$3,029,121Average Value$1,115Average Price per Sq Ft1Home For Sale
Upper Brookville is a lush village on Long Island's famed Gold Coast
Upper Brookville’s winding roads are lined with large estates, woods and farms, giving it a calming rural atmosphere that many seek to call home. “People come for its larger homes and larger lots, and the privacy, beauty and nature of the area with access to great country clubs, good schools, both public and private school options, and the close proximity to the beaches,” says Regina Rogers, a licensed real estate salesperson at Douglas Elliman Real Estate with 25 years of experience in the business. “And it’s truly a lifestyle here. People tend to live a very active lifestyle.”
Living in Upper Brookville provides a sense of calm and privacy when residents want it, but it doesn’t have to feel isolating. Those who want it can tap into the village’s thriving community. “If one wants privacy, they can certainly achieve that here,” Rogers says. “If they don’t want to get to know their neighbors, they don’t have to, but if they do, there’s generally a lovely community throughout the area. They’ll join the local country clubs or participate in community events, there’s a local library, or school involvement. There’s a variety of ways that people get together here.” Upper Brookville’s mix of large homes and properties, calm rural atmosphere and proximity to essentials and entertainment make it a popular place to call home. “It’s just a beautiful, picturesque community,” Rogers says. “Another hidden jewel.”
Upper Brookville students explore nearby beaches on a field trip.
Oyster Bay is a great place for a boat ride and just minutes from Upper Brookville.
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Stately homes with multi-acre lots tend to move fast in a tight market
Upper Brookville’s large homes and luxurious estates are on a minimum of two acres, providing a great opportunity for residents to own large parcels of land. Home prices in the village start at $1.5 million for a house that needs upgrades or renovations and between $2 million and $2.5 million for a home that is fully updated. Luxury homes in Upper Brookville, which tend to be on lots of at least three or four acres, can climb as high as $10 million.
Upper Brookville’s housing market is strong, with the small number of homes that make it onto the market selling relatively quickly. “It’s still very active and there’s very little inventory here,” Rogers says. “So unlike other parts of the country, they’re showing signs of slowing, but not here on Long Island. It’s still extremely active. And I suspect it’s because of our close proximity to New York City. We have always lived here in a bit of a bubble and are somewhat insulated in the housing market because of that sole reason. People have jobs in New York City.”
Beautiful flowering trees line the driveway of this Upper Brookville mansion.
A perfectly manicured mansion sits in Upper Brookville.
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Two A-rated school districts serve students in the area
The village is split between the Oyster Bay-East Norwich Central School District and the Locust Valley Central School District, both of which have A ratings on Niche. The Oyster Bay-East Norwich district is a smaller district with just three schools, so children attend Theodore Roosevelt School, James H. Vernon School and Oyster Bay High School, where they can participate in extracurricular activities like the literary magazine, robotics club and Model UN. In the Locust Valley district, children attend schools like Ann MacArthur Primary School, Locust Valley Intermediate School, Locust Valley Middle School and Locust Valley High School. The high school’s newspaper and music programs are both incredibly highly rated, with a third of its approximately 700 students participating in the music program.
Theodore Roosevelt Elementary School serves students from grades Pre K to 2nd.
Oyster Bay High School offers many extracurricular activities to the students.
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Active community with a scenic arboretum by country clubs and beaches
When locals want to get outside and enjoy the nature surrounding them, they have plenty of options. Many enjoy hiking or biking through Hope Iselin Preserve, while others enjoy exploring the Planting Fields Arboretum. Its 409 acres of gardens and greenhouses provide more than you could possibly explore and enjoy in a single visit, so there’s always something new to see. “One can enjoy a beautiful stroll among incredible specimen trees and planting and be in nature for hours at a time,” Rogers says. While there, residents can also tour the Coe Hall Historic House Museum or the Tea House, part of the 1920s Gold Coast estate that has become the garden’s grounds. The arboretum hosts weekly and annual events for the community, including twilight tours, festivals and 5K runs. Joining a nearby club like The Mill River Club gives members access to additional community events and amenities like an 18-hole golf course, pool, tennis courts and more, further adding to many residents’ active lifestyles.
With North Shore beaches less than 4 miles away, the water also plays an important role in life in Upper Brookville. “In the summer months, people are out swimming and enjoying some fun in the sun, they’re walking, they’re enjoying sunsets,” Rogers says. “That’s an event here on Long Island, where people are drawn to the beach for the sunsets—or for the morning risers, the sunrise.”
An open gate frames a view of the gardens at Planting Fields Arboretum.
Roosevelt Beach near Upper Brookville is a great place for a walk.
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Downtown Oyster Bay offers shops, restaurants and transit nearby
And although Upper Brookville can feel rural and remote, the shopping and restaurants in Oyster Bay’s downtown are also within 4 miles, and some options can be found even closer in East Norwich. Commuters often get on the train at Oyster Bay Station, which takes them to New York City in about 80 minutes, and easy access to the Northern State Parkway makes traveling simple.
Christina's Epicure in nearby East Norwich meets all your grocery needs.
Try the Santa Fe steak sandwich at Coach Meeting House near Upper Brookville.
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Photography Contributed By
Jeff Rainone
Video By
Alex Finneran
Interested in learning more about homes in this area?
Reach out to
Kieran Rodgers,
an experienced agent in this area.
GreatSchools:
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