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$10,250,000
7 Beds 12 Baths 1050255 MLS
An extraordinary custom-built estate set within one of Old Brookville’s most prestigious gated communities, this magnificent residence offers an exceptional setting for grand-scale living and refined entertaining. The seven-bedroom, 12-bathroom home is complemented by an impressive eight-car garage and an array of resort-style amenities, including a luxurious pool house, swimming pool, hot tub, and private tennis and multi-sport court. A rare offering that seamlessly combines scale, privacy, and sophistication in one of Long Island’s most coveted enclaves. A grand entrance hall with soaring ceilings introduces the home’s elegant interiors. The main level features a chef’s eat-in kitchen, breakfast room, formal living room, formal dining room, family room, library, and lounge, providing an ideal balance of formal and informal living spaces. The second floor is anchored by a commanding primary suite with expansive his-and-her walk-in closets and separate his-and-her bathrooms. The remaining bedrooms are generously proportioned and each includes a private full bathroom. The finished basement extends the home’s exceptional amenities with a gym, spa, entertainment room, and lounge, creating a private retreat for wellness, recreation, and relaxation.An extraordinary custom-built estate set within one of Old Brookville’s most prestigious gated communities, this magnificent residence offers an exceptional setting for grand-scale living and refined entertaining. The seven-bedroom, 12-bathroom home is complemented by an impressive eight-car garage and an array of resort-style amenities, including a luxurious pool house, swimming pool, hot tub, and private tennis and multi-sport court. A rare offering that seamlessly combines scale, privacy, and sophistication in one of Long Island’s most coveted enclaves. A grand entrance hall with soaring ceilings introduces the home’s elegant interiors. The main level features a chef’s eat-in kitchen, breakfast room, formal living room, formal dining room, family room, library, and lounge, providing an ideal balance of formal and informal living spaces. The second floor is anchored by a commanding primary suite with expansive his-and-her walk-in closets and separate his-and-her bathrooms. The remaining bedrooms are generously proportioned and each includes a private full bathroom. The finished basement extends the home’s exceptional amenities with a gym, spa, entertainment room, and lounge, creating a private retreat for wellness, recreation, and relaxation.

18 Evergreen Way, Old Brookville

$1,449,000
4 Beds 2 Baths 1048833 MLS
Sea Cliff charm takes on a whole new meaning at “Herbert’s Hill,” a truly one-of-a-kind 4-bedroom, 2-bathroom Tudor with a remarkable artistic history. Built in 1912 by an artist, the home, formerly known as “The Artist Tudor”, still showcases the original owner and builder’s work throughout, including original murals, painted glass, and handcrafted architectural details. Rich walnut wood, exposed ceiling beams, archways, and other period details create a warm and captivating sense of character and eccentricity at every turn. The kitchen features a hand-painted tile backsplash which is a treat from the current artists and owners, while a second floor room with oversized windows offers an ideal setting for a home office, studio, or creative retreat. Downstairs, the “Beer Garden Cellar” is perhaps the home's most intriguing space, preserving the original artist's work with painted glass windows, timbered ceilings, and an angled brick fireplace featuring a Viking ship. It is a space that begs to be explored and offers a fascinating glimpse into the home's past. Outside, a wrap-around path winds through a peaceful garden oasis with a koi pond and waterfall. This is not simply a house, it is a piece of Sea Cliff history filled with artistry, craftsmanship, and unmistakable personality. A must walk through for those who appreciate originality and have the vision to thoughtfully maintain and preserve something truly special.

230 Littleworth Lane, Sea Cliff

$2,200,000
4 Beds 4 Baths 1042500 MLS
Quintessential Colonial in the Heart of Sea Cliff Beautifully appointed, spacious, and thoughtfully updated, this classic Colonial offers an exceptional layout with incredible flow, abundant natural light, and generous living space throughout, all in one of Sea Cliff’s most desirable locations. From the moment you enter, soaring cathedral ceiling and skylights create a dramatic, light-filled foyer, complete with two closets and an immediate sense of space. The floor plan is truly one of the highlights of this home, you simply couldn’t ask for a better layout. The main level features gracious formal living and dining rooms, while the heart of the home is the chef’s kitchen, flowing naturally into a sun-filled breakfast area and spacious den. Beautiful glass doors open directly to the private backyard, patio, and built-in fire pit, creating the perfect indoor-outdoor connection for everyday living, entertaining, summer evenings, and crisp fall nights. Upstairs, the expansive primary suite is a true retreat with cathedral ceilings, skylights, a beautifully renovated primary bath, and generous closet space. Three additional bedrooms, a full bath, and conveniently located second-floor laundry complete this level. Abundant closet and storage space can be found throughout the entire home, something you truly appreciate once you live here. The fully CO’d finished lower level provides incredible additional living space with a wet bar, large bathroom, and plenty of room for a playroom, movie room, gym, home office, or whatever suits your lifestyle. A finished two-car garage adds even more convenience. With high ceilings, wonderful proportions, an exceptional floor plan, and effortless flow from one room to the next, this is truly the quintessential Sea Cliff Colonial. And the location is hard to beat, just moments from the village, shops, restaurants, parks, beaches, and everything that makes Sea Cliff such a special place to feel right at home.

60 Lafayette Avenue, Sea Cliff

$8,250,000
6 Beds 8 Baths 1048329 MLS
Set behind the gates of an exclusive community in the Village of Old Brookville, this exceptional modern residence offers more than 7,000 square feet of luxurious living space on over three acres of beautifully manicured, private grounds. Walls of windows fill the home with natural light while showcasing serene views of the surrounding landscape, inground pool and hot tub. A dramatic two-story entry introduces the impressive main level, featuring a soaring two-story great room with a striking stone wet bar, a formal dining room and a private home office. The expansive eat-in kitchen includes a spacious breakfast area and provides an inviting setting for both everyday living and entertaining. A generously sized junior primary suite and an additional bedroom completes the first floor. Upstairs, the expansive primary suite serves as a private retreat with dual walk-in closets, a luxurious primary bathroom and a generous terrace. Three additional bedroom suites each feature their own private bathrooms, while a conveniently located laundry room completes the second level. The finished lower level is designed for recreation, relaxation and wellness, offering a golf simulator, entertainment room, play area and full bathroom. A private spa features a hot tub, sauna and steam room, creating a resort-like experience without ever leaving home. Surrounded by lush, meticulously maintained grounds, this remarkable Old Brookville property delivers exceptional privacy, modern sophistication and resort-style living in one of Long Island’s most prestigious communities.

160 Hegemans Lane, Old Brookville

$949,000
2 Beds 4 Baths 1048063 MLS
Welcome to this sun-drenched and stylish Glen Head fully-updated townhouse in the Fairway View development, perfectly positioned with ideal southern exposure that bathes the home in natural light all day long. Step into a dramatic entry foyer with soaring cathedral ceilings that flow seamlessly into an open-concept living area. Sleek black hardwood floors anchor the residence, creating a sophisticated backdrop for both daily living and effortless entertaining. The gourmet eat-in kitchen features timeless quartz countertops, a matching backsplash, an expansive island with abundant storage, and a dedicated laundry area with pantry space. Step through sliders from the main living space onto your private back deck—an idyllic setting for outdoor dining or peaceful morning coffee. Upstairs, the primary suite serves as a true sanctuary, complete with a generous closet system and a tranquil, Zen-inspired en-suite bathroom. A spacious second bedroom, an additional full bath, and a versatile den/office space with its own private upper-deck access offer endless flexibility for work or guests. The fully finished basement adds exceptional living space, featuring an open layout, a third full bathroom, and an egress window. Situated in the prestigious, award-winning North Shore School District, this home offers the ultimate blend of privacy and convenience—just minutes from top-rated schools, local dining, community amenities, Tappen Beach, and the Glen Head LIRR for a effortless commute.

40 Cedar Lane N Unit #40, Glen Head

$2,995,000
5 Beds 6 Baths 1044302 MLS
5 Woodfield Lane! Set on beautiful landscaped grounds, this impressive residence offers a wonderful blend of space, comfort, and privacy. Totally renovated in 2019! 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

$1,149,000
3 Beds 2 Baths 1042818 MLS
Welcome to this bright and inviting 3–4 bedroom, 2 full bath Cape Cod, filled with natural light throughout. The entry foyer opens to the dining room, leading to a comfortable den and a beautiful living room/sunroom with fireplace, abundant windows, and skylights that create a warm and airy atmosphere. The light-filled kitchen features a center island and stainless steel appliances, offering a wonderful space for everyday living and entertaining. A first-floor bedroom and full hall bath complete the main level. Upstairs, an open landing leads to the primary bedroom, an additional bedroom, and a full hall bath. Fresh white interiors, plentiful windows, and skylights enhance the home’s bright, open feel throughout. Outside, enjoy a private yard with patio, perfect for relaxing or entertaining, along with a 1-car detached garage. A charming Cape offering flexible living space, great natural light, and a welcoming feel throughout.

9 Robert Road, Glen Cove

$998,639
3 Beds 2 Baths 1039571 MLS
Welcome to this inviting 3-bedroom, 2-full-bath Colonial with a Contemporary feel, featuring a charming covered front porch and a comfortable, functional layout with wonderful indoor and outdoor living space. The main level features a spacious living room with a wood-burning fireplace, flowing seamlessly into the dining room and kitchen for an open and welcoming feel. Sliding glass doors from the kitchen lead to a deck overlooking the large backyard, perfect for relaxing, entertaining, and outdoor gatherings. The first floor also offers a bedroom and full bath, providing flexible space for guests, a home office, or additional living needs. Just off the kitchen is a mudroom with laundry and access to the finished basement with outside entry. Upstairs, you’ll find the primary bedroom and an additional bedroom, connected by a Jack-and-Jill full bath featuring a Jacuzzi tub. With its inviting covered front porch, warm fireplace, open living spaces, flexible floor plan, deck, and expansive backyard, this charming Colonial is ready to welcome you home.

3 Woodland Avenue, Glenwood Landing

$1,699,900
4 Beds 3 Baths 1039834 MLS
Experience Modern Living with Historic Charm. 4 Beds | 2.5 Baths | Meticulously Expanded & Rebuilt in 2017. Welcome to a stunning example of comfortable living nestled in the charming community of Sea Cliff. Originally built in 1898, this exquisite Colonial home has been meticulously expanded and completely rebuilt in 2017 by a builder ensuring top-quality materials, premium finishes, and meticulous craftsmanship throughout. Elegant & Intelligent Living Spaces: * Grand Welcome: A classic covered front porch leads into a spacious living space perfectly designed for today's lifestyle. * Chef's Heart: A modern kitchen equipped with state-of-the-art appliances and high-end finishes. * Smart Home Technology: Fully integrated SMART home automation paired with custom automated Hunter Douglas blinds. * Premium Finishes: Rich hardwood floors run seamlessly throughout the entire home. * Daily Convenience: A functional mudroom features custom built-ins alongside a stylish powder room. Your Second-Floor Sanctuary: * Primary Suite Oasis: A luxurious retreat featuring a spacious walk-in closet and a spa-like marble bathroom complete with radiant heat, a steam shower, and a separate soaker tub. * House Accommodations: Three additional bright bedrooms, a centrally located hall bath, and a dedicated upstairs laundry area. Bonus Spaces & Private Resort Grounds: * Finished Basement: Provides a dedicated play area for guests, plus abundant extra storage. * Oversized Property: A custom-made fence with a beautiful arbor completely surrounds the property, offering ample private outdoor space. * Outdoor Entertaining: Enjoy a private patio, custom landscaping, professional exterior lighting, and hassle-free in-ground sprinklers. * Ample Parking & EV Ready: A 2-car detached garage recently updated with sleek epoxy flooring and an electric car charger, plus room for 3–4 additional cars in the private driveway. The Sea Cliff Lifestyle: Perfectly located close to beautiful North Shore beaches and quaint village shops, this home offers the absolute best of Sea Cliff living. Enjoy the dual benefits of exceptionally low taxes and enrollment in the highly acclaimed North Shore School District.

18 20th Avenue, Sea Cliff

$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

$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

$1,650,000
5 Beds 5 Baths 1032997 MLS
Welcome to this custom 5-bedroom, 5-bath Colonial, thoughtfully designed with architectural angles throughout. Perfectly situated on a quiet picturesque lane, this property offers the ideal blend of style, comfort, and functionality. From the moment you enter, you'll be impressed by the home's light-filled interiors, high ceilings, and design. The open-concept floor plan is ideal for both everyday living and entertaining. The first floor primary suite offers a private retreat, while four additional bedrooms and bathrooms provide comfort and flexibility. New kitchen with fireplace, formal dining room with fireplace, living room with fireplace and oversized windows, study with fireplace, and home office. Outside, this property offers endless possibilities for outdoor entertaining, recreation, or creating your own private backyard oasis. This inviting home combines interesting architecture in a convenient location. Don't miss this opportunity to make this truly distinctive property a home that delivers elevated living.

9 Addison Lane, Greenvale

$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

$5,999,999
7 Beds 9 Baths 1021590 MLS
Old Brookville | Welcome to 3 Valentine Farm Court, where timeless architecture, exceptional craftsmanship, and an unmatched collection of luxury amenities define one of the North Shore's most impressive private estates. Positioned behind double iron gates at the end of a secluded cul-de-sac, this stately brick center hall colonial is situated on more than three meticulously landscaped acres, combining remarkable privacy with an extraordinary level of recreation and entertaining amenities. The residence is introduced by a spectacular two-story domed foyer showcasing a sparkling chandelier, intricate hand-painted ceiling details, and extensive custom millwork carried throughout every level of the home. Formal and informal living spaces are thoughtfully arranged, including an expansive formal living room, richly appointed mahogany library, inviting family room with one of three wood-burning fireplaces, formal dining room, powder room, and a spacious first-floor en-suite bedroom with separate exterior access. The custom kitchen is appointed with premium gas appliances, custom cabinetry, a center island with seating, an adjoining breakfast area, and an expansive butler's pantry connecting directly to the formal dining room. Extending from the main level, an elevated terrace with a built-in outdoor kitchen overlooks the estate grounds and pool complex below. The second level features five bedroom suites, each with their own full bathroom. Occupying its own wing of the home, the primary suite includes a private balcony overlooking the property, separate sitting room, two oversized walk-in closets, and an expansive en-suite bathroom with dual vanities and a jetted soaking tub. Designed as an exceptional recreational and entertaining space, the lower level features a custom wet bar, expansive gathering areas, a fully equipped fitness center, additional bedroom and full bathroom, oversized laundry room, and a below-grade indoor sports court with min. 15-foot ceilings—a rarely available amenity in residential construction. The outdoor amenities are equally impressive. The resort-inspired grounds are centered around an oversized gunite swimming pool with an integrated spa and water features, surrounded by expansive patios and mature landscaping. A fully equipped pool house includes a full bathroom, laundry facilities, and an indoor kitchen with a built-in grill opening directly onto the pool terrace. Completing the estate is a full-size sports court configured for both tennis and basketball, along with an oversized three-car garage equipped with vehicle lifts offering additional space for the car enthusiast. Representing an exceptional combination of scale, craftsmanship, and amenities on more than three private acres, 3 Valentine Farm Court presents a rare opportunity within one of the North Shore's most distinguished settings.

3 Valentine Farm Court, Old Brookville

$2,199,000
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

$2,995,000
4 Beds 5 Baths 1023631 MLS
Just Completed to Perfection. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location. Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for today's lifestyle. The chef's kitchen boasts an oversized center island, quartz countertops, Sub-Zero and Wolf appliances, a breakfast area, and opens to the spacious great room with a fireplace and French doors leading to a beautiful patio for seamless indoor/outdoor entertaining. The main level also includes a formal dining room with coffered ceiling, butler's pantry, living room, office/den, powder room, and attached two-car garage. Upstairs, the luxurious primary suite offers tray ceilings, walk-in closets, and a spa-inspired bath with Carrara marble, soaking tub, walk-in shower, and dual vanities. Three additional en-suite bedrooms and a second-floor laundry room complete the upper level. A full basement with 9-foot ceilings offers exceptional potential to create additional living space tailored to your needs. Additional features include Pella windows, 4-inch wide-plank oak floors, premium fixtures, multi-zone HVAC, energy-efficient construction, hardie plank,and professionally landscaped grounds, all within the award-winning North Shore School District. *Current property taxes reflect land value only.*

738 Motts Cove Road N, Glen Head

$2,995,000
4 Beds 5 Baths 1023543 MLS
Nearing Completion – See 738 Motts Cove N for Finished Home. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location. Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for today's lifestyle. The chef's kitchen boasts an oversized center island, quartz countertops, Sub-Zero and Wolf appliances, a breakfast area, and opens to the spacious great room with a fireplace and French doors leading to a beautiful patio for seamless indoor/outdoor entertaining. The main level also includes a formal dining room with coffered ceiling, butler's pantry, living room, office/den, powder room, and attached two-car garage. Upstairs, the luxurious primary suite offer tray ceilings, walk-in closets, and a spa-inspired bath with Carrara marble, soaking tub, walk-in shower, and dual vanities. Three additional en-suite bedrooms and a second-floor laundry room complete the upper level. A full basement with 9-foot ceilings offers exceptional potential to create additional living space tailored to your needs. Additional features include Pella windows, 4-inch wide-plank oak floors, premium fixtures, multi-zone HVAC, energy-efficient construction, and professionally landscaped grounds, all within the award-winning North Shore School District.*Current property taxes reflect land value only.*

734 Motts Cove Road N, Glen Head

$2,995,000
4 Beds 5 Baths 1023531 MLS
Nearing Completion – See 738 Motts Cove N for Finished Home. Stunning new construction on a charming tree-lined cul-de-sac shared by only six homes, this exceptional 4-bedroom, 4.5-bath Hamptons-inspired residence offers the perfect blend of luxury, craftsmanship, and location. Filled with natural light, the home features exquisite millwork, designer finishes, and an open floor plan ideal for today's lifestyle. The chef's kitchen boasts an oversized center island, quartz countertops, Sub-Zero and Wolf appliances, a breakfast area, and opens to the spacious great room with a fireplace and French doors leading to a beautiful patio for seamless indoor/outdoor entertaining. The main level also includes a formal dining room with coffered ceiling, butler's pantry, living room, office/den, powder room, and attached two-car garage. Upstairs, the luxurious primary suite offer stray ceilings, walk-in closets, and a spa-inspired bath with Carrara marble, soaking tub, walk-in shower, and dual vanities. Three additional en-suite bedrooms and a second-floor laundry room complete the upper level. A full basement with 9-foot ceilings offers exceptional potential to create additional living space tailored to your needs. Additional features include Pella windows, 4-inch wide-plank oak floors, premium fixtures, multi-zone HVAC, energy-efficient construction, and professionally landscaped grounds, all within the award-winning North Shore School District.*Current property taxes reflect land value only.*

730 Motts Cove Road N, 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

$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

$699,000
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

$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

$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

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.