luxury houses for sale Old Brookville, United States

Perfectly set on a winding country lane, this charming colonial combines timeless craftsmanship with modern luxury on over two level, landscaped acres designed by Steven Dubner. The home showcases fine millwork and mouldings with hardwood flooring throughout the first floor. A welcoming entry leads to a gracious living room with a gas fireplace, dentil moulding surround, and built -in bookcases leading into a formal dining room. French doors open to a new bluestone terrace with flower beds, a full outdoor kitchen, views of the saltwater, and gunite pool with an electric cover and expansive grounds. The gourmet kitchen features black marble countertops, imported tile backsplash, a quartz center island with a prep sink and top -tier appliances, including a Wolf cooktop, double wall ovens, Subzero refrigerator/freezer, Miele dishwasher, Sharp microwave and wine refrigerator. A breakfast room with banquette flows into the spectacular great room with cathedral ceilings, exposed beams, a brick wood-burning fireplace, built-in bar, Palladium window and terrace access. An office, laundry/mudroom and guest room with en suite bath complete the first floor. Upstairs, the Primary suite offers a sunlit sitting room/office, spacious bedroom, a luxurious marble bath with radiant heat, dual sinks, vanity, and two fully fitted dressing rooms. Additional accomodations include an en suite bedroom, two additional bedrooms with a shared new bath, a second washer/dryer and ample storage. A finished basement provides a playroom, storage, and easy access to the mechanicals. This is an exceptional home blending the charm of classic Long Island living with every modern convenience.

Lovingly updated, this warm and inviting home in the Promenade section of prime Glen Head offers a versatile multi-level layout with 3 bedrooms and 2.5 bathrooms, including a spacious primary ensuite. Featuring multiple living and entertaining spaces across different levels, including a lower-level den/playroom and a generous backyard with multi-level decking. This home blends comfort and functionality with ease. Centrally located, near the Glen Head train station, local shops and restaurants at the four corners, and within the sought-after North Shore School District.

OLD BROOKVILLE Far from ordinary, this extraordinary custom built brick Mansion is designed for luxurious entertaining, Set on a private cul-de-sac, wrought iron gates open to the courtyard of this pristine 3acre estate surrounded by lush landscaping and colorful gardens. You'll greet your guests in the breathtaking Foyer where soaring domed ceiling sits 30' above a double bridal staircase. Throughout the home, each room is spacious and beautifully detailed. Featuring mahogany doors & trim, mahogany & marble floors, coffered ceilings, private Library, 2 story Great room, chef's Kitchen with abundance of appliances, 7 Bedrooms with private Balconies,6 full Bathrooms, 5 half Bathrooms, 5 Fireplaces, Elevator to all floors ,and 5 car heated garage. To cater to your entertaining needs, the walkout lower level features a banquet hall capable of hosting hundreds of guests, complete with a commercial-grade prep kitchen, a walk-in pantry, and 2 separate multi-stall bathrooms and 500 bottle Wine Cellar. This lower level opens up to the Pool, Pool House, and Tennis Sports Court, providing ample outdoor enjoyment. If you seek something truly exquisite and extraordinary, 4 Valentine Farm Court is sure to win your heart and leave a lasting impression on your guests.

Set on five flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville’s prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated level of security and exclusivity. A grand double height foyer welcomes you, anchored by a magnificent Baccarat chandelier, immediately setting a tone of timeless elegance. The home is thoughtfully designed for both grand scale entertaining and comfortable everyday living, featuring 4 fireplaces, a formal living room, elegant dining room, refined library, and a luxury bar area. The main level includes two bedrooms with two full bathrooms nearby, ideal for guests or extended living, along with a fully equipped laundry room. At the heart of the home, the sun-drenched chef’s kitchen is enhanced by skylights and oversized custom windows, creating a bright and inviting atmosphere. Completed with premium appliances including a double wall Wolf oven, Wolf gas cooktop, and two Bosch dishwashers, breakfast nook and two pantries. The space seamlessly connects to the main living areas and opens to the patio, where retractable awnings provide effortless indoor to outdoor living. Upstairs, four spacious en-suite bedrooms include a luxurious primary suite featuring its own fireplace and a spa-inspired bath, offering a true private retreat. A Juliet balcony giving a view of serene front outdoor space. A finished attic adds a versatile open space suitable for a variety of lifestyle needs. The outdoor grounds are equally exceptional, showcasing expansive flat land, a heated gunite pool, tennis court, and multiple areas for entertaining and al fresco dining, all set within one of the most picturesque locations on Colonial Drive. Additional highlights include a finished basement with extra high ceilings, a whole house surround sound system, a recently updated roof (approximately 4 years old), and newer windows (approximately 1 year old). Updated Kitchen and bathrooms. Custom-made furnishings imported from Italy are included, further elevating the home’s refined aesthetic. This extraordinary estate seamlessly blends classic Georgian architecture with modern upgrades, offering unparalleled privacy, scale, and sophistication in one of the North Shore’s most coveted locations.

Welcome to this charming Ranch in Glen Knolls, offering 3 bedrooms and 2 beautifully renovated bathrooms. Sunlight pours through skylights, filling the home with an easy, uplifting feel, while multiple fireplaces bring comfort and charm through every season. A cozy den creates the perfect spot to unwind, gather, or simply enjoy a quiet moment. Set on a nicely sized property, the home extends effortlessly outdoors with a large deck, spacious yard, and sprinkler system—ideal for relaxing, entertaining, or play. Ideally located near the LIRR and within the North Shore School District, this home offers everyday convenience with a special bonus for train lovers: the gentle, passing sound of the train can be enjoyed right from your backyard, adding a uniquely nostalgic touch to this special setting.

Glen Head Center Hall Colonial updated and expanded offering 5 bedrooms and inviting living spaces. Impressive entrance, custom stairs and millwork, open floor plan, spacious living room with fireplace, formal dining room, private rear patio with complete outdoor kitchen. Sundrenched primary bedroom with 11 foot ceilings and bath with heated floor. Lower level recreation area and more, conveniently located closed to Glenwood Landing Elementary School, North Shore Middle School and North Shore High School as well as Tappen Beach.

Tucked away in the sought-after North Shore Acres neighborhood of Glen Head you will find this refined home combining contemporary flair with traditional details. Reimagined within the last 10 years to include all new wood floors, moldings, stairs, kitchen and baths. This property checks all the boxes, a bespoke wood-mode kitchen w/calcutta marble counters, center island and premium appliances. A first floor guest suite includes a new full bath. Soaring ceilings with new skylights drenching the living spaces with natural light. The primary suite w/spa-like marble bath, soaking tub, steam shower and double vanities. Additional 3 bedrooms and new full bath all located on second floor. The full walk-out lower level features additional living spaces, additional bedroom and full bath. Sliders provide access to the outdoor oasis where you will find the in-ground saltwater pool with wading area, hot - tub, firepit, new pavers where you can enjoy it all in complete privacy. You have a found a home that has been loved and renovated with the utmost quality including a new roof, gutters, skylights and exterior painting all done this year. Nothing to do but enjoy living in this beautiful home in an exclusive neighborhood that is also convenient to schools, LIRR, shopping and dining. Taxes have been successfully grieved for upcoming year.

Beautiful Colonial-style home with North shore school and located in a desirable tree-lined community, totally renovated in 2023, modern amenities include curb appeal, when entering you will find a thoughtfully designed layout that maximizes space and lots of natural sunlight, 4 Bedrooms, 2 Full Baths with radiant heated floors, large laundry room with custom cabinetry and window, washer and dryer, crown & base moldings, recessed lighting throughout, living room with fireplace and large bay window with views of the stone patio and large yard, new double hung windows, Dining area with wainscoting, All new kitchen with stainless steel appliances, Quartz counter tops and all custom white cabinetry and new fixtures, soft close draws and over the gas stove with pot filler an exhaust range, pantry coat closet, Primary bedroom on the first floor, plus first floor full bath with radiant heated floors. second bedroom /office with windows for natural light and closet, Second floor with 2 bedrooms, Full Bath with radiant heated floors, lots of custom storage, whether you're enjoying the home or entertaining in the private backyard and expansive patio with large porcelain tiles great for Alfresco dining and gas for a BBQ, this residence is a perfect blend of modern amenities and effortless living, ideal for those who appreciate modern amenities in every detail, lush professional landscaping, privacy trees around the property and lovely rose bushes in the front, one car detached renovated garage with the driveway that accommodates 6+ cars. generator hook up, Amenities list available and North Shore School district.

Introducing An Unparalleled Masterpiece Of Luxury Living On Estate Suited For A Celebrity. This Prestigious And Exclusive Private Brick Compound Situated On 7 Acres Of Lush, Sprawling Grounds In Upper Brookville Offers A Lifestyle That Seamlessly Combines Timeless Elegance With Modern Luxury. Vaulted Ceilings, Creating A Sense Of Openness. Oversized Windows With An Abundance Of Natural Light & Panoramic Views Of The Property. 6 Oversized Bedrooms W/En-Suite Baths, 7 1/2 baths, Large EIK With Generous Counter Space & Storage. For The Car Lover Enthusiast W/10 Car Garage, Top-Of-The-Line Car Lifts & Car Port. Entertainers Exclusive Front & Backyard. Custom-Designed 22,000 Gallon Koi Pond With Thoughtfully Placed Stone Work, Fountains & Lighting. Newly Resurfaced Har-Tru Tennis Court, Gunite Heated Pool, 8 Person Hot Tub, Pool House W/Kitchenette, Full Bath & Changing Room. Custom Outdoor Kitchen, Premium Speaker System Both Inside & Out. Embrace A Lifestyle In Your Private Sanctuary! Google Maps, Waze

Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Beautifully appointed with crisp white cabinetry, honed Absolute Black granite countertops, top-of-the-line appliances, and radiant heated floors, the kitchen flows effortlessly into the informal dining area and family room, complete with a raised-hearth stone fireplace. Additional highlights include pristine condition throughout, Newly painted and redone guest quarters, separate living and dining rooms, and a separate hot water heater., New generator, new gas line (2025), House newly painted and redecorated and grounds re landscaped. The Property in Spring is filled with an abundance of color with the Hellebores, Azaleas, Rhododendron. It is private and magical.

Poised on nearly half an acre of manicured grounds in one of the North Shore's most storied waterfront villages, this newly constructed residence offers an exceptional standard of living where coastal serenity meets refined modern design. Spanning approximately 4,900 square feet across three thoughtfully finished levels, the home presents five bedrooms, four full and one half bathrooms, and an architectural sensibility that honors the timeless character of Sea Cliff while delivering every contemporary luxury. Soaring nine-foot ceilings on both the first and second floors create an atmosphere of effortless grandeur, while sun-drenched, open-concept living spaces flow seamlessly from a chef's kitchen — appointed for serious entertaining — to an expansive great room that opens directly to a private backyard retreat. Upstairs, the primary suite is a study in quiet indulgence, featuring a spa-inspired bath and generous walk-in closets designed for the discerning eye. Additional bedrooms offer gracious flexibility for family and guests alike. The fully finished lower level — with eight-foot ceilings — lends itself equally to a state-of-the-art fitness studio, a private media lounge, or an elegant recreation space. Situated within the award-winning North Shore School District, and moments from the Sea Cliff Marina, private beach, and the Sunset Club at Tappen Beach, this address places the very best of village life at your doorstep. Sailboats drift across Hempstead Harbor at dusk. The village beckons with coffee, galleries, and art fairs. North Shore Country Club and Glen Head Country Club are minutes away. This is coastal living at its most refined — a sanctuary where every detail speaks to quality, craftsmanship, and the rare beauty of a place truly unlike any other.

This beautifully maintained side hall Colonial is ideally situated on the border of Old Brookville, offering convenient access to Glen Cove Road while tucked away on a quiet cul-de-sac. Set on a shy third of an acre of flat, usable property, this home combines comfort, space, and functionality. The interior features a welcoming entrance foyer that flows into a spacious living room and a formal dining room, perfectly positioned off the open-concept kitchen. A bright, sun-filled bonus area enhances the home’s appeal, creating the perfect setting for entertaining guests. The inviting family room with a fireplace, along with a convenient powder room, completes the main level. Upstairs, the home boasts a luxurious primary suite with a renovated ensuite bathroom and a walk-in closet, along with an additional generously sized bedroom comparable to a second primary. Three more spacious bedrooms share a beautifully updated hall bathroom. A full finished basement adds even more versatile living space. Located within the North Shore School District, this home offers an exceptional lifestyle in a prime location.

Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless elegance with modern comforts. A truly iconic Georgian estate nestled in the heart of Upper Brookville, this 17,587 square feet of total living space, this sprawling residence features 9 bedrooms, 9.555+ bathrooms, 10 wood-burning fireplaces, and exquisite architectural details, including vintage millwork, antique hand-painted wallpaper, and Samuel Yellin wrought-iron gates from the JP Morgan estate. Designed in 1924 by renowned architect James W. O’Connor and landscape architect Robert Ludlow Fowler, Gray Horse Farm is where classic architecture meets nearly 9 acres of pristine, equestrian-ready grounds. Perfectly suited for multigenerational living, the estate includes three separate guest/staff quarters (two 1-bedrooms and one 3-bedroom), offering privacy while staying connected. For those who love to entertain and enjoy the outdoors, the estate features a 20' x 55' heated saltwater pool with a pool house that's fully equipped, tennis and basketball courts, and a secret meditation garden you don't want to miss. For the car enthusiast there's a 7-car garage. Equestrian enthusiasts will appreciate the 3-stall stable, multiple paddocks, and run-in horse shed, all designed for top-tier country living. Additional highlights include a whole-house generator, —all just 27 miles from Manhattan. Whether you're seeking a premier equestrian retreat or an expansive generational compound, Gray Horse Farm delivers an unmatched lifestyle of luxury, privacy, and prestige. A rare offering close to top universities,marinas, beaches, golf, museums and americana shopping!

Beautifully renovated Colonial in Hill Terrace area of Glen Head. Classic charm and modern update. Sun filled living room with cozy fireplace, formal dining room, updated kitchen with granite countertops and stainless steel appliances. Nice deck overlooks yard with patio and shed. Located in North Shore School District. Close to shops, dining and Tappen Beach.

Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a grand living room, banquet-sized dining room, inviting family room, and a serene primary suite with fireplace, sitting area, and generous mirrored closets. A spacious country eat-in kitchen and a lower entertainment level with bar and gym further enhance the home’s appeal. Outdoors, the estate opens to multi-tiered gardens, expansive terraces and patios, an in-ground pool, pool house with full kitchen, 2 full baths and guest quarters, tennis/sport court, golf hole with 3 tee boxes, apple orchard, trellis, and outdoor barbecuing area. A rare offering that captures the privacy, grace, and enduring appeal of the North Shore Gold Coast.

Opportunity awaits! Welcome to the classic center hall colonial, built in 1986, offering timeless charm and spacious living throughout. With a traditional layout, this home is perfect for both everyday living and entertaining. The main level features a large eat-in kitchen, a generous den with a fireplace, a formal living room and dining room, along with a dedicated home office and convenient powder room. Upstairs, the primary suite offers a private ensuite bath and walk in closet, along with three additional bedrooms and full hall bath. Enjoy year round comfort with central air, and take advantage of the expansive finished basement. Step outside to relax on the welcoming front porch or entertain on the back deck. Complete with a 2 car garage and conveniently located near shopping, transportation and dining this home presents an incredible opportunity. This home is being sold as is!

Set on 3.1 breathtaking park-like acres along a quiet country lane, this immaculate 5 Bedroom Colonial offers an exceptional lifestyle with over 7200 square feet of beautifully appointed living space. Sunny and bright throughout, the home features expansive rooms, soaring ceilings, and hardwood floors that create an elegant yet welcoming atmosphere. Designed for both grand entertaining and comfortable everyday living, the residence boasts a gourmet chef's kitchen along with multiple gathering spaces enhanced by fireplaces in the dining room, den, game room and luxurious oversized primary bedroom suite. Step outside to experience resort-style living at its finest. Expansive terraces with awnings and a built in BBQ area are steps away from the stunning heated gunite saltwater pool complete with sun deck, surrounding terraces and an exceptional pool house featuring a living/dining room, kitchen and full bath-the perfect retreat for entertaining family and friends all summer long. Ideally located close to major roadways, schools, shopping and clubs. This extroadinary property combines privacy, luxury and convenience in one remarkable offering. A rare opportunity that will not last long!

This meticulously maintained private North Shore gem is the epitome of move-in ready, reflecting the pride of an owner who has obsessively cared for every detail. From the brand-new ventilated roof, vinyl siding, and energy-efficient windows to the top-tier mechanical upgrades—including a new 200-amp electric panel, ductless HVAC, and a high-efficiency gas boiler with classic cast iron radiators—no expense has been spared in its modernization. The interior shines with a beautifully updated kitchen featuring granite countertops and stainless appliances, quartz-clad bathrooms, and flawlessly refinished hardwood floors. Perfectly situated just moments from the sparkling waters of Hempstead Harbor, residents can enjoy easy access to the park, the beach, the schools, highways, vibrant sunsets at the Sunset Club, and elite amenities like the North Shore Country Club, TOB pool, pickleball, basketball, and hockey games. This home offers a rare blend of structural integrity and a small-town lifestyle...you get a rock-solid house in a location that feels like a permanent vacation!

19 Gruber Drive, Glen Cove, NY 11542