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Oyster Bay: Beaches, events, history draw buyers to Teddy Roosevelt's old digs

The heart of Oyster Bay's downtown centers around South Street... — The heart of Oyster Bay's downtown centers around South Street and E. Main Street. Credit: Debbie Egan-Chin

By Aidan JohnsonSpecial to NewsdayUpdated August 3, 2026 11:53 am

THE SCOOP With access to beautiful beaches and a boatload of events, the scenic hamlet of Oyster Bay has much to offer to both residents and visitors alike.

"It's just been getting better and better every year," said Oyster Bay Town Clerk Richard LaMarca.

"There's been a big renaissance going on with restaurants, and we've been doing a lot of work with the local chambers and civic associations to make it more of a destination for those even outside of the hamlet," said LaMarca, who serves on the board of the Oyster Bay-East Norwich Chamber of Commerce.

The hamlet is rife with activity; in May, Oyster Bay Day is celebrated, June sees the Empire State Ride Long Island, a bike ride that raises money for cancer research, and in October, the hamlet hosts their biggest festival, the Oyster Fest, which includes live music, a carnival and plenty of food vendors.

Bonanza’s 1897 is an iconic eatery in Oyster Bay that... — Bonanza’s 1897 is an iconic eatery in Oyster Bay that sells hot dogs, ice cream and more. Credit: Debbie Egan-Chin

Every Tuesday night during the summer, the hamlet has Cruise Nights in Oyster Bay, a car show that also sees participation from the local businesses and includes food, music, and activities for the children.

The heart of Oyster Bay's downtown lies on Audrey Avenue, where the township's town hall is located.

"We have a pretty bandstand in the center of the hamlet, where President Teddy Roosevelt used to give speeches and where I currently [perform] many of the weddings I officiate," LaMarca said.

Overlooking Oyster Bay Harbor is the popular Theodore Roosevelt Memorial... — Overlooking Oyster Bay Harbor is the popular Theodore Roosevelt Memorial Park. Credit: Debbie Egan-Chin

Other important roadways in the hamlet include Route 106, which starts in North Bellmore and ends in Oyster Bay, Pine Hollow Road, which turns into South Street, and East Main Street and West Main Street.

The Long Island Rail Road's Oyster Bay station is a four-minute walk from Theodore Roosevelt Memorial Park.

With a population that's just over 7,000, LaMarca described Oyster Bay as "a place where everybody knows everybody."

Chloe Blog, of Huntington, is the general manager at Theodore’s... — Chloe Blog, of Huntington, is the general manager at Theodore’s Books, and independent bookshop on E. Main Street. Credit: Debbie Egan-Chin

Real estate agent Regina Rogers shared how Oyster Bay got its name, originating from Dutch settlers in the 1600s who noted the great amount of oysters found in what is now known as Oyster Bay Harbor.

Oyster Bay still has a strong maritime culture, "with The Waterfront Center offering sunset cruises discussing the history of the harbor," Rogers said.

"There's nothing like being on the water, whether it's on a paddle board or sailboat or a larger vessel," she said.

"It's just a very peaceful, incredible place to be," Rogers said.

Homes along Peerless Drive, top, and Sidney Street. Credit: Debbie Egan-Chin

SALE PRICES Between Aug. 1, 2025, and July 31, 2026, there were 47 home sales with a median sale price of $909,962, according to OneKey MLS. During the same period a year earlier, there were 48 home sales with a median sale price of $910,000.

CONDOS AND CO-OPS There are five co-ops, priced between $304,999 and $489,000, on the market.

OTHER STATS

Population 7,308

Median age 38

Median home value $882,500

Monthly LIRR ticket from Oyster Bay $299.75

School district, graduation rate Oyster Bay-East Norwich (95%)

Library Oyster Bay-East Norwich

Transit (no nearby bus routes)

Sources: 2024 American Community Survey; OneKey MLS via InfoSparks by ShowingTime; LIRR; data.nysed.gov; Nassau Inter-County Express

RECENTLY SOLD

$920,000