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Upper Brookville Real Estate

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    • Behold Applewood Estate, an expansive 35+ acre serene property nestled within the prestigious Village of Upper Brookville. This unmatched North Shore architectural masterpiece with 6+ dwellings, offers both grandeur and elegance. The unrivaled property was meticulously designed with professional landscaping, decorated with mature privacy hedges, formal gardens with water features and rolling green lawn space. Rooted in history, this magnificent estate was once an Apple Orchard Farm back in the early 1900’s and was also formerly owned by the celebrated 19th-century American Artist Montague Flagg. The bespoke Main Residence encompasses an impressive 13, 000 Sq.Ft. of living space, was custom built with Slate, Brick and Stone in 2005 and is a testament to high-end design and luxury living. Designer details include Onyx Marble installations, spacious primary rooms, oversized parquet wood floors, handmade iron fireplaces, thick-cut millwork and more. A grand Foyer with a winding staircase, a Great Room with intricate coffered 23 foot ceilings and a magnificent Library loft and a handcrafted Meditation Room, a Billiards/Game room with a Wet-Bar and a Eat-In-Kitchen with a Breakfast Room overlooking the peaceful backyard are just a few of the interior highlights that make this home truly special. Additionally, this unrivaled estate features several detached houses including a 2 Bedroom Colonial Residence and a meticulously reconstructed circa 1914 Stone Barn, now serving as a guest retreat. This distinguished horse-property includes a newly resurfaced tennis court, a separate sports court, a 6-door detached garage, a commercial-grade 150kW generator, a long tree-lined driveway and a secure gated entrance, ensuring peace, beauty and privacy. Equestrian enthusiasts will appreciate the formal horse stables complete with a training ring. The property further boasts a heated in-ground pool pavilion with a jetted jacuzzi spa and a built-in outdoor kitchen, as well as a 1 bedroom Pool House and numerous other refined amenities, making it a Gold Coast sanctuary of relaxation and sophistication. 36
      Applewood Estate Upper Brookville, NY 11545
      $29,900,000
      13 Bedrooms 11 Full Baths 6 Half Baths Sq. Ft. 12892.00:#
      Single Family For Sale ML# 3578383
      Behold Applewood Estate, an expansive 35+ acre serene property nestled within the prestigious Village of Upper Brookville. This unmatched North Shore architectural masterpiece with 6+ dwellings, offers both grandeur and elegance. The unrivaled property was meticulously designed with professional landscaping, decorated with mature privacy hedges, formal gardens with water features and rolling green lawn space. Rooted in history, this magnificent estate was once an Apple Orchard Farm back in the early 1900’s and was also formerly owned by the celebrated 19th-century American Artist Montague Flagg. The bespoke Main Residence encompasses an impressive 13, 000 Sq.Ft. of living space, was custom built with Slate, Brick and Stone in 2005 and is a testament to high-end design and luxury living. Designer details include Onyx Marble installations, spacious primary rooms, oversized parquet wood floors, handmade iron fireplaces, thick-cut millwork and more. A grand Foyer with a winding staircase, a Great Room with intricate coffered 23 foot ceilings and a magnificent Library loft and a handcrafted Meditation Room, a Billiards/Game room with a Wet-Bar and a Eat-In-Kitchen with a Breakfast Room overlooking the peaceful backyard are just a few of the interior highlights that make this home truly special. Additionally, this unrivaled estate features several detached houses including a 2 Bedroom Colonial Residence and a meticulously reconstructed circa 1914 Stone Barn, now serving as a guest retreat. This distinguished horse-property includes a newly resurfaced tennis court, a separate sports court, a 6-door detached garage, a commercial-grade 150kW generator, a long tree-lined driveway and a secure gated entrance, ensuring peace, beauty and privacy. Equestrian enthusiasts will appreciate the formal horse stables complete with a training ring. The property further boasts a heated in-ground pool pavilion with a jetted jacuzzi spa and a built-in outdoor kitchen, as well as a 1 bedroom Pool House and numerous other refined amenities, making it a Gold Coast sanctuary of relaxation and sophistication.
      Presented By: Daniel Gale Sothebys Intl Rlty  516-466-4036
      Call Today: or  Email: Daniel Gale Assoc Inc
    • The seller is willing to hold the mortgage to a qualified buyer. Located in a gated community in Upper Brookville, this 10, 000-square-foot majestic Gold Coast estate welcomes you with a circular driveway, soaring ceilings, and a grand double staircase. This luxurious home boasts a balcony on the second floor, a raised panel mahogany ceiling, and built-in cabinets and bookcases. It contains a Chef’s custom eat-in kitchen with double all Wolf appliances. This Estate features six fireplaces. All bedrooms enjoy en suite baths. The Main bedroom has four closets and an en suite bath with a fireplace, jacuzzi, and an enormous walk-in shower. The main house has seven elegant bedrooms, nine full baths, and two half baths. For the car lover, there is a three-car garage attached to the main house and a nine-car detached garage with heat and air conditioning. Over the detached garage, there is an elegant one-bedroom apartment. The basement contains a state-of-the-art media room, a 1200-bottle wine cellar, perfect for the collector or investor, a humidor for the cigar smoker, a game room, and a gym for those who enjoy staying fit at home. The full-house generator ensures uninterrupted power for this five-acre estate. For all those who appreciate nature, this home enjoys a garden that contains a variety of unique trees, vegetable gardens, and marvelous sprawling lawns. The Olympic pool is complemented by a pool house, a one-bedroom guest cottage, two outdoor kitchens, and a travertine patio for dining. Summer fun can be enjoyed by playing tennis and basketball, visiting nearby beaches, and enjoying North Shore luxury and amenities. 36
      9 Colonial Drive Upper Brookville, NY 11545
      $8,499,900
      9 Bedrooms 11 Full Baths 2 Half Baths Sq. Ft. 10000.00:#
      Single Family For Sale ML# 3559974
      The seller is willing to hold the mortgage to a qualified buyer. Located in a gated community in Upper Brookville, this 10, 000-square-foot majestic Gold Coast estate welcomes you with a circular driveway, soaring ceilings, and a grand double staircase. This luxurious home boasts a balcony on the second floor, a raised panel mahogany ceiling, and built-in cabinets and bookcases. It contains a Chef’s custom eat-in kitchen with double all Wolf appliances. This Estate features six fireplaces. All bedrooms enjoy en suite baths. The Main bedroom has four closets and an en suite bath with a fireplace, jacuzzi, and an enormous walk-in shower. The main house has seven elegant bedrooms, nine full baths, and two half baths. For the car lover, there is a three-car garage attached to the main house and a nine-car detached garage with heat and air conditioning. Over the detached garage, there is an elegant one-bedroom apartment. The basement contains a state-of-the-art media room, a 1200-bottle wine cellar, perfect for the collector or investor, a humidor for the cigar smoker, a game room, and a gym for those who enjoy staying fit at home. The full-house generator ensures uninterrupted power for this five-acre estate. For all those who appreciate nature, this home enjoys a garden that contains a variety of unique trees, vegetable gardens, and marvelous sprawling lawns. The Olympic pool is complemented by a pool house, a one-bedroom guest cottage, two outdoor kitchens, and a travertine patio for dining. Summer fun can be enjoyed by playing tennis and basketball, visiting nearby beaches, and enjoying North Shore luxury and amenities.
      Presented By: Signature Premier Properties  631-368-6800
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Discover Residenza Di Serenita An Exquisite Estate Where Luxury Meets Tranquility, Just 45 Minutes Outside Of Manhattan. Located On Prestigious Pine Valley Road In Upper Brookville, Offers A Harmonious Blend Of Elegance And Modern Living. As You Enter Through The Grand Two-Story Marble Foyer, The Gentle Shimmer Of A Restored French 100-Year-Old Antique Crystal Chandelier Welcomes You. The Expansive Family Room, Adorned With A Fireplace, Flows Seamlessly Into A Gourmet Chef’s Kitchen Featuring Top-Of-The-Line Appliances, A Stunning Brick Pizza Oven, And An Oversized Center Island-Perfect For Culinary Adventures And Unforgettable Gatherings. The Opulent Primary Suite Serves As A Tranquil Sanctuary With Soaring Ceilings, A Cozy Fireplace, And A Private Terrace Overlooking Beautifully Landscaped Grounds. Six Additional En-Suite Bedrooms Provide Comfort And Elegance For Family And Guests, Ensuring Everyone Feels At Home. Step Outside To Your Backyard Oasis, Complete With A Shimmering Fully Tile Pool, Inviting Spa, And State-Of-The-Art Outdoor Kitchen Equipped For Summer Barbecues And Alfresco Dining. Gather Around The Gas Fire Pit Under The Stars, Surrounded By Enchanting Landscapes That Set The Perfect Ambiance For Evening Entertaining. Entertainment Options Abound In The Finished Basement, Featuring A Media Room, Fitness Center, Steam Shower, And Direct Access To The Backyard, Creating Seamless Indoor-Outdoor Flow. Located Near Esteemed Golf And Country Clubs, This Estate Provides An Unmatched Lifestyle Of Luxury, Leisure, And Convenience. Experience The Epitome Of Refined Living At Residenza Di Serenita, Where Every Detail Has Been Thoughtfully Curated To Elevate Your Lifestyle. Don’t Miss Your Chance To Make This Extraordinary Estate Your Own! 36
      Upper Brookville, NY 11771
      $7,950,000
      7 Bedrooms 7 Full Baths 1 Half Bath
      Single Family For Sale ML# 3583754
      Discover Residenza Di Serenita An Exquisite Estate Where Luxury Meets Tranquility, Just 45 Minutes Outside Of Manhattan. Located On Prestigious Pine Valley Road In Upper Brookville, Offers A Harmonious Blend Of Elegance And Modern Living. As You Enter Through The Grand Two-Story Marble Foyer, The Gentle Shimmer Of A Restored French 100-Year-Old Antique Crystal Chandelier Welcomes You. The Expansive Family Room, Adorned With A Fireplace, Flows Seamlessly Into A Gourmet Chef’s Kitchen Featuring Top-Of-The-Line Appliances, A Stunning Brick Pizza Oven, And An Oversized Center Island-Perfect For Culinary Adventures And Unforgettable Gatherings. The Opulent Primary Suite Serves As A Tranquil Sanctuary With Soaring Ceilings, A Cozy Fireplace, And A Private Terrace Overlooking Beautifully Landscaped Grounds. Six Additional En-Suite Bedrooms Provide Comfort And Elegance For Family And Guests, Ensuring Everyone Feels At Home. Step Outside To Your Backyard Oasis, Complete With A Shimmering Fully Tile Pool, Inviting Spa, And State-Of-The-Art Outdoor Kitchen Equipped For Summer Barbecues And Alfresco Dining. Gather Around The Gas Fire Pit Under The Stars, Surrounded By Enchanting Landscapes That Set The Perfect Ambiance For Evening Entertaining. Entertainment Options Abound In The Finished Basement, Featuring A Media Room, Fitness Center, Steam Shower, And Direct Access To The Backyard, Creating Seamless Indoor-Outdoor Flow. Located Near Esteemed Golf And Country Clubs, This Estate Provides An Unmatched Lifestyle Of Luxury, Leisure, And Convenience. Experience The Epitome Of Refined Living At Residenza Di Serenita, Where Every Detail Has Been Thoughtfully Curated To Elevate Your Lifestyle. Don’t Miss Your Chance To Make This Extraordinary Estate Your Own!
      Presented By: Compass Greater NY LLC  516-703-3360
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Chateau de L’ Amour is an immaculate 10, 500 Sq.Ft. estate located within the heart of Upper Brookville, New York. Fully redesigned in 2023, this bespoke Gold Coast showpiece boasts unmatched interior customizations including thick-cut millwork, unique parquet floors, stained glass windows, round-top doors, coffered ceilings and hand-carved staircases. At 7 Bedrooms and 7.55 Bathrooms, this residence features multiple formal entertaining rooms, beautiful stone gas fireplaces, a finished walk-out basement and a sunlit eat-in-kitchen with marble countertops, Butler’s Pantry, Viking and True Kitchen Appliances and a round, sunlit Breakfast nook. The spacious Primary Wing has tall ceilings, a sizable walk-in closet and a luxurious ’His & Hers’ marble en-suite bathroom with a freestanding tub. An exceptional piece of North Shore architecture, the exterior of the home was masterfully constructed with brick, stone, slate and cedar shake. The 5+ acre property features a private electric gate, Porte Cochere, 4 Car Attached Garage, professionally landscaped gardens, a heated Salt Water Pool & Spa, a built-in firepit and a detached poolside cabana with a brand new center-island kitchen. Located close to esteemed Golf/Country Clubs, the vibrant village of Locust Valley and the LIRR. 35
      35 Chestnut Hill Drive Upper Brookville, NY 11771
      $5,980,000
      7 Bedrooms 7 Full Baths 2 Half Baths Sq. Ft. 10500.00:#
      Single Family For Sale ML# 3561364
      Chateau de L’ Amour is an immaculate 10, 500 Sq.Ft. estate located within the heart of Upper Brookville, New York. Fully redesigned in 2023, this bespoke Gold Coast showpiece boasts unmatched interior customizations including thick-cut millwork, unique parquet floors, stained glass windows, round-top doors, coffered ceilings and hand-carved staircases. At 7 Bedrooms and 7.55 Bathrooms, this residence features multiple formal entertaining rooms, beautiful stone gas fireplaces, a finished walk-out basement and a sunlit eat-in-kitchen with marble countertops, Butler’s Pantry, Viking and True Kitchen Appliances and a round, sunlit Breakfast nook. The spacious Primary Wing has tall ceilings, a sizable walk-in closet and a luxurious ’His & Hers’ marble en-suite bathroom with a freestanding tub. An exceptional piece of North Shore architecture, the exterior of the home was masterfully constructed with brick, stone, slate and cedar shake. The 5+ acre property features a private electric gate, Porte Cochere, 4 Car Attached Garage, professionally landscaped gardens, a heated Salt Water Pool & Spa, a built-in firepit and a detached poolside cabana with a brand new center-island kitchen. Located close to esteemed Golf/Country Clubs, the vibrant village of Locust Valley and the LIRR.
      Presented By: Daniel Gale Sothebys Intl Rlty  516-466-4036
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Welcome to GRAY HORSE FARM! This magnificent iconic equestrian estate on desirable Piping Rock Road is situated on 9 gorgeous acres and offers 13, 324 square feet of gracious living with 10 bedrooms, 7.555 baths and 10 fireplaces, plus beautiful apartments, exquisite 20’ x 55’ pool and pool house with kitchen and full bath , stable, paddocks, run-in horse shed, tennis and sports courts. The impressive scale of the home is enhanced by vintage millwork, antique hand-painted wallpaper, and priceless Samuel Yellin front gates from the JP Morgan estate. Built in 1924 and designed by architect James W. O’Connor and landscape architect Robert Ludlow Fowler, this classic brick Georgian Colonial resonates with old-world charm and grace and boasts a slate roof. Original architectural details provide the perfect canvas for a modern lifestyle and exceptional entertaining. Renovations include the apartments, pool, pool house, tennis court, and HVAC system, ready for you to make this home your own spectacular residence! Part of Locust Valley School District, convenient to private schools, fine dining, Americana shopping, 27 miles to Manhattan. Equestrian’s delight! keep your favorite horses near you! 7-car garage, 600-AMP electrical service, whole house generator. Must see Special Features and video of antique wall covering- (click virtual tour link above to view). Taxes are being grieved., Additional information: Appearance:Excellent, ExterioFeatures:Tennis, Interior Features:Guest Quarters, Lr/Dr, Marble Bath, Separate Hotwater Heater:yes 36
      60 Piping Rock Rd Upper Brookville, NY 11545
      $5,890,000
      10 Bedrooms 7 Full Baths 3 Half Baths Sq. Ft. 13324.00:#
      Single Family For Sale ML# 3554087
      Welcome to GRAY HORSE FARM! This magnificent iconic equestrian estate on desirable Piping Rock Road is situated on 9 gorgeous acres and offers 13, 324 square feet of gracious living with 10 bedrooms, 7.555 baths and 10 fireplaces, plus beautiful apartments, exquisite 20’ x 55’ pool and pool house with kitchen and full bath , stable, paddocks, run-in horse shed, tennis and sports courts. The impressive scale of the home is enhanced by vintage millwork, antique hand-painted wallpaper, and priceless Samuel Yellin front gates from the JP Morgan estate. Built in 1924 and designed by architect James W. O’Connor and landscape architect Robert Ludlow Fowler, this classic brick Georgian Colonial resonates with old-world charm and grace and boasts a slate roof. Original architectural details provide the perfect canvas for a modern lifestyle and exceptional entertaining. Renovations include the apartments, pool, pool house, tennis court, and HVAC system, ready for you to make this home your own spectacular residence! Part of Locust Valley School District, convenient to private schools, fine dining, Americana shopping, 27 miles to Manhattan. Equestrian’s delight! keep your favorite horses near you! 7-car garage, 600-AMP electrical service, whole house generator. Must see Special Features and video of antique wall covering- (click virtual tour link above to view). Taxes are being grieved., Additional information: Appearance:Excellent, ExterioFeatures:Tennis, Interior Features:Guest Quarters, Lr/Dr, Marble Bath, Separate Hotwater Heater:yes
      Presented By: Compass Greater NY LLC  516-551-5241
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with Waterfall, Gazebo, Koa Pond, Bocce Court & Generator. A Must See 27
      5 Peacock Lane Upper Brookville, NY 11545
      $3,699,000
      5 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Sale ML# 3574927
      Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with Waterfall, Gazebo, Koa Pond, Bocce Court & Generator. A Must See
      Presented By: Douglas Elliman Real Estate  516-759-0400
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Discover Luxury Living on the Gold Coast of Long Island in this pristine, recently renovated Farm Colonial, nestled on just over 2 Acres at the end of a long, private driveway on prestigious Wolver Hollow Road. This Sun-filled gem exudes charm and luxury, boasting opulent moldings with granite accents, along with hardwood floors throughout. The eat-in-kitchen features sleek cabinetry with built-ins and stunning marble countertops, perfect for both culinary adventures and casual family gatherings. The expansive family room, with its vaulted and large windows, offers impeccable views of the vast property and includes a large wood-burning fireplace as the centerpiece of this open-concept floor plan. On the first level, you’ll also find a formal living room, dining room, half bath, and entertainment room-perfect for hosting guests. The full basement provides additional living space, laundry, and ample storage. Upstairs, the primary bedroom is a sanctuary with built-ins, a sizable marble bathroom, and a walk-in closet. Another large bedroom includes an ensuite bathroom, and generous-sized additional bedrooms offer comfort, with one featuring a staircase leading to a unique loft or attic area. Generator, Propane, Roof 2yrs., French Drain, Granite Walkway, plus 27-Zone Inground Sprinkler system, and more. With taxes, including village, at just $20, 000, this marvel won’t last long. Don’t miss your chance to experience luxury living in Upper Brookville., Additional information: Appearance:Immaculate, Interior Features:Marble Bath, Separate Hotwater Heater:Y 24
      100 Wolver Hollow Rd Upper Brookville, NY 11545
      $1,749,000
      $1,625,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Sale PRICE REDUCED ML# 3580392
      Discover Luxury Living on the Gold Coast of Long Island in this pristine, recently renovated Farm Colonial, nestled on just over 2 Acres at the end of a long, private driveway on prestigious Wolver Hollow Road. This Sun-filled gem exudes charm and luxury, boasting opulent moldings with granite accents, along with hardwood floors throughout. The eat-in-kitchen features sleek cabinetry with built-ins and stunning marble countertops, perfect for both culinary adventures and casual family gatherings. The expansive family room, with its vaulted and large windows, offers impeccable views of the vast property and includes a large wood-burning fireplace as the centerpiece of this open-concept floor plan. On the first level, you’ll also find a formal living room, dining room, half bath, and entertainment room-perfect for hosting guests. The full basement provides additional living space, laundry, and ample storage. Upstairs, the primary bedroom is a sanctuary with built-ins, a sizable marble bathroom, and a walk-in closet. Another large bedroom includes an ensuite bathroom, and generous-sized additional bedrooms offer comfort, with one featuring a staircase leading to a unique loft or attic area. Generator, Propane, Roof 2yrs., French Drain, Granite Walkway, plus 27-Zone Inground Sprinkler system, and more. With taxes, including village, at just $20, 000, this marvel won’t last long. Don’t miss your chance to experience luxury living in Upper Brookville., Additional information: Appearance:Immaculate, Interior Features:Marble Bath, Separate Hotwater Heater:Y
      Presented By: Nest Seekers LLC  516-922-2878
      Call Today: or  Email: Daniel Gale Assoc Inc
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