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$5,599,000
6 Beds ⋅ 7 Baths ⋅ 1026409 MLS
Introducing an Extraordinary new Construction Estate in the prestigious Village of Muttontown, Set on approximately 3 Private acres overlooking a Picturesque Golf Couse. This Exceptional 2026 built residence offers the perfect blend of Modern Luxury , Elegance, and Sophistication. Featuring Six (6) Spacious Bedrooms and 6.5 designer bathrooms, with Radiant Heated Floors. The home showcases impeccable craftsmanship and high-end finishes throughout. A Grand Entrance welcomes you into a breathtaking Great Room, with soring ceilings, expansive windows, and abundant natural light, creating an impressive setting for both everyday living and entertaining. Designed for comfort and style, the residence includes two fireplaces- One Gas and One Electric, adding warmth and ambiance to the home's thoughtfully designed living spaces. The open and flowing floor plan seamlessly connects formal and informal areas while maximizing the stunning Golf Course Views. Nestled on a beautifully situated 3-acre property, this Magnificent estate offers privacy, tranquility, and resort style living in one of Long Island's most sought after communities. A rare opportunity to own a newly built luxury home in the Heart of Muttontown.

730 Remsens Lane, Muttontown
$12,250,000
7 Beds ⋅ 10 Baths ⋅ 1017340 MLS
This is an exclusive opportunity to own a turn-key Modern Mansion, perfectly positioned on 5 manicured acres on the Gold Coast of Long Island. Constructed in 2022, this designer residence showcases oversized windows, 12ft ceilings, multiple marble gas fireplaces, pocket doors, glass railings and more. Both captivating and secluded, this residence offers the warmth of a traditional home with a contemporary flair. The first floor has a two story foyer, spacious formal living and dining rooms, an office and a lounge with a built-in bar and billiards area. The state-of-the-art modern kitchen is outfitted with top-of-the-line Viking appliances, Neo Marble countertops, numerous pantries and a sweeping center island with bar seating. Off of the kitchen is a beautiful light-filled eating area, with doors leading out to the backyard, an inviting family room and a bespoke homework area/ work space. The main house boasts 6 vast bedrooms, all with en-suite bathrooms and large closets. The Primary Wing is on the first floor and is outfitted with a private sitting room, 2 patios, a laundry area, 'His and Her' spa-like bathroom with a stand-alone tub and two glass enclosed showers, as well as 2 custom walk-in closets, one totaling over 3,000 Sq.Ft. of storage space. Upstairs also features a playroom with a media center, a crafts room, a matted fitness area and a massive flex room over the 8 car attached garage. Additional interior details include 4 stylish powder rooms, an elevator, 2 full service laundry rooms, a whole-house Smart Camera and Alarm System, a central vacuum system, surround sound speakers and an unfinished basement, with an indoor sports court, spanning the entire length of the home. The exterior is fashioned with a gated entry, a long blue stone and pebble driveway, a solid stucco facade, steel windows and decorative metal gutters. The property is elegantly landscaped and has a 60ft x 25ft Saltwater Heated Pool and Hot Tub, a Cabana with a Kitchenette, a fenced-in Dog Run and a covered patio with an outdoor lounge area, great for entertaining. In proximity to The Village of Locust Valley, the LIRR, charming local beaches and some of Long Island's most prominent Country/Golf Clubs. Zoned for the acclaimed Locust Valley Central School District.

199 Lattingtown Road, Locust Valley
$8,975,000
6 Beds ⋅ 9 Baths ⋅ 1011822 MLS
A Legacy Estate of Uncommon Distinction — Buttonball Hill Conceived in 1929 for Vanderbilt heir Aldred Coster Schermerhorn, Buttonball Hill is a masterwork of Georgian architecture set amid sweeping manicured grounds. The classic red brick and clapboard exterior — crowned by a slate roof and crisp black shutters — announces itself with quiet authority. Inside, a double-height foyer with hand-carved moldings and a gracefully curved staircase sets the tone. Soaring ceilings and a natural flow make the principal rooms equally suited to intimate daily living and grand entertaining. The formal living room opens through French doors into a sun-filled solarium; the chestnut-paneled library and cozy den each offer their own fireplace and garden access. The chef’s kitchen is a true centerpiece — expansive and impeccably appointed, with top-of-the-line appliances, custom cabinetry, and generous counter space designed for serious cooking and effortless hosting. Multiple seating areas make it the natural heart of the home: a sun-drenched breakfast nook overlooking the gardens, a sprawling island ideal for casual dining, and a comfortable sitting area perfect for gathering with family and guests. The primary suite is a sanctuary: sitting room, two ensuite baths, fireplace, and a private balcony with sweeping estate views. Outside, a heated pool, Har-Tru tennis court, and beautifully landscaped gardens round out the resort-caliber grounds. A superbly maintained estate where historic soul meets modern ease — minutes from top schools, village amenities, and convenient rail access to the city.

52 Piping Rock Road, Locust Valley
$4,900,000
6 Beds ⋅ 5 Baths ⋅ 1003784 MLS
Enter the wrought iron gates, crowned with classic gas lanterns that cast a warm, welcoming glow and along a private drive, Rolling Meadows reveals itself with the quiet authority of architecture built without haste -a classic brick Georgian residence with stately columns and a slate roof, set amid nine-plus acres of gracious formal gardens and mature specimen trees. Inside, wide plank oak floors create genuine character. A sweeping staircase rises from the entry foyer; the living room and imported Filipino mahogany-paneled library each offer wood-burning marble fireplaces; the formal dining room features a distinct china showcase; and the chef’s kitchen — with its substantial center island and adjoining breakfast room — is designed for both daily living and entertaining. The principal suite is positioned on the main floor, offering exceptional privacy, generous dressing, and a unique ensuite bath. A first-floor guest suite, three additional second floor bedrooms, a substantial bonus room and a three-car attached garage complete the residence. The grounds are as fully realized as the interiors. An Innocenti and Webel pool and dedicated pool house provide an effortless setting for outdoor entertaining. The equestrian facility comprises a seven-stall barn, multiple paddocks and on-site staff quarters. The serious equestrian infrastructure is complemented by a three-car attached garage. There are two additional outdoor garages on the estate. Rolling Meadows is that increasingly rare proposition: a fully equipped country estate where architectural pedigree, equestrian infrastructure, and the warmth of a well-appointed home meet without compromise. A property of this character is best understood in person.

550 Chicken Valley Road, Locust Valley
$25,000,000
13 Beds ⋅ 17 Baths ⋅ 1001064 MLS
Experience Applewood Estate — a generational North Shore compound where timeless architecture, historic provenance, and resort-caliber living unfold across more than 35 secluded acres in the esteemed Village of Upper Brookville. Once an operating apple orchard in the early 1900s and later owned by renowned American artist Montague Flagg, this extraordinary estate carries a legacy as rich as the land itself. Hidden behind a gated, tree-lined approach, the property reveals a breathtaking landscape of rolling lawns, mature specimen trees, formal gardens, peaceful water features, and open meadows designed to evoke the grandeur of Long Island’s historic Gold Coast estates. Inspired by Tudor Cotswold architecture, the compound is a masterclass in cohesive design, blending old-world craftsmanship with modern luxury across multiple residences and lifestyle amenities. The centerpiece is a magnificent custom-built Manor residence encompassing approximately 13,000 square feet of refined living space. Constructed in 2005 with slate, brick, and stone, the home showcases extraordinary craftsmanship through onyx marble accents, oversized parquet flooring, handcrafted iron fireplaces, detailed millwork, and dramatic entertaining spaces throughout. A grand foyer anchored by a sweeping staircase introduces interiors defined by warmth and scale, including a soaring ballroom with 23-foot coffered ceilings, an elegant library loft, meditation room, billiards lounge with wet bar, and a sun-filled eat-in kitchen with breakfast room overlooking the estate grounds. Designed as a true multi-structure compound, Applewood Estate includes several additional residences and guest accommodations, including a beautifully renovated barn residence with attached two-bedroom cottage, an additional two-bedroom cottage, a two-bedroom pool house, a one-bedroom studio, and a meticulously reconstructed circa-1914 stone barn now transformed into a luxurious retreat. Outdoor living is equally exceptional. The estate features a heated swimming pool and spa pavilion, built-in outdoor kitchen, resurfaced tennis court, separate sports court, expansive paddocks, and formal equestrian facilities complete with horse stables and a training ring. Additional highlights include a six-car detached garage, maintenance barn, commercial-grade 150kW generator, and secure gated entry, all thoughtfully integrated into the estate’s serene natural surroundings. Rarely does a property offer this level of acreage, architectural integrity, historical significance, and lifestyle versatility within one of the North Shore’s most coveted enclaves. Applewood Estate is not simply a home — it is a private world crafted for legacy living, grand entertaining, and timeless retreat.

1 Applewood Estate, Upper Brookville
$5,495,000
6 Beds ⋅ 8 Baths ⋅ 985121 MLS
An exceptional private brick estate compound set on approximately 7 meticulously manicured acres in Upper Brookville. This impressive residence offers grand scale, timeless elegance, luxurious landscaping, and a true lifestyle experience both inside and out. Filled with natural light, the home features vaulted ceilings, oversized windows, sweeping property views, 6 spacious bedrooms with en-suite baths, 7.5 baths, large eat-in kitchen with generous counter space and storage, and full finished basement. Designed for both daily living and elevated entertaining, every space offers comfort, presence, and functionality. The meticulously designed grounds create a resort style setting with a custom 22,000 gallon koi pond, custom lighting, newly resurfaced Har-Tru tennis court, heated gunite pool, 8-person hot tub, pool house with kitchenette, full bath and changing room, custom outdoor kitchen, and premium speaker system inside and out. Complete with space for 10-cars, car lifts, and carport, this rare Upper Brookville estate delivers privacy, scale, luxury, and an unmatched indoor and outdoor lifestyle. A rare opportunity to own a private Upper Brookville estate with exceptional amenities and beautifully maintained grounds.

45 Wolver Hollow Road, Upper Brookville
$8,800,000
7 Beds ⋅ 11 Baths ⋅ 973001 MLS
Apple Trees Is A Place Where Time Slows And Life Feels Richer. Down A Winding Drive, Past More Than 15 Private Acres Of Specimen Trees, Flowering Gardens, And Sprawling Lawns, A 1916 Tudor Revival Manor By Renowned Architect Roger H. Bullard Reveals Itself With Quiet Grace. Its Slate Roof And Ornamental Brickwork Glow In The Morning Light, While Ten Fireplaces Warm Rooms Filled With Coffered Ceilings, Hand-Finished Millwork, And Over A Century Of History. Built As A Wedding Gift For Junius Spencer Morgan, Son Of J.P. Morgan, Apple Trees Is A Home With Soul A Home Where Laughter Spills From The Sunroom, Music Drifts From The Grand Piano In The Salon, And Evenings End With Candlelight And Conversation On The Bluestone Patio. Daily Life Here Feels Effortless. Mornings Begin With Sunlight Spilling Through The Greenhouse As Roses And Rhododendrons Stir In The Breeze. Stroll Through Arboretum-Like Grounds, Savor A Match On The Har-Tru Tennis Court, Or Swim Laps In The Gunite Pool. Further Back, A Putting Green And Your Own One-Hole Golf Course Create Moments Of Playfulness And Escape. Evenings Might Bring Wine From The Climate-Controlled Cellar, Dinner Al Fresco Under Century-Old Trees, And Firelight Shared With Friends. Inside, The Estate’s Scale And Details Inspire. Spanning Over 13,000 Square Feet, Apple Trees Offers Far More Than Seven Bedrooms And Seven Full Baths; It Offers A Canvas For A Richly Layered Life. A Mahogany-Paneled Study, A Chef’s Kitchen Built For Bold Meals And Late-Night Stories, And Gracious Entertaining Spaces Framed By Windows That Capture The Beauty Of The Surrounding Grounds. The Boutique-Style Primary Suite Is Its Own Sanctuary, Complete With Dual Baths, A Steam Room, Sauna, Fireplace, And A Dressing Room Designed For Mornings That Matter. The Grounds Are A World Unto Themselves. Specimen Trees, Perennial Gardens, A Greenhouse, And A Barn Nestle Seamlessly Into The Landscape, Believed To Have Been Influenced By The Legendary Olmsted Brothers. These Private Acres Offer Room For Your Next Vision, Whether That Means A Sculpture Garden, A Vineyard, An Outdoor Cinema Beneath The Stars, Or Stables And A Riding Trail. This Is Land That Listens, Ready To Reflect Whatever Inspires You Next. Behind The Scenes, Thoughtful Infrastructure Provides Peace Of Mind. A Whole-Property Gas Generator Supports The Main House, Guest Apartment, And Garage, Ensuring Seamless Continuity In Any Season. The Three-Bedroom Apartment Above The Garage Adds Flexible Space For Guests, Staff, Or Extended Family, Further Enhancing The Estate’s Versatility. Every Inch Of Apple Trees Respects Its History, Yet Nothing Here Is Frozen In Time. Move In And Live Beautifully As-Is Or Reimagine The Home Through Your Own Modern Lens. Its Craftsmanship, Scale, And Setting Are Already In Place The Rest Is Limited Only By Your Imagination. In A World That Moves Too Fast, Apple Trees Doesn’t Chase; It Invites You To Breathe. Here, Luxury Is Not Loud. It Is Quiet Confidence, Permanence, And Provenance Wrapped In Storied Walls And Sunlit Windows. This Is One Of Locust Valley’s Last Great Legacy Estates, Built To Impress In Its Time And Still Breathtaking Today. And Now, It Is Ready For Its Next Chapter.

95 Piping Rock Road, Locust Valley
$3,850,000
6 Beds ⋅ 6 Baths ⋅ 973588 MLS
Tucked away on a serene private road just minutes from the storybook charm of Locust Valley, this Mediterranean-style Colonial is a true estate of distinction. Sited on 5+ pristine acres, seamlessly blends classic elegance with modern luxury. Designed with both grandeur and comfort in mind, the home features two gracious primary suites on the main level, a total of 6 spacious bedrooms, 5 full bathrooms, and one half bath. Soaring 10-foot ceilings enhance the sense of openness throughout, while rich oak hardwood floors provide warmth and sophistication in every room. The heart of the home is a massive chef’s kitchen, thoughtfully appointed for both entertaining and everyday living. A timeless oak-paneled library offers a refined retreat for work or leisure. The layout is perfectly made for making entertaining a seamless, enjoyable experience. Recently renovated, upstairs bathrooms, along with brand new HVAC systems, and a newly constructed three-car garage, ensure turnkey ease and modern comfort. Full partially finished basement, with walkout to outside. "The Last of the Mohicans" on a highly desirable private road in Matinecock, this extraordinary property offers rare privacy and elegance in one of Long Island’s most coveted enclaves. Close proximity to LIRR (train), renowned golf courses, and schools makes this a desired location. A truly unique offering that must be seen to be appreciated.

406 Duck Pond, Locust Valley
$8,937,200
6 Beds ⋅ 12 Baths ⋅ 958234 MLS
660 Chicken Valley Road | Locust Valley, Long Island Gold Coast Positioned within the most coveted enclave of Locust Valley on Long Island’s historic Gold Coast, 660 Chicken Valley Road is not merely a residence—it is a private estate of enduring significance, designed for a highly discerning buyer who values legacy, discretion, and uncompromising quality. Set across approximately 5.33 acres of secluded, manicured grounds and encompassing nearly 16,500 square feet of interior living space, the estate embodies a rare combination of architectural integrity, refined craftsmanship, and long-term asset strength—an offering seldom available in today’s market. Architectural Integrity & Engineering Excellence The residence far exceeds conventional residential standards, delivering exceptional structural durability and long-term stability. Every element—from roofing systems to drainage engineering, from acoustic insulation to thermal efficiency—has been executed to a near commercial-grade level, ensuring the property performs as beautifully as it presents over time. A fully integrated geothermal heating system, paired with advanced climate and humidity control, provides year-round comfort while preserving fine art, furnishings, and materials at an optimal level. Smart home integration allows full remote operation globally, supported by central vacuum, multi-zone climate control, and a whole-house generator—ensuring seamless living without compromise. Security and privacy are paramount, with dual gated access, an extended private drive, and discreet contingency features that elevate the estate to a level of true residential security. Interiors | Bespoke Craft, Quiet Luxury The interior experience is defined not by excess, but by precision. From hand-finished hardwood floors to finely executed crown moldings, each detail reflects a commitment to craftsmanship that is increasingly rare. The kitchen and service areas are appointed with best-in-class appliances—including Wolf, Sub-Zero, and Miele—integrated with custom millwork and carefully selected stone surfaces. These spaces function equally as a private culinary environment and a sophisticated setting for entertaining. The primary suite is conceived as a private retreat, featuring a fireplace, a fully appointed dressing room, and a spa-caliber bathroom with radiant heated floors, a freestanding soaking tub, and a multi-function shower system—delivering a daily experience of understated indulgence. Technology is seamlessly embedded throughout the home, integrating lighting, climate, and security into a unified system that supports effortless, modern living while preserving warmth and timeless character. Grounds | A Private Landscape of Distinction The estate grounds offer a level of scale and privacy rarely achieved. A defining feature is the approximately 2,000-foot cherry blossom-lined drive, creating a seasonal spectacle that transforms the approach into an experience of quiet grandeur—both cinematic and deeply personal. The landscape unfolds with expansive lawns, mature trees, and curated outdoor environments designed for both solitude and large-scale entertaining. Recreational amenities further enhance the lifestyle offering, positioning the estate as a true private resort. Location & Investment Perspective Locust Valley remains one of the most tightly held and supply-constrained markets on the Gold Coast. Properties of this caliber—combining land scale, construction quality, and privacy—are increasingly rare. This offering represents not only a primary or secondary residence, but a strategic long-term asset with strong preservation of value and generational appeal. 660 Chicken Valley Road is not defined by square footage alone, but by what it represents. It is a residence for those who understand that true luxury is not declared—it is recognized. Here, ownership is not simply acquired. It is inherited forward.

660 Chicken Valley Road, Matinecock
$5,585,000
9 Beds ⋅ 12 Baths ⋅ 885874 MLS
Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless elegance with modern comforts. A truly iconic Georgian estate nestled in the heart of Upper Brookville, this 17,587 square feet of total living space, this sprawling residence features 9 bedrooms, 9.555+ bathrooms, 10 wood-burning fireplaces, and exquisite architectural details, including vintage millwork, antique hand-painted wallpaper, and Samuel Yellin wrought-iron gates from the JP Morgan estate. Designed in 1924 by renowned architect James W. O’Connor and landscape architect Robert Ludlow Fowler, Gray Horse Farm is where classic architecture meets nearly 9 acres of pristine, equestrian-ready grounds. Perfectly suited for multigenerational living, the estate includes three separate guest/staff quarters (two 1-bedrooms and one 3-bedroom), offering privacy while staying connected. For those who love to entertain and enjoy the outdoors, the estate features a 20' x 55' heated saltwater pool with a pool house that's fully equipped, tennis and basketball courts, and a secret meditation garden you don't want to miss. For the car enthusiast there's a 7-car garage. Equestrian enthusiasts will appreciate the 3-stall stable, multiple paddocks, and run-in horse shed, all designed for top-tier country living. Additional highlights include a whole-house generator, —all just 27 miles from Manhattan. Whether you're seeking a premier equestrian retreat or an expansive generational compound, Gray Horse Farm delivers an unmatched lifestyle of luxury, privacy, and prestige. A rare offering close to top universities,marinas, beaches, golf, museums and americana shopping!

60 Piping Rock Road, Upper 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.