Browse All Old Brookville NY 5 Bedroom Properties for Sale

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

$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

$2,089,000

5 Beds ⋅ 4 Baths ⋅ 1006685 MLS

Wonderful opportunity to own a home on two lush acres in the heart of Old Brookville. Situated on a quiet cul-de-sac, this five bedroom immaculate and well maintained Center Hall Colonial is detailed with hardwood floors and two fireplaces. It offers buyers the chance to reimagine and update a gracious residence with exceptional potential. The beautifully landscaped property features an in-ground pool, tennis court and gazebo. Additional amenities include a two-car attached garage, an additional 3-car detached garage and generator. A rare opportunity to bring your vision and create your own private estate in a premier location.

14 Oak 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

$2,500,000

5 Beds ⋅ 4 Baths ⋅ 954210 MLS

Set on 2 flat, park-like acres in the sought-after North Shore School District, 19 Carlisle Drive is a home that can be updated to today's modern family while maintaining everyday luxury. This 5-bedroom, 3.5-bathroom property is designed to impress, with thoughtful details and amenities that elevate both form and function. The heart of the home is its first-floor primary suite—a true sanctuary featuring generous proportions, a spa-like en-suite bathroom, and ample closet space. The open-concept living areas are bathed in natural light, seamlessly connecting to an entertainer’s dream backyard. Imagine summer days spent lounging by the in-ground heated gunite pool or unwinding in the indoor jacuzzi when the weather cools. Perfectly nestled in the quiet charm of Old Brookville, this property offers not just a home but a lifestyle. Whether hosting friends or enjoying a peaceful evening surrounded by manicured greenery, you’ll feel worlds away while still being close to it all. Don’t miss your chance to make this stunning property your own.

19 Carlisle Drive, 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

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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.

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