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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
    2,150 sqft   lot 21,780 sqft
    MLS 3568549
    1 Days on Market
  2. 2 Beds,  1 Bath
    lot 12,197 sqft
    MLS 3568394
    1 Days on Market
  3. 3 Beds,  2 Baths
    1,425 sqft   lot 8,712 sqft
    MLS 3568382
    1 Days on Market
  4. 4 Beds,  2.5 Baths
    2,500 sqft   lot 2.10 ac
    MLS 3565665
    1 Days on Market
  5. 4 Beds,  2.5 Baths
    2,450 sqft   lot 41,382 sqft
    MLS 3568309
    2 Days on Market
  6. 6 Beds,  5.5 Baths
    lot 22,216 sqft
    MLS 3567891
    3 Days on Market
  7. 4 Beds,  4 Baths
    3,100 sqft   lot 40,947 sqft
    MLS 3567805
    3 Days on Market
  8. 4 Beds,  4.5 Baths
    3,400 sqft   lot 40,947 sqft
    MLS 3567804
    3 Days on Market
  9. 3 Beds,  2.5 Baths
    lot 2.04 ac
    MLS 3567569
    5 Days on Market
  10. 2 Beds,  1 Bath
    lot 10,890 sqft
    MLS 3567148
    6 Days on Market
  11. 4 Beds,  2.5 Baths
    2,400 sqft   lot 41,818 sqft
    MLS 3567104
    7 Days on Market
  12. 4 Beds,  3 Baths
    lot 12,633 sqft
    MLS 3566268
    10 Days on Market
  13. 3 Beds,  2 Baths
    lot 4,792 sqft
    MLS 3566875
    12 Days on Market
  14. 3 Beds,  2 Baths
    1,422 sqft   lot 2.35 ac
    MLS 3564140
    13 Days on Market
  15. 3 Beds,  1.5 Baths
    lot 13,068 sqft
    MLS 3565566
    14 Days on Market
  16. 4 Beds,  4 Baths
    lot 15,682 sqft
    MLS 3565387
    15 Days on Market
  17. 3 Beds,  1 Bath
    lot 5,228 sqft
    MLS 3565361
    15 Days on Market
  18. 2 Beds,  1 Bath
    lot 12,633 sqft
    MLS 3565186
    16 Days on Market
  19. 4 Beds,  2.5 Baths
    2,100 sqft   lot 14,375 sqft
    MLS 3565045
    16 Days on Market
  20. 4 Beds,  3.5 Baths
    2,950 sqft   lot 25,265 sqft
    MLS 3565010
    16 Days on Market
  21. 3 Beds,  3 Baths
    2,556 sqft   lot 20,909 sqft
    MLS 3565060
    17 Days on Market
  22. 4 Beds,  2.5 Baths
    2,100 sqft   lot 20,909 sqft
    MLS 3564841
    17 Days on Market
  23. 1 Bed,  1 Bath
    432 sqft   lot 4,356 sqft
    MLS 3564812
    17 Days on Market
  24. 2 Beds,  1 Bath
    805 sqft  
    MLS 3564729
    17 Days on Market
  25. 5 Beds,  4 Baths
    4,723 sqft   lot 5.82 ac
    MLS 3564723
    17 Days on Market
  26. 2 Beds,  1 Bath
    1,320 sqft   lot 40,511 sqft
    MLS 3564725
    17 Days on Market
  27. 3 Beds,  1.5 Baths
    lot 20,909 sqft
    MLS 3564682
    17 Days on Market
  28. 2 Beds,  1 Bath
    1,050 sqft   lot 3,485 sqft
    MLS 3564481
    18 Days on Market
  29. 4 Beds,  4 Baths
    4,000 sqft   lot 5,228 sqft
    MLS 3564345
    18 Days on Market
  30. 2 Beds,  2 Baths
    1,100 sqft   lot 7,841 sqft
    MLS 3564290
    19 Days on Market
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