Refine Search
Sort by
$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

$2,995,000
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

$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

$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

$6,850,000
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

$849,000
4 Beds 2 Baths 986170 MLS
Step into timeless charm with this 1888 Colonial, where classic character meets everyday comfort. A welcoming front porch sets the tone—perfect for morning coffee or relaxing evenings. Inside, the living room offers a warm and inviting space centered around a gas fireplace, creating the ideal spot to gather on cooler nights. A large den adds flexibility. The formal dining room provides for entertaining, while the kitchen features a center island, ample cabinetry, and room to cook, connect, and enjoy daily life. Plus there is a Full Bath & Office. Upstairs, you’ll find two bedrooms filled with natural light, along with a full bathroom. The home also includes a full basement offering storage and laundry. Outside, a detached garage provides added functionality, while the yard is designed for both relaxation and entertaining, complete with a patio and a charming fire pit area.

75 Grove Street, Glenwood Landing

$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

$1,850,000
5 Beds 4 Baths 943383 MLS
This one-of-a-kind home combines modern style, thoughtful design, and custom craftsmanship throughout. The main level features a welcoming entry foyer, a formal living room with fireplace, dining room, and a spacious, open kitchen with a wood-burning stone fireplace. A main-level bedroom with full bath, powder room, and family room complete the floor. Upstairs, the primary suite is a modern retreat with double sinks, a spa-style bathtub, and a large walk-in shower. Two additional bedrooms share a Jack-and-Jill bath and a fifth bedroom in the loft area. Custom wooden staircases and design elements give the home warmth and character. The fully finished basement includes expansive storage and a laundry area. Modern amenities abound: 3-zone central heat and air, radiant heat in first-floor living areas, solar panels with an extra battery functioning as a generator, indoor and outdoor cameras, tesla charger, and a speaker system in the living room, dining room, kitchen, and primary bath. Outside, enjoy a putting green, Japanese style dry garden, and turf yard- all low-maintenance for easy living. The expansive driveway accommodates multiple cars. Every inch of this home was thoughtfully customized, creating a modern, stylish space that’s both functional and cool, ideal for today’s lifestyle.

3 Maple Street, Glenwood Landing

$2,099,000
4 Beds 3 Baths 920526 MLS
Exceptional Custom-Built Colonial in the Heart of Glen Head Don’t miss this rare opportunity to own a truly one-of-a-kind custom-built home in the desirable Glen Head community. Thoughtfully designed and built with no expense spared, this residence is a masterpiece of quality craftsmanship, luxury finishes, and modern functionality — far beyond basic or “just to code.” Step into a grand center hall colonial featuring a dramatic entry foyer, stunning custom white oak flooring, and intricate moldings throughout. The expansive open-concept layout flows seamlessly into a gourmet chef’s eat-in kitchen, complete with a massive 2” quartz island, top-of-the-line GE Cafe appliances, LED lighting, and custom cabinetry — ideal for everyday living and entertaining. Unmatched Construction & Features: Radiant heat throughout all levels, including the basement, Superior 2"x6" framing and steel beam construction, 10' ceilings on lower level, 9' on main and 8' upstairs, One-foot-thick foundation for durability and insulation. All principal rooms are generously sized, filled with natural light, and designed for both comfort and elegance. Outside, enjoy your private backyard oasis with a beautiful in-ground pool featuring a smart filtration system and automated retractable cover, plus a sleek outdoor kitchenette area — perfect for relaxing and entertaining year-round. All perfectly situated on over a quarter-acre of manicured property in a prime location. This home is a rare gem offering the perfect blend of timeless design and cutting-edge construction.

9 Hill Drive, Glen Head

$5,490,000
6 Beds 6 Baths 845880 MLS
Where Drama Meets Design Welcome to nearly 8,000 square feet of pure fabulous in one of the North Shore’s most prestigious enclaves. This newly reimagined estate has been transformed from top to bottom in the last 24 months, creating a home that is equal parts glamorous, playful, and unforgettable. From the moment you step inside, you’re swept into a world of high style and high impact. The soaring ceilings set the stage, while bold architectural details and designer finishes bring a sense of drama to every room. The custom chef’s kitchen is as functional as it is stunning—perfect for hosting everything from cozy family dinners to glamorous cocktail parties. Every detail was designed to delight. The pink laundry room will make you smile every time you walk in, and the sleek, sophisticated man bar is party-ready for unforgettable nights with friends. Every corner of this home tells a story of creativity, luxury, and fun. Step outside and it only gets better. The grounds are your private resort: a sparkling pool glistening in the sun, a full tennis court for a quick match, and beautifully landscaped gardens that feel like your own private park. Whether you’re entertaining on a grand scale or enjoying quiet evenings under the stars, this property delivers it all.

89 Pound Hollow Road, 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.