luxury houses with pool for sale Upper Brookville, United States

Set on two flat, quiet and bucolic acres surrounded by beautiful park-like plantings, mature specimen trees and colorful perennials, this renovated four-bedroom Center Hall Colonial offers serene country setting with exceptional convenience for commuting. A dramatic and elegant entry hall welcomes you with marble flooring and a striking staircase with decorative wrought-iron banister. Just off the foyer is a beautifully appointed full bath featuring custom, high-end porcelain and marble finishes. At the heart of the home is the sleek and stunning eat-in kitchen, thoughtfully designed with two sinks, two dishwashers and a quartzite waterfall center island with seating. GE Café appliances, a French oven and porcelain farmhouse sink complete the sophisticated space. Recessed ceiling lighting and motion-activated floor lighting provide both ambiance and effortless nighttime navigation. Radiant heat adds an additional level of comfort. The spacious formal living room features a wood-burning fireplace with marble surround and an abundance of natural light fro a wall of windows and French doors opening to the bluestone rear patio-ideal for seamless indoor-outdoor entertaining. The sunny formal living room showcases beautiful new wood floors and flows into a private office/den with French doors opening to a covered concrete patio. Upstairs are four bright bedrooms, including a spacious primary en-suite. All bathrooms have been custom designed with luxurious European finishes, including Grohe fixtures, heated towel bars and radiant heat. Outside, the spectacular, level property creates a truly dreamy setting. Expansive lawns, established perrenials and magnificent mature specimen trees surround a fenced, heated Gunite in-ground pool, offering exceptional privacy and a resort-like atmosphere. Numerous recent improvements include new Pella windows throughout, an updated cesspool, roof and plumbing, a new boiler and a full-house generator. Smart-home features allow heating, cooling, washer and dryer functions to be conveniently controlled from your phone. A beautifully renovated home combining timeless elegance, modern amenities and magnificent grounds in an exceptionally peaceful setting.

Introducing An Unparalleled Masterpiece Of Luxury Living On Estate Suited For A Celebrity. This Prestigious And Exclusive Private Brick Compound Situated On 7 Acres Of Lush, Sprawling Grounds In Upper Brookville Offers A Lifestyle That Seamlessly Combines Timeless Elegance With Modern Luxury. Vaulted Ceilings, Creating A Sense Of Openness. Oversized Windows With An Abundance Of Natural Light & Panoramic Views Of The Property. 6 Oversized Bedrooms W/En-Suite Baths, 7 1/2 baths, Large EIK With Generous Counter Space & Storage. For The Car Lover Enthusiast W/10 Car Garage, Top-Of-The-Line Car Lifts & Car Port. Entertainers Exclusive Front & Backyard. Custom-Designed 22,000 Gallon Koi Pond With Thoughtfully Placed Stone Work, Fountains & Lighting. Newly Resurfaced Har-Tru Tennis Court, Gunite Heated Pool, 8 Person Hot Tub, Pool House W/Kitchenette, Full Bath & Changing Room. Custom Outdoor Kitchen, Premium Speaker System Both Inside & Out. Embrace A Lifestyle In Your Private Sanctuary! Google Maps, Waze

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!

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

Set on five magnificent acres of sprawling, level grounds along one of Long Island’s most coveted residential streets, this extraordinary contemporary estate, designed by acclaimed architectural firm Mojo Stumer, represents a sophisticated expression of modern luxury, architectural innovation, and resort-inspired living. Distinguished by dramatic proportions, soaring ceilings, expansive walls of glass, and a seamless connection between indoor and outdoor spaces, the residence offers an exceptional combination of architectural significance, privacy, and grand-scale entertaining. A grand entrance foyer introduces interiors defined by remarkable volume and natural light, leading to a breathtaking double-height great room anchored by a striking marble fireplace. Expansive windows frame picturesque views of the surrounding landscape, enhancing the home's connection to its private, park-like setting. The thoughtfully designed main level features an elegant formal dining room, spacious eat-in kitchen, inviting family room, and sophisticated lounge with a wet bar. A powder room and first-floor laundry provide additional convenience. Occupying a private wing of the main level, the luxurious first-floor primary suite offers an exceptional retreat, complete with a generous his and her walk-in closet and a beautifully appointed bathroom featuring a steam shower. An additional first-floor bedroom with a full bathroom provides ideal accommodations for guests or extended family. The second level features four generously proportioned guest bedrooms complemented by two full bathrooms. Additionally an expansive loft with its own balcony and full bathroom offers a versatile space ideally suited for a private office, additional lounge, or secluded retreat. Designed for recreation, wellness, and entertaining, the expansive lower level features a dramatic double-sided fireplace connecting the game room and entertainment spaces. A spacious recreation area with a wet bar provides the perfect setting for gatherings, while a substantial private gym with its own full bathroom creates a dedicated fitness retreat. Additional accommodations include a staff or guest bedroom and another full bathroom. Beyond the residence sits a remarkable private resort featuring a swimming pool, hot tub, and tennis court. A substantial poolside cabana offers a full indoor kitchen, outdoor wet bar, comfortable lounge, full bathroom, and dedicated laundry facilities. A built-in outdoor grill completes the exceptional entertaining amenities, providing an effortless transition between indoor luxury and outdoor leisure. A four-car garage further complements the estate, providing generous space for automobiles and storage. The property presents a remarkable opportunity to experience architectural distinction, privacy, and an uncompromising lifestyle.

Bold, sophisticated and entirely of the moment, 7 Brookville Road represents a new level of luxury. Set on 2.5+ magnificent acres in Brookville’s prestigious Estate Section, this newly constructed modern estate offers 8,700 square feet under roof. A rare opportunity to own a truly distinctive Brookville residence—thoughtfully designed for an exceptional way of life. Built and designed by Willard Holmes, the residence is dramatic in scale yet refined in every detail. Highlights include two luxurious primary suites, a spectacular chef’s kitchen with separate catering kitchen, and expansive living spaces for relaxed daily living and grand-scale entertaining. Outside, a pool and pool house complete the private retreat. For the discerning buyer seeking an elevated lifestyle, this estate offers room for everyone, with inviting spaces to gather and retreat in privacy. Equally compelling as a year-round residence or an escape from the city, it brings a sense of ease to everyday living.

Built in 2001 and privately set on five pristine acres, this extraordinary estate is a residence of rare character and enduring elegance, blending old-world craftsmanship, architectural drama, and gracious modern living. From richly detailed formal rooms to expansive spaces designed for entertaining, every level reveals another layer of thoughtful design. The home makes an immediate impression with a distinguished foyer featuring classic checkered flooring, where graceful archways establish a sense of symmetry and sophistication. Beyond, the formal living room is beautifully appointed with intricate hardwood floors, a marble fireplace and mantel, and French doors opening directly to the terrace, creating an effortless connection between the interiors and gardens. A formal office boasts distinguished rich hardwood paneling, an intricately finished plaster ceiling, and its own wood-burning fireplace. The formal dining room is equally refined, framed by substantial moldings and anchored by another fireplace—an elegant setting for both intimate dinners and grand-scale entertaining. One of the home's most memorable architectural moments is a discreet curved staircase leading to the dramatic family room. Here, soaring vaulted ceilings, exposed wood beams, and a monumental stone fireplace create a remarkable sense of scale. A concealed door reveals a private wet bar, adding an unexpected and sophisticated element for entertaining. The kitchen and service areas have been conceived with both beauty and function in mind. A handsome butler's pantry features a hand-painted tile backsplash, marble countertops, and abundant preparation space. The expansive farmhouse-inspired eat-in kitchen is finished with warm terracotta floors, two porcelain farmhouse sinks, oversized chef's appliances, a substantial center island, and a sun-filled breakfast area overlooking the grounds. A pantry and discreetly positioned powder room are located just off the kitchen, while a circular rear staircase provides convenient access between levels. A separate side entrance opens to a practical mudroom with an additional service pantry, complete with sink and refrigerator. Ascending to the second floor, an oval wood architectural ceiling crowns a gracious landing overlooking the level below, creating a striking transition to the private bedroom quarters. The secondary accommodations include four generously proportioned bedrooms, one with its own loft space, each appointed with a marble en-suite bath. Near the rear-stair landing, a convenient preparation or household station with sink adds functionality, while a private office provides a dedicated workspace. The primary suite is an extraordinary private retreat. Generous in scale and beautifully secluded, it offers separate dressing rooms and walk-in closets, along with a spa-inspired bath featuring a jetted soaking tub and oversized walk-in shower. An adjoining sitting room creates a quiet sanctuary, with access to a walk-up attic offering additional possibilities. The lower level rivals the principal entertaining spaces in both scale and amenities. Remarkably high ceilings enhance an expansive den and recreation area, complemented by a powder room, full bar, billiards and game room, wine cellar, professionally matted gym, and an impressive 15-seat private theater. Two additional staff or guest rooms, supported by two full baths, complete this exceptionally versatile level. Across the estate's five pristine acres, the grounds unfold as a private resort. Expansive slate and brick terraces provide multiple settings for dining and entertaining, while covered patios framed by graceful archways offer shaded retreats overlooking the property. Beyond, a swimming pool and spa form the centerpiece of the property's recreational amenities, accompanied by a substantial, one-of-a-kind pool house that further elevates the estate's resort-like appeal.

Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a grand living room, banquet-sized dining room, inviting family room, and a serene primary suite with fireplace, sitting area, and generous mirrored closets. A spacious country eat-in kitchen and a lower entertainment level with bar and gym further enhance the home’s appeal. Outdoors, the estate opens to multi-tiered gardens, expansive terraces and patios, an in-ground pool, pool house with full kitchen, 2 full baths and guest quarters, tennis/sport court, golf hole with 3 tee boxes, apple orchard, trellis, and outdoor barbecuing area. A rare offering that captures the privacy, grace, and enduring appeal of the North Shore Gold Coast.

Set amid mature, beautifully landscaped grounds in the coveted Village of Matinecock, this distinguished brick North Shore residence, built in 2006, offers an exceptional combination of scale, craftsmanship, privacy, and resort-inspired living. Rich hardwood floors, substantial millwork, designer wallcoverings, and thoughtfully updated interiors create a home that is at once impressive and inviting. A dramatic, columned double-height foyer with graceful bridal staircases sets an elegant tone upon arrival. The formal dining room is distinguished by a coffered ceiling, while a handsome wood-burning fireplace anchors the spacious den. French doors extend the living spaces to an expansive slate-and-brick terrace overlooking the lush grounds. Designed for both everyday living and effortless entertaining, the eat-in chef’s kitchen features custom cabinetry extending to the ceiling, marble countertops, an oversized center island, generous pantry storage, wine refrigeration, and professional-grade Thermador stainless steel appliances. The first floor primary suite is a private retreat, entered through double doors and appointed with a fireplace, sitting den, two closets, substantial moldings, and an en-suite bath. A formal living room, sunroom with terracotta floors, beautifully appointed laundry room with abundant storage, an elegant powder room, and a bedroom with an attached full bath complete the first floor. Outdoors, the residence unfolds as a private North Shore oasis. The fully fenced 2.06-acre property is framed by mature landscaping and enhanced by multiple fountains and water features. An inviting saltwater swimming pool with an electric cover is framed by handsome slate terraces, while a built-in spa with a cascading waterfall flowing into the pool enhances the resort-like setting. A beautifully designed teak outdoor shower and playset complete an environment equally suited to sophisticated entertaining and leisurely summer days. For the automobile enthusiast or collector, an extraordinary combination of attached and detached garaging accommodates up to eight vehicles - a rare and remarkably versatile offering. Additional amenities include radiant heat beneath tiled areas, central vacuum, whole-house water filtration, natural gas, a generator, integrated audio, Lutron lighting system, seamless speaker systems, and an electric privacy gate at the entrance to the property. The expansive unfinished lower level, with tall ceilings and concrete floors, includes a matted fitness area, provides direct access to the attached garage, and offers substantial storage along with exciting potential for future recreation, wine, or entertainment spaces. Private yet welcoming, refined yet eminently livable, this exceptional Matinecock residence captures the enduring appeal of North Shore estate living, with gracious interiors, expansive grounds, resort-like amenities, and an extraordinary setting designed to be enjoyed in every season. Located within the esteemed Locust Valley Central School District.

Tucked behind a private gated drive and set across over eight pristine acres, this iconic 1916 manor estate has been comprehensively restored and strategically enhanced to meet the expectations of today’s most discerning buyer. Historic architecture remains intact, while modern systems, technology, and amenities have been elevated to a truly exceptional level. Grand formal living and dining rooms feature museum-quality moldings and millwork, offering a refined backdrop for both intimate gatherings and large-scale entertaining. The gourmet kitchen is designed for serious cooking and seamless hosting, flowing naturally into the home’s main living spaces. A striking paneled library with wood-burning fireplace provides a moody, private retreat, while the showstopping 23’ x 44’ great room by Smiros & Smiros commands attention with 16-foot ceilings and a dramatic stone fireplace—engineered for memorable entertaining. The primary suite functions as a true private residence within the home, complete with a separate sitting room, coffee bar, and half bath, a spa-caliber marble bathroom with radiant heated floors, and dual dressing rooms. Five additional en-suite bedrooms, including a fully ADA-accessible suite, along with an office overlooking the gardens, complete the second level. Amenities rival those of a private resort, including a paneled elevator, indoor endless lap pool, catering kitchen, dog spa, a fully refreshed gym, and a discreet panic room / walk-in vault offering an elevated level of security. For the automotive collector, the estate delivers rare flexibility: a heated three-car garage with soaring ceiling heights designed to accommodate lifts for up to six vehicles, complemented by two additional single-car garages. The grounds are equally intentional. A new slate roof, heated gunite pool, Har-Tru tennis court with lighting (recently resurfaced and fenced), putting green, English gardens, playhouse, and curated outdoor lighting create a private, park-like setting designed for year-round enjoyment. Extensive masonry restoration, irrigation repair, landscape clearing, and exterior upgrades have been executed at scale. Behind the scenes, the home has undergone substantial systems modernization, including new and serviced HVAC, complete attic insulation, comprehensive electrical upgrades, restored fireplaces, upgraded pool infrastructure, a fully serviced gate and telecom system, and enterprise-grade security with AI-enabled cameras and property-wide WiFi coverage. The interior has been fully refreshed with newly painted finishes, refinished hardwood floors, custom window screens throughout, and exterior trim replaced with durable Azek for longevity. This is not simply a restored estate—it is a fully realized modern compound, where legacy architecture meets forward-thinking execution

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

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.

A long driveway opens to a large courtyard with a classic fountain, revealing a magnificent Château-style Mansion on 2.03 acres of verdant property on a private cul-de-sac. Custom built for grand entertaining and everyday living, this incredible residence masterfully blends old-world European charm with modern luxury. A majestic 2-story entry foyer features a stunning domed-vaulted ceiling with a curved staircase, showcasing antiqued mirrored panels and an ornate wrought iron railing. Through a series of exquisite arches, the foyer leads to an expansive formal living room with a detailed ceiling and wall-to-wall windows as well as a palatial-sized dining room with a butler’s pantry that offers a wet bar and additional storage. The comfortable family room has a unique curved wall and a marble fireplace flanked by marble goddesses. Adjacent is a sitting room with a floor-to-ceiling built-in display wall and a cozy hexagonal built-in bay window seating area. Next door, an elegant study offers a productive place to work from home. A spectacular chef-inspired kitchen boasts a large breakfast area, dual islands, marble counters, a beautiful ILVE range with a show-stopping backsplash, Wolf, Miele and Sub-Zero appliances, plus an additional service kitchen to ensure effortless hosting. An opulent master suite retreat has a private sitting room with a fireplace, a convenient wet bar with refrigeration, 2 sets of French doors to front and rear balconies, and 2 walk-in closets – both with custom closet systems and one with a generous center island with storage – and features an incredible spa-like bath with a steam shower and a magnificent stand-alone soaking tub. All additional en-suite bedrooms are comfortable with ample walk-in closets and tastefully appointed baths with showers. The lower level is designed with a home gym, expansive recreation space, games area, raised stage, and handsome tufted leather doors leading to a state-of-the-art movie theater. An additional bonus space also offers a bedroom, closet, and a full bath with a shower. Flowing seamlessly outdoors, the lush, park-like property features an expansive bluestone terrace anchored by an outdoor fireplace and a gourmet summer kitchen equipped with a premium built-in grill, integrated refrigeration, and an artisanal pizza oven. Alongside the sparkling heated pool and large sun deck, a gorgeous cabana with a full bath and laundry provides an open yet covered space to relax, while dramatic torches illuminate the pool area at night, creating a resort-caliber experience. This exceptional smart home is complete with a Generac generator, central vacuum, Crestron security system, interior/exterior sound system, sprinkler system, radiant flooring, 3 fireplaces, fine millwork, and a 3-car garage. Just 27 miles from NYC, this French-inspired masterpiece of 5 bedrooms and 8 full baths/4 half baths, offers a tranquil retreat for the discerning buyer who appreciates a Gold Coast luxury lifestyle.

Set on over 2.5 exceptionally private and beautifully landscaped acres in the prestigious Village of Brookville, 25 Old Wheatley Road is a distinguished European-inspired estate offering timeless architecture, impressive scale, and an exceptional indoor-outdoor lifestyle. The residence makes an immediate impression with its masonry exterior, slate rooflines, sculptural chimneys, arched windows and openings, wrought-iron balconies, and beautifully articulated architectural detailing. Projecting bays, dormers, and varied roof forms create depth and character, while a sweeping stone-paved motor court provides an elegant approach to the home and its integrated three-car garage. Inside, the residence is defined by grand proportions, refined finishes, and a thoughtful floor plan designed for both formal entertaining and comfortable everyday living. A gracious central entry hall and gallery establish the main axis of the home, connecting an expansive formal living room, private library, formal dining room, kitchen, breakfast room, and den. The formal living room occupies a substantial wing of the residence and provides an impressive setting for entertaining, while the adjoining library offers a more intimate retreat. At the heart of the home, the kitchen is complemented by a dedicated breakfast room, pantry, mudroom entry, and separate den, creating an ideal balance between elegant entertaining spaces and relaxed daily living. Architectural details throughout the main level add distinction to the interiors, including projecting bays, octagonal room configurations, and expansive window arrangements that bring natural light and views of the surrounding property into the home. The second floor is dedicated to the home’s private bedroom accommodations. The expansive primary suite offers a luxurious retreat with a generously proportioned bedroom, dedicated dressing room, substantial primary bath, private anteroom, and direct access to outdoor terraces. Additional bedrooms are thoughtfully arranged as private suites, each with its own bathroom and individual character. The lower level has been designed as a complete recreation and wellness destination. A spacious entertainment room with bar provides an ideal setting for gatherings, accompanied by a dedicated home theater and gym. A private wellness suite includes a steam room, sauna, shower, changing room, and pool bath, creating a resort-like experience within the residence. Additional guest or staff accommodations, laundry facilities, cedar storage, and extensive service areas further enhance the functionality of the home. The outdoor spaces are equally impressive. Across more than 2.5 acres of mature, meticulously maintained grounds, expansive stone terraces create multiple settings for dining, entertaining, and lounging, while an outdoor kitchen and masonry fireplace establish a sophisticated environment for open-air gatherings. Broad stone steps lead from the upper terrace toward the pool and surrounding gardens, creating a seamless connection between the residence and the landscape. The swimming pool serves as the centerpiece of the outdoor environment, surrounded by natural stone terraces, manicured gardens, mature specimen trees, flowering hydrangeas, clipped hedges, and dense woodland. The acreage and established landscaping provide an extraordinary degree of privacy, giving the property the secluded atmosphere of a true country estate. Combining refined architecture, gracious formal spaces, private bedroom suites, extensive recreation and wellness amenities, and over 2.5 acres of beautifully landscaped grounds, 25 Old Wheatley Road offers a rare opportunity to own a significant estate in the Village of Brookville, one of Long Island’s most distinguished residential enclaves.

Welcome to this commanding five-bedroom contemporary residence, a spectacular home where soaring architecture, abundant natural light, and resort-style amenities combine to create an extraordinary living experience. From the moment you enter the dramatic two-story foyer, you are captivated by three magnificent floor-to-ceiling Palladian windows that frame breathtaking views of the terraced, verdant grounds beyond. The home's impressive two-story ceilings, rich hardwood floors, four fireplaces, and generously proportioned principal rooms create an atmosphere that is both grand and inviting, while seamlessly blending the beauty of the outdoors with every interior space. Designed for both everyday living and elegant entertaining, the home features a stunning culinary kitchen appointed with lacquered cabinetry, dual center islands, and an extraordinary Redwood Triple Glass Conservatory that bathes the space in natural sunlight. After dining in the elegant dinig room enhanced by a fireplace, a comfortable den provides the perfect place to unwind, while a private home office offers an ideal remote work environment. The main-level primary suite serves as a luxurious retreat, complete with a sitting room, spa-inspired bath, and custom-fitted closets. Upstairs, three additional bedrooms are complemented by a welcoming loft with a fireplace—a wonderful gathering space for relaxation and recreation. The home's most exceptional feature awaits on the walk-out lower level: a meticulously maintained heated indoor swimming pool that can be enjoyed year-round, creating a private resort within your own home. Outside, the beautifully terraced landscape is anchored by impressive natural boulders that enhance the property's architectural beauty and park-like setting. A serene, Zen-inspired brook gently winds through the grounds, creating a soothing sense of tranquility, while expansive bluestone patios, an outdoor kitchen, and lush lawns provide the perfect setting for entertaining, recreation, and peaceful reflection. This is a rare opportunity to experience luxury living at its finest. Generator and Level 3EV Charging

Experience pristine living in this exquisite diamond Brookville home, offering unsurpassed value in a highly coveted location. The prestigious approach features a long circular driveway, welcoming you to a serene retreat. The exterior boasts mature specimen plantings and estate fencing encircling a country club style yard with a Gunite inground gas heated pool. The flat entertaining backyard and brick patio, provides ample space to add tennis, pickleball or sport court. This serene oasis is perfect for relaxation and entertainment. Inside the kitchen features hardwood cabinets, complimented by gleaming hardwood flooring throughout the home. The architectural roof adds to the home's timeless elegance. First floor bedroom with en-suite bath and his and hers walk in closets, laundry, and a versatile bedroom/office with a walkout to the fabulous yard. There is so much more to this exceptional property that must be seen to be fully appreciated. Don't miss this rare opportunity to own a true retreat in a serene oasis.

Classic elegance and timeless sophistication define this stately Colonial estate set on approximately 2.73 private acres in the prestigious Village of Muttontown. Offering 6 bedrooms, 6 full bathrooms, and 2 half bathrooms, this exceptional residence showcases a grand center hall foyer, gracious formal entertaining rooms, a spacious chef's kitchen with expansive breakfast area, multiple family and gathering spaces, a private home office, and a luxurious primary suite designed as a private sanctuary complete with dual walk-in closets and a spa-inspired bath. Rich architectural details, generous proportions, and abundant natural light create an atmosphere of refined comfort throughout. Surrounded by beautifully landscaped, park-like grounds, the estate offers a true resort-style lifestyle complete with a heated gunite pool, a three-stall barn, access to preserved nature trails, and serene wooded vistas. Additional highlights include a substantial bonus room, a sprawling lower level offering exceptional recreation and storage space, and a three-car garage. Combining extraordinary privacy, scale, and elegance with the convenience of nearby shopping, dining, transportation, and the highly acclaimed Jericho School District, this remarkable property represents Gold Coast living at its finest.

Beyond a long, tree-lined driveway, an exceptional brick Center Hall Colonial awaits on four private acres in prestigious Old Brookville. Defined by timeless architecture, grand proportions, and resort-caliber amenities, this extraordinary estate embodies the elegance, privacy, and refined lifestyle synonymous with Long Island’s Gold Coast. A dramatic two-story foyer with a sweeping staircase welcomes you into beautifully appointed interiors designed for both grand-scale entertaining and comfortable everyday living. The thoughtfully designed floor plan offers expansive formal and informal living spaces, including a gracious living room that flows seamlessly into the inviting den. At the heart of the home is an exceptional chef’s kitchen, thoughtfully designed with premium appliances, custom cabinetry, expansive workspace, and a generous center island. The kitchen opens effortlessly to the outdoor entertaining spaces, creating a seamless connection between indoor and outdoor living. Step outside to your own private resort, where multiple stone patios, a fully equipped outdoor kitchen, sparkling in-ground pool, and beautifully appointed pool house provide the ultimate setting for entertaining or quiet relaxation, all surrounded by meticulously landscaped grounds and unmatched privacy. The luxurious primary suite serves as a private retreat, complete with a large dressing room and a spa-inspired bath featuring a soaking tub, oversized shower, and refined finishes. Five additional spacious bedrooms, along with seven full bathrooms and three half bathrooms, provide exceptional accommodations. The finished lower level is designed for both recreation and relaxation, offering a custom wine cellar, state-of-the-art home theater, fitness center, expansive recreation room, and abundant storage. Perfectly blending timeless design with modern luxury, this remarkable estate offers an unparalleled lifestyle in one of Old Brookville’s most sought-after locations, where privacy, sophistication, and exceptional entertaining come together in a truly extraordinary setting.

‘Haut Bois’ is a refined brick-and-stucco French chateau nestled in the heart of Brookville, New York. Inspired by the Louis XIV hunting lodge that later became the Palace of Versailles, this extraordinary 18-room estate is steeped in history, elegance, and timeless beauty. Originally built in 1916 by renowned architect Ogden Codman Jr. and meticulously restored in the late 20th century, this one-of-a-kind masterpiece sits at the end of a private road on eight pristine acres. Beyond its wrought-iron gates, a long, tree-lined stone driveway leads to the stately residence, where every detail reflects exceptional craftsmanship and sophistication - from antique stone fireplace mantels and hand-painted wallpaper to crystal chandeliers and bespoke finishes throughout. A grand entrance hall with a sweeping marble staircase welcomes you to the main level. The formal living and dining rooms, each adorned with French doors, open seamlessly to the outdoor entertaining terraces and overlook the breathtaking formal gardens. The chef’s eat-in kitchen features a spacious center island, custom cabinetry, a La Cornue range with matching hood, premium appliances, and granite countertops. Completing the main level are a wet bar, library, den, powder room, and a private guest bedroom with an en-suite bath. Upstairs, the luxurious primary suite offers separate dressing rooms, multiple walk-in closets, and two exquisite marble bathrooms. Three additional generously sized bedrooms, two full baths, and elevator access complete the upper level. The lower level is thoughtfully designed for both recreation and comfort, featuring separate guest quarters, a billiards room, playroom, laundry room, fitness area, spa, and sauna. The basement level includes abundant storage, a temperature-controlled wine cellar, and access to the attached four-car garage. Originally landscaped by famed French architect Jacques Gréber, the grounds are nothing short of spectacular. Highlights include a stunning step-down courtyard, irrigated vegetable garden, gated tennis court, in-ground pool with pool house, chipping and putting green, and an outdoor fireplace and grilling area. Cloaked in ivy and grandeur, and tucked away along Long Island’s storied Gold Coast, ‘Haut Bois’ stands as one of the last remaining architectural treasures of its era.

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

Discover the pinnacle of everyday living where sophistication meets serenity in Old Brookville. Nestled away on its own private and unique compound, this expansive and meticulous ranch boasts 4 bedrooms, 5.5 baths, finished walkout basement. Spacious living areas perfect for entertaining, custom eat-in chef's kitchen boasting top-of-the-line appliances with two islands, granite counter tops, custom cabinetry & storage. Gunite heated pool with new patio and tennis court set amidst 2.4 acres. The 2 story pool house retreat with full kitchen, 2.5 baths & loft. Charming private guest cottage with 2 beds, 1 bath and kitchen, provides an additional space perfect for visitors or extended family. Award-winning North Shore schools, conveniently located to shopping, fine dining, country clubs and prestigious golf courses. This 1-of-a-kind residence offers a lifestyle of unparalleled opportunity, convenience & sophistication. Must see! Google Maps, Waze

Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 15+ acre equestrian estate formally named 'Westward' presents a rare opportunity to acquire a significant piece of North Shore history. Privately nestled amid rolling pastures, mature woodlands, and formal gardens, the estate seamlessly blends timeless architectural elegance with an unparalleled country lifestyle just moments from New York City. Originally commissioned in 1924 for noted industrialist and financier Benjamin Brewster Jennings - President and Chairman of Socony-Mobil and a prominent figure in New York's financial and corporate circles - this Georgian Revival brick residence with a cascading slate roof was masterfully designed by renowned architect Walter B. Chambers. The estate's distinguished landscape plan was created by legendary landscape architect Ellen Biddle Shipman, whose formal gardens and thoughtfully designed grounds continue to define the property's enduring beauty. Approached by a long, tree-lined drive framed by classic stone walls, the stately residence commands a setting of exceptional privacy and serenity. Encompassing three full levels of living space, the home is distinguished by grand entertaining rooms, soaring proportions, multiple wood-burning fireplaces, graceful arched windows, leaded-glass details, and an abundance of natural light. A gracious entrance vestibule opens to a sweeping curved staircase, while expansive formal living and dining rooms provide an elegant backdrop for entertaining on any scale. The 10 bedroom, 9.5 bathroom primary residence also features a spacious eat-in kitchen, indoor spa pool, vast slate patios and an outdoor swimming pool with cabana set against picturesque grounds, providing an idyllic backdrop for outdoor enjoyment. For equestrian enthusiasts, the property offers a turnkey horse facility. The grounds include a well-maintained main barn, run-in sheds (equipped with stalls, water, and electricity), a hot walker, extensive paddocks, and open acreage ideal for riding and grazing. Additionally, this unmatched property includes charming gatehouse cottages, staff apartments, and multiple ancillary structures, most of which have been recently renovated, creating flexibility for guests, caretakers, or income-producing opportunities. Located within one of the North Shore's most prestigious and historically significant communities, the estate enjoys close proximity to Long Island Sound beaches, renowned equestrian facilities, and some of the region's finest private clubs and golf courses. Zoned within the esteemed North Shore Central School District. Rarely does a property of this caliber come to market - offering a remarkable combination of provenance, architectural distinction, equestrian amenities, acreage, and development potential. A legacy estate of exceptional character and enduring significance, representing the very essence of North Shore country living.

Steeped in architectural pedigree and timeless elegance, this extraordinary Muttontown estate, on 3.84 bucolic acres, was designed by renowned architect Marion Sims Wyeth, celebrated for his iconic work on Mar-a-Lago in Palm Beach. Privately tucked behind an impeccably landscaped half mile-long drive off Route 106, the property unfolds as a secluded North Shore sanctuary of exceptional beauty and distinction. Set amidst sweeping lawns, manicured gardens, and picturesque equestrian grounds, the stately brick residence, crowned with a slate roof and introduced by a charming courtyard entry, exudes enduring sophistication. Inside, grand formal entertaining rooms showcase exquisite millwork, original hardwood floors, dramatic wrought-iron railings, and an abundance of French doors that flood the interiors with natural light while seamlessly connecting the home to its breathtaking surroundings. Offering five bedrooms and five-and-a-half baths, the home masterfully balances grandeur with comfort. The formal living room, complete with a fireplace and built-in wet bar, creates an inviting setting for entertaining, while the sunlit breakfast turret and updated chef’s kitchen, appointed with premium professional-grade appliances, provide effortless everyday functionality. A spacious family room and elegant powder room complete the main living spaces. The first-floor primary suite serves as a luxurious private retreat, featuring dual full baths, a fireplace, expansive walk-in closets, and an intimate sitting room. The upper level offers two generously proportioned bedrooms and a beautifully appointed full bath with a thoughtfully separated vanity and shower area. Completing the space is an expansive unfinished attic, presenting exceptional potential for storage or future customization. Additional highlights include a walk-out finished lower level with laundry, bedroom with full bathroom and direct access to the attached two-car garage. Designed for both gracious living and sophisticated entertaining, the residence boasts expansive slate terraces spanning the length of the home, overlooking the stone courtyard driveway, private gardens, charming pergola, and in-ground gunite pool - evoking the romance and refinement of a storybook North Shore estate. A true horse property, the fully fenced equestrian amenities are equally exceptional, featuring a pristine multi-stall barn built-by Morton, thoughtfully designed grazing paddocks, and scenic walking trails woven throughout the grounds. A truly rare offering, this remarkable estate presents an unparalleled opportunity to own a significant piece of Long Island history, all within the esteemed Syosset Central School District.

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.