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$2,399,000
6 Beds ⋅ 5 Baths ⋅ 979551 MLS
Welcome to this beautifully transformed Carriage House, where historic charm meets modern living! This impressive main residence offers a spacious open floorplan, featuring three generous bedrooms and 2.5 bathrooms. The heart of the home is illuminated by a stunning wall of windows, flooding the space with natural light and providing gorgeous views of your serene graveled French garden—perfect for entertaining friends or enjoying quiet moments in nature. But that’s not all! Just steps away, you’ll find a Guest House fully renovated and ready for your creative touch. This charming second dwelling is an excellent option for a cozy studio, or an in-law suite. It includes a full kitchen, a sunny sunroom, a handy laundry room, and a half bath on the main floor. Head up the stylish spiral staircase to discover three additional bedrooms and a full bath, offering even more versatile living space. Set on over 2 level acres, this property is a rare find that beautifully combines historic elegance with contemporary comforts, providing you the perfect canvas to create your dream lifestyle. Whether you’re seeking a multi-generational living arrangement or simply a uniquely charming estate to call home, this property invites you to write the next chapter in its wonderful story. Don’t miss out on the opportunity to own this exceptional home that seamlessly blends history and modernity. Tours 24/7

22 Brookville Road, Muttontown
$1,250,000
978154 MLS
This extraordinary 8.5+ acre parcel in the heart of Lattingtown offers a rare opportunity to design and build your dream estate. Set in a prestigious village known for its natural beauty and exclusivity, this expansive property is a blank canvas for creating a private retreat. Work with your own architect, the opportunity to craft a custom home of unparalleled scale and sophistication awaits.

Taylor Court, Locust Valley
$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
$4,475,000
5 Beds ⋅ 9 Baths ⋅ 974091 MLS
A rare offering where tranquil water views meet timeless natural surroundings; Privately positioned at the end of a quiet cul-de-sac and approached by a long treelined drive, 8 Mill Pond Lane is set across nine acres of pristine waterfront with unobstructed views along Mill Neck Creek. Originally built as a builder’s own residence, which has had extensive and comprehensive remodeling by the current owner in recent years, the home reflects a seamless blend of bold contemporary design and modern luxury. Located within the coveted Lattingtown community and the Locust Valley School District, the property offers a rare balance of privacy and accessibility—just moments from renowned yacht clubs, golf courses, private schools and white sandy beaches. Elevated rolling lawns with panoramic waters views and breathtaking sunrise and sunset define the natural scenic setting. Inside you are greeted by soaring ceilings and walls of glass which create a light-filled, seamless indoor/outdoor living concept. Stepping into a grand foyer, you are greeted with a stunning 25-foot great room with stone fireplace. The recently updated chef’s kitchen, complete with dual butler’s pantries, flows effortlessly into formal/informal living and dining spaces designed for both intimate gatherings and flow into indoor/outdoor entertaining. The first-floor primary suite serves as a private sanctuary, featuring vaulted ceilings, a fireplace, and a spa-like bath while capturing waterfront views. The abundantly-lit foyer leads to a sculptural curved staircase taking you to the second level, where three en-suite guest bedrooms, additional living spaces, and a library open to wraparound balconies overlooking expansive vistas. Outdoor amenities include a recently redesigned, heated, saltwater Gunite pool and spa; a dedicated pool bathroom; expansive entertaining areas; and direct kayak access. Completing the offering is a three-car garage with EV charging and discreet interior access to a guest wing with butler’s pantry. A rare opportunity to experience refined waterfront living on Long Island’s Gold Coast— just moments from Locust Valley Village with LIRR connection.

8 Mill Pond Lane, Lattingtown
$3,750,000
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
$8,995,000
6 Beds ⋅ 10 Baths ⋅ 970669 MLS
OFFERS OF $7,000,000 OR GREATER RECEIVED ON OR BEFORE SEPTEMBER 21, 2026 TO BE CONSIDERED. ENTIRE PROPERTY WAS COMPLETELY RENOVATED FROM 2023 T0 2026. Maison Blanche: An Architectural Icon in Upper Brookville Experience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated (2023–2026) masterpiece. The residence features six bedrooms with en-suite bathrooms, four additional half-baths, to include an expansive first-floor primary suite. Architectural highlights include two custom floating staircases with glass railings, porcelain and white oak floors, and frameless full-bodied Belldinni doors. The chef’s kitchens in the main and guest houses are equipped with Wi-Fi-controlled Thermador appliances and specialty quartz islands. Uniquely designed for wellness and entertainment, the second-floor features 3 bedrooms and a private gym and Finnish sauna, while the lower level boasts a Dolby-Atmos theater, wine tasting room, a yoga/massage spa, and a wet bar. Outside, a heated saline pool and spa are framed by a porcelain patio and an unobstructing glass railing, and an outdoor wet kitchen. App-controlled for the modern age, the estate features smart management of the custom steel entry gate, five-zone HVAC, motorized shades, security, and a whole-house generator. This is the new standard of Gold Coast living.

31 Chestnut Hill Drive, Upper Brookville
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 967360 MLS
UPPER BROOKVILLE. Privately set behind sweeping lawns on over two acres in the Village of Upper Brookville, this elegant North Shore residence offers the privacy, scale, and timeless character synonymous with Gold Coast estate living. The home features 4 bedrooms, with primary suite on the main, and 3 full and 2 half baths, along with sun-filled living spaces, hardwood and tiled (radiant heated) floors, where seen, and classic architectural details throughout. A gracious entry leads to beautifully proportioned interiors designed for both everyday comfort and sophisticated entertaining. The formal living room with fireplace flows seamlessly into the dining room and adjoining sun room, creating an inviting setting for gatherings large or small. At the heart of the home, the chef’s kitchen features custom cabinetry, stone countertops, and a generous center island, opening naturally to the main living areas. The first-floor primary suite provides a private retreat complete with a walk in closet and a beautifully appointed bath with soaking tub and oversized shower. Additional bedroom/library on the first floor offers the perfect space for a home office or quiet relaxation. The second level includes additional bedrooms and bath, while the finished lower level offers exceptional entertaining amenities including a home theater, wine cellar, and bar/kitchenette. Outdoors, the property features expansive lawns and patios, mature landscaping, koi pond, fire pit, and an inground heated Gunite pool with detached guest/pool house (featuring full bath, kitchenette, living room with fireplace, and rec area), and 2 outdoor BBQ spaces, creating an ideal setting for summer entertaining and weekend gatherings. Conveniently located to world-class golf courses, equestrian estates, yacht clubs, and the charming villages of Locust Valley, Roslyn, and Manhasset, with Manhattan just a short commute away. A rare opportunity to enjoy refined estate living in the heart of Upper Brookville. Additional features: whole house generator, exterior lighting throughout, built in speakers throughout interior and exterior, 2 car attached heated garage, cul-de-sac location, and more.

1017 Friendly Road, Upper Brookville
$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
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 947764 MLS
BEACHFRONT BLISS on Long Island Sound! Legal 2-family home consisting of 2 separate structures: a 2-bedroom/ 2 bath home plus a separate 1-BR cottage on a single lot! This totally rebuilt residence offers amazing 180-degree views of Long Island Sound with spectacular sunsets and access to the beach right in your own back yard! The cottage offers a fantastic opportunity for an extended family or as a legal income-producing rental. Located in the exclusive Pine Lane HOA, this home is part of the Locust Valley School District and is close to restaurants and boutique shopping. Amenities include a brand-new electrical system, 3-zone gas heat, new appliances, new flooring throughout both homes, a new roof on the cottage, a 5-year roof warranty on the main house, 10-year windows, and exterior steps to the beach. The 1-year renovations include structural reinforcing and waterproofing of the basement. The basement features a high ceiling, a half-bath, and an outside entrance. Long driveway provides room for 4 cars plus cut-out for separate car space. Low taxes: less than $16,000! (Also available for Rent see MLS# 950020)

19 Pine Lane, Bayville
$5,495,000
944325 MLS
Stunning 18-Acre Estate in Lattingtown - A Unique Blend of History and Natural Beauty Discover an exceptional opportunity to own the last major parcel of the historic Underhill Farm, nestled within the prestigious Oyster Bay National Wildlife Refuge. This breathtaking 18-acre property set on two separate buildable approved lots on Factory Pond Road offers over 1,100 feet of pristine waterfront along Mill Neck Creek, providing an unparalleled setting for nature enthusiasts and history buffs alike. Embrace the serenity of this picturesque landscape, featuring a sweeping open field ideal for a variety of uses, from serene pastoral views to expansive gardens. A charming small wooded area adds a touch of tranquility, while mature trees offer privacy and an enchanting natural backdrop. Rich in history, this land was once home to a factory renowned for crafting Revolutionary War uniforms, imbuing the property with a unique historical significance. The legacy of this factory adds an intriguing layer to this already compelling site. This rare piece of real estate combines the allure of a wildlife haven with the charm of historical heritage, all set against the stunning backdrop of Mill Neck Creek. Whether you envision a private estate, a conservation project, or a legacy property, this unparalleled offering is a once-in-a-lifetime opportunity. Seize the chance to own a slice of Lattingtown's storied past and its spectacular natural beauty.

31 Factory Pond Road, Locust Valley
$2,799,000
5 Beds ⋅ 4 Baths ⋅ 938081 MLS
Tucked at the end of a quiet cul-de-sac, this timeless contemporary sits on two perfectly level acres offering exceptional privacy and a deep, usable yard. The property features an in-ground heated pool with a waterfall and beautiful outdoor space ideal for gatherings or relaxation. Inside, the home provides plenty of opportunity with its dramatic ceilings and walls of glass that create a bright, open feel throughout. The sunken living room flows into a dining area with a wet bar. The first floor includes a spacious primary suite, a dedicated home office, and both formal and casual living areas—all thoughtfully laid out and generously proportioned. With its solid foundation and impressive architectural details, this home offers an incredible opportunity to update and customize to your personal style.

7 Pin Oak Court, Old Brookville
$1,190,000
3 Beds ⋅ 3 Baths ⋅ 936207 MLS
Just steps from a private beach, this stunning brick ranch at 9 Oak Shore Drive in Bayville offers quintessential Sound-side living. With three bedrooms and 2.5 baths, the home’s open layout and hardwood floors create an inviting, sunlit atmosphere. The spacious living room, complete with skylights and a gas-burning fireplace, flows to a large eat-in kitchen with tile floors and sliding glass doors that open to a backyard deck—perfect for quick walks to the sand or watching evening sunsets over the water. A recently updated half bath and a main-level full bath with a deep soaking tub and separate shower add modern comfort. The fully finished basement includes a renovated full bath, laundry room, boiler room and exterior egress. Outdoor amenities feature a swimming pool and pool house with a half bath and storage, plus a one-car garage. Embrace a rare opportunity to live just steps from your private beach.

9 Oak Shore Drive, Bayville
$6,000,000
919385 MLS
12.6 Acres of Prime Land for Sale – Planned for 4 Homes – 3-Acre Zoning – Cul-de-Sac Access A rare development opportunity awaits with this 12.6-acre parcel of land, ideally situated at the end of a peaceful cul-de-sac. Zoned for 3-acre minimum lots, this property comes with a concept plan for 4 single-family homes, making it perfect for a small subdivision, custom home builder, or a private family estate. This is a perfect opportunity for developers, builders, or investors looking for a manageable project with strong potential and desirable zoning. With all entrances planned from the cul-de-sac, this layout ensures privacy, safety, and minimal traffic—ideal for a quiet residential enclave.

5694 Northern Boulevard, Muttontown
$1,988,888
7 Beds ⋅ 4 Baths ⋅ 897325 MLS
A Rare Investment Opportunity in the Historic Village of Bayville, NY Nestled in the heart of the Incorporated Village of Bayville, this rare offering presents a once-in-a-lifetime opportunity to own a unique vacation compound just 500 feet from a pristine private beach. Located on Long Island’s North Shore, Bayville has long been a beloved seaside destination for travelers near and far. Originally settled in the 1600s and later incorporated in 1919, Bayville evolved into a charming beach community known for its serene coastal views, laid-back lifestyle, and strong sense of community. Today, it remains a hidden gem—offering the perfect blend of nostalgia, natural beauty, and convenience. This exceptionally unique property features four separate homes on one parcel, totaling 7 bedrooms and 4 bathrooms—making it ideal for a large gathering retreat, income-generating rental property, or private compound. Three of the four cottages have been beautifully renovated with modern finishes while preserving their beachy charm. The fourth cottage is partially renovated, offering the next owner the chance to customize it to their taste. With unobstructed, year-round views of the Long Island Sound, the setting is nothing short of spectacular. Enjoy morning visits to the beach, sunset bonfires, and the peaceful sounds of nature—all just minutes from your front door. Whether you're looking for a peaceful getaway or an investment in one of Long Island’s most picturesque communities, this property delivers Four separate cottages on one parcel 7 bedrooms / 4 bathrooms total Three fully renovated, one partially renovated Approximately 500 feet to private beach access Unmatched, unobstructed views year-round Located in the historic and charming Village of Bayville Create your own legacy on the North Shore—this Bayville retreat offers charm, flexibility, and the lifestyle dreams are made of.

347 Bayville Avenue, Bayville
$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.