On the Great South Bay, Islip is a coastal hamlet punctuated by lakes, canals, parks and a lively Main Street with restaurants and shops. In the Town of Islip, it’s almost exactly halfway between New York City and the Hamptons, as well as a short ferry ride away from Fire Island and its access to the Atlantic Ocean — but the town itself is home to a popular South Shore beach and access to the water for boaters, fishers and swimmers. People are drawn to Islip for more than just its waterfront, though. “Islip is a tight-knit community,” says David Restrepo, an associate broker at Arbo Realty who has sold homes here for 15 years. “It has a fantastic school district, and the town itself offers a lot of parades and festivals where they close the street down and everybody gets to meet and enjoy carnival-type activities, so it’s a great place for kids to grow up and for people that are looking to meet their neighbors.”
Locals relax on the beach at the Islip Town Beach.
Dock spaces are abundant for waterfront homes in Islip, which is adorned with canals and lakes.
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Swimming and enjoying the views at Islip Beach, private clubs
For many, the water is a key part of life in Islip. Boating and fishing are favorite pastimes, and locals head to Islip Beach to relax in the sand or swim in the bay. It’s open only to residents of the town of Islip and has a playground in the sand for local children, and Restrepo says the views are gorgeous. Residents can also choose to get memberships at private waterfront clubs like the Bayberry Yacht Club or the Bayberry Beach & Tennis Club, which is member-owned and run. The Seatuck National Wildlife Refuge spans 209 acres and generally isn’t open to the public, but from November through January, it opens 100 of its acres to white-tailed deer hunters. Anglers are also allowed to fish from boats in sections of the refuge on the Great South Bay. Pardee Avenue Park is home to abundant athletic spaces. There are tennis, pickleball and basketball courts alongside a playground and fields that can be used for soccer, lacrosse or football.
The Yacht club is very prevalent the Islip area.
Brookwood Hall Park playground in Islip offer fun times for the little ones.
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Homes north of Main Street start around $450,000
Islip has a very wide range of home prices, with different sections of the town falling into different price ranges. The least expensive homes are the ranch-style houses, hi-ranches and Cape Cods found north of Main Street, which is also known as Montauk Highway; small fixer-uppers start as low as $450,000 and bigger, updated homes typically max out at $850,000. South of Main Street, homes start at $700,000. Homes on the water usually have private boat slips. They start around $1.5 million and can easily climb to $5 million for a large, updated house. Homes here are a mix of older Victorian and colonial-style homes and custom-built houses in a wider range of styles, including Mediterranean and new traditional.
According to Robert Caggiano, a licensed associate broker at Coldwell Banker who lives in Islip and has sold homes there for 12 years, the area known as Bayberry Point is where many of Islip’s most expensive homes are, including historic Moorish Revival homes along Bayberry Road. These homes, which Caggiano compares to something from The Great Gatsby, were designed and built in the early 1900s by an architect named Grosvenor Atterbury. Caggiano says a lot of these original homes have been knocked down, but there are still a handful of them. “That’s a very desirable and yet expensive street because toward the end of Bayberry you have panoramic, gorgeous views of the Great South Bay and the sunset,” Caggiano says.
Cape cod and ranch style homes are very common in Islip.
Many colonial homes sit on large tracts of land in Islip.
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Hurricane season in Islip
Hurricanes and tropical storms can hit Islip. When they do, they bring a major risk of both flooding and high wind. Getting insurance to help protect homes from this is an essential part of living here, especially directly along the waterfront.
Holiday parades, street fairs and summer movie nights
Islip holds community events throughout the year, including an annual parade and Christmas tree lighting in December and a big St. Patrick’s Day Parade. The fire department hosts street fairs where the hamlet shuts down Main Street to enjoy games, local vendors, food trucks and bouncy houses. “In the summer, on weekends, they have outdoor movie nights,” Caggiano says. “Families can take their beach chairs and towels and enjoy an old-time outdoor movie with their family.”
Special events take place around the city hall in Islip.
Main street in Islip sometimes gets closed down for special occasions.
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Local restaurants and businesses on Main Street
Main Street is a walkable stretch of shops and restaurants. Oconee Diner has been an Islip staple for over half a century. The family-owned and operated diner is open until the early morning hours and serves everything from omelets to burgers, Greek dishes and Italian specialties. It also has a full bar, but it’s best known for going all out on their holiday decorations — whether that holiday is Christmas or Halloween. Tellers: An American Chophouse is also well-known, with upscale dining in an old, converted bank. “That’s probably the most famous place in Islip to eat,” Restrepo says. Nearby, Harp & Hound is a bar with Irish pub-style food and live music on the weekends. The little downtown is also home to banks and local businesses, including hair salons, a yoga studio and a photography gallery. Lidl, Aldi and ShopRite all have groceries right in Islip, and there are two Stop & Shop locations just outside the town.
Oconee Diner is a great spot for the people of Islip wanting a tasty meal.
ShopRite on Sunrise Highway is a popular supermarket for the locals of Islip.
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Academics and athletics at Islip schools
Niche gives the Islip Union Free School District an A-minus. Children in Islip can attend Wing Elementary School, which has an A-minus, for kindergarten and first grade before moving on to the B-rated Maud S. Sherwood Elementary School for second through fifth grade. Islip Middle School has a B-plus and Islip High School has an A-minus. The high school earned recognition as a Scholar-Athlete School of Excellence for the 2023-2024 school year.
Islip High School is a highly rated, public school located in Islip, NY.
The Islip High Schools Turf Foodball Field is the home of the Buccaners.
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Major highways, LIRR station to Manhattan
Montauk Highway, which is primarily called Main Street here, isn’t Islip’s only major road. Sunrise Highway, state Route 111 and Southern State Parkway all cross through it, making it easy for residents to drive in almost any direction. The Long Island Rail Road’s Islip Station is also a major draw, especially for those who work in Manhattan. The station has a free onsite parking lot that fits 150 cars. From there, the train reaches Penn Station in about an hour and 15 minutes. “You’re still close enough to Manhattan to be able to experience all the shows and the sports venues that they have but still have the peacefulness and tranquility of living on the water and enjoying the environment,” Restrepo says. Bay Shore’s ferry to Fire Island is also less than 3 miles away. South Shore University Hospital is less than 2 miles away, and Long Island MacArthur Airport is about 9 miles away.
Margaret (Meg) Smith has more than 30 years of experience as a real estate professional. She graduated with honors as an Education Major and Spanish Minor from Purdue University. In 1984, she opened Kidnastics, a preschool in Babylon Village, NY. While looking to expand this business, she became interested in Real Estate. In 1987, she sold her preschool, and her real estate career began. In 2010 she started her own brokerage, Meg Smith and Associates Real Estate, which was acquired by Daniel Gale Sotheby’s International Realty in February 2022.
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