Refine Search
Map
Sort by
$1,111,000
4 Beds ⋅ 3 Baths ⋅ 1032630 MLS
Classic architectural design meets serene waterfront living in this 4-bedroom 2 and a half bath Center Hall Colonial situated in Glen Cove. Spanning 2,798 square feet across 8 spacious rooms, this residence offers a flowing floor plan crafted for effortless daily living and gracious entertaining. At the heart of this home, an expansive living room and den, each with their own fireplaces, serve as inviting, light-filled gathering spaces. Set on a picturesque property overlooking a private neighborhood pond, the property delivers calming water views and a peaceful natural backdrop. Positioned within the North Shore School District, this home provides an ideal blend of suburban comfort and natural beauty.

40 Knott Drive, Glen Cove
$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
$2,695,000
4 Beds ⋅ 4 Baths ⋅ 906140 MLS
ARCHITECTURAL MILLWORK... COFFERED CEILING... RAISED MOLDINGS....DESIGNER BATHS... CUSTOM KITCHEN WITH 10 FT ISLAND .... STAINLESS APPLIANCES ...QUARTZ COUNTERTOPS ...SUN ROOM OFF KITCHEN....HARDWOOD FLOORING... ALL NEW ANDERSEN BLACK FRAME WINDOWS ...HARDIE PLANK SIDING TOTAL RENOVATION JUST COMPLETED SHOWS LIKE A MODEL

19 MICHAELS Lane, Old Brookville
$999,000
5 Beds ⋅ 2 Baths ⋅ 1029568 MLS
Newly renovated 5-bedroom, 2-bath Hi-Ranch home in the North Shore School District. Situated on two lots (Lots 432 & 485) with a combined lot size of approximately 60' × 178' irregular, this exceptional property offers an expansive backyard. The home features a modern kitchen with sleek finishes, stylishly updated bathrooms, and a thoughtfully designed layout with a finished basement ideal for additional storage, recreation, or a home office. The additional lot provides enhanced privacy and abundant outdoor space with endless possibilities for outdoor living and entertaining. Conveniently located close to local beaches, parks, shops, and amenities, this move-in-ready home combines comfort, style, and convenience.

120 Glenwood Road, Glenwood Landing
$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
$2,775,000
4 Beds ⋅ 4 Baths ⋅ 1025463 MLS
Nestled on two private acres, this stunning 4-bedroom, 3.5-bath ranch combines timeless comfort with resort-style living, featuring over 3,100 square feet, an in-ground pool, and beautifully designed indoor-outdoor spaces, all within the acclaimed North Shore School District.

153 Brookville Lane, Glen Head
$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
$1,188,000
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
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 1023642 MLS
New Construction in North Shore School District: Enjoy the perfect home with 4 bedrooms, 3.5 bathrooms, a mudroom, and a one car garage. Situated on a level 60’ x 100’ property, on a quiet cul-de-sac, this home provides a lovely primary suite with tray ceilings, two spacious closets and a primary bath featuring a double sink vanity and a soaker tub. The kitchen boasts quality finishes with Fabuwood cabinets, under cabinet lighting, quartz countertops, a 36” gas Bertazzoni range and a large center island including a wine cooler. You can finish the full basement which already has 10’ ceilings and outside entrance. Don’t miss this opportunity to make this dream home yours!

9 First Street, Glenwood Landing
$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
$999,000
3 Beds ⋅ 2 Baths ⋅ 1021621 MLS
This home features a kitchen that opens to the formal dining room, with direct access to a private deck overlooking a beautifully tree-lined backyard. The inviting living room offers a cozy wood-burning fireplace, while the formal dining room showcases hardwood flooring. Hardwood floors extend throughout much of the home, adding warmth and timeless character. A separate guest area with its own private exterior entrance provides exceptional flexibility for visitors, extended family, or a home office. Additional amenities include a garage and a full basement with a washer and dryer, offering ample storage and everyday convenience. This property is being sold as is and presents a fantastic opportunity for investors, contractors, or buyers looking for a handyman special. With some TLC, this home has tremendous potential to make it your own or add value as an investment.

21 Laurel Avenue, Sea Cliff
$975,000
4 Beds ⋅ 2 Baths ⋅ 1022186 MLS
Welcome to 22 Locust Avenue, a legal two-family residence ideally located in the heart of Glen Head. This property offers two spacious apartments, each featuring two bedrooms, one full bath, hardwood floors, comfortable living areas, updated kitchens and baths, and separate entrances for added privacy and convenience. Additional highlights include a fenced backyard, detached two-car garage, and conveniently located to local shops, dining, parks, and the Long Island Rail Road. With its flexible layout, desirable location, and income producing potential, this property presents an excellent opportunity for investors or owner occupants.

22 Locust Avenue, Glen Head
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 1021581 MLS
Roslyn Harbor, North Shore Schools, on cul-de-sac. 0.86 of an acre, opportunity to build your dream home.

11 Mary Lane, Roslyn Harbor
$2,695,000
2 Beds ⋅ 3 Baths ⋅ 1021582 MLS
One of the most unique luxury condos at The Residences at Glen Harbor with the largest patio over 1,200 that fully wraps around and is ideally situated on the first floor with panoramic waterfront views of the harbor and LI Sound. Unit #101 is being offered fully furnished as an option allowing for immediate enjoyment on day one with many upgrades made too, including custom entertainment built-ins, bedroom closets and a functional in unit mud room with storage, plus laundry. In addition, this particular condo also comes with a private secure storage space inside the building located just by the unit. 2 parking spaces in the garage. This newly listed condo is spacious and a beautiful open floor plan. The kitchen has two islands now, quartz countertops featuring Sub-Zero and Wolf appliances. Dining Room open to Living Room with walls of windows bringing in the natural light and looking out to the direct waterfront view. Modern and effortless living at this luxury condo building full of amenities. The primary bedroom suite offers a serene oasis overlooking the water, custom built-in closets throughout and the two walk-in closets, porcelain spa bathroom. The guest bedroom was created to become an en-suite experience, very private and comfortable. The Residences at Glen Harbor delivers a luxury waterfront lifestyle with exceptional amenities including 24 hour doorman and concierge services, welcome lobby, clubhouse lounge, coffee bar, two fitness centers including a cardio room and free weight room, resort-style heated swimming pool outside, pool house pavilion, sun decks, bbq area and so much more. Full building generator. Residents also enjoy a scenic boardwalk along the waterfront, unobstructed views of Hempstead Harbor and the Long Island Sound, beautifully landscaped grounds, and a private community atmosphere. Conveniently located near shopping, dining, transportation, and North Shore conveniences. Fully furnished option. Move in immediately and enjoy, just bring your toothbrush.

10 Shore Road Unit #101, Glenwood Landing
$775,000
3 Beds ⋅ 2 Baths ⋅ 1020045 MLS
Colonial Set On Private Grounds. Formal Living Room And Dining Room, Hardwood Floors Throughout. Eat In Kitchen, Half Bath And Stackable Washer Dryer Located On First Floor With Sliders Out To Covered Deck. Upstairs Ther Are 3 Nice Size Bedrooms With Walk In Closet In Hallway And Full Bath With Bathtub. Large Fully Fenced Yard. Close To Sea Cliff Village And Beach.

3 Altamont Avenue, Sea Cliff
$2,849,000
5 Beds ⋅ 4 Baths ⋅ 1019591 MLS
ROSLYN HARBOR. Beautifully positioned on a private, park-like acre in the heart of Roslyn Harbor, this exquisitely renovated ranch seamlessly blends sophisticated design with the ease of luxurious single-level living. Completely reimagined in 2017, meticulously kept and renovated again in 2022 by the current owners, this exceptional residence offers 5 bedrooms, 3 full and 1 half baths, and an expansive open-concept floor plan thoughtfully designed for both elegant entertaining and everyday comfort. Bathed in natural light from 15 strategically placed skylights and expansive walls of glass, the home's sun-drenched interiors create a seamless connection between indoor and outdoor living. Refined architectural details, generous proportions, and impeccable craftsmanship are showcased throughout. The formal living room, anchored by a fireplace, is thoughtfully defined by a custom wood bench that creates a subtle transition into the designer kitchen. A true showpiece, the kitchen features stainless steel appliances, quartz countertops, custom cabinetry, and a dramatic suspended architectural truss lighting installation with museum-quality adjustable LED illumination. The adjoining formal dining room is equally impressive, appointed with custom built-in cabinetry, a Sub-Zero wine cooler, and floor-to-ceiling windows overlooking the picturesque grounds. The inviting family room, complete with a second fireplace and direct access to the outdoor patio, provides the perfect setting for effortless indoor-outdoor living. Privately situated, the luxurious primary suite serves as a tranquil retreat, featuring two walk-in closets—including one with a dedicated vanity—and a spa-inspired bath appointed with radiant heated floors, a double vanity, bidet, private water closet, and designer finishes. Four additional bedrooms, including one en-suite, a beautifully appointed full bath, powder room, and a spacious laundry/mudroom complete the home's thoughtfully designed layout. Outside, the beautifully manicured grounds offer exceptional privacy and an idyllic backdrop for entertaining and relaxation. A rare offering that pairs timeless architecture with contemporary sophistication, this move-in-ready Roslyn Harbor residence presents an extraordinary opportunity to enjoy refined North Shore living just moments from shopping, fine dining, golf courses, country clubs, and major parkways.

3 Engineers Road, Roslyn Harbor
$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 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
$691,100
3 Beds ⋅ 2 Baths ⋅ 1016764 MLS
AUCTION/OCCUPIED. 3- bedroom, 2 bath 1,499 square feet home sitting on 6,200 square foot lot in Glenwood Landing. Home is a short distance from Glen Head LIRR station, 3 different golf courses and Sea Cliff Beach. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or guarantee occupancy status. NO VIEWINGS of this property. Please DO NOT DISTURB the occupant. Buyer is responsible for obtaining possession of the property upon closing.

31 Glenwood Road, Glen Head
$1,990,000
4 Beds ⋅ 3 Baths ⋅ 1015549 MLS
Get ready, the perfect Sea Cliff home is here! Welcome to this idyllic 4-bedroom, 3-bath gem on coveted Lafayette Avenue, right in the heart of prime Sea Cliff. Set on flat land, just blocks from the school and vibrant town, this home offers the lifestyle everyone dreams about; from sunny afternoons by the pool, to unforgettable Halloween nights as nearby Carpenter Avenue fills with laughter, costumes, and neighborhood magic. Warm, welcoming, and full of charm, this is more than a home — it’s the perfect place to make lifelong memories.

73 Lafayette Avenue, Sea Cliff
$21,500,000
10 Beds ⋅ 10 Baths ⋅ 1010319 MLS
Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 33+ 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, four 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 Pound Hollow Road, Old Brookville
$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
$790,000
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 luxurious 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 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

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.