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Brookville Real Estate Search

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Old Brookville, Brookville & Upper Brookville Homes and Condos for Sale

Nestled within the picturesque Town of Oyster Bay in Nassau County, Long Island, New York, lie three charming villages collectively known as "The Brookvilles": Brookville, Upper Brookville, and Old Brookville. This trio forms a unique inverted triangle, its northern base embracing a rich tapestry of history, nature, and luxury living.

Steeped in history, The Brookvilles trace their roots back to English and Quaker settlers who, in the 17th and 18th centuries, were attracted to the area's serene landscape, graced by several brooks and springs. Dutch settlers soon followed suit, acquiring expansive properties. By the 1900s, The Brookvilles had evolved into a playground for New York's elite, with renowned families such as the Posts, Vanderbilts, and DuPonts crafting magnificent estates. Today, remnants of this golden era blend seamlessly with modern developments, creating a captivating fusion of old-world charm and contemporary luxury.

Brookville, spanning 4 square miles with a population of 3,465, offers an idyllic retreat characterized by meticulously maintained golf courses and verdant countryside. Its neighboring villages, Old Brookville and Upper Brookville, boast similarly enchanting landscapes and a rich equestrian heritage, with bridle paths winding past horse farms and nature preserves. The legacy of legendary sportswoman Hope Goddard Iselan lives on, as Upper Brookville proudly bears her name, reflecting its elevated status within the community.

One of The Brookvilles' most esteemed features is its exceptional educational system, ranked among the nation's finest. Families are drawn to the area not only for its stunning homes but also for the unparalleled opportunities it affords their children.

Despite their affluent reputation, The Brookvilles exude a welcoming ambiance, fostering a sense of community akin to a cherished preserve. Residential offerings range from contemporary masterpieces on sprawling two-acre plots to grand estates spanning up to 100 acres, catering to diverse tastes and preferences. Currently, homes on the market span from $1,350,000 for a charming 4-bedroom, 3-bathroom abode to $9,995,000 for an opulent 8-bedroom, 11-bathroom mansion, with the average listing price hovering around $3,400,000.

Beyond its lavish residences, The Brookvilles offer an array of amenities to suit every lifestyle. From upscale boutiques and gourmet restaurants to tranquil parks and cultural attractions, there's no shortage of delights to explore. Whether you're savoring a leisurely afternoon on the polo fields or embarking on a scenic stroll through lush gardens, each moment in The Brookvilles is infused with a sense of tranquility and refinement.

If you're ready to discover the unparalleled beauty and luxury of The Brookvilles, we invite you to explore our curated selection of homes for sale. With their timeless elegance and modern comforts, these residences promise a lifestyle beyond compare. Contact us today to embark on your journey to find the perfect home in this coveted enclave of Long Island.

Latest Old Brookville,Brookville & Upper Brookville Homes and Condos for Sale

1 Applewood Estate, Upper Brookville image
1 Applewood Estate, Upper Brookville $25,000,000
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  • 13 Beds
  • 17 Baths
  • 1001064 MLS
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1985-4 Cedar Swamp Road, Brookville image
1985-4 Cedar Swamp Road, Brookville $14,900,000
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  • 7 Beds
  • 9 Baths
  • 1004738 MLS
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97 A Pound Hollow Road, Old Brookville image
97 A Pound Hollow Road, Old Brookville $13,600,000
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  • 10 Beds
  • 10 Baths
  • 1034316 MLS
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39 Chestnut Hill Drive, Upper Brookville image
39 Chestnut Hill Drive, Upper Brookville $12,750,000
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  • 8 Beds
  • 12 Baths
  • 1056809 MLS
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18 Evergreen Way, Old Brookville image
18 Evergreen Way, Old Brookville $10,250,000
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  • 7 Beds
  • 12 Baths
  • 1050255 MLS
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7 Covey Court, Upper Brookville image
7 Covey Court, Upper Brookville $8,995,000
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  • 5 Beds
  • 12 Baths
  • 1031340 MLS
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25 Old Wheatley Road, Brookville image
25 Old Wheatley Road, Brookville $8,250,000
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  • 6 Beds
  • 10 Baths
  • 1058948 MLS
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160 Hegemans Lane, Old Brookville image
160 Hegemans Lane, Old Brookville $8,250,000
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  • 6 Beds
  • 8 Baths
  • 1048329 MLS
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30 Evans Drive, Brookville image
30 Evans Drive, Brookville $7,988,000 ▼
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  • 7 Beds
  • 10 Baths
  • 983498 MLS
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97 B Pound Hollow Road, Old Brookville image
97 B Pound Hollow Road, Old Brookville $7,900,000
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  • 1034323 MLS
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31 Chestnut Hill Drive, Upper Brookville image
31 Chestnut Hill Drive, Upper Brookville $7,850,000
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  • 6 Beds
  • 10 Baths
  • 1061123 MLS
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7 Brookville Road, Brookville image
7 Brookville Road, Brookville $7,250,000
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  • 6 Beds
  • 8 Baths
  • 1055002 MLS
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Brookville image
Brookville $6,499,000
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  • 6 Beds
  • 8 Baths
  • 1038793 MLS
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6 Evergreen Way, Old Brookville image
6 Evergreen Way, Old Brookville $6,450,000 ▼
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  • 7 Beds
  • 10 Baths
  • 991638 MLS
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14 Wenwood Drive, Brookville image
14 Wenwood Drive, Brookville $6,399,999
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  • 6 Beds
  • 8 Baths
  • 989641 MLS
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3 Valentine Farm Court, Old Brookville image
3 Valentine Farm Court, Old Brookville $5,999,999 ▼
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  • 7 Beds
  • 9 Baths
  • 1021590 MLS
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2 Vista Lane, Brookville image
2 Vista Lane, Brookville $5,698,000
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  • 5 Beds
  • 7 Baths
  • 1053488 MLS
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12 Quaker Ridge Drive, Brookville image
12 Quaker Ridge Drive, Brookville $5,599,999 ▼
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  • 6 Beds
  • 9 Baths
  • 901446 MLS
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20 Knollwood Road, Brookville image
20 Knollwood Road, Brookville $5,499,999 ▼
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  • 6 Beds
  • 8 Baths
  • 986988 MLS
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16 Cowpath, Brookville image
16 Cowpath, Brookville $5,499,000
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  • 6 Beds
  • 7 Baths
  • 1056991 MLS
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8 Stonegate Lane, Old Brookville image
8 Stonegate Lane, Old Brookville $5,499,000
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  • 9 Beds
  • 8 Baths
  • 1005247 MLS
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952 Cedar Swamp, Old Brookville image
952 Cedar Swamp, Old Brookville $5,498,000
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  • 7 Beds
  • 8 Baths
  • 1009813 MLS
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63 Fruitledge Road, Brookville image
63 Fruitledge Road, Brookville $5,299,000
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  • 6 Beds
  • 7 Baths
  • 1044684 MLS
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7 Fairway Court, Upper Brookville image
7 Fairway Court, Upper Brookville $4,998,000 ▼
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  • 6 Beds
  • 7 Baths
  • 1010689 MLS
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27 Victorian Lane, Brookville image
27 Victorian Lane, Brookville $4,988,888 ▼
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  • 6 Beds
  • 8 Baths
  • 953450 MLS
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18 Chestnut Hill Drive, Upper Brookville image
18 Chestnut Hill Drive, Upper Brookville $4,980,000
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  • 7 Beds
  • 9 Baths
  • 1061600 MLS
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1 Penny Pond Court, Old Brookville image
1 Penny Pond Court, Old Brookville $4,795,999
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  • 11 Beds
  • 14 Baths
  • 1016829 MLS
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1 Penny Pond Court, Old Brookville image
1 Penny Pond Court, Old Brookville $4,795,999
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  • 1016857 MLS
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24 Emerson Road, Brookville image
24 Emerson Road, Brookville $4,595,000
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  • 6 Beds
  • 8 Baths
  • 1029380 MLS
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93 Hoaglands Lane, Old Brookville image
93 Hoaglands Lane, Old Brookville $4,399,000 ▼
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  • 5 Beds
  • 8 Baths
  • 987442 MLS
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3 Rock Hill Lane, Brookville image
3 Rock Hill Lane, Brookville $4,295,000
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  • 6 Beds
  • 6 Baths
  • 1028751 MLS
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10 Laurel Woods Drive, Upper Brookville image
10 Laurel Woods Drive, Upper Brookville $4,200,000
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  • 6 Beds
  • 8 Baths
  • 1043804 MLS
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5 Victorian Lane, Brookville image
5 Victorian Lane, Brookville $3,900,000 ▼
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  • 5 Beds
  • 7 Baths
  • 1017067 MLS
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23 Overbrook Lane, Upper Brookville image
23 Overbrook Lane, Upper Brookville $3,795,000
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  • 6 Beds
  • 6 Baths
  • 996646 MLS
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343 Chicken Valley Road, Upper Brookville image
343 Chicken Valley Road, Upper Brookville $3,700,000 ▼
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  • 4 Beds
  • 4 Baths
  • 955669 MLS
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61 Linden Lane, Upper Brookville image
61 Linden Lane, Upper Brookville $3,500,000 ▼
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  • 5 Beds
  • 5 Baths
  • 1018330 MLS
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5 Carol Lane, Upper Brookville image
5 Carol Lane, Upper Brookville $3,495,000 ▼
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  • 6 Beds
  • 9 Baths
  • 1045340 MLS
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8 Victorian Lane, Brookville image
8 Victorian Lane, Brookville $3,299,000 ▼
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  • 6 Beds
  • 5 Baths
  • 1017003 MLS
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33 High Farms Road, Old Brookville image
33 High Farms Road, Old Brookville $3,249,888 ▼
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  • 6 Beds
  • 6 Baths
  • 977675 MLS
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7 Mac Lean Drive, Brookville image
7 Mac Lean Drive, Brookville $2,998,000 ▼
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  • 5 Beds
  • 5 Baths
  • 1045154 MLS
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5 Woodfield Lane, Old Brookville image
5 Woodfield Lane, Old Brookville $2,995,000
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  • 5 Beds
  • 6 Baths
  • 1044302 MLS
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1017 Friendly Road, Upper Brookville image
1017 Friendly Road, Upper Brookville $2,749,000 ▼
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  • 4 Beds
  • 5 Baths
  • 967360 MLS
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14 Pheasant Hill Lane, Old Brookville image
14 Pheasant Hill Lane, Old Brookville $2,742,000
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  • 7 Beds
  • 6 Baths
  • 1060861 MLS
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19 Pheasant Hill Lane, Old Brookville image
19 Pheasant Hill Lane, Old Brookville $2,499,999
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  • 5 Beds
  • 4 Baths
  • 1019434 MLS
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4 Roads End, Brookville image
4 Roads End, Brookville $2,445,000 ▼
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  • 4 Beds
  • 4 Baths
  • 998655 MLS
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19 MICHAELS Lane, Old Brookville image
19 MICHAELS Lane, Old Brookville $2,295,000 ▼
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  • 4 Beds
  • 4 Baths
  • 906140 MLS
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89 Mill River Road, Upper Brookville image
89 Mill River Road, Upper Brookville $2,199,000
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  • 3 Beds
  • 3 Baths
  • 949536 MLS
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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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