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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
Photography Contributed By
Jeff Rainone
Video By
Alex Finneran
Interested in learning more about homes in this area?
Reach out to
Dee Dee Brix,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Upper Brookville, NY sell after 8 days on the market compared to the national average of 55 days. The median sale price for homes in Upper Brookville, NY over the last 12 months is $2,500,000.
A Rare 2-Acre North Shore Estate-Like Setting Offering Privacy, Presence, and Endless Potential Set on approximately 2 acres of private, park-Like grounds, this timeless Colonial with vintage charm presents a truly rare opportunity in the heart of Glen Head. Privately set back and gently elevated from the road along a long, tree-lined approach, the property offers an exceptional sense of space
Welcome to 1678 Cedar Swamp Road, Brookville! Set on a sprawling 2.01-acre property in Brookville and located within the Jericho School District, this beautifully maintained 4-bedroom, 3.5-bath Colonial offers exceptional space, comfort, and lifestyle amenities. The home features wood floors throughout, new moldings, and a freshly painted interior, creating a bright and inviting atmosphere from
12.6 Acres of Prime Land for Sale – Planned for 4 Homes – 3-Acre Zoning – Cul-de-Sac AccessA rare development opportunity awaits with this 12.6-acre parcel of land, ideally situated at the end of a peaceful cul-de-sac. Zoned for 3-acre minimum lots, this property comes with a concept plan for 4 single-family homes, making it perfect for a small subdivision, custom home builder, or a private
Maison Blanche: An Architectural Icon in Upper BrookvilleExperience the pinnacle of ultra-modern luxury at 31 Chestnut Hill Drive. Set on five flat, private acres at the crest of a premier cul-de-sac, this architectural sanctuary was originally designed by the renowned architect Gary Gallagher and redesigned by award-winning FAIA architect Stuart Narofsky, leading to an extensively renovated
Set on nearly 10 private acres in the heart of Upper Brookville, Red Fox is a distinguished Gold Coast estate of exceptional character and scale. This 17-room French Tudor is marked by classic architectural details, including turrets, a slate roof, and striking 3-story bay windows that lend timeless elegance. Richly detailed interiors feature beautifully proportioned principal rooms, including a
A Rare 2-Acre North Shore Estate-Like Setting Offering Privacy, Presence, and Endless Potential Set on approximately 2 acres of private, park-Like grounds, this timeless Colonial with vintage charm presents a truly rare opportunity in the heart of Glen Head. Privately set back and gently elevated from the road along a long, tree-lined approach, the property offers an exceptional sense of space
UPPER BROOKVILLE. Privately set behind sweeping lawns on over two acres in the Village of Upper Brookville, this elegant North Shore residence offers the privacy, scale, and timeless character synonymous with Gold Coast estate living. The home features 4 bedrooms, with primary suite on the main, and 3 full and 2 half baths, along with sun-filled living spaces, hardwood and tiled (radiant heated)
This gorgeous Brick Colonial, located in Upper Brookville, is a beautiful and elegant estate that sits on 2.53 acres. Built in 2007, this residence offers an impressive 6 bedrooms and 7 bathrooms within its expansive 6,921 square feet of living space. Step inside to find a home designed for both grand entertaining and comfortable living. The first floor features a formal living room, a formal
Elegance redefined in this stunning gem that blends an eclectic mix of mid-century modern design with a touch of contemporary sophistication, nestled on two lush, gated acres in Upper Brookville. From the moment you enter, the home captivates your imagination with its soaring 30-foot ceilings and dramatic windows and wood architectural elements. Clean lines, warm textures, and artful finishes
Beautiful Flat 2 Acre Home in Jericho SD in Upper Brookville. Cabana with Gunite Pool, Elevator, Top Appliances, High Ceilings, Great Room w/ Linear Fire Place, Chefs Kitchen+Spice Kitchen, Top Appliances. Hide-A-Hose Central Vacuum. 5 Central Air Zones. Huge Backyard, Professionally designed landscaping. 10 ft first Floor, 10 ft basement, 12” 2nd floor in bedrooms. 4 Panel Slider in Basement!!
Upper Brookville. Brand New Construction on 5 Serene Acres. Move Right In to this Warm & Comfortable Sun Drenched Home! State of the Art Chef's Kitchen w Top of the Line Wolf & Sub Zero Stainless Steel Appliances Throughout. Oak Wood Floors Throughout Entire 2nd Floor. Primary Suite with Brand New Bathroom w His & Her Sinks, Oversized Shower, Luxurious Free Standing Tub & Private Water Closet. 2
Private Hilltop Estate with Mother-Daughter Layout in Upper Brookville Located in the prestigious community of Upper Brookville, this exceptional 4,000 sq. ft. home sits on over 2 private acres at the top of a hill, offering outstanding privacy and beautiful natural surroundings. The property borders the Mill River Club and is surrounded by mature trees, creating a peaceful and secluded setting
Beautiful Cape Style Cedar Shake Home, First Floor, Large Entry, Large Living Room W/Fireplace, Formal Dining Room, Large Open Eat In Kitchen With Great Room With Fireplace And Beautiful Wood Beams On Ceiling, Master Bedroom With Her And Him Closet, Primary Bathroom, Office Or Sitting Room Off Primary, Additional Bedroom With Full Bathroom, Landry Room. Second Floor Has Bedroom With Full
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
A destination to relax, live, and indulge in Long Island’s distinguished north shore highlights—this is Norwich Gate Apartments! As a picturesque country club community sheltered by tree-lined hills, we’re ready to surpass your expectations for high-quality living with our Oyster Bay apartments’ latest features, amenities, and easy access to elite work, retail, and leisure venues. Find
$20,000 per month
3 Beds
3 Baths
Welcome to Barn Owl, a timeless summer retreat set on beautifully landscaped grounds with peaceful garden views on the North Shore of Long Island. This inviting three-bedroom, three-bath cottage offers a rare blend of tranquility, character, and understated elegance for the summer season. Inside, a dramatic great room with soaring ceilings and exposed rustic beams creates a warm and striking
Charming one-bedroom cottage with an additional room that could easily make a wonderful office space. Set on an estate of 3+ acres, surrounded by beautifully landscaped grounds—very peaceful location.
Donna ScalaLAFFEY REAL ESTATE
$15,000 per month
6 Beds
5 Baths
3,031 Sq Ft
Experience unparalleled privacy and space in this sprawling 3,000 sq. ft. expanded ranch, nestled on 3 acres of lush, manicured grounds within the prestigious Jericho School District. A long, private driveway leads you to a home designed for both grand entertaining and quiet relaxation.• The Main Level: Features a bright living room with a cozy wood-burning fireplace and an inviting open
Completely renovated 1 bedroom apartment on 2nd floor in 4 family home. Driveway parking and shared back yard. All new kitchen and full bath. Finished attic, perfect for home office, family room and extra storage. Close to all that the village of Oyster Bay has to offer such as Theodore Roosevelt beach, picnic & play ground, restaurants, shopping, library & LIRR. Pets will be considered.
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
