$799,108Average Value$352Average Price per Sq Ft6Homes For Sale
A waterfront community with echoes of the past in Oakdale
The Gilded Age was a time of opulence for the rich elite, and it’s an era that has its fingerprints all over Oakdale. The waterfront community was a summertime playground for Gilded Age luminaries, dotted with elaborately furnished mansions — including one built by William Vanderbilt in the late 1800s. Originally called Idle Hour, the mansion has been renamed the Bourne Mansion and restored to its original grandeur; it currently serves as an events venue overlooking the Connetquot River. Everyday people left their mark in Oakdale, too, through areas like the Artists' Colony, which is full of historic homes.
Today, the hamlet is most well-known for the same features that called Vanderbilt and his contemporaries to build mansions here: its position right where the mouth of the Connetquot River meets Nicoll Bay on Long Island’s South Shore. “I think one of the best things about Oakdale is how it wraps around the Connetquot River,” says Larry McKenna, a licensed real estate salesperson at Signature Premier Properties who has been selling in the area for 17 years. “It’s really geared for boaters; it’s a boating community.” Boaters are drawn here not just for its marinas, but for the canals that now cut through the land. Homes back up to these canals, offering small private boat slips for residents.
These waterfront homes in Oakdale have an unforgettable view of the bay every day.
The Wharf and The Snapper Inn are two local favorites.
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Boating on Nicoll Bay, swimming at Byron Lake Park’s new pool
The water that surrounds Oakdale on two sides and runs through its canals provides plenty of space for marinas and private docks as well as launching points for jet skis, paddle boards and kayaks. According to McKenna, many residents join the Oakdale Yacht Club. And although Oakdale lacks a beach, Byron Lake Park’s pool completed a $20 million renovation project just in time for summer 2024. The new pool is accessible, with equipment in place to lower and raise people with limited mobility into the water. It also has a huge, curving water slide, a splash pad and a concession stand, and its building and septic system have been updated as well. Even the park’s lake got a facelift in the form of a new bulkhead to improve water quality. “I haven’t had the pleasure of visiting yet, but I’ve been told that it actually has everything from a beautiful pool — just a great place for kids — to a very beautiful recreation area,” says Ted Gounelas, an associate real estate broker at Coldwell Banker M&D Life.
Connetquot River State Park Preserve borders the north side of Oakdale. The nearly 3,500-acre preserve is home to local wildlife, including rare birds and native plants. It has at least 50 miles of trails for hiking, horseback riding and cross-country skiing. The park allows fly fishing for permit holders.
Cruise down the river in Oakdale or head into the bay for a fun day on the water.
Head over to cool off in the Oakdale Beach Club Pool.
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Oakdale's waterfront and historic homes
Oakdale’s homes vary greatly in style and size — ranch-style homes, hi-ranches and Garrison Colonials built between the 1940s and 1980s and more recently built new traditionals can all be found on many of its streets. But so can large Colonial Revivals, huge Beau Arts-style houses and historic estates. “Within reason, there are some houses that have been there for about 200 years, and they’re located on 2 to 3 acres, including its own private little pond,” Gounelas says. “You can find properties on upwards of an acre, but for the most part they’re probably mostly on a smaller quarter acre all the way to half-acre or 1-acre lots.” Inland homes typically cost between $600,000 and $850,000, aside from a few large, renovated houses with larger lots and amenities like pools that can go for $1.3 million. Waterfront homes with private docks are also very common here, whether they back into canals or look over the river. Depending on their size, age and renovation status, they typically cost between $750,000 and $2 million.
Historic homes aren’t limited to just massive estates, though — in Oakdale, even some normal residences bear the echoes of the Gilded Age. The original Idle Hour was surrounded by a 900-acre farm, whose outbuildings, including a creamery, a horse barn and a duck house, were designed to look like residences. In 1926, an artist bought these buildings and turned them into true homes. Her artist friends flocked there, and the little area is now called Artists' Colony. It’s known for its narrow streets and houses that are often described as looking like they belong in a storybook. Some are attached and some semi-attached, while others stand on their own, adding even more variety to the community. A small, attached home in Artists' Colony could start in the high $400,000 range. In 2024, Gounelas helped sell a renovated home here for $1.5 million. “I think it started off as a chapel because part of the renovation involved the original stained-glass windows being put into the den — the actual formal dining room,” he says. Most homes in Artists' Colony seem to cost well under $1 million, but it’s hard to pin down an exact price point because it’s a small area, and many residents stay there for decades, making it hard to pull pricing data.
Like many waterfront communities, flooding can be a concern here, especially during hurricane season. Wind damage during these storms, though, is an even bigger concern in Oakdale. Purchasing insurance to protect against these types of damage is an essential part of living here. The CAP Index crime score is 1 out of 10, below the national average of 4.
Modern waterfront homes overlooking the bay in Oakdale.
Oakdale is the perfect south shore town on Long Island.
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Community events through the Oakdale Yacht Club
Oakdale is a quiet community, but there are events for those who want to seek them out. “Their main thing in the summer is the Oakdale Yacht Club,” McKenna says. “That’s the place to be, it’s a lot of fun.” A few miles away, the West Sayville Seafood Festival draws thousands every year on the third weekend in August.
Oakdale has a slew of marinas to choose from if you need a slip for your boat.
Hang out at the Oakdale Yacht Club, go for a dip in the pool or have a drink at the bar.
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Fresh seafood and live music at local restaurants
“Oakdale is a hip and up-and-coming [community],” says Karen Roth, a licensed associate broker at RE/MAX Integrity. Montauk Highway is lined with a collection of local eateries. Mannino’s serves Italian classics and Village Idiot Irish Pub hosts live music every Friday night. On the water, The Snapper Inn has been a popular brunch and dinner spot since 1929 and View is known for its lobster rolls and lobster bisque. Both fine dining restaurants have waterfront decks with views of the water and frequent live music performances. For dinner and drinks on the water with a little bit of a lower price tag, locals head to The Wharf, which also has frequent live music and stays open until 3 a.m. on the weekend. There are a few small businesses and a veterinary clinic along Montauk Highway as well, and Lidl is on Sunrise Highway.
The Wharf is a town favorite in Oakdale.
Great live music is always at The Apple Festival.
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Extracurriculars at Connetquot High
The Connetquot Central School District gets an A-minus from Niche. Children can attend Idle Hour Elementary School, which has an A, and Oakdale-Bohemia Middle School, which has an A-minus. Students then move on to Connetquot High School. The high school has a B-plus from Niche and a student-to-teacher ratio of 11-to-1 — despite serving over 2,000 students. Students can participate in extracurricular activities like animal conservation, robotics and sign language clubs.
Students enjoying the tennis courts at Connetquot High School.
Connetquot public high school serves students from the 9th–12th grades in Bohemia.
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Montauk and Sunrise Highway, LIRR options for daily commutes
Montauk Highway and Sunrise Highway both run through the area, making it easy to travel across Long Island by car. From Oakdale Station, the Long Island Rail Road takes commuters the 53 miles to Manhattan’s Penn Station in about an hour and 20 minutes. “People who live in central Suffolk County don’t mind the commute at all,” Roth says. She adds that some people drive about 7 miles north to Ronkonkoma Station for a better chance at nabbing a seat. “It’s one of the best parts of living in this area. You’re almost guaranteed a seat on the train, and you can enjoy your morning coffee,” she says. Long Island MacArthur Airport is less than 6 miles away, and it’s about 10 miles to both Long Island Community Hospital and Good Samaritan University Hospital.
Take a ride on the Long Island Rail Road at Oakdale Station.
Waterfront properties are common in the area.
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Written By
Michael Crouch
Photography Contributed By
Anthony Costa
Video By
Adam Lapallo
Interested in learning more about homes in this area?
Reach out to
Patricia Duggan,
an experienced agent in this area.
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On average, homes in Oakdale, NY sell after 53 days on the market compared to the national average of 49 days. The median sale price for homes in Oakdale, NY over the last 12 months is $701,500, up 11% from the median home sale price over the previous 12 months.
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