Brookville NY Historical Real Estate, Homes for Sale

Set on 2.5 private, beautifully landscaped acres in Brookville, this dramatic 9,485-square-foot contemporary offers exceptional scale, architectural interest and resort-style amenities within the Jericho School District. The 18-room residence features 6 bedrooms and 7 full and 1 half baths, including an expansive main-level primary suite with a spa-like bath and multiple walk-in closets. A grand foyer and soaring ceilings introduce generously proportioned living and dining spaces, a spacious sitting room and a chef’s kitchen with a large center island, breakfast nook and high-end Sub-Zero and Bosch appliances. Radiant-heated floors enhance the kitchen, primary suite and an additional bedroom. Walls of glass create a seamless connection to the extensive decking, swimming pool, cascading stone water feature and lush grounds. The finished lower level is designed for recreation and wellness, with a large recreation room, gym, sauna, wine cellar, laundry and abundant storage. Additional highlights include a home office, flexible guest accommodations, five-zone central air, a backup generator, a newer roof, an oversized three-car garage and a private tennis court. A rare Brookville estate offering privacy, space and exceptional indoor-outdoor living.

24 Emerson Road, Brookville

$3,799,000

5 Beds ⋅ 5 Baths ⋅ 1027379 MLS

Set on two flat, beautifully landscaped acres along a low-traffic street in Brookville, yet just minutes from major highways and shopping, this classic Colonial built in 1964 offers thoughtfully updated living space throughout. An extensive renovation touched nearly every corner of the home, from all new Marvin windows and doors to central air, updated heating, and a full repaint inside and out. The kitchen underwent its own complete transformation, emerging with high end appliances, a center island, and gas cooking, ideal for anyone who loves to cook and entertain. Three fireplaces warm the home throughout, found in the den, the living room, and the sunroom, where a new gas fireplace adds year round comfort. Upstairs, five bedrooms include a primary suite with a walk-in closet and an en suite bath featuring a soaking tub, stall shower, and double vanity, while a sixth bedroom was converted into a convenient laundry room. Three full baths and two half baths serve the home's living spaces, and a full unfinished basement offers ample storage or future potential. The three car garage, expanded from its original two car footprint, sits above with a second story that shares a wall with the primary suite. Comfort continues with three zone heating and air conditioning, a 400 amp electrical service, an automatic propane generator, and a Control4 smart home system managing sound, lighting, and video throughout. Outside, mature landscaping surrounds a brand new in-ground pool, a pergola, and an outdoor kitchen with a gas BBQ, perfect for warm weather gatherings. A new thirty year asphalt roof, new driveway, and updated sprinkler system round out a home where every major system and finish has been thoughtfully addressed. Colonial in style and scaled for gracious living, 15 Dogwood Hill offers a rare combination of space, setting, and easy access to everything Long Island's North Shore has to offer.

15 Dogwood Hill, Brookville

$2,799,999

7 Beds ⋅ 5 Baths ⋅ 1023664 MLS

Experience pristine living in this exquisite diamond Brookville home, offering unsurpassed value in a highly coveted location. The prestigious approach features a long circular driveway, welcoming you to a serene retreat. The exterior boasts mature specimen plantings and estate fencing encircling a country club style yard with a 20x40 Gunite gas heated pool. The flat 2 acres of entertaining backyard and brick patio, provides ample space to add tennis, pickleball or sport court. This serene oasis is perfect for relaxation and entertainment. Inside the kitchen features hardwood cabinets, complimented by gleaming hardwood flooring throughout the home. 4,717 of finished living space and an additional 1,148 of unfinished basement to create a media room, play room or entertainment cave. The architectural roof adds to the home's timeless elegance. First floor bedroom with en-suite bath and dual walk in closets, laundry, and a versatile bedroom/office with a walkout to the fabulous yard. There is so much more to this exceptional property that must be seen to be fully appreciated. Don't miss this rare opportunity to own a true retreat in a serene oasis.

15 Tappentown Lane, Brookville

$3,299,000

5 Beds ⋅ 6 Baths ⋅ 1014653 MLS

Welcome to 11 Wenwood Drive, an exceptional residence nestled in the prestigious, highly sought-after Village of Brookville. The home is located within the Jericho Union Free School District and offers convenient access to shopping, dining, parks, major highways and public transportation. From the moment you arrive, you'll be captivated by the home's impressive curb appeal and thoughtfully designed floor plan, perfectly suited for both everyday living and elegant entertaining. A double-door front entry welcomes you into a two-story foyer featuring elevated ceilings and a dramatic staircase. Filled with natural light and timeless elegance, the gracious interior offers an ideal balance of sophistication and comfort. At the heart of the home is the open-concept chef's kitchen featuring an oversized center island with seating, a spacious breakfast area, high-end appliances, abundant custom cabinetry, and generous counter space. The kitchen flows seamlessly into a stunning formal dining room perfect for everyday dining and memorable celebrations. There is also step down access to a spectacular great room featuring a floor to ceiling stone wall with an oversized wood burning fireplace, creating a warm and inviting gathering space. Just off the foyer, the formal living room, with soaring ceilings, is bathed in natural light from oversized windows. It is enhanced by an elegant classic mantel encasing a wood-burning fireplace and hardwood floors. The spacious first-floor primary suite provides a private retreat with generous proportions and the convenience of main-level living. There is a vast seating area, surrounded by beautiful windows, two large closets and an ensuite bathroom with a double vanity, jacuzzi spa bathtub and a separate shower. An additional first-floor bedroom, complete with an adjacent half bath and a separate private entrance, offers exceptional flexibility for guests, a home office, or live-in accommodations. The second level features three additional bedrooms and two full bathrooms, providing comfort and privacy for guests. The upper level den has an oversized window overlooking the rear property which creates the perfect space for relaxation or exercise. With a built-in work station, it also creates a perfect setting for studying or working from home. Step outside to a beautifully designed bluestone patio complete with an outdoor gas barbeque and ample space for al fresco dining and entertaining. The pristine property offers a stunning, in-ground , heated, gunite pool with a summer kitchen including a sink and mini refrigerator; covered by a beautiful pergola, perfect for outdoor entertaining. The 2.03 acre property also allows plenty of room for an outdoor playset with lots of green space for all types of sporting activities. The finished basement has a craft room with shelving and a closet as well as room for a home theatre, gym or playroom. There is also a separate room with a closet, a full bathroom and an outside egress window. Additional highlights include a main level separate laundry room and a wrap-around private driveway leading to an oversized two car attached garage.

11 Wenwood Drive, Brookville

$4,400,000

5 Beds ⋅ 7 Baths ⋅ 1017067 MLS

Welcome to this commanding five-bedroom contemporary residence, a spectacular home where soaring architecture, abundant natural light, and resort-style amenities combine to create an extraordinary living experience. From the moment you enter the dramatic two-story foyer, you are captivated by three magnificent floor-to-ceiling Palladian windows that frame breathtaking views of the terraced, verdant grounds beyond. The home's impressive two-story ceilings, rich hardwood floors, four fireplaces, and generously proportioned principal rooms create an atmosphere that is both grand and inviting, while seamlessly blending the beauty of the outdoors with every interior space. Designed for both everyday living and elegant entertaining, the home features a stunning culinary kitchen appointed with lacquered cabinetry, dual center islands, and an extraordinary Redwood Triple Glass Conservatory that bathes the space in natural sunlight. After dining in the elegant dinig room enhanced by a fireplace, a comfortable den provides the perfect place to unwind, while a private home office offers an ideal remote work environment. The main-level primary suite serves as a luxurious retreat, complete with a sitting room, spa-inspired bath, and custom-fitted closets. Upstairs, three additional bedrooms are complemented by a welcoming loft with a fireplace—a wonderful gathering space for relaxation and recreation. The home's most exceptional feature awaits on the walk-out lower level: a meticulously maintained heated indoor swimming pool that can be enjoyed year-round, creating a private resort within your own home. Outside, the beautifully terraced landscape is anchored by impressive natural boulders that enhance the property's architectural beauty and park-like setting. A serene, Zen-inspired brook gently winds through the grounds, creating a soothing sense of tranquility, while expansive bluestone patios, an outdoor kitchen, and lush lawns provide the perfect setting for entertaining, recreation, and peaceful reflection. This is a rare opportunity to experience luxury living at its finest. Generator and Level 3EV Charging

5 Victorian Lane, Brookville

$2,598,000

4 Beds ⋅ 4 Baths ⋅ 1016868 MLS

Set on two meticulously landscaped acres, this exceptional Brookville residence showcases refined design, expansive living spaces, and resort-style outdoor amenities. The grounds feature an inground saltwater pool, elegant stone patio, and outdoor kitchen equipped with a barbecue, refrigerator, and sink. A dramatic entry opens to soaring ceilings and impressive window walls that flood the home with natural light. The spacious floor plan includes a sprawling living room/dining room, two inviting dens, and a recently renovated eat-in kitchen designed for both daily living and entertaining. Four beautifully updated bedrooms and three-and-a-half baths provide comfortable accommodations throughout. The finished ground level offers versatile additional living space, while the seamless connection between indoor and outdoor areas enhances the home's exceptional functionality and appeal. Move-in ready and thoughtfully updated. Ideally situated near transportation, shopping, dining, parks, universities, golf and tennis facilities, this is a remarkable offering in Brookville.

19 Tappentown Lane, Brookville

$3,499,000

6 Beds ⋅ 5 Baths ⋅ 1017003 MLS

Welcome to this exceptional Colonial-style residence situated on 2 private acres in the highly sought-after Village of Brookville, within the award-winning Jericho School District. This beautifully maintained home offers a timeless colonial floor plan featuring a desirable first-floor primary suite, spacious living areas, and quality craftsmanship throughout. The elegant stucco exterior enhances the home's curb appeal, while modern updates, including a new roof, a new central air conditioning system, and a whole-house gas generator, provide peace of mind for years to come. The home is designed for comfortable living and entertaining, featuring natural gas cooking, a fully finished basement with a ground-level exit, and abundant living space for family and guests. Step outside to your private backyard retreat complete with a stunning inground gunite swimming pool, surrounded by expansive flat grounds offering endless possibilities for recreation, gardening, or future expansion. Located in one of Long Island's most desirable neighborhoods, this property offers luxury, privacy, and convenience, with easy access to major highways, shopping, dining, and transportation.

8 Victorian Lane, Brookville

$4,200,000

5 Beds ⋅ 6 Baths ⋅ 1012827 MLS

This exceptional two acre Brookville estate offers the perfect blend of luxury, privacy, and resort-style living. Surrounded by pristine, professionally landscaped grounds, the property is a true outdoor oasis designed for both relaxation and entertaining. Filled with an abundance of natural light, the residence showcases hardwood floors throughout and beautifully appointed living spaces designed for both comfortable living and elegant entertaining. The gourmet chef’s kitchen is equipped with top-of-the-line appliances, custom cabinetry, and a spacious breakfast area that opens seamlessly to an inviting den with a fireplace. The kitchen also provides direct access to the expansive wraparound porch, creating effortless indoor-outdoor living. Additional first-floor highlights include a formal dining room, a sun-filled living room with access to the porch, a first-floor bedroom, and a convenient laundry room. The second level is anchored by a luxurious primary suite retreat featuring two expansive closets, a spa-inspired bath, and private office with a balcony overlooking the pool and spectacular backyard. Three additional en-suite bedrooms offer comfort and privacy, while a versatile recreation room provides flexible space for a playroom, media room, fitness studio, or additional office. The finished lower level offers an expansive entertainment area along with abundant storage space. Outside, the property evokes the ambiance of a private country club. The breathtaking grounds feature a sparkling pool, sport court, cabana-style pavilion, sprawling lawns, and mature landscaping that create a serene and picturesque setting. Completing this extraordinary estate is a three-car garage and ample space for entertaining on a grand scale. A rare opportunity to own a private Brookville retreat offering timeless elegance, exceptional amenities, and an unparalleled North Shore lifestyle.

209 Brookville Road, Brookville

$14,900,000

7 Beds ⋅ 9 Baths ⋅ 1004738 MLS

‘Haut Bois’ is a refined brick-and-stucco French chateau nestled in the heart of Brookville, New York. Inspired by the Louis XIV hunting lodge that later became the Palace of Versailles, this extraordinary 18-room estate is steeped in history, elegance, and timeless beauty. Originally built in 1916 by renowned architect Ogden Codman Jr. and meticulously restored in the late 20th century, this one-of-a-kind masterpiece sits at the end of a private road on eight pristine acres. Beyond its wrought-iron gates, a long, tree-lined stone driveway leads to the stately residence, where every detail reflects exceptional craftsmanship and sophistication - from antique stone fireplace mantels and hand-painted wallpaper to crystal chandeliers and bespoke finishes throughout. A grand entrance hall with a sweeping marble staircase welcomes you to the main level. The formal living and dining rooms, each adorned with French doors, open seamlessly to the outdoor entertaining terraces and overlook the breathtaking formal gardens. The chef’s eat-in kitchen features a spacious center island, custom cabinetry, a La Cornue range with matching hood, premium appliances, and granite countertops. Completing the main level are a wet bar, library, den, powder room, and a private guest bedroom with an en-suite bath. Upstairs, the luxurious primary suite offers separate dressing rooms, multiple walk-in closets, and two exquisite marble bathrooms. Three additional generously sized bedrooms, two full baths, and elevator access complete the upper level. The lower level is thoughtfully designed for both recreation and comfort, featuring separate guest quarters, a billiards room, playroom, laundry room, fitness area, spa, and sauna. The basement level includes abundant storage, a temperature-controlled wine cellar, and access to the attached four-car garage. Originally landscaped by famed French architect Jacques Greber, the grounds are nothing short of spectacular. Highlights include a stunning step-down courtyard, irrigated vegetable garden, gated tennis court, in-ground pool with pool house, chipping and putting green, and an outdoor fireplace and grilling area. Cloaked in ivy and grandeur, and tucked away along Long Island’s storied Gold Coast, ‘Haut Bois’ stands as one of the last remaining architectural treasures of its era.

1985-4 Cedar Swamp Road, Brookville

$2,499,000

5 Beds ⋅ 3 Baths ⋅ 1002763 MLS

Welcome to this exceptional Ranch-style retreat nestled on over 2 private acres in the prestigious Brookville and located within the award-winning Jericho School District. Offering 5 spacious bedrooms and 3 full bathrooms, this move-in ready home perfectly blends warmth, elegance, and serene living. Designed with both comfort and entertaining in mind, the home features an open-concept eat-in kitchen with high-end finishes, premium appliances, and stunning granite countertops flowing seamlessly into the formal dining room and expansive living room with soaring cathedral ceilings and an abundance of natural light. The fully finished basement provides incredible additional living and recreational space, while the backyard oasis offers the ultimate private escape with a heated in-ground pool and a charming pool house thoughtfully designed as a beautiful one-bedroom apartment complete with a full bathroom — ideal for guests, extended family, or private work-from-home living. Full house Water Filtration System. Surrounded by tranquil grounds and offering timeless charm with modern updates, this special property captures luxury, comfort, and peaceful living all in one remarkable residence.

14 Horse Hill Road, Brookville

$2,595,000

4 Beds ⋅ 4 Baths ⋅ 998655 MLS

An exceptional piece of North Shore history, “Lily Pond Hollow” is nestled in the heart of Brookville. This gentleman’s farmhouse was seamlessly and thoughtfully expanded with a great room, grand primary suite, and 3 car garage to make it comfortable for modern living. Standing as a reminder of Long Island’s rich history, the estate spreads out over two spectacular acres with an arboretum-like property featuring rolling lawns, formal gardens, mature specimen trees, and original stone garden walls. It is named for the home’s serene direct views overlooking a large freshwater lily pond that creates an extraordinary setting of privacy and natural beauty. Offering exceptional natural light, the residence strikes the perfect balance between grand, flowing entertaining spaces and cozy, intimate nooks tailored for remote work or quiet relaxation. A banquet-sized dining room, an inviting sitting room, a charming breakfast room, and a sun-drenched great room lined with French doors open to panoramic views of the picturesque grounds and pond which can be enjoyed year-round. Upstairs, there are four comfortable bedrooms with fireplaces and the possibility of creating a fifth guest room. The primary suite is located within its own dedicated wing, catching light from three exposures. Complete with a high ceiling, crown molding, and a fireplace. There are numerous built-ins and a spacious seating area with a large Palladian window. The large primary bathroom is complete with a separate soaking tub room with its own fireplace. Located within the nationally recognized Jericho Union Free School District, “Lily Pond Hollow” is a captivating historic estate offering a rare combination of privacy, community, and unmatched New England charm, just moments from major highways and only 25 miles from Manhattan by car or a direct 43-minute train ride. It is not just a house, but a complete lifestyle that must be experienced in person to be fully appreciated.

4 Roads End, Brookville

$2,695,000

5 Beds ⋅ 4 Baths ⋅ 993165 MLS

Tucked away in the heart of Brookville, this exceptional 2-acre estate at 1 Glenby Lane offers the perfect blend of luxury, privacy, and comfort within the highly regarded Locust Valley Central School District. Surrounded by lush, expansive grounds, the property unfolds into a sprawling, park-like setting complete with a full tennis court and a beautiful in-ground pool creating your own private retreat. A sweeping, estate-style U-shaped driveway makes a striking first impression, offering a grand approach and elegant arrival experience that sets the tone for the home. Inside, this warm and inviting 5 bedroom, 3.5 bath residence balances comfort with refined living, featuring thoughtfully designed interiors ideal for both everyday living and effortless entertaining. The spacious family room seamlessly extends to the outdoor entertaining area, leading directly out to the pool creating a natural indoor-outdoor lifestyle. At the center of the home is a stunning chef’s kitchen, featuring premium Wolf and Sub-Zero appliances that combine style with top-tier performance. Seamless indoor outdoor flow enhances the experience, with the expansive property offering endless opportunities to relax and entertain. Whether hosting by the pool, enjoying a match on your private court, or simply taking in the beauty of the grounds, this home delivers a lifestyle that is both luxurious and inviting. Brookville is one of Long Island’s most coveted and established communities, known for its expansive estates, privacy, and natural beauty. Perfectly positioned on the Gold Coast, it offers close proximity to the charming villages, the waterfront towns along the North Shore, renowned golf courses and country clubs, as well as convenient access to the Long Island Rail Road for an easy commute to Manhattan. The area combines a quiet, refined setting with access to some of the region’s finest dining, shopping, and lifestyle amenities. A rare offering in one of Brookville’s most prestigious and desirable locations.

1 Glenby Lane, Brookville

$2,499,000

5 Beds ⋅ 4 Baths ⋅ 983513 MLS

Rare Is The Opportunity To Secure Over Two Acres Of Flat, Usuable Land In The Highly Sought-After Jericho School District. Along One Of Brookville's Most Picturesque Roads And Nestled In A Cul-De-Sac, 18 Quaker Ridge Drive Is An Idyllic Retreat Backing Onto A Private Equestrian Property - Providing Unmatched Tranquility And Pastoral Vistas. Currently Featuring A Classic 5 Bedroom Colonial, The Grounds Are Expansively Landscaped, Designed For Both Relaxation And Entertaining. With A 20x40 In-Ground Pool And Professional Specimen Plantings, The Sprawling Acreage Provides A Magnificent Canvas For A Luxury Expansion Or The Addition Of High-End Amenities That Suit Your Lifestyle - Such As A Tennis Court or Even Your Own Horse And Stable. With Low Taxes, This Is The Perfect Blend Of A Secluded Retreat And A Smart Investment.

18 Quaker Ridge Drive, Brookville

$1,990,000

4 Beds ⋅ 4 Baths ⋅ 971322 MLS

Welcome to 1678 Cedar Swamp Road, Brookville! Set on a sprawling 2.01-acre property in Brookville and located within the Jericho School District, this beautifully maintained 4-bedroom, 3.5-bath Colonial offers exceptional space, comfort, and lifestyle amenities. The home features wood floors throughout, new moldings, and a freshly painted interior, creating a bright and inviting atmosphere from the moment you enter. The first floor includes a welcoming living room, a cozy den with a wood-burning fireplace, a powder room, laundry room, and a convenient coat closet. The updated eat-in kitchen features radiant heat and flows seamlessly into the formal dining room, making it perfect for everyday living and entertaining. Upstairs, the second floor offers a spacious primary bedroom with a full ensuite bath, a second bedroom, and a third bedroom with a walk-in attic/closet. A linen closet and second full bathroom complete the level. The fully finished basement, recently refurbished, adds excellent bonus space and includes a new dual-zone electric heat pump heating system, recessed lighting, a gym room, and an additional full bathroom. The expansive backyard is designed for recreation and relaxation, featuring a running track, basketball court, fenced gate, patio with a built-in grill, a 4,000 sq ft park area, and a trampoline. The property also includes an in-ground swimming pool (currently not in use but can be restored for enjoyment). Additional highlights include new washer and dryer appliances and abundant outdoor space offering privacy and versatility. This unique property combines classic Colonial charm with modern updates and exceptional outdoor amenities—an outstanding opportunity in Brookville.

1678 Cedar Swamp Road, Brookville

$3,995,000

12 Beds ⋅ 10 Baths ⋅ L3109690 MLS

Brookville. Unimaginable Opportunity To Purchase An Incredible Part Of History. This Brick Manor Estate Built in 1925 Has Been Meticulously And Lovingly Taken Care Of And Restored. Featuring Dining Room With Hand Painted Gracie Mural, Black Walnut Library, And All The Glamour Of Old World Charm In Each Space With Architectural Detail Throughout Reflecting Timeless Luxury. Incomparable Home On Over Seven Acres Of Gardens, With Pool and Pool House, and 3 Par Golf Course. With Much More!, Additional information: Business Located At:,Rental Income:,Separate Hotwater Heater:Yes

11 Evans Drive, Brookville

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Brookville Historical Real Estate