expanded ranch, rebuilt in 2001 and nestled on 2.2 flat acres in the heart of Old Brookville. Offering over 5,100 sq ft of living space, this 6-bedroom, 3.5-bath home combines generous scale with a versatile open floor plan—perfect for both everyday living and entertaining. Highlights include a large living room with fireplace that flows seamlessly into the gourmet kitchen featuring a center island with seating for 8 , Wolf stove, and Sub-Zero refrigerator. A beautifully crafted library with custom mahogany millwork and a second fireplace adds warmth and sophistication. A spacious laundry room with double washers and dryers adds convenience. The primary suite includes a walk-in closet and a roughed-in en-suite bath awaiting your vision to complete. Upstairs offers a large bonus room with a full bath and ample storage—ideal for guests, office, or recreation. Outside, enjoy a peaceful, private setting with a vinyl in-ground pool, expansive patio, and lush grounds. The home also has a partial unfinished basement. Endless potential.

9 Chicken Valley Road, Old Brookville
$5,399,999
6 Beds ⋅ 8 Baths ⋅ 937193 MLS
Welcome to 35 Chicken Valley Road, an extraordinary, gated estate set far off the road and approached by an approximately 825-foot private driveway entrance, culminating in a prestigious circular drive that announces arrival with quiet grandeur. Nestled within the coveted enclave of Old Brookville, this Brick Center Hall Colonial—masterfully built by the renowned Worrell Group—rests on 4.5 acres of impeccably manicured, estate-quality grounds and offers nearly 10,000 square feet of finished living space across all levels. The circular drive leads to a stately entryway accented by a stunning fountain, anchoring the home’s grand approach. Step inside to a breathtaking 22-foot entry foyer with soaring ceilings, intricate moldings, and refined wainscot paneling framing the sweeping staircase. The double-height foyer introduces elegant formal spaces, including a living room with a wood-burning fireplace featuring an ornamental mantel, marble inlay, and classic dental molding. Double columns guide you into the sophisticated sitting room, where French doors open to the terrace, creating effortless indoor–outdoor flow. The formal dining room is designed for grand entertaining, showcasing wainscot paneling, a decorative ceiling medallion, egg-and-dart crown molding, and exquisite millwork throughout. The renovated gourmet eat-in kitchen features top-of-the-line appliances, custom cabinetry, a large center island, and direct access to multiple outdoor dining terraces. Adjacent formal rooms—also with French doors—further connect the interior to the resort-like grounds beyond. The luxurious primary suite is a true sanctuary, offering 22-foot tray ceilings, hardwood floors, serene estate views, a private sitting room with fireplace, a custom dressing room, and a spa-inspired bath with soaking tub and double vanities. Four additional en-suite bedrooms provide exceptional comfort and privacy, ideal for multigenerational living or long-term guests. The expansive lower level elevates entertainment and wellness with a billiards lounge, wet bar, sound-proof private screening room, 3,100-bottle wine cellar, gym, sauna, and full bath. Outdoors, the breathtaking grounds include a heated gunite saltwater pool, regulation tennis court, outdoor kitchen, sweeping lawns, and multiple blue stone terraces—offering both privacy and scale rarely found. Additional features include a three-car garage and a Generac whole-house backup generator. Ideally located in Old Brookville, close to universities, country clubs, golf, marinas, museums, farms, and premier North Shore amenities, and situated within the award-winning North Shore School District.

35 Chicken Valley 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.