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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. 3 Beds,  2 Baths
    2,200 sqft   lot 32,670 sqft
    MLS 3304553
    1 Days on Market
  2. 3 Beds,  7 Baths
    2,238 sqft  
    MLS H6109306
    4 Days on Market
  3. 3 Beds,  1 Bath
    lot 10,019 sqft
    MLS 3303399
    5 Days on Market
  4. 2 Beds,  1 Bath
    lot 12,633 sqft
    MLS 3303182
    5 Days on Market
  5. 3 Beds,  3 Baths
    2,400 sqft   lot 21,780 sqft
    MLS 3303167
    5 Days on Market
  6. 4 Beds,  3 Baths
    2,000 sqft   lot 32,670 sqft
    MLS 3303159
    5 Days on Market
  7. 2 Beds,  1 Bath
    lot 5,228 sqft
    MLS 3303000
    6 Days on Market
  8. 4 Beds,  4 Baths
    lot 10,890 sqft
    MLS 3302952
    6 Days on Market
  9. 4 Beds,  4 Baths
    2,500 sqft   lot 19,167 sqft
    MLS 3302509
    7 Days on Market
  10. 4 Beds,  3 Baths
    2,400 sqft   lot 23,087 sqft
    MLS 3302218
    10 Days on Market
  11. 2 Beds,  2 Baths
    lot 872 sqft
    MLS 3302064
    10 Days on Market
  12. 4 Beds,  2 Baths
    lot 43,560 sqft
    MLS 3301928
    10 Days on Market
  13. 5 Beds,  6 Baths
    5,100 sqft   lot 37,462 sqft
    MLS 3301795
    11 Days on Market
  14. 1 Bed,  2 Baths
    lot 8,712 sqft
    MLS 3301593
    11 Days on Market
  15. 3 Beds,  2 Baths
    lot 10,890 sqft
    MLS 3301489
    11 Days on Market
  16. 2 Beds,  2 Baths
    1,300 sqft   lot 1,307 sqft
    MLS 3301177
    12 Days on Market
  17. 3 Beds,  3 Baths
    2,100 sqft   lot 11,762 sqft
    MLS 3300953
    13 Days on Market
  18. 4 Beds,  4 Baths
    lot 26,136 sqft
    MLS 3300726
    13 Days on Market
  19. 4 Beds,  2 Baths
    2,500 sqft   lot 24,830 sqft
    MLS 3299694
    18 Days on Market
  20. 3 Beds,  4 Baths
    5,000 sqft   lot 14,375 sqft
    MLS 3299403
    19 Days on Market
  21. 3 Beds,  4 Baths
    1,850 sqft   lot 13,504 sqft
    MLS 3299169
    19 Days on Market
  22. 4 Beds,  4 Baths
    2,800 sqft   lot 21,345 sqft
    MLS 3298391
    24 Days on Market
  23. 3 Beds,  4 Baths
    2,700 sqft   lot 22,652 sqft
    MLS 3298214
    24 Days on Market
  24. 4 Beds,  3 Baths
    2,400 sqft   lot 20,909 sqft
    MLS 3298213
    24 Days on Market
  25. 4 Beds,  4 Baths
    lot 20,474 sqft
    MLS 3297849
    25 Days on Market
  26. 2 Beds,  1 Bath
    1,000 sqft   lot 22,652 sqft
    MLS 3297517
    26 Days on Market
  27. 3 Beds,  2 Baths
    lot 29,621 sqft
    MLS 3296875
    28 Days on Market
  28. 4 Beds,  3 Baths
    2,750 sqft   lot 25,265 sqft
    MLS 3296764
    29 Days on Market
  29. 4 Beds,  3 Baths
    lot 10.82 ac
    MLS 3295917
    33 Days on Market
  30. 4 Beds,  3 Baths
    lot 7,406 sqft
    MLS 3295589
    33 Days on Market
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