At the top of the 20th century, Shirley was a popular getaway for a few New York City elites. “Walter T. Shirley owned this beautiful mansion there off the water, and that’s where he would entertain socialites and movie stars like Tony Bennett and Marilyn Monroe,” says Ted Gounelas, an associate broker with Coldwell Banker M&D Good Life who grew up in the area. “That happened before the Hamptons, so I don’t want to say it was the original Hamptons, but it’s basically the Hamptons that never were.” In the 1960s, Walter T. Shirley then developed the community as a collection of bayside bungalows for working-class families. Today, the hamlet on Long Island's South Shore carries on his surname — and his vision. “It’s the last affordable waterfront community,” says Tina Jahrsdoerfer, a licensed real estate salesperson at Signature Premier Properties who has lived in the neighborhood for 29 years and has sold homes here for 10 years. “You can get waterfront property for less than $1 million here, which is unheard of — and actually, a lot less than that.”
Even for those who don’t live on the water, the beach is often only a short drive or bike ride away. “People love being right by the beach,” Jahrsdoerfer says. “Shirley is kind of big. But if you live south of Montauk, you’re only 5 miles from the beach, right down the road. You can hop on your bike and ride over there, which people like because then you don’t have to pay for parking. That’s what I usually do. People who live on those canal streets, they can just walk over the bridge.” Home to just under 26,500 people, Shirley offers access to the natural beauty of Long Island and the urban amenities of New York City, about 70 miles away. The hamlet also embraces the spirit of its motto “Long Island’s Best Kept Secret.” “I tell people all the time. My mother lives in Upstate New York, that’s too little. The city, that’s too much. Long Island is just perfect,” says Andrew Chrzanowski, team leader of the Manhattan to Montauk Group with Real Broker NY.
Shirley's various neighborhoods have easy access to the water.
Wertheim National Wildlife refuge is a great place to hike and see various bird life.
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Fishing, boating and swimming in Bellport Bay and on Fire Island
Shirley embraces its waterfront location, with opportunities for fishing, boating and swimming. “Everywhere you look, we have a fishing pier,” Jahrsdoerfer says. “We never have to buy clams or crabs because if we’re in the mood for them, my husband just buys chicken legs, grabs the traps and gets them.” On the edge of Bellport Bay is Shirley Beach, which features a sandy beachfront, playground and splash pad. “I bring popsicles down there while the kids hang out and go to the splash park to cool off,” Jahrsdoerfer says. Those looking to get out on the water can head to the boat ramp at Smith Point Marina County Park. The 2,550-acre Wertheim National Wildlife Refuge stretches into the western half of Shirley and is a popular spot for hiking, wildlife watching and paddle boating on the Carmans River.
The hamlet is also home to the Long Island Skydiving Center. “I was driving down William Floyd Parkway with my daughter the other day and there were six parachuters coming down,” Jahrsdoerfer says. The Smith Point Bridge connects residents to the eastern end of Fire Island, where Smith Point County Park is a haven for beachgoers on the Atlantic Ocean. There’s also live music in the park every weekend throughout the summer at Tiki Joe’s Beach Club. After undergoing a $26.7 million renovation project, the Mastics-Moriches-Shirley Community Library reopened in 2024 and continues to support the Tri-Hamlet area with educational and recreational programming for all ages. Shirley sees all four seasons, with humid summers and relatively mild winters.
Take a boat out from Smith Point Marina through Narrow Bay or Bellport Bay en route to the Ocean
Take a boat out from Smith Point Marina through Narrow Bay or Bellport Bay en route to the Ocean
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Shirley offers comparative affordability on Long Island
A variety of architectural styles complement the hamlet’s waterfront location. “In the 1950s and ‘60s, this area was full of bungalows and summer homes for people in the city. As more people started moving to Long Island, those bungalows became full-time homes,” Chrzanowski says. “Some of the homes are still the original bungalows, and then there are also some ranch-style houses and Capes.” Those looking for newer construction will find properties built from the 2000s through the early 2020s. “There’s more space out this way, so they’re building a lot of newer homes. Most of those are Colonials,” Chrzanowski says.
Comparative affordability is a big draw for homebuyers in Shirley. The median price of single-family homes is $505,000, significantly less than the median sales price of over $700,000 across all of Long Island. “Where else are you getting that?” Jahrsdoerfer asks. “You’re not getting that anywhere else, and you’re looking right out your bedroom window at the canal. The waterfront lifestyle is here just like it is anywhere else that’s more expensive; it’s just more affordable, and the taxes are lower.” Homes right on the bay can fetch up to $1.4 million, and flood insurance is a must for residents who live along the waterfront. Shirley’s overall CAP Index crime score is 3 out of 10, lower than the national average of 4.
Plenty of dock space for your boat or jetski, right in your backyard.
Spacious ranch home on the canal.
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Top-rated school districts, nearby community college and Stony Brook University
Shirley is split between two school districts. The William Floyd Union Free School District serves the southern three-quarters of the hamlet, while the Longwood Central School District covers the northern quarter. Both school districts earn an overall grade of A-minus from Niche. Nearby options for higher education include Suffolk County Community College, which is less than 15 miles away and serves more than 20,000 students. Residents are also around 25 miles from Stony Brook University, which Niche ranks as the fourth-best public university in the state. “One of the big draws to Long Island is Stony Brook University,” Chrzanowski says. “It’s a top-rated university, and your kids can still live at home without paying for dorms and all of that stuff.” SCCC and SBU are part of the State University of New York system.
NID 537933 Longwood Sr. High School has a fairly large campus with many well maintained fields.
William Floyd High School has one of the largest school campus in the area.
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Events in the Tri-Hamlet area include the Annual Christmas Parade
Shirley, Mastic and Mastic Beach are three intertwining hamlets known together as the Tri-Hamlet area. Residents from all three communities come together for annual events hosted by the Mastics & Shirley Chamber of Commerce. Popular festivities include the Food Truck Rally & Car Show and the Annual Christmas Parade, which brings more than 6,000 people to the hamlets each year and stands out as the largest Christmas parade in the Town of Brookhaven. Locals can also join community organizations like the Tri-Hamlet Mom’s Group.
Get an early start on your Christmas shopping at the Christmas Craft Fair.
Enjoy some live music at the North Meets South Fair.
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Commercial corridors along William Floyd Parkway and Sunrise Highway
Shopping and dining are concentrated in the heart of Shirley along William Floyd Parkway and Sunrise Highway. Residents will find a mix of shopping centers, chain retailers and local restaurants lining both thoroughfares. “As far as dining goes, there’s pretty much every type of food you can think of,” Chrzanowski says. “They just put in this amazing brewery called Southpaw, and they actually fill your beer from the bottom up. It seems like the beer is just better that way.” For more shopping and dining, residents can head to the Tanger Outlets Riverhead, one of the largest outlet malls on Long Island, with more than 130 retailers.
Access to the Long Island Expressway, LIRR and NYC commutes
In addition to shopping and dining, William Floyd Parkway and Sunrise Highway are Shirley's main transportation routes. William Floyd Highway provides access to Interstate 495, which runs along the hamlet’s northern edge. Also known as the Long Island Expressway, I-495 leads about 70 miles west into New York City. Those who prefer to take public transportation can head to Mastic-Shirley station, where the Montauk Branch of the Long Island Rail Road connects commuters to Manhattan’s Penn Station in about an hour and 45 minutes. For air travel, Long Island MacArthur Airport is about 13 miles away, and USA Today ranks it as the third-best small airport in the country. The closest international airport is John F. Kennedy International Airport, about 53 miles from Shirley.
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