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$8,995,000

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.

5 Beds ⋅ 12 Baths ⋅ 1031340 MLS

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.

7 Covey Court, Upper Brookville

$3,500,000

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.

5 Beds ⋅ 5 Baths ⋅ 1018330 MLS

Dream homes do exist. Perfectly situated on 2+ private, meticulously landscaped acres on a winding country lane, this charming 5-bedroom residence offers an unparalleled lifestyle. Every sun-drenched room provides stunning, expansive views of lush lawns, specimen trees, and vibrant perennial gardens. Exquisite Craftsmanship & Main Level Living. The main level showcases exceptional millwork, fine moldings, and rich hardwood flooring. A vaulted foyer welcomes you, leading to an elegant music room, a spacious living room, and a handsome cherry library with custom built-ins. The gourmet kitchen features premium appliances and custom Wood-Mode cabinetry, overlooking your private backyard oasis. A thoughtfully placed butler’s bar with a Sub-Zero wine cooler connects the kitchen to the formal dining room for seamless entertaining. A first-floor bedroom with a private en-suite bath is ideal for guests or multi-generational living. The second level hosts four additional bedrooms. The serene primary suite features a luxurious en-suite bath. Two additional bedrooms boast private en-suite baths, while the fourth bedroom enjoys access to a well-appointed hall bath. Step outside to your private resort, featuring an expansive deck that overlooks a heated, saltwater gunite pool. The entire property is fully fenced, private, and beautifully framed by mature landscaping. Car enthusiasts and organizers will love the two separate garages: a convenient main-level attached garage near the mudroom/kitchen, plus a second 2-car garage/storage area at the basement level. A massive, unfinished basement offers endless customization potential and features a direct walk-out entrance to the pool area. Enjoy the perfect balance of privacy and convenience. Located just moments from the village, this home offers an excellent commute while placing you in the highly coveted North Shore School District.

61 Linden Lane, Upper Brookville

$5,288,000

A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a two-story entryway, a luxurious primary suite on the main level, a free-form inground heated gunite pool with a waterfall, a covered outdoor kitchen, and a 3-car garage. Luxurious living with hidden privacy and easy access.

6 Beds ⋅ 7 Baths ⋅ 1010689 MLS

A Private Oasis in Upper Brookville. Timeless elegance prevails in this custom-built, majestic brick 6-bedroom, 6.5-bath manor home in Upper Brookville. Masterfully set at the end of a cul-de-sac, a private driveway leads to a spacious courtyard and impressive, stately residence set on 6 prime, serene acres. For a qualified buyer, this is an exceptional opportunity. Many many features include: a two-story entryway, a luxurious primary suite on the main level, a free-form inground heated gunite pool with a waterfall, a covered outdoor kitchen, and a 3-car garage. Luxurious living with hidden privacy and easy access.

7 Fairway Court, Upper Brookville

$25,000,000

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.

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

$4,000,000

Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Beautifully appointed with crisp white cabinetry, honed Absolute Black granite countertops, top-of-the-line appliances, and radiant heated floors, the kitchen flows effortlessly into the informal dining area and family room, complete with a raised-hearth stone fireplace. Additional highlights include pristine condition throughout, Newly painted and redone guest quarters, separate living and dining rooms, and a separate hot water heater., New generator, new gas line (2025), House newly painted and redecorated and grounds re landscaped. The Property in Spring is filled with an abundance of color with the Hellebores, Azaleas, Rhododendron. It is private and magical.

4 Beds ⋅ 4 Baths ⋅ 955669 MLS

Move right into this stunning four-bedroom ranch residence set on 5.5 beautifully landscaped acres. Thoughtfully updated and impeccably maintained, this light-filled home offers an open-concept floor plan designed for today’s modern lifestyle. There is an updated one bedroom guest cottage and a separate office. Built on one level, the home showcases expansive floor-to-ceiling windows and doors that frame picturesque garden views and flood the interiors with natural light. The gracious living and dining areas are anchored by a striking double-sided stone fireplace, creating architectural interest and a warm, inviting ambiance. A sophisticated bar room with wine refrigeration and custom painted cabinetry enhances the cozy den, offering the perfect setting for entertaining. The expansive kitchen and family room serve as the heart of the home, featuring a dramatic double-height vaulted ceiling with loft above and seamless access to a side terrace ideal for outdoor dining and gatherings. Beautifully appointed with crisp white cabinetry, honed Absolute Black granite countertops, top-of-the-line appliances, and radiant heated floors, the kitchen flows effortlessly into the informal dining area and family room, complete with a raised-hearth stone fireplace. Additional highlights include pristine condition throughout, Newly painted and redone guest quarters, separate living and dining rooms, and a separate hot water heater., New generator, new gas line (2025), House newly painted and redecorated and grounds re landscaped. The Property in Spring is filled with an abundance of color with the Hellebores, Azaleas, Rhododendron. It is private and magical.

343 Chicken Valley Road, Upper Brookville

$5,495,000

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.

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

$5,585,000

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!

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