Old Brookville Real Estate

Set on 2.61 beautifully landscaped acres in the prestigious enclave of Old Brookville, this stately brick Georgian Colonial offers an exceptional blend of timeless architecture, generous living spaces, privacy, and versatility. A sweeping circular driveway creates a grand arrival, framed by mature plantings and lush grounds that provide a serene and secluded setting. Designed to embrace natural light, the residence features oversized windows throughout all three levels, complemented by natural oak hardwood floors that lend warmth and a refined feel. A two-story entry foyer establishes an elegant first impression, opening to an expansive main level with multiple distinct living spaces, including a formal living room, formal dining room, family room, and a versatile secondary sitting room or private office. The family room features a fireplace, while a thoughtfully designed eat-in kitchen offers a propane gas range, pantry, and sun-filled breakfast area surrounded by walls of windows. Sliding glass doors open onto a beautiful deck overlooking the expansive backyard, creating a seamless connection between indoor living and the surrounding landscape. A desirable first floor primary suite adds convenience and flexibility to the home’s well designed layout. The second level features four additional bedrooms and two full bathrooms, with two of the bedrooms enjoying their own private balconies overlooking the grounds. A striking spiral staircase, complemented by a secondary staircase, provides convenient access to the fully finished, above ground walkout lower level, offering an exceptional extension of the home’s living and entertaining spaces. The lower level is thoughtfully equipped with a full kitchen, wet bar, two additional bedrooms, 1.5 bathrooms, and a spacious living area anchored by a fireplace, creating a warm and inviting atmosphere for relaxation and entertaining. Additional flexible space offers endless possibilities for a home gym, media room, recreation lounge, or customized leisure space. With its generous accommodations and direct walkout access to the grounds, this level offers outstanding versatility for multigenerational living, extended guests, or a variety of lifestyle needs. Additional highlights include a three car garage, smart thermostats, Ring security cameras and doorbell, and mature landscaping throughout the private grounds, newly resealed driveway, brand new recessed LED lighting throughout, newly finished floors, and much more. With seven bedrooms, four full bathrooms, two half bathrooms, and an abundance of indoor and outdoor living spaces, this distinguished Old Brookville residence presents a remarkable opportunity to enjoy privacy, space, and timeless architectural character in a coveted North Shore setting.

14 Pheasant Hill Lane, Old Brookville

$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

$8,250,000

6 Beds ⋅ 8 Baths ⋅ 1048329 MLS

Set behind the gates of an exclusive community in the Village of Old Brookville, this exceptional modern residence offers more than 7,000 square feet of luxurious living space on over three acres of beautifully manicured, private grounds. Walls of windows fill the home with natural light while showcasing serene views of the surrounding landscape, inground pool and hot tub. A dramatic two-story entry introduces the impressive main level, featuring a soaring two-story great room with a striking stone wet bar, a formal dining room and a private home office. The expansive eat-in kitchen includes a spacious breakfast area and provides an inviting setting for both everyday living and entertaining. A generously sized junior primary suite and an additional bedroom completes the first floor. Upstairs, the expansive primary suite serves as a private retreat with dual walk-in closets, a luxurious primary bathroom and a generous terrace. Three additional bedroom suites each feature their own private bathrooms, while a conveniently located laundry room completes the second level. The finished lower level is designed for recreation, relaxation and wellness, offering a golf simulator, entertainment room, play area and full bathroom. A private spa features a hot tub, sauna and steam room, creating a resort-like experience without ever leaving home. Surrounded by lush, meticulously maintained grounds, this remarkable Old Brookville property delivers exceptional privacy, modern sophistication and resort-style living in one of Long Island’s most prestigious communities.

160 Hegemans Lane, Old Brookville

$2,995,000

5 Beds ⋅ 6 Baths ⋅ 1044302 MLS

Spacious Old Brookville Retreat with Private Tennis Court Set on two beautifully landscaped acres in the heart of Old Brookville, this impressive residence offers an exceptional combination of space, privacy, comfort, and timeless elegance. Completely renovated in 2019, the home welcomes you with a gracious entry and expansive living spaces featuring soaring ceilings, abundant natural light, beautiful stone and hardwood floors, and multiple gathering areas designed for both relaxed everyday living and sophisticated entertaining. At the heart of the home, the spacious eat-in kitchen features extensive custom cabinetry, generous counter space, a large center island, and a wall of windows overlooking the lush grounds. The adjoining living and dining areas create an inviting flow, while two fireplaces add warmth and character. Step outside and discover what makes this property truly special. The two-acre grounds offer privacy and tranquility, with mature landscaping, expansive lawns, and a private tennis court creating an extraordinary setting for recreation, entertaining, or simply enjoying the outdoors. A long, impressive driveway welcomes you to the property and provides abundant parking for family and guests. The finished lower level expands the living space even further, with high ceilings, a home office, gym, and recreation room. With its generous proportions, sophisticated architectural details, exceptional outdoor space, and rare private tennis court, 5 Woodfield Lane offers the opportunity to experience the space and privacy of a true Old Brookville retreat—while remaining close to everything the North Shore has to offer.

5 Woodfield Lane, 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

$7,900,000

1034323 MLS

Set on more than 17 pristine and level acres in the heart of prestigious Old Brookville, this exceptional farm property presents a rare opportunity to own a significant piece of Long Island's North Shore history. Once part of the renowned Westward estate, the grounds were originally assembled in the early 1900s for distinguished industrialist and financier Benjamin Brewster Jennings, President and Chairman of Socony-Mobil and one of the most influential figures in New York's corporate and financial circles. Offering endless possibilities for equestrian pursuits, agricultural use, or the creation of a remarkable private estate, the property is improved with multiple run-in sheds, garages, and supporting outbuildings. Located within the highly regarded North Shore Central School District, this is an extraordinary offering that combines historic provenance, exceptional acreage, and limitless potential.

97 B 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

$2,399,000

4 Beds ⋅ 4 Baths ⋅ 906140 MLS

A completely reimagined Old Brookville residence offering 4,200 square feet of turnkey luxury on a private one acre property. Thoughtfully renovated from top to bottom, this sophisticated modern ranch combines exceptional craftsmanship with effortless single level living. The designer kitchen features a 10 ft island quartz counter tops hardwood flooring and stainless appliances. A beautiful sunroom off the kitchen adds more space to relax and enjoy the private property. Custom millwork throughout including coffered ceilings and a full 15 ft wall of architectural molding . New Andersen black frame windows and Hardie Plank siding . North Shore Schools Low property taxes .... Shows like a model ...furnishing are ai generated

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

$4,795,999

1016857 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

Old Brookville Real Estate

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