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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,  3 Baths
    3,000 sqft   lot 15,246 sqft
    MLS 858803
    1 Days on Market
  2. 8 Beds,  7 Baths
    5,600 sqft   lot 2.28 ac
    MLS 859020
    2 Days on Market
  3. 3 Beds,  1.5 Baths
    1,550 sqft   lot 11,326 sqft
    MLS 858018
    2 Days on Market
  4. 3 Beds,  2 Baths
    2,100 sqft   lot 27,443 sqft
    MLS 857773
    2 Days on Market
  5. 4 Beds,  4.5 Baths
    3,500 sqft   lot 1.20 ac
    MLS 857922
    3 Days on Market
  6. 4 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 858113
    3 Days on Market
  7. 3 Beds,  2 Baths
    1,655 sqft   lot 14,811 sqft
    MLS 856401
    3 Days on Market
  8. 4 Beds,  1.5 Baths
    1,600 sqft   lot 7,406 sqft
    MLS 857635
    4 Days on Market
  9. 4 Beds,  2.5 Baths
    2,400 sqft   lot 20,909 sqft
    MLS 857324
    4 Days on Market
  10. 3 Beds,  2 Baths
    2,000 sqft   lot 28,750 sqft
    MLS 855331
    5 Days on Market
  11. 3 Beds,  3 Baths
    2,300 sqft   lot 33,542 sqft
    MLS 857115
    6 Days on Market
  12. 3 Beds,  3 Baths
    1,599 sqft   lot 17,424 sqft
    MLS 856972
    7 Days on Market
  13. 4 Beds,  4 Baths
    3,500 sqft   lot 23,087 sqft
    MLS 856031
    7 Days on Market
  14. 5 Beds,  3.5 Baths
    2,600 sqft   lot 15,595 sqft
    MLS 853979
    7 Days on Market
  15. 3 Beds,  3 Baths
    2,100 sqft   lot 21,780 sqft
    MLS 856377
    8 Days on Market
  16. 3 Beds,  2 Baths
    1,551 sqft   lot 5,228 sqft
    MLS 845202
    8 Days on Market
  17. 5 Beds,  4.5 Baths
    5,200 sqft   lot 40,511 sqft
    MLS 856176
    9 Days on Market
  18. 4 Beds,  2.5 Baths
    2,700 sqft   lot 1.19 ac
    MLS 855923
    9 Days on Market
  19. 3 Beds,  1.5 Baths
    1,350 sqft   lot 13,068 sqft
    MLS 855491
    9 Days on Market
  20. 4 Beds,  2 Baths
    2,600 sqft   lot 23,087 sqft
    MLS 844613
    9 Days on Market
  21. 4 Beds,  3 Baths
    2,800 sqft   lot 27,879 sqft
    MLS 854688
    9 Days on Market
  22. 5 Beds,  2 Baths
    2,190 sqft   lot 5.20 ac
    MLS 854848
    11 Days on Market
  23. 3 Beds,  1.5 Baths
    1,800 sqft   lot 20,474 sqft
    MLS 854500
    11 Days on Market
  24. 3 Beds,  1 Bath
    MLS 854454
    11 Days on Market
  25. 3 Beds,  2 Baths
    1,750 sqft   lot 14,811 sqft
    MLS 854267
    11 Days on Market
  26. 5 Beds,  4.5 Baths
    4,000 sqft   lot 1.66 ac
    MLS 853662
    14 Days on Market
  27. 4 Beds,  3.5 Baths
    3,000 sqft   lot 2.47 ac
    MLS 852892
    15 Days on Market
  28. 4 Beds,  3 Baths
    3,756 sqft   lot 27,008 sqft
    MLS 851840
    16 Days on Market
  29. 3 Beds,  3.5 Baths
    3,210 sqft   lot 34,848 sqft
    MLS 851749
    16 Days on Market
  30. 3 Beds,  3 Baths
    2,400 sqft   lot 13,417 sqft
    MLS 849591
    17 Days on Market
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