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A peaceful Hamptons neighborhood nestled on the North Fork of eastern Long Island, the exquisite Southold hamlet invites residents to enjoy wide-open farmland and small-town charms from antique shops to roadside produce stands. Established in 1640 as New York’s oldest English settlement, Southold continues to evolve today.

Dotted with acres of open farmland, world-renowned vineyards, and ample space devoted to public parks, the delightful community with a rich heritage continues to thrive with unique shopping opportunities, top casual and fine dining fare, historic buildings, beautiful museums, and unlimited recreational opportunities.

Its countrified qualities, culture, and history make Southold a special place to live, especially for those who prefer homes set on well-tended acres of farmland rather than tracts best measured by the square foot. Southold is a nirvana for residents who prefer natural island beauty over suburban life or summer hotspot festivities.

The hamlet of Cutchogue is home to not just Long Island’s first winery (established in 1973) but also one of best surviving examples of domestic English architecture in the United States. Peconic—named for Peconic Bay and once home to Albert Einstein—has roots as a noted artists’ haven dating back to the early 20th century.

Walk the unspoiled beaches along the Long Island Sound and Noyack Bay, rich with stretches of pristine sand. Known for its wine culture, Southold’s North Fork features sprawling vineyards and wineries open year-round for tours and tastings. Also part of the township are Robins Island, Plum Island, and Fisher’s Island.

Contact Team Rita today to schedule viewings for homes in Southold, New York. Call to schedule a free consultation with one of our real estate agents.


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  1. 4 Beds,  2 Baths
    2,000 sqft   lot 1.74 ac
    MLS L3548646
    402 Days on Market
  2. 3 Beds,  2 Baths
    lot 17,337 sqft
    MLS L3547425
    407 Days on Market
  3. 4 Beds,  3.5 Baths
    4,000 sqft   lot 41,818 sqft
    MLS H6303191
    408 Days on Market
  4. 4 Beds,  3 Baths
    lot 2.22 ac
    MLS L3569738
    409 Days on Market
  5. 3 Beds,  1.5 Baths
    1,504 sqft   lot 21,650 sqft
    MLS L3544978
    417 Days on Market
  6. 4 Beds,  3.5 Baths
    lot 14,375 sqft
    MLS L3539656
    442 Days on Market
  7. 5 Beds,  4.5 Baths
    4,900 sqft   lot 39,814 sqft
    MLS L3528746
    493 Days on Market
  8. 6 Beds,  2.5 Baths
    3,200 sqft   lot 29,447 sqft
    MLS L3509055
    610 Days on Market
  9. 4 Beds,  3.5 Baths
    2,604 sqft   lot 29,883 sqft
    MLS L3494242
    680 Days on Market
  10. 3 Beds,  1.5 Baths
    1,068 sqft   lot 43,299 sqft
    MLS L3487080
    715 Days on Market
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