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Overview


Anglophiles are quick to point out that Southold, which was founded in 1640, is the oldest English settlement in New York.

Farmland still abounds here, forming scenic swathes of open spaces. Dotted with produce stands, antique shops, and top restaurants, Southold also is a hamlet of exquisite homes and farms. And, like other towns on the North Fork, it's made for individuals who prefer to live in homes set on well-tended acres instead of tracts better measured by the square foot.

Living in Southold

The peaceful Hamptons neighborhood of Southold treats residents to acres of open farmland, world-renowned vineyards and plenty of space devoted to public parks. Beachfront access is available, too, with can't-miss sunset views and access to Long Island Sound and Peconic Bay.

With a variety of locally-owned restaurants, friendly watering holes and ample opportunities to sample wine at the local vineyards, Southold also offers plenty to do indoors. Its combination of wide-open farmland dating back to the 1600s and small town charms like antique shops and roadside produce stands make Southold a great choice for Long Island real estate shoppers.

Southold real estate

Southold real estate options consist primarily of single-family homes with tree-filled manicured yards and views of surrounding farmland or water. The New England-style properties, spacious in size with three or more bedrooms, often mix brick with clapboard siding and bright window shutters. Cozy interior features like wood-burning stoves and enormous sliding-glass doors combine with outdoor amenities such as hot tubs, wrap-around decks and in-ground swimming pools.  

Southold history

Southold, the proclaimed oldest English settlement in the state of New York, began its storied history in 1640 when a group of Puritans from the New Haven Colony in present-day Connecticut made their way south and settled on Long Island. New arrivals brought their livestock and received four-acre lots spreading out from a central church, which also served as Southold's arsenal and town hall.

The community continued to grow and a new church, built in 1684, ushered in a period of agricultural and textile development aimed at trade with neighboring colonies. Flourishing economically, Southold grew to just over 3,000 residents by the time of the Revolutionary War.

Railroad construction in the 19th century brought visitors escaping the heat and crowds of Manhattan every June. As summer homes and leisure time became part of everyday life for well-to-do New Yorkers, the area grew again in population. Older farmland turned into horse farms, vineyards and idyllic country estates, giving present-day Southold much of its charm and old-town feel.

Southold restaurants

Erik's Breakfast and Lunch, also known as Erik's in Southold, serves scrumptious breakfast dishes like egg sandwiches and heaping omelets in a relaxed setting with ample outdoor seating and personable service. The bustling eatery also serves some of the area's best coffee, and a popular homemade chili later in the day.

For a formal meal in an elegant setting, you'll find no better option in Southold than The North Fork Table and Inn. American cuisine like truffled macaroni and cheese and Australian grass-fed beef are served in the converted New England-style mansion with a wide selection of wines and cocktails. With its popular food truck parked right outside serving boxed lunches and unique takes on American favorites like artisan hot dogs on bakery rolls and Berkshire pulled pork, locals can also grab a quick bite on the go.

Southold attractions

Dog owners, fishing enthusiasts and hikers all flock to the Peconic Dunes County Park for time outside in a gorgeous beachfront setting. Locals rave about the sunset views, too, and use the 36 acres of untouched wilderness year-round to explore the great outdoors.

The historic Horton Point Lighthouse, built in 1857, towers over Southold and still retains many examples of a bygone era with rickety chairs and old lanterns on display as visitors make their way up the 58-foot beacon of light. With educational programs, community outreach events and tours during the summer by the Southold Historical Society, the lighthouse shares insightful stories about Southold's notable past.

Southold shopping

Locals rave about Sparkling Pointe's wines, available for sale at their stunning vineyard in the heart of Southold. The local winery and vineyard, which practices sustainable agriculture and hand-tends its grapes, sits on 40 acres and treats visitors to a one-of-a-kind tour and tasting experience under elegant crystal chandeliers and a vaulted ceiling. With a VIP lounge, tranquil outdoor terrace areas and educational sessions with food pairings, wine connoisseurs have every excuse for a repeat visit.

Music lovers are hard-pressed to find a better selection of vintage guitars on Long Island than at Rothman's Guitars. The local hub for everything related to music also sells banjos, harmonicas and doubles as an art gallery showcasing local talent.

Southold events

With weekly movie nights, book clubs and special events from local authors and artists, the Southold Free Public Library is the area's hot spot for events the whole family can enjoy. Physical activity gets into the act, too, with events like story time yoga and bulb planting in the library's garden. The library hosts five to seven events a week at all times of day to bring the community together for fun and entertainment.

Southold nightlife

Southold's under-the-radar nightlife centers on a few low-key and unique watering holes right in the heart of downtown. North Fork Taps & Corks, as the name suggests, serves craft beer and local wine in a welcoming setting with live acoustic music and fun events like painting your own masterpiece and open mic nights.

Locals frequent Founders Tavern to watch all the games on big-screen TVs while taking advantage of drink specials and local micro brews from Long Island breweries. The establishment serves pub fare until late, too, with favorites like baby back ribs, fried flounder and build-your-own burgers.

Southold golf

Cedars Golf Club, the closest golf course to Southold, sits in nearby Cutchogue on 13 acres of rolling hills, tranquil ponds and soaring cedar trees. The nine-hole par-three course also features an indoor golf club with snacks, gear and a simulator for improving your swing between rounds.

Beyond Yummy

"Southold Town is home to the Famous North Fork Table and Inn this restaurant is an absolute must dine- Sit up at the bar and tell Ricky the bartender Sheri sent you! "
Sheri Winter Clarry
Sheri Winter         Clarry
Explore Properties in the Neighborhood
1515 Anchor Lane, Southold $999,000Featured
1515 Anchor Lane 3 Beds / 4 Baths / 3,300 Sq. Ft.

What's In The Area: Southold

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Local tips and information for going out in the Southold from The Corcoran Group. Explore dining, shopping and nightlife.

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