Browse All Brookville NY 5 Bedroom Properties for Sale

BROOKVILLE. Perfectly nestled on two private acres at the end of a quiet cul-de-sac in the heart of Brookville, this exceptional residence offers a harmonious blend of timeless architecture, modern sophistication, and resort-inspired living. Offering five bedrooms, with primary suite on the main, four full and two half baths, this remarkable home welcomes you with a striking two-story arched entry leading into sun-drenched interiors where expansive living spaces, soaring ceilings, and walls of glass create an effortless connection to the surrounding natural landscape. Designed with both elegance and comfort in mind, the thoughtfully crafted layout features gracious principal rooms, refined architectural details, and seamless transitions between formal entertaining spaces and relaxed everyday living. The heart of the home opens beautifully to the outdoors, where an expansive wraparound deck overlooks beautifully manicured grounds, a sparkling in-ground pool, and tranquil wooded vistas, creating a private retreat that feels worlds away. Whether hosting grand-scale gatherings or enjoying quiet moments surrounded by nature, the outdoor spaces provide the perfect backdrop for every season. Set amidst lush landscaping and complete with exceptional privacy, this remarkable Brookville residence offers a rare opportunity to experience sophisticated living on the Gold Coast of Long Island.

3 Rock Hill Lane, 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

$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

$3,699,000

5 Beds ⋅ 5 Baths ⋅ 1016352 MLS

Brookville | Tucked away on two lush, manicured acres in the heart of Brookville, 5 Hemlock Drive is an exceptional five-bedroom estate that blends timeless architecture with modern comforts and resort-style amenities. A gravel driveway and stately facade welcome you into a dramatic two-story foyer, where soaring ceilings and a sparkling chandelier set the tone for the thoughtfully designed interiors beyond. The main level is anchored by a luxurious first-floor primary suite, offering dual walk-in closets, a grand spa-inspired bath with a clawfoot soaking tub and steam shower, and private access to a secluded deck overlooking the picturesque grounds. A second first-floor bedroom, currently utilized as a home office, provides flexibility for guests or multi-generational living. Designed for both intimate gatherings and large-scale entertaining, the recently redesigned living room features lofted ceilings, a marble-encased wood-burning fireplace, modern finishes, and integrated Sonos speakers. The expansive chef's kitchen is equally impressive, appointed with a breakfast bar, oversized center island with prep sink and storage, Thermador gas range, additional wall oven, warming drawer, microwave, and paneled Sub-Zero refrigerator and freezer. The adjoining dining area seamlessly extends outdoors to a mahogany deck complete with a built-in outdoor kitchen. Privately tucked behind French doors, the rustic den offers a warm and inviting retreat with custom wood finishes, built-in shelving, a second wood-burning fireplace, and a wet bar featuring both a wine refrigerator and paneled beverage refrigerator. The second level hosts three additional bedrooms, including two en-suite bedrooms and an oversized bonus room currently serving as a children's playroom. Additional highlights include a mudroom with laundry and full bath just off the three-car garage, generator for essential systems, and abundant storage throughout. The grounds are nothing short of spectacular. Surrounded by mature landscaping and complete privacy, the backyard is a true resort destination featuring an inviting in-ground swimming pool and a full-sized tennis court tucked discreetly among the greenery—creating an unparalleled setting for recreation, relaxation, and entertaining. A rare offering that captures the essence of Gold Coast living, this Brookville residence presents an extraordinary opportunity to enjoy privacy, luxury, and lifestyle in one of Long Island's most coveted enclaves.

5 Hemlock Drive, Brookville

$3,680,000

5 Beds ⋅ 5 Baths ⋅ 1009371 MLS

Welcome to 14 Norgate Road, a magnificent estate nestled in the prestigious Brookville, offering timeless elegance, exceptional craftsmanship, and luxurious living throughout. A grand two-story entry foyer welcomes you into this distinguished residence, setting the tone for the exquisite details found in every room. Designed for both sophisticated entertaining and everyday comfort, the home features an elegant formal dining room complemented by a butler’s pantry with an additional dishwasher. The expansive den showcases a beautiful fireplace, while the richly appointed library/office features custom mahogany cabinetry and its own fireplace, creating the perfect private retreat. The spacious eat-in chef’s kitchen is equipped with a gas cook top and opens to a generous breakfast area with picturesque views of the professionally landscaped grounds. The home is thoughtfully designed with two staircases, including a grand main staircase and a separate service staircase with direct access to the garage, prep kitchen, bedroom, bathroom and laundry. The luxurious primary suite is a serene sanctuary featuring soaring ceilings, a spa-inspired bathroom complete with radiant heated floors and a steam shower. The second level offers two additional bedrooms connected by a Jack-and-Jill bath, an additional spacious bedroom with an en-suite bathroom, and a large finished bonus room with its own separate heating zone, ideal for a recreation room, home gym, or guest retreat. A full unfinished lower level provides endless possibilities for customization and additional living space. Outside, the expansive stone patio creates the perfect setting for elegant entertaining or peaceful relaxation while overlooking the lush, beautifully maintained private backyard. 14 Norgate Road is a rare opportunity to own an exceptional Brookville estate where luxury, comfort, and refined living come together seamlessly.

14 Norgate Road, 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

$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

$2,695,000

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

$4,500,000

5 Beds ⋅ 8 Baths ⋅ 860682 MLS

Incredible price reduction! Incredible Value! For the Discerning Client who seeks only the Finest....Welcome to 8 Vista Lane in Brookville--where Timeless Design and Bespoke Materials are blended to create this Sophisticated Modern Luxury. A Grand Courtyard leads to the Entrance of this Spectacular Private Estate. The Tone is set as Guests are greeted in the Breathtaking 30'high Domed Circular Reception Gallery adorned with Magnificent Crystal Chandelier, Stunning Marble Floors, Marble Fireplace, Intricate Plaster Moldings & Delicately Hand Painted Gold Leaf Wall Accents. Grandeur continues to an Elaborate Formal Living Room with Mahogany Floors, Shimmering Designer Textured Walls, Built-In Bar/Wine Cabinet, French Marble Fireplace & 2 sets of French Doors leading to an enclosed bluestone Patio for Indoor/Outdoor entertaining ease. Elegant Dinner Parties can be hosted from the private Banquet Dining Room graced with Antique Crystal Chandeliers & wall Sconces surrounded by elegant Venetian Plaster walls with soft handpainted Topiary silhouettes. The spacious Family Room is complimented by beautifully detailed coffered ceiling, Magnificent stone Fireplace and custom Drapery covering 3 sets of French Doors that open to a covered patio with brick archways. The Dream Kitchen is a Gourmet's delight with the most exquisite custom High Resin Wood Cabinetry, Meile & Wolf appliances, a 350 Bottle Wine Refrigerator, custom Illuminated Glass countertops, heated porcelain floors & Breakfast Room overlooking lush greenery. A private Office/Bedroom with soaring Architectural ceiling & doors to a Juliet Balcony and rear Patio is set off a private Hallway. Intricate custom wrought iron railings with gleaming mahogany handrails adorn each of this Manor Homes 4 floors. A circular Hallway embraces the 2nd floor leading to the elaborate Primary Bedroom. This lavish retreat is the epitome of Luxury with custom built-in wardrobe closets, French Marble carved Fireplace,2 separate Full Baths, one in Onyx, the other Marble with large custom walk-in closet, electronic blackout shades & expansive private outdoor patio. 3 additional large bedrooms, each with generous closets, private baths and electric shades complete this floor. The lower level is an open floor plan with play rooms, game room, gym,laundry and full indoor sports court. An entrance to the 4 car garage and stairway to rear property are accessed from this level. A life of privilege and a sanctuary of luxury await the next owners of this extraordinary residence set on two acres with pool/jacuzzi ,tennis, built-in outdoor kitchen, bluestone patios & professional gardens. Jericho SD By Appointment

8 Vista Lane, Brookville

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