Southold offers easy beach access and a small-town feel
Southold is a peaceful coastal community on Long Island’s North Fork, where you can stroll the locally owned businesses along Main Road and be at a beach within minutes. The area attracts a blend of seasonal and year-round residents, many of whom are retired or work remotely. Home styles here vary widely, ranging from modest cottages to expansive luxury builds. Kids have access to highly rated schools, and commuters can get to New York via the Long Island Rail Road.
How much it costs to buy in Southold
The median home sale price in Southold is in the upper $800,000s, lower than the nearby communities of Greenport and Mattituck. Size, condition and proximity to the water influence price, which can vary widely. Timothy O'Keefe, who grew up in the area and is a Realtor with Signature Premier Properties, says you can find anything from “a small beach cottage to a brand new 3,000 to 5,000 square foot new build.” In general, ranch-style homes, Cape Cods and small cottages range from the upper $500,000s to the upper $900,000s, while historic properties and newer builds range from the mid-$900,000s to over $2.7 million. O’Keefe adds that the market here stays competitive. “Any time a home pops up, it gets a lot of attention,” he says.
A mix of seasonal and year-round residents
Many people buying in Southold are looking for seasonal vacation homes, but O’Keefe says he sees a good share of year-round buyers as well, many of whom are retired. “Summer is busy, and in winter it quiets down, but there’s still action going on year-round,” he says, adding that businesses remain open throughout the year and winter weather isn’t bad, just chilly with occasional snow. Summer tourism traffic can occasionally slow you down, but O’Keefe says the worst traffic is during pumpkin-picking season.
Two highly rated schools serve the area
The area is served by the highly rated Southold Union Free School District, which has two schools. Southold Elementary School serves kindergarten through sixth grade, and then students move on to Southold Junior/Senior High School. Both campuses are right next to each other near Southold’s town center.
Commute to New York City on the LIRR or by car
Many of the jobs in Southold revolve around the area’s service, agriculture and marine industries, and O’Keefe says that many who live here work remotely or travel into New York City a couple of days a week. The LIRR’s station in Southold has train service into the city. The trip can take around two hours and 40 minutes, and it requires a transfer at the station in Ronkonkoma. Driving there can take over two hours, depending on traffic. As for getting around Southold itself, O’Keefe says the area is bike-friendly, and some residents can walk to businesses and restaurants from their homes.
Beaches and other ways to have fun
In Southold, you can be at a beach within minutes. “We’re in a great spot where we’re sandwiched between the Peconic Bay and the Long Island Sound, so it gives you the best of both beach worlds,” O’Keefe says. “The bay side has more sandy beaches and a little bit calmer water, and then on the opposite side is the Long Island Sound, which is known for being a little rocky, but some of us like that and it’s always great for a swim.” There are several places to have fun here, including:
- Founders Landing Park, which has a playground and a sandy beach on the bay
- Kenney’s Beach, a sandy swimming spot on the sound
- The Horton Point Lighthouse, which offers tours and has a museum
- Goldsmith’s Inlet County Park, a tidal area known for fishing and bird-watching
- The Custer Institute and Observatory, which hosts night sky observation sessions on Saturdays
Restaurants, markets and wineries along Main Road
Southold’s Main Road is lined with locally owned businesses and restaurants, including:
- North Fork Table and Inn, an upscale eatery serving freshly caught seafood
- Wayside Market, a butcher shop that also serves sandwiches
- Southold Fish Market, a seafood market and counter-serve restaurant offering seafood baskets and sandwiches
- White Flower Farmhouse, a high-end home goods store
The North Fork is known for its wineries, and there are several just outside of the hamlet along Main Road. For groceries, you can head to Southold IGA and farm stands like KK’s the Farm, which sell locally sourced produce. For national retailers like Target and Costco, you’ll have to head to Riverhead, around 30 minutes away.
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Written By
Annie Franklin
