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$2,995,000
5 Beds ⋅ 6 Baths ⋅ 1044302 MLS
5 Woodfield Lane! Set on beautifully landscaped grounds, this impressive residence offers a wonderful blend of space, comfort, and privacy. A gracious entry welcomes you into expansive living areas with soaring ceilings, abundant natural light, Stone and hardwood floors, multiple gathering spaces designed for both everyday living and entertaining. The spacious eat-in kitchen features extensive custom cabinetry, generous counter space, a large center island, and a wall of windows overlooking the lush property. The adjoining living and dining areas create an open, inviting flow, while two fireplaces add warmth and character to the home. The generously sized grounds provide a rare sense of privacy and tranquility, with mature landscaping, expansive lawns, and a private tennis court creating an exceptional outdoor setting. The long driveway provides a striking approach to the residence and ample space for guests. With its generous proportions, sophisticated architectural details, multiple living spaces, and extraordinary property, this residence offers a unique opportunity to enjoy an elegant home in a truly private setting. Finished basement features high ceilings, home office, gym, recreation room.

5 Woodfield Lane, Old Brookville
$789,000
5 Beds ⋅ 2 Baths ⋅ 1040374 MLS
This double dormered Cape Cod features a living room, formal dining room, a kitchen, a den, two bedrooms and a full bath on the main floor and three bedrooms including the primary bedroom ( full with primary bedroom is huge and could easily be divided into two separate bedrooms ) and a bath on the second floor. There is a full basement, a one car garage that is not in good shape, an in-ground pool that needs to be repaired or replaced, hardwood floors, tile floors, a newer main roof, all gas cooking and Heating and a very quiet location that is walk to most things. This house needs a lot of work but is a diamond in the rough.

1 Glen Cove Drive, Glen Head
$929,000
4 Beds ⋅ 2 Baths ⋅ 1039687 MLS
A Builder’s Dream in Hill Terrace! Bring your vision and your contractor—this well-located home offers an exciting opportunity for buyers looking to renovate, customize, and create their dream home. Nestled in the desirable Hill Terrace neighborhood of Glen Head, this property is surrounded by beautiful homes and offers incredible potential. Enjoy a top-rated school district and a prime location close to everything—charming village shops and dining, beautiful beaches, schools, and the railroad for an easy commute. Whether you're looking to build, renovate, or invest in a sought-after community, this is an opportunity not to be missed. Builders and savvy buyers—come now! The possibilities are endless.

35 Washington Avenue, Glen Head
$1,099,998
3 Beds ⋅ 2 Baths ⋅ 1038251 MLS
Welcome to this charming three-bedroom, two-bathroom home in the heart of Glen Head, offering comfortable living spaces, thoughtful updates, and wonderful outdoor amenities. The formal living room features a beautiful fireplace, creating a warm and inviting setting for relaxing or entertaining, while the adjacent dining room provides an ideal space for family meals and gatherings. The updated kitchen offers modern convenience and functionality, and the spacious family room provides plenty of room for everyday living, movie nights, or entertaining guests. The primary bedroom is a private retreat with its own balcony, while two additional bedrooms provide comfortable spaces for children, guests, or a home office. With ample storage throughout and a full unfinished basement, there is plenty of space for organization, hobbies, recreation, or future expansion. Outside, enjoy a fully fenced backyard designed for both relaxation and entertaining. A covered patio provides a comfortable outdoor living area, while a separate fire pit area creates the perfect spot for gathering with family and friends. Ideally located in Glen Head, this home offers convenient access to the Long Island Rail Road, Tappan beach, nearby parks and recreational areas, and the highly sought-after North Shore community and school district. A wonderful opportunity to enjoy the space, charm, and convenience of Glen Head living.

40 Plymouth Drive S, Glen Head
$3,500,000
3 Beds ⋅ 3 Baths ⋅ 1031287 MLS
Set on two level acres surrounded by mature trees in the sought-after Village of Old Brookville, this distinctive three-bedroom, three-bath residence offers a peaceful setting with expansive lawns and exceptional privacy. A long driveway provides abundant parking in addition to the attached two-car garage. Inside, the main level features a dramatic living room with approximately 16-foot ceilings, creating an open and impressive gathering space. Two fireplaces add warmth and character, while the flexible floor plan provides comfortable areas for everyday living, entertaining and working from home. The spacious primary suite includes a private loft that can serve as a home office, workout area or quiet retreat, along with a walk-in closet and generously sized full bathroom. Outside, a deck and adjoining patio provide inviting spaces for dining, entertaining or relaxing while overlooking the broad, level grounds and natural surroundings. Conveniently located within the North Shore School District, this Old Brookville property presents a rare combination of acreage, privacy, parking and versatile interior and outdoor living space, with an opportunity for the next owner to personalize the home to suit their individual vision.

1 Stonegate Lane, Old Brookville
$5,250,000
6 Beds ⋅ 10 Baths ⋅ 1031994 MLS
Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

33 Chicken Valley Road, 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
$888,000
3 Beds ⋅ 1 Baths ⋅ 1027250 MLS
Charming Corner Property "The Promenade" – Glen Head Tucked into one of Glen Head's most walkable and welcoming pockets, this Charming 3-bedroom, 1-bath ranch sits proudly on a coveted corner lot along The Promenade — offering both character and convenience in equal measure. Step inside and be greeted by warm, original wood floors that flow throughout the home, adding timeless charm to every room. The cozy fireplace serves as a natural gathering point, perfect for quiet evenings in or entertaining friends and family on a crisp fall night. Sun-filled rooms and a comfortable layout make this home as practical as it is inviting. Outdoor living is just as special here. Start your mornings on the classic front porch with a cup of coffee, or unwind in the evening on the spacious back deck — both finished with durable, low-maintenance Trex decking designed to look beautiful for years to come. Whether you're hosting a summer barbecue or simply enjoying some fresh air, these outdoor spaces extend your living area beautifully. Practicality meets opportunity with the attached 1-car garage, offering easy parking and extra storage, while the unfinished basement is a blank canvas — ideal for a home gym, workshop, media room, or simply valuable extra storage space. Perhaps best of all is the unbeatable location. Situated within the highly regarded North Shore School District, this home is just moments from the elementary school, making morning drop-offs a breeze. Commuters will love the close proximity to the train station, while everyday errands are simplified with a grocery store and local shops just around the corner, and the Long Island Sound down the road. Here, small-town charm meets everyday convenience — a rare combination that's hard to find. This is more than just a house — it's a place to put down roots, build memories, and enjoy the very best of Glen Head living. 3 Bedrooms | 1 Bathroom | 1-Car Garage | Unfinished Basement | North Shore Schools Schedule your private showing today — homes like this in The Promenade don't come along often!

38 Hill Drive, Glen Head
$6,999,000
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
$2,199,000
5 Beds ⋅ 5 Baths ⋅ 1026272 MLS
Welcome to 23 Wildwood Lane - an expansive modern contemporary located on a Old Brookville Street and set on .60 flat usable acres. This spacious home includes 5 oversized bedrooms and 5 well-appointed baths, including two primary ensuites with one located on the main level. Designed with flexibility in mind, this layout is ideal for multi-generational living. A dramatic entry foyer features 20-ft. soaring ceilings and the elegant and timeless marble floors set the tone for the rest of this unique home. Multiple sun-filled living spaces, and an open floor plan are designed for both everyday living and hosting large gatherings. The meticulously constructed eat-in kitchen flows seamlessly into generous living, dining and lounge areas overlooking the deck and yard while the rear property offers endless opportunities to create your own private oasis with room for a pool, and/or outdoor kitchen and more. Conveniently located near parks, shopping, dining, and transportation, this move-in ready home is a rare opportunity in one of the area’s most desirable neighborhoods. North Shore School District.

23 Wildwood Lane, Greenvale
$1,088,000
4 Beds ⋅ 2 Baths ⋅ 1024196 MLS
Located in the highly coveted, award-winning North Shore School District.Welcome home to this move-in-ready, newly renovated Colonial perfectly situated at the beginning of a charming, quiet cul-de-sac. This 4-bedroom, 2-full-bath home beautifully balances classic warmth with modern upgrades and an open space concept. The expanded 2,300 sq. ft. layout (1,561 sq. ft. livable) begins on the first floor with an inviting living room, a beautifully updated open-concept kitchen/dining room, a full bathroom, and an attached garage. Upstairs, find 4 spacious, sun-drenched bedrooms and a second full bath. Full finished basement provides incredible additional space for a home gym, media room, or play area. Enjoy seamless everyday living with unbeatable convenience—just minutes to the LIRR for an easy commute, plus nearby supermarkets, fine dining, and premier shopping. All information is deemed reliable but not guaranteed. Don't miss this Blue-ribbon North Shore gem!

7 Locust Street, Glen Head
$3,500,000
5 Beds ⋅ 5 Baths ⋅ 1018330 MLS
Dream homes do exist. Perfectly situated on 2+ private, meticulously landscaped acres on a winding country lane, this charming 5-bedroom residence offers an unparalleled lifestyle. Every sun-drenched room provides stunning, expansive views of lush lawns, specimen trees, and vibrant perennial gardens. Exquisite Craftsmanship & Main Level Living. The main level showcases exceptional millwork, fine moldings, and rich hardwood flooring. A vaulted foyer welcomes you, leading to an elegant music room, a spacious living room, and a handsome cherry library with custom built-ins. The gourmet kitchen features premium appliances and custom Wood-Mode cabinetry, overlooking your private backyard oasis. A thoughtfully placed butler’s bar with a Sub-Zero wine cooler connects the kitchen to the formal dining room for seamless entertaining. A first-floor bedroom with a private en-suite bath is ideal for guests or multi-generational living. The second level hosts four additional bedrooms. The serene primary suite features a luxurious en-suite bath. Two additional bedrooms boast private en-suite baths, while the fourth bedroom enjoys access to a well-appointed hall bath. Step outside to your private resort, featuring an expansive deck that overlooks a heated, saltwater gunite pool. The entire property is fully fenced, private, and beautifully framed by mature landscaping. Car enthusiasts and organizers will love the two separate garages: a convenient main-level attached garage near the mudroom/kitchen, plus a second 2-car garage/storage area at the basement level. A massive, unfinished basement offers endless customization potential and features a direct walk-out entrance to the pool area. Enjoy the perfect balance of privacy and convenience. Located just moments from the village, this home offers an excellent commute while placing you in the highly coveted North Shore School District.

61 Linden Lane, Upper 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
$899,000
3 Beds ⋅ 3 Baths ⋅ 1019592 MLS
Welcome to The Knolls, a beautifully landscaped and meticulously maintained gated condominium community offering effortless, low maintenance living in a prime location. This exceptional 1944 square foot residence features 3 bedrooms and 3 full baths, thoughtfully designed with spacious living areas, abundant natural light, and a highly functional floor plan. The sun-filled gourmet eat-in kitchen offers generous cabinetry, ample workspace, and room for casual dining. The elegant living room is anchored by a wood burning fireplace and open to a private wood deck, creating the perfect setting for indoor-outdoor entertaining and relaxation. The spacious primary suite is a true retreat, featuring deck access, abundant closet space, and the convenience of an upstairs laundry area. A second laundry room on the lower level provides added flexibility and convenience. The expansive lower level offers exceptional additional living space with outside access, making it ideal for a family room, home office, gym, guest quarters, or recreation area. Ample storage throughout the home ensures space for all of your belongings. Additional features include two outdoor parking spaces conveniently located on the first level near the front door, making everyday living easy and accessible. Residents of The Knolls enjoy a host of amenities and services, including a gated entrance with entry code access, weekend attendant, beautifully maintained grounds, roof decks, and exterior windows and doors maintained by the condo association. The community is known for its pristine appearance, mature landscaping, and welcoming atmosphere. The monthly HOA fee is $1,780.26 per month which includes the taxes, assessment for $233.22 which lasts for 18 months. Also included in the monthly fee is snow removal, landscaping, exterior maintenance, and community upkeep, allowing residents to enjoy a carefree lifestyle. No board approval is required. Offering the perfect combination of space, comfort, convenience, and a maintenance-free living, the exceptional home presents a rare opportunity to enjoy one of the area's most desirable condominium communities.

112 The Glen Unit #112, Glen Head
$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
$1,550,000
4 Beds ⋅ 5 Baths ⋅ 1016195 MLS
Welcome to The Knolls, a Prestigious Gated Community located in the North Shore Coveted Gold Coast. This Sun-Drenched, Spacious Residence Set in a Prime Location, features a Secluded Backyard. A True Sanctuary that Offers a Combination of Tranquility, Privacy, and Beauty. This Elegant Multi-Level Home has a flowing Open Floor Plan, Hardwood Floors, and an abundance of Natural Light. This home offers you two master bedrooms with full bathroom with lots of closet space. one on the first floor with jacuzzi, stand up shower, sky lights, second master bedroom on the 2nd floor with full bathroom lots of closet space, wood oak floors, new Recessed Lighting, sliding doors to the deck to enjoy nature. Many updates have been done throughout the house, new oak wood floors, new Recessed Lighting, new paint. THIS CO-OP IS RUN AS A CONDO – WITH NO BOARD APPROVAL REQUIRED. TAXES AND MAINTENANCE ARE CONVENIENTLY INCLUDED IN THE TAX PORTION

12 The Glen Lane Unit #12, Glen Head
$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
$749,888
3 Beds ⋅ 1 Baths ⋅ 1002991 MLS
Charming one-level ranch offering easy living and modern updates! This well-maintained home features three spacious bedrooms, a beautifully updated full bath, and a brand-new eat-in kitchen perfect for everyday living and entertaining. The inviting living room includes a door leading directly to the backyard, creating a seamless indoor-outdoor flow. Additional highlights include a versatile bonus room ideal for a home office, den, plus a one-car attached garage for convenience. Nestled on a quiet, tree-lined street with low taxes, this home is perfectly located close to downtown, beaches, shopping, and restaurants. A wonderful opportunity for comfortable and convenient living! North Shore School District with a Glen Cove address.

12 Ronan Road, Glen Cove
$765,000
2 Beds ⋅ 2 Baths ⋅ 1003795 MLS
Nestled within the prestigious gated community of The Knolls and adjacent to the renowned Glen Head Country Club, this beautifully appointed residence at 19 The Circle offers a seamless blend of elegance, comfort, and effortless living. Bathed in natural light from an abundance of windows and multiple skylights, the home showcases gleaming hardwood floors, crown and base moldings, recessed lighting, and timeless craftsmanship throughout. The well-appointed kitchen is designed for both function and style, featuring granite countertops, tile backsplashes, stainless steel appliances, gas cooking, generous cabinetry, and a sun-drenched dining area illuminated by skylights. Its open-concept layout flows seamlessly into the main living space, creating the perfect environment for everyday living and entertaining alike. The dramatic living room boasts soaring vaulted ceilings, additional skylights, a cozy fireplace, and oversized sliding glass doors that open to a private deck spanning the full length of the unit. The spacious primary suite serves as a private retreat, complete with a walk-in closet, direct deck access through sliding glass doors, and an abundance of natural light. The recently updated luxurious primary en-suite bath features a double vanity, soaking tub, and separate shower, creating a spa-like experience at home. A generously sized second bedroom, full guest bath, and dedicated laundry closet with washer and dryer provide comfort and convenience. Additional highlights include a four-year-young hot water heater (installed in Nov 2022) covered assigned garage parking, a private storage area, and exclusivity of gated community living. Ideally located near transportation, shopping, dining, and recreation, this exceptional residence presents a rare opportunity to enjoy one of Glen Head's most sought-after communities.

19 The Circle Unit #19, Glen Head
$5,499,000
9 Beds ⋅ 8 Baths ⋅ 1005247 MLS
Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. Inside, the richly paneled foyer and wide pegged oak floors set the stage for exquisite architectural details, including a sweeping staircase and intricate custom millwork. The first floor offers a seamless blend of grandeur and comfort. The magnificent living room and banquet-sized dining room both feature elegant fireplaces, while the gourmet kitchen boasts a spacious center island and a bright breakfast room. A butler’s pantry adds convenience, and the library, adorned with built-in bookcases and a fireplace, offers a cozy retreat. Additional highlights include a sunroom, two en suite guest bedrooms, a first-floor washer/dryer, and a powder room. Oversized windows throughout the home provide breathtaking views of the lush grounds. The expansive primary suite is a private sanctuary, complete with a fireplace, spa-like bath, dressing area, and a large balcony overlooking the manicured gardens. This level also features four additional bedrooms with two Jack-and-Jill baths, two additional fireplaces, a gracious hall bath, a gym/bedroom, an office/bedroom, and a second-floor laundry room. The lower level offers an abundance of recreational space, including a playroom, arts and crafts area, and a full bath. The exquisitely landscaped grounds provide something for everyone, offering endless opportunities for relaxation and entertainment. The sunken gardens, originally designed by renowned landscape architect Robert Ludlow Fowler Jr., are a marvel to behold. They gracefully lead the way to a serene 20x50 saltwater gunite pool that is complemented by a spacious, elegant pool house. Sports enthusiasts will appreciate the lighted clay tennis court and a heated, enclosed outdoor structure, perfect for squash or basketball. Adding to the estate’s appeal, a charming three-bedroom, two-bath guest cottage provides comfortable accommodations, while a three-car heated garage with a separate workroom ensures ample space for vehicles and storage. This extraordinary estate is a timeless masterpiece inside and out, seamlessly blending historic charm with modern refinement.

8 Stonegate Lane, Old Brookville
$4,399,000
5 Beds ⋅ 8 Baths ⋅ 987442 MLS
Set within the rarefied landscape of Old Brookville, this striking Mid-Century Modern residence is a study in architectural drama and refined design. Celebrated in Luxe Interiors + Design at the time of its transformation, the home reflects the visionary collaboration between its owners and the acclaimed firm Garcia/Maldonado, Inc.. The result is a masterwork where every line, material, and proportion has been considered with uncompromising precision. A rich palette of exotic woods—mahogany, oak, and birch—anchors the interiors with warmth and texture, while the architecture itself unfolds with quiet grandeur. The great room is nothing short of breathtaking: a soaring vaulted ceiling, commanding fireplace, and an expansive wall of glass dissolve the boundary between indoors and out, flooding the space with natural light and framing the surrounding landscape as living art. An elegant dining room overlooks the property and is the perfect venue for entertaining. At the heart of the home, the kitchen is both generous and inviting—designed for gathering and everyday luxury—with a substantial center island, sunlit breakfast room, and seamless connection to an open den. A separate media room, complete with a built-in bar and sliding doors, offers the flexibility for both intimate evenings and vibrant entertaining. The first-floor primary suite is a private sanctuary, opening directly to the grounds and featuring its own fireplace. A dramatic staircase leads to a secluded study—an architectural moment that elevates both function and form. The suite is further enhanced by a bespoke fitted closet room and a spa-like bath, exquisitely detailed in teak wood to evoke a sense of serenity, complete with dual vanities, a soaking tub, and a separate glass-enclosed shower. Upstairs, three oversized ensuite bedrooms, each with their own bath are complemented by an open lounge, creating a natural gathering space bathed in light. The lower level extends the lifestyle with a recreation room, additional den, and dedicated gym. Set across three exquisitely landscaped acres, the property evokes a private country club experience: a newly crafted Ipe deck, sparkling in-ground pool, Har-tru tennis court, and cabana complete this exceptional offering—where architecture and setting exist in perfect harmony.

93 Hoaglands Lane, Old Brookville
$3,795,000
6 Beds ⋅ 6 Baths ⋅ 996646 MLS
Framed by sweeping pond views and surrounded by over 2 private acres of beautifully landscaped grounds, this beautifully renovated brick estate offers a rare blend of luxury, privacy, and serene waterfront living. Tucked away on a quiet cul-de-sac, the home is perfectly positioned to capture the beauty of the pond from both the interior living spaces and the resort-style outdoor setting. A circular driveway and expansive paving-stone walkway introduce this impressive 6-bedroom, 5.5-bath residence featuring a bright, flowing layout designed for both everyday comfort and elegant entertaining. The custom gourmet kitchen overlooks the scenic backyard with tranquil water views, while the first-floor primary suite serves as a private retreat within the home. Designed with exceptional functionality, every bedroom enjoys direct bathroom access through either private en-suite baths or thoughtfully designed Jack-and-Jill layouts, offering comfort and convenience. Additional highlights include hardwood floors throughout, spacious entertaining areas, a full finished basement, guest accommodations, a full-house natural gas generator, and a 3-car attached garage. Outdoors, beautifully crafted stone patios and a fully equipped outdoor kitchen create the ideal backdrop for entertaining beside the pond, with direct water access and breathtaking year-round views completing this extraordinary Upper Brookville offering. **Some photos have been virtually staged for illustrative purposes to showcase the potential use and design of the space.**

23 Overbrook Lane, Upper Brookville
$6,450,000
7 Beds ⋅ 10 Baths ⋅ 991638 MLS
Set behind private gates in the prestigious Estates at Greenfield, this stately brick Georgian Colonial is perfectly positioned on three + magnificently landscaped acres, offering an exceptional blend of timeless architecture and resort-style living. A gracious approach leads to a generous courtyard, creating a striking first impression and a true sense of arrival. Inside, a dramatic two-story center hall marble foyer showcases a sweeping wrought iron circular staircase and exquisite, detailed millwork that sets the tone for the home’s refined interiors. The formal living room is both elegant and inviting, complete with a custom built-in bar and hardwood floors while the generous dining room is perfectly suited for grand entertaining. A warm and inviting den with a fireplace sits just off the chef’s kitchen and sunlit breakfast nook, creating an ideal flow for everyday living. A richly appointed home office features its own fireplace, custom built-in shelving, and a convenient half bath. The first floor is further enhanced by a private ensuite bedroom, perfect for guests or extended family. The second level offers a luxurious primary en-suite retreat with a fireplace, a gracious sitting room, and multiple custom-fitted closets. The spa-like marble bathroom adds to the sense of indulgence. Four additional ensuite bedrooms provide comfort and privacy, while a fabulous bonus room offers flexibility as a second den, media lounge, or computer room. The lower level has been thoughtfully designed for recreation and relaxation, featuring a game room, media area, gym, and abundant storage. Outdoors, the property is truly extraordinary—lush, expansive, and beautifully curated with mature specimen trees that provide both privacy and natural beauty. Designed for both relaxation and recreation, the grounds include a sparkling pool and hot tub, a full-service cabana, and a fully equipped outdoor kitchen ideal for seamless entertaining. A sports court and playground complete this exceptional offering. The property is simply divine—an all-encompassing retreat in The Estates at Greenfield, where every amenity has been thoughtfully curated, offering a lifestyle so complete there is truly no reason to ever leave home.

6 Evergreen Way, Old Brookville
$3,899,000
6 Beds ⋅ 5 Baths ⋅ 957864 MLS
Nestled in the heart of Old Brookville, this private oasis offers the perfect blend of luxury, tranquility, and modern living. Set on a sprawling, flat 3.2 -acre lot within the prestigious North Shore School District, this property feels like your own year-round retreat. As you approach via the picturesque private driveway, you're greeted by lush, mature landscaping that ensures complete seclusion. The property boasts a sparkling gunite saltwater pool with a chic pool house, a clay tennis court, and plenty of open space to enjoy outdoor living at its finest. Step inside this contemporary gem, and you'll find a thoughtfully designed floor plan that caters to comfort and style. The main level features a stunning primary ensuite with its own private deck—your perfect sanctuary for morning coffee or evening relaxation. The home has been meticulously updated with hardy plank siding, new windows, a modern A/C system, and a hot water heater. Simply move in and make it your own! Whether you're lounging by the pool, hosting friends on the tennis court, or unwinding in your serene retreat, this home truly offers a vacation lifestyle all year long. Don’t miss your chance to experience the ultimate in privacy and luxury living.

91 Hoaglands Lane, Old Brookville
$3,299,888
6 Beds ⋅ 6 Baths ⋅ 977675 MLS
Welcome to a rare opportunity to own a fully renovated and extended estate—rebuilt from the studs up and reimagined for modern luxury in the heart of one of Long Island’s most coveted neighborhoods. Set on a beautifully manicured 2 acre lot, this 6-bedroom, 5.5-bathroom smart residence combines sophisticated design, premium finishes, and cutting-edge amenities, offering a seamless blend of elegance. Every inch of the home reflects quality and intention—from the radiant heated floors throughout the entire main level and every bathroom to the sleek, designer fixtures and finishes throughout. The gracious first floor features a private guest suite with a separate entrance, ideal for extended family and guests. The chef’s kitchen is the true centerpiece—a culinary dream outfitted with a massive center island, top-tier stainless steel appliances, including a 48” Bertazzoni induction range with double ovens, oversized refrigerator and freezer, dual dishwashers, custom cabinetry, beverage drawers, and thoughtful built-ins—all designed to inspire both intimate dinners and large-scale entertaining. The second floor is home to a luxurious primary suite with a spa-inspired en-suite bath, radiant heated floors, oversized closet, and tranquil views of the property. Three additional spacious bedrooms upstairs offer generous closets, and large windows that flood the rooms with natural light. With a dedicated second-floor laundry area, convenience meets everyday function for busy households. The fully finished basement features its own private exterior entrance and offers an abundance of versatile space, including a wine cellar, gym, recreation, full laundry room, and more— The home's brand-new exterior features include a new roof, striking black energy-efficient windows, and a large Trex deck that opens from the kitchen to your own private oasis complete with an in-ground pool. Every system has been updated—new electrical, plumbing, floors, HVAC, and insulation—ensuring true turnkey luxury living. This is more than a home—it's a statement. A rare offering of timeless craftsmanship and modern design in one of the most distinguished enclaves.

33 High Farms Road, Old Brookville
$2,699,900
5 Beds ⋅ 4 Baths ⋅ 974758 MLS
Stunning Old Brookville Estate on 2 Acres with Pool & Outdoor Oasis Welcome to this exquisite 5-bedroom, 4-bathroom home nestled on 2 acres of beautifully landscaped property in the prestigious area of Old Brookville. This elegant residence offers the perfect blend of luxury, comfort, and privacy. Step inside to discover spacious living areas filled with natural light, including a grand living room with a cozy fireplace, a formal dining room, and a gourmet kitchen. The primary suite is a private retreat, complete with a spa-like en-suite bathroom. The fully finished basement is an entertainer’s dream, featuring a custom bar and ample space for gatherings. Outdoors, enjoy a serene backyard paradise with an in-ground pool, a charming gazebo, and a spacious patio—perfect for relaxing or entertaining. This exceptional property offers a rare opportunity to own a piece of paradise in one of Long Island’s most desirable locations. Don’t miss out on this remarkable home!

Glen Head
$3,800,000
974655 MLS
Lovely 7.09 Acres of Residential Land a Great Builders Opportunity! This is not all flat land, it has beautiful hills. Located in Village of Old Brookville, The Address can be Brookville or Glen Head according to Village of Old Brookville same postal zip code. There is 2 acres zoning for this property, so 3 Beautiful Homes can be built on this property. All approvals would go to Village of Old Brookville. North Shore School District, close to shopping & Beaches.

559 Cedar Swamp Road, Old Brookville
$12,000,000
954864 MLS
Glen Head Commons is a rare, fully approved shovel-ready new residential development opportunity in the heart of Glen Head, NY within the Town of Oyster Bay, one of Long Island's most desirable North Shore communities in Nassau County. Situated on 7.7 acres, the completely flat site is ideally located close to town amenities and nearby to the Glen Head Long Island Railroad Station. The subject property falls within the North Shore School District, including Glen Head Elementary, and has very close proximity to the North Shore Middle School and North Shore High School, plus numerous private school options nearby. The property is fully approved for total 53 residential units, thoughtfully designed to blend seamlessly into the surrounding neighborhood. The approved site plan consists of 15 single family residences and 38 townhomes. Glen Head offers a classic North Shore of Long Island lifestyle characterized by strong community identity, tree-lined streets, and proximity to beaches, marinas, parks, town shops, a variety of food options and village centers. The location provides outstanding regional connectivity, offering exceptional transit-oriented appeal just 26 miles from Manhattan and LIRR train access to both Penn Station and Grand Central in about an hour to New York City plus easy access to major roads and multiple international airports. With all approvals in place and utilities accessible, including sewers available, Glen Head Commons represents an exceptional opportunity to deliver high-quality for-sale housing in a supply-constrained, North Shore market. Buyers to verify all information and process to further develop this land parcel including physical improvements such as new road and utilities. The most ready to go new residential development in the immediate area and a truly exciting prospect not seen in over 40-50 years here.

Glen Head

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