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Upper Brookville Real Estate

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    • Nestled in the prestigious Chestnut Hill Estate Section of Upper Brookville and overlooking the esteemed Mill River Golf Club, this extraordinary oasis offers unparalleled luxury and sophistication. This magnificent home boasts 7 bedrooms and 13 bathrooms, Spanning nearly 11, 000 square feet of pure luxury and set on over 5.25 acres of meticulously landscaped grounds with specimen trees and plantings, this residence epitomizes elegance and grandeur. A double-height entry foyer creates a dramatic entrance, providing a stunning view of the indoor pool upon arrival. The expansive gourmet chef’s kitchen features dual center islands, custom cabinetry, and top-of-the-line appliances. The grand formal dining room comfortably seats 14, making it ideal for lavish gatherings. The deluxe primary suite is a serene retreat with views of the indoor pool and offers dual en-suite bathrooms and expansive walk-in closets. A sophisticated library, perfect for a home office, also offers pool views, and features a warm fireplace, high ceilings, rich mahogany detailing, and a spiral staircase leading to the lower level. Inside, unparalleled amenities include a fitness center and world class spa with a sauna, steam and massage room, a state-of-the-art home theater, bowling alley and a billiard room, ensuring endless entertainment options. Outside, enjoy the outdoor pool with a relaxing waterfall feature and a private tennis court. Designed for grand-scale entertaining, this estate offers expansive living areas and outdoor terraces perfect for hosting memorable gatherings. Security and privacy are paramount, with a gated entrance and advanced security systems. Warm and inviting yet grand and impressive, this exceptional estate offers the epitome of luxury living in an exclusive Upper Brookville sanctuary. Experience unmatched sophistication and elegance in this one-of-a-kind property. 29
      43 Chestnut Hill Drive Upper Brookville, NY 11771
      $9,950,000
      7 Bedrooms 10 Full Baths 3 Half Baths Sq. Ft. 10861.00:# Square Feet
      Single Family For Sale NEW ML# 3556951
      Nestled in the prestigious Chestnut Hill Estate Section of Upper Brookville and overlooking the esteemed Mill River Golf Club, this extraordinary oasis offers unparalleled luxury and sophistication. This magnificent home boasts 7 bedrooms and 13 bathrooms, Spanning nearly 11, 000 square feet of pure luxury and set on over 5.25 acres of meticulously landscaped grounds with specimen trees and plantings, this residence epitomizes elegance and grandeur. A double-height entry foyer creates a dramatic entrance, providing a stunning view of the indoor pool upon arrival. The expansive gourmet chef’s kitchen features dual center islands, custom cabinetry, and top-of-the-line appliances. The grand formal dining room comfortably seats 14, making it ideal for lavish gatherings. The deluxe primary suite is a serene retreat with views of the indoor pool and offers dual en-suite bathrooms and expansive walk-in closets. A sophisticated library, perfect for a home office, also offers pool views, and features a warm fireplace, high ceilings, rich mahogany detailing, and a spiral staircase leading to the lower level. Inside, unparalleled amenities include a fitness center and world class spa with a sauna, steam and massage room, a state-of-the-art home theater, bowling alley and a billiard room, ensuring endless entertainment options. Outside, enjoy the outdoor pool with a relaxing waterfall feature and a private tennis court. Designed for grand-scale entertaining, this estate offers expansive living areas and outdoor terraces perfect for hosting memorable gatherings. Security and privacy are paramount, with a gated entrance and advanced security systems. Warm and inviting yet grand and impressive, this exceptional estate offers the epitome of luxury living in an exclusive Upper Brookville sanctuary. Experience unmatched sophistication and elegance in this one-of-a-kind property.
      Presented By: Nest Seekers LLC  516-922-2878
      Call Today: or  Email: Daniel Gale Assoc Inc
    • UPPER BROOKVILLE. An incredible renovation, and new story to tell, within this Architectural Gem in Upper Brookville. A modernized spin, exquisitely crafted and designed with the finest of materials and craftmanship to provide luxury and casual elegance, on the Old World Charm estate, sitting privately and serenely on over 5 acres of formal gardens, with several patios, inground pool, pool house, porte cochere, and more. Incredible floor plan that encompasses a unique and open feeling, with spectacular staircases on either sides of the home. Featured in the May 2000 Issue of Architectural Digest. 36
      N Chestnut Hill Drive Upper Brookville, NY 11771
      $6,998,000
      7 Bedrooms 7 Full Baths 2 Half Baths
      Single Family For Sale ML# 3485647
      UPPER BROOKVILLE. An incredible renovation, and new story to tell, within this Architectural Gem in Upper Brookville. A modernized spin, exquisitely crafted and designed with the finest of materials and craftmanship to provide luxury and casual elegance, on the Old World Charm estate, sitting privately and serenely on over 5 acres of formal gardens, with several patios, inground pool, pool house, porte cochere, and more. Incredible floor plan that encompasses a unique and open feeling, with spectacular staircases on either sides of the home. Featured in the May 2000 Issue of Architectural Digest.
      Presented By: Douglas Elliman Real Estate  516-629-2242
      Call Today: or  Email: Daniel Gale Assoc Inc
    • SIGNIFICANT $800, 000.00 PRICE REDUCTION! MOTIVATED SELLER! Exquisite Chateau de L’ Amour is a stunning interpretation of the original creativity of renowned architects, Ike Kligerman Barkley, known for enhancing Life through Design. With a talented eye for design, the owners of this magnificent property succeeded in completely transforming this exquisite Gold Coast Estate and created a Masterpiece that defines Living a Life of Luxury. Spanning over 10, 000 sqft w 7 bedrooms & 7.55 Baths, the Interior boasts a balance of modern & traditional design elements with a harmonious blend of artisan woods, soft palettes & bespoke materials. The privacy & relaxed seclusion of this property creates entertaining ease with an indoor/outdoor flow for social engagement, whether grand scale or more intimate gatherings. Additional Interior features include Lower Level Playroom, MediaRm, Salon, MassageRm, WineRm & Gym. This Magnificent Gem is set on 5 acres w Landscape Lighting, Gated Courtyard Entrance, Porte Cochere passage to Service Courtyard & Heated Four-Car Garage, Enchanting Vistas, Formal Gardens, Multiple Patios, Expansive Pool Patio, IG Salt Water Pool/Jacuzzi, Fire Pit, & Fully Renovated Pool House with expansive Kitchen/Entertainment Rm/2 Full Baths/ Private Changing Room 36
      A Chestnut Hill Drive Upper Brookville, NY 11771
      $6,998,000
      7 Bedrooms 7 Full Baths 2 Half Baths Sq. Ft. 10500.00:# Square Feet
      Single Family For Sale ML# 3485634
      SIGNIFICANT $800, 000.00 PRICE REDUCTION! MOTIVATED SELLER! Exquisite Chateau de L’ Amour is a stunning interpretation of the original creativity of renowned architects, Ike Kligerman Barkley, known for enhancing Life through Design. With a talented eye for design, the owners of this magnificent property succeeded in completely transforming this exquisite Gold Coast Estate and created a Masterpiece that defines Living a Life of Luxury. Spanning over 10, 000 sqft w 7 bedrooms & 7.55 Baths, the Interior boasts a balance of modern & traditional design elements with a harmonious blend of artisan woods, soft palettes & bespoke materials. The privacy & relaxed seclusion of this property creates entertaining ease with an indoor/outdoor flow for social engagement, whether grand scale or more intimate gatherings. Additional Interior features include Lower Level Playroom, MediaRm, Salon, MassageRm, WineRm & Gym. This Magnificent Gem is set on 5 acres w Landscape Lighting, Gated Courtyard Entrance, Porte Cochere passage to Service Courtyard & Heated Four-Car Garage, Enchanting Vistas, Formal Gardens, Multiple Patios, Expansive Pool Patio, IG Salt Water Pool/Jacuzzi, Fire Pit, & Fully Renovated Pool House with expansive Kitchen/Entertainment Rm/2 Full Baths/ Private Changing Room
      Presented By: Compass Greater NY LLC  516-817-7300
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Welcome to GRAY HORSE FARM! This magnificent iconic 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 pool and pool house, 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 17-year old 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, whole house generator. Must see video of antique wall covering- (click virtual tour link above to view). 29
      60 Piping Rock Rd Upper Brookville, NY 11545
      $5,890,000
      10 Bedrooms 7 Full Baths 3 Half Baths Sq. Ft. 13324.00:# Square Feet
      Single Family For Sale ML# 3554087
      Welcome to GRAY HORSE FARM! This magnificent iconic 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 pool and pool house, 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 17-year old 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, whole house generator. Must see video of antique wall covering- (click virtual tour link above to view).
      Presented By: Compass Greater NY LLC  516-551-5241
      Call Today: or  Email: Daniel Gale Assoc Inc
    • NEW CONSTRUCTION, currently under construction by one of North Shore’s premium builders and to be completed 4th QTR 2024. The time to customize is now! Architectural plans available for review. Make this luxury residence your dream home, with 6 bedrooms, in-ground heated salt-water pool and outdoor cabana on 2 beautiful acres in Upper Brookville. 9
      3 Donna Drive Upper Brookville, NY 11771
      $5,875,000
      7 Bedrooms 7 Full Baths 2 Half Baths Sq. Ft. 7000.00:# Square Feet
      Single Family For Sale ML# 3468763
      NEW CONSTRUCTION, currently under construction by one of North Shore’s premium builders and to be completed 4th QTR 2024. The time to customize is now! Architectural plans available for review. Make this luxury residence your dream home, with 6 bedrooms, in-ground heated salt-water pool and outdoor cabana on 2 beautiful acres in Upper Brookville.
      Presented By: Douglas Elliman Real Estate  516-759-0400
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Brookhaven selected as a Masterpiece Collection Property is situated on 2.0 prime acres located on a quiet lane in coveted Upper Brookville. This stately colonial feature 7, 200 sq.ft. of sophisticated decor, impeccable craftsmanship, state-of-the-art infrastructure and security systems, convenient to schools, nature preserves, shops, dining, and waterfront creating an enviable country lifestyle. The luxurious main floor flows from the gracious double height entry hall with handsome millwork to the elegant living room with fireplace and formal dining room to the richly paneled library with fireplace then onto the spacious family room with fireplace. The sun-filled gourmet kitchen is equipped with top-of-the-line appliances and informal dining overlooking the sweeping lawn, glorious gardens, and shimmering new heated 20x50 gunite pool designed by Gibbons. The graceful spiral center stairway leads to the luxurious primary suite and boasting three spacious bedrooms/baths with a second staircase. The lower level where every detail has been considered for your enjoyment: Guest bedroom and bath; Theatre Room; Recreation Room; Storage. A magical setting to enjoy a true haven and to create memories! 33
      12 Locust Lane Upper Brookville, NY 11545
      $4,250,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 7200.00:# Square Feet
      Single Family For Sale ML# 3534999
      Brookhaven selected as a Masterpiece Collection Property is situated on 2.0 prime acres located on a quiet lane in coveted Upper Brookville. This stately colonial feature 7, 200 sq.ft. of sophisticated decor, impeccable craftsmanship, state-of-the-art infrastructure and security systems, convenient to schools, nature preserves, shops, dining, and waterfront creating an enviable country lifestyle. The luxurious main floor flows from the gracious double height entry hall with handsome millwork to the elegant living room with fireplace and formal dining room to the richly paneled library with fireplace then onto the spacious family room with fireplace. The sun-filled gourmet kitchen is equipped with top-of-the-line appliances and informal dining overlooking the sweeping lawn, glorious gardens, and shimmering new heated 20x50 gunite pool designed by Gibbons. The graceful spiral center stairway leads to the luxurious primary suite and boasting three spacious bedrooms/baths with a second staircase. The lower level where every detail has been considered for your enjoyment: Guest bedroom and bath; Theatre Room; Recreation Room; Storage. A magical setting to enjoy a true haven and to create memories!
      Presented By: Daniel Gale Sothebys Intl Rlty  516-759-4800
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Beautiful 6-bedroom, 4.5 bath brick colonial sitting on over 2 acres of flat land with a scenic pond view. The house was completely renovated in 2019 featuring an open and airy floor plan with a 18 feet high ceiling foyer. First floor primary suite, spacious custom-built gourmet kitchen, full, finished basement, hardwood floors and terra cotta tiles (where seen), bidets in almost every bathroom, 3 car attached garage, stone patios with outdoor kitchen, pond access and views, and much more! 36
      23 Overbrook Lane Upper Brookville, NY 11545
      $3,895,000
      6 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 5911.00:# Square Feet
      Single Family For Sale OPEN HOUSE ML# 3534852
      Beautiful 6-bedroom, 4.5 bath brick colonial sitting on over 2 acres of flat land with a scenic pond view. The house was completely renovated in 2019 featuring an open and airy floor plan with a 18 feet high ceiling foyer. First floor primary suite, spacious custom-built gourmet kitchen, full, finished basement, hardwood floors and terra cotta tiles (where seen), bidets in almost every bathroom, 3 car attached garage, stone patios with outdoor kitchen, pond access and views, and much more!
      Presented By: Keller Williams Rty Gold Coast  516-482-0200
      Call Today: or  Email: Daniel Gale Assoc Inc
      Upcoming Open House View Location
      06/16/2024 - 06/16/2024 1:30PM - 3:30PM
    • Magnificent Colonial set on 4.5 flat acres in the desirable Village of Upper Brookville. This stately Colonial has grand entertaining rooms, 7 bedrooms, 6.55 baths. Spacious Eat in Kitchen with Granite Counter tops. Mud room with cubbies, Elevator, pantry. Huge Primary Suite with (2) fireplaces, sitting room, balcony, walk in closet, bath with steam shower. 2 additional bedrooms on suite, 2 bedrooms with jack & jill bath and den. 2 additional bedrooms and 2 baths. Spectacular property with in-ground gunite pool, cabana, barn, stable and paddock. Professionally landscaped with things blooming all summer. Convenient to 25A, Hwys, Schools, Shopping, LIRR, Town, Restaurants, Parks and Library. 32
      963 Ripley Lane Upper Brookville, NY 11771
      $3,698,000
      7 Bedrooms 6 Full Baths 2 Half Baths
      Single Family For Sale ML# 3551746
      Magnificent Colonial set on 4.5 flat acres in the desirable Village of Upper Brookville. This stately Colonial has grand entertaining rooms, 7 bedrooms, 6.55 baths. Spacious Eat in Kitchen with Granite Counter tops. Mud room with cubbies, Elevator, pantry. Huge Primary Suite with (2) fireplaces, sitting room, balcony, walk in closet, bath with steam shower. 2 additional bedrooms on suite, 2 bedrooms with jack & jill bath and den. 2 additional bedrooms and 2 baths. Spectacular property with in-ground gunite pool, cabana, barn, stable and paddock. Professionally landscaped with things blooming all summer. Convenient to 25A, Hwys, Schools, Shopping, LIRR, Town, Restaurants, Parks and Library.
      Presented By: Daniel Gale Sothebys Intl Rlty  516-759-4800
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Upper Brookville - Casa Blanca This stunning residence offers an unparalleled blend of sophisticated elegance, modern amenities, and exceptional craftsmanship. With 4/5 spacious bedrooms and 4 meticulously designed bathrooms, this home provides the perfect sanctuary for both relaxation and entertainment. As you approach the property, you are greeted by a beautifully landscaped front yard, featuring lush greenery and elegant stone pathways that lead you to the grand entrance. Step inside to a breathtaking foyer, showcasing high ceilings, a sweeping wrought iron staircase, and an abundance of natural light that floods through expansive windows. Off the entry foyer you have a beautiful space which can be used as a first floor bedroom ensuite or a private office. The main level features numerous intricate moldings and detailed wainscoting throughout. The formal dining room offers and large space suited for large scale formal dinner parties. The open concept living spaces are thoughtfully designed to offer seamless flow and connectivity, perfect for modern living. The living room, adorned with exquisite light fixtures, custom moldings & gas fireplace, transitions into the kitchen creating a grand open entertaining space. Sliding glass doors off the living room/kitchen open to a paved patio creating a beautiful indoor/outdoor living concept. The heart of the home is the state-of-the-art kitchen, a culinary enthusiast’s dream. This gourmet kitchen boasts top-of-the-line stainless steel appliances, custom cabinetry, large center island with stunning granite countertops, wetbar as well as a large pantry. The second level features a one of a kind second floor living space with double glass doors which open to a gorgeous balcony overlooking the property. The four upstairs bedrooms are generously proportioned, each offering serene views and ample closet space. The primary suite is a true retreat, featuring a spa-like en-suite bathroom with a soaking tub, a glass-enclosed steam shower, and double vanities. The additional bathrooms are equally luxurious, with high-end fixtures, designer tiles, and elegant finishes. The finished basement is perfect for entertaining and includes a beautiful glass enclosed wine storage space. The backyard oasis features an in-ground pool, cabana as well as multiple patio spaces. Luxury living at its finest. A Masterpiece Listing. 36
      9 Locust Lane Upper Brookville, NY 11545
      $3,495,000
      5 Bedrooms 4 Full Baths
      Single Family For Sale NEW ML# 3557123
      Upper Brookville - Casa Blanca This stunning residence offers an unparalleled blend of sophisticated elegance, modern amenities, and exceptional craftsmanship. With 4/5 spacious bedrooms and 4 meticulously designed bathrooms, this home provides the perfect sanctuary for both relaxation and entertainment. As you approach the property, you are greeted by a beautifully landscaped front yard, featuring lush greenery and elegant stone pathways that lead you to the grand entrance. Step inside to a breathtaking foyer, showcasing high ceilings, a sweeping wrought iron staircase, and an abundance of natural light that floods through expansive windows. Off the entry foyer you have a beautiful space which can be used as a first floor bedroom ensuite or a private office. The main level features numerous intricate moldings and detailed wainscoting throughout. The formal dining room offers and large space suited for large scale formal dinner parties. The open concept living spaces are thoughtfully designed to offer seamless flow and connectivity, perfect for modern living. The living room, adorned with exquisite light fixtures, custom moldings & gas fireplace, transitions into the kitchen creating a grand open entertaining space. Sliding glass doors off the living room/kitchen open to a paved patio creating a beautiful indoor/outdoor living concept. The heart of the home is the state-of-the-art kitchen, a culinary enthusiast’s dream. This gourmet kitchen boasts top-of-the-line stainless steel appliances, custom cabinetry, large center island with stunning granite countertops, wetbar as well as a large pantry. The second level features a one of a kind second floor living space with double glass doors which open to a gorgeous balcony overlooking the property. The four upstairs bedrooms are generously proportioned, each offering serene views and ample closet space. The primary suite is a true retreat, featuring a spa-like en-suite bathroom with a soaking tub, a glass-enclosed steam shower, and double vanities. The additional bathrooms are equally luxurious, with high-end fixtures, designer tiles, and elegant finishes. The finished basement is perfect for entertaining and includes a beautiful glass enclosed wine storage space. The backyard oasis features an in-ground pool, cabana as well as multiple patio spaces. Luxury living at its finest. A Masterpiece Listing.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-921-2918
      Call Today: or  Email: Daniel Gale Assoc Inc
    • Nestled on the beautiful Overbrook Lane in Upper Brookville, this full brick estate sits on 1.24 acres of land with a view of a pond. This masterpiece offers the ultimate luxury living experience with over 7, 300 sq. ft. boasting 5 bedrooms and 5 baths. Custom designed millwork, and hand painted ceilings throughout. From the moment you step inside, you are astonished with immaculate craftsmanship and modern elegance. Every detail has been flawlessly thought out with the highest quality finishes. The kitchen features a large center island that is open to the spacious family and breakfast room, making it perfect for entertaining and family gatherings. The primary suite features a luxurious bath, and 3 walk-in closets. Four Additional bedrooms, with ample space. Second floor has a separate spa/sauna for ultimate relaxation. The full finished basement is the perfect space for recreational activities with high ceilings and lots of potential. The backyard is an oasis, featuring a pond and clear beautiful grounds for lots of potential. The solar panels offer an extra convenience of lower electricity cost. The round driveway leads to a 3-car garage. Large MUST SEE! 26
      21 Overbrook Lane Upper Brookville, NY 11545
      $2,950,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 7300.00:# Square Feet
      Single Family For Sale ML# 3552198
      Nestled on the beautiful Overbrook Lane in Upper Brookville, this full brick estate sits on 1.24 acres of land with a view of a pond. This masterpiece offers the ultimate luxury living experience with over 7, 300 sq. ft. boasting 5 bedrooms and 5 baths. Custom designed millwork, and hand painted ceilings throughout. From the moment you step inside, you are astonished with immaculate craftsmanship and modern elegance. Every detail has been flawlessly thought out with the highest quality finishes. The kitchen features a large center island that is open to the spacious family and breakfast room, making it perfect for entertaining and family gatherings. The primary suite features a luxurious bath, and 3 walk-in closets. Four Additional bedrooms, with ample space. Second floor has a separate spa/sauna for ultimate relaxation. The full finished basement is the perfect space for recreational activities with high ceilings and lots of potential. The backyard is an oasis, featuring a pond and clear beautiful grounds for lots of potential. The solar panels offer an extra convenience of lower electricity cost. The round driveway leads to a 3-car garage. Large MUST SEE!
      Presented By: Daniel Gale Sothebys Intl Rlty  347-531-7099
      Call Today: or  Email: Daniel Gale Assoc Inc
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