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$12,800,000
10 Beds ⋅ 15 Baths ⋅ 922932 MLS
Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary. A striking stone and stucco facade with oversized black-trim windows sets a sophisticated tone upon arrival. Inside, a dramatic marble foyer with a sweeping spiral staircase unveils the heart of the home: a voluminous great room featuring soaring ceilings, a sleek gas fireplace, bespoke wet bar, and walls of glass that dissolve the boundary between indoors and out. Every inch of this residence speaks to thoughtful luxury. The chef’s kitchen is clad in two-toned cabinetry, boasts a suite of chef-grade stainless steel appliances and thick-cut stone countertops. The welcoming family room has a warm fireplace with a custom, stone mantel and beautiful natural wood built-ins. Entertain effortlessly in the formal dining room, designed to host 14+ guests, supported by a fully outfitted butler’s pantry. Designed for both grand entertaining and intimate day-to-day living, the main level also features a spacious home office with a private sitting area, two elegant powder rooms, a guest-ready first-floor bedroom suite, an elevator and a mudroom conveniently located off of the 4-car attached garage. Upstairs, the primary wing evokes the atmosphere of a five-star hotel, complete with a private lounge, dressing and vanity area, spa-like bath with an oversized rain shower and soaking tub, radiant heated floors, and multiple walk-in closets, with custom wardrobe installations. There are four additional bedrooms, four marble full-bathrooms and an expansive laundry room. The walk-out lower level is a world unto itself, beginning with a dramatic foyer framed by a floor-to-ceiling wine display wall. Details include a one-bedroom guest suite, media or den space, full bath, a state-of-the-art gym with sound system and sauna, and a full-scale golf simulator for year-round recreation. Outdoors, the resort-quality amenities continue with a covered patio with a fireplace, a built-in kitchen, and a sparkling in-ground pool and spa. A poolside cabana offers yet another luxe retreat, complete with a kitchenette, lounge, changing rooms, and full bath. Beyond the main residence, a two-story barn with a loft serves as an 8-stall equestrian facility or an extraordinary car collector's gallery, accompanied by a fully-appointed 3/4 bedroom guest house for extended stays or guest quarters. Nestled in a picturesque and ultra-private setting, this 20,000+ Sq.Ft. Old Brookville masterpiece redefines modern estate living with unmatched elegance, scale, and functionality. Located within the North Shore School District.

53 Simonson Road, 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
$4,199,999
4 Beds ⋅ 5 Baths ⋅ 989235 MLS
Why escape to a luxury resort for the weekend when you can come home to one every single day? This extraordinary residence delivers the kind of lifestyle most people only experience on vacation—private, peaceful, and effortlessly elegant. A rare opportunity to own a home that feels like a permanent getaway. Welcome to "Casa De Luce" a French Chateau style palace, a truly exceptional luxury retreat where resort-style living meets modern design and privacy. Set on 1.11 acres with sweeping pond views and no visible neighbors beyond, this one-of-a-kind property offers the rare feeling of owning nearly double the land—your own private escape. From the moment you arrive through the gated entrance with smartphone access, the home makes a statement. Step inside to a dramatic glass staircase and soaring floor-to-ceiling windows that immediately draw your eye through the home and out to the breathtaking backyard. Designed with both elegance and comfort in mind, the main level features a spacious dining area, an oversized eat-in kitchen with an impressive 15-foot countertop, and expansive living spaces ideal for entertaining. A separate living room with a gas fireplace provides a warm, inviting retreat, complemented by a stylish powder room. All bedrooms are located upstairs, the primary suite is a sanctuary of its own—complete with a massive walk-in closet, a luxurious spa-like bathroom, and a Juliet balcony overlooking the tranquil yard and pond. Three additional bedrooms 2 share a well-appointed Jack and Jill bathroom, the third has its own private full bathroom and a convenient upper-level laundry station adds everyday ease. A fully equipped attic level with HVAC and an automatic skylight with retractable shade provides additional flexible living space. This home is designed for elevated living and entertaining, offering a dedicated theater room, custom bar area, and expansive recreation space—perfect for hosting, relaxing, or creating your own private retreat. Step outside to your private resort. The backyard is designed for ultimate enjoyment with a heated gunite pool, built-in BBQ, wet bar, and a retractable imported European cabana. The premium patio stays cool under the sun, allowing for comfortable outdoor living all summer long—all set against the peaceful backdrop of the pond. Additional highlights include 10 foot ceilings on every level, a geothermal HVAC system, whole-house generator, and a 2-car garage with 18-foot ceilings—ideal for car lifts or a collector’s setup. Every finish throughout the home has been thoughtfully curated to deliver a true 5-star living experience. This is more than a home—it’s a lifestyle.

22 Eastview Lane, Old Brookville
$4,150,000
6 Beds ⋅ 6 Baths ⋅ 1034020 MLS
Old Brookville with choice of North Shore or Locust Valley Schools. 2 Acre Property Welcome to 17 Hunt Court, nestled within the coveted Pheasant Chase section of Old Brookville and tucked behind the area's renowned equestrian center. This exceptional brick colonial blends timeless architecture with beautifully updated interiors, resort-inspired outdoor living, and the peaceful surroundings that define the quintessential Old Brookville lifestyle. A tranquil wrap-around porch welcomes your arrival before double entry doors open to an impressive 18-foot foyer, highlighted by a sweeping wrapped staircase and gracious proportions that set the tone throughout the home. Designed for both refined entertaining and comfortable everyday living, the main level offers a formal living room anchored by a wood-burning fireplace, an elegant formal dining room connected to the kitchen through a butler's pantry, and a spacious family room featuring tray ceilings, a second wood-burning fireplace, and French doors opening seamlessly to the backyard. The beautifully appointed chef's kitchen serves as the heart of the home, thoughtfully designed with a breakfast nook, built-in office area, Sub-Zero refrigerator and freezer, refrigerator drawers, two dishwashers, a wine refrigerator, built-in Miele coffee system, television nook, and a gas range with pot filler, creating an inviting space for gathering and entertaining. A country club-inspired mudroom offers exceptional functionality with direct access to the backyard, second level, and attached three-car garage. Completing the first floor is a home office which can also be used as a first-floor bedroom. The second level is highlighted by a luxurious primary suite featuring hidden laundry, an expansive spa-inspired bathroom with dual vanities, a soaking tub overlooking the beautifully landscaped grounds, water closet, beverage refrigerator, oversized walk-in shower, generous walk-in closet, and a private retreat designed for comfort and relaxation. Four additional bedrooms and two recently renovated full bathrooms complete the upper level. The finished lower level expands the home's exceptional living and entertaining space, offering a wet bar, dedicated fitness room, expansive recreation area, and direct outdoor access to the backyard. Outdoors, the property has been extensively transformed into a private resort-inspired retreat. An expansive patio surrounds the heated gunite pool and fully equipped outdoor kitchen, creating an exceptional setting for entertaining while overlooking meticulously maintained landscaping and sprawling lawns. The shared common green space beyond enhances the sense of privacy and openness, further contributing to the quiet, secluded setting that makes this neighborhood so desirable. Offering six bedrooms, beautifully curated indoor and outdoor living spaces, and an exceptional location within one of the North Shore's most sought-after communities, 17 Hunt Court presents a rare opportunity to experience the very best of Gold Coast living in the heart of Old Brookville.

17 Hunt Court, Old Brookville
$3,100,000
5 Beds ⋅ 7 Baths ⋅ 969013 MLS
Built by the renowned Farrell Building Company in 1996, whose homes are recognized among Long Island’s finest for their exceptional quality and enduring craftsmanship, this exceptional brick Gold Coast estate blends timeless architecture with today’s luxury amenities, offering over 5,480 square feet of elegantly appointed living space on two private acres in the heart of prestigious Old Brookville. Designed for both grand entertaining and comfortable everyday living, the home showcases five bedrooms, five full baths, two powder rooms, grandly scaled interiors, rich hardwood floors, custom solid wood built-ins, abundant natural light, and four fireplaces that add warmth and character throughout. At the heart of the home is a beautifully appointed eat-in kitchen featuring granite countertops, a large center island, double ovens, two dishwashers, and generous dining space. The kitchen flows seamlessly into the inviting family room with custom built-ins and a dramatic stone wood-burning fireplace. Formal living and dining rooms, a private study, a spacious laundry room, and a cabana bath with direct access to the backyard complete the thoughtfully designed main level. The luxurious primary suite is a private retreat, offering a gas fireplace, a spa-inspired bath with radiant heated floors, dual vanities, a double shower, and extraordinary walk-in closets. A rare walk-out lower level, entirely move grade offering an additional 1,800 square feet of finished living space, thoughtfully designed to function as an extension of the home. This level includes a spacious a recreation room, fireplace, gym, guest suite with an en-suite bath, powder room, and direct access to the backyard. Designed for exceptional outdoor living, the resort-inspired grounds feature a heated saltwater gunite pool, an outdoor fireplace, a built-in barbecue, expansive bluestone patios, a gazebo and mature landscaping, creating an exceptionally private setting. Additional highlights include a heated four-car garage with hot and cold water, a private driveway accommodating over 10 cars and a whole-house generator. Perfectly positioned near waterfront dining, Long Island Sound beaches, championship golf courses, nature preserves, and the charming villages of Roslyn, Oyster Bay, and Locust Valley, this is a rare opportunity to own a timeless Gold Coast estate where exceptional craftsmanship, refined living, and today’s comforts come together in one extraordinary residence.

10 Overbrook Lane, Old Brookville
$2,799,000
5 Beds ⋅ 4 Baths ⋅ 938081 MLS
Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright, open feel throughout. The sunken living room flows into a dining area with a wet bar. The first floor includes a spacious primary suite, a dedicated home office, and both formal and casual living areas—all thoughtfully laid out and generously proportioned. With its solid foundation and impressive architectural details, this home offers an incredible opportunity to update and customize to your personal style.

7 Pin Oak Court, 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

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.