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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,  3 Baths
    2,150 sqft   lot 21,780 sqft
    MLS 861719
    18 Days on Market
  2. 5 Beds,  4.5 Baths
    3,500 sqft   lot 1.20 ac
    MLS 857922
    18 Days on Market
  3. 4 Beds,  4.5 Baths
    4,028 sqft   lot 24,830 sqft
    MLS 828111
    19 Days on Market
  4. 4 Beds,  3 Baths
    1,800 sqft   lot 17,337 sqft
    MLS 862801
    19 Days on Market
  5. 3 Beds,  1 Bath
    1,100 sqft   lot 11,762 sqft
    MLS 856542
    19 Days on Market
  6. 3 Beds,  3 Baths
    3,000 sqft   lot 15,246 sqft
    MLS 858803
    23 Days on Market
  7. 8 Beds,  7 Baths
    5,600 sqft   lot 2.28 ac
    MLS 859020
    24 Days on Market
  8. 3 Beds,  2 Baths
    2,100 sqft   lot 27,443 sqft
    MLS 857773
    24 Days on Market
  9. 3 Beds,  2 Baths
    1,584 sqft   lot 3,877 sqft
    MLS 854289
    25 Days on Market
  10. 4 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 858113
    25 Days on Market
  11. 4 Beds,  1.5 Baths
    1,600 sqft   lot 7,406 sqft
    MLS 857635
    26 Days on Market
  12. 4 Beds,  2.5 Baths
    2,400 sqft   lot 20,909 sqft
    MLS 857324
    26 Days on Market
  13. Price Drop
    3 Beds,  2 Baths
    2,000 sqft   lot 28,750 sqft
    MLS 855331
    27 Days on Market
  14. Price Drop
    3 Beds,  3 Baths
    2,300 sqft   lot 33,542 sqft
    MLS 857115
    28 Days on Market
  15. Price Drop
    3 Beds,  3 Baths
    1,599 sqft   lot 17,424 sqft
    MLS 856972
    29 Days on Market
  16. 4 Beds,  4 Baths
    3,500 sqft   lot 23,087 sqft
    MLS 856031
    29 Days on Market
  17. Price Drop
    4 Beds,  3.5 Baths
    2,600 sqft   lot 15,595 sqft
    MLS 853979
    29 Days on Market
  18. 3 Beds,  3 Baths
    2,100 sqft   lot 21,780 sqft
    MLS 856377
    30 Days on Market
  19. 3 Beds,  2 Baths
    1,924 sqft   lot 5,228 sqft
    MLS 845202
    30 Days on Market
  20. 5 Beds,  4.5 Baths
    5,200 sqft   lot 40,511 sqft
    MLS 856176
    31 Days on Market
  21. 4 Beds,  2.5 Baths
    2,700 sqft   lot 1.19 ac
    MLS 855923
    31 Days on Market
  22. Price Drop
    3 Beds,  1.5 Baths
    1,350 sqft   lot 13,068 sqft
    MLS 855491
    31 Days on Market
  23. 4 Beds,  2 Baths
    2,600 sqft   lot 23,087 sqft
    MLS 844613
    31 Days on Market
  24. 3 Beds,  1.5 Baths
    1,800 sqft   lot 20,474 sqft
    MLS 854500
    33 Days on Market
  25. Price Drop
    3 Beds,  2 Baths
    1,750 sqft   lot 14,811 sqft
    MLS 854267
    33 Days on Market
  26. 5 Beds,  4.5 Baths
    4,000 sqft   lot 1.66 ac
    MLS 853662
    36 Days on Market
  27. 4 Beds,  3 Baths
    3,756 sqft   lot 27,008 sqft
    MLS 851840
    38 Days on Market
  28. 3 Beds,  3.5 Baths
    3,210 sqft   lot 34,848 sqft
    MLS 851749
    38 Days on Market
  29. 3 Beds,  3 Baths
    2,400 sqft   lot 13,417 sqft
    MLS 849591
    39 Days on Market
  30. 2 Beds,  1 Bath
    885 sqft   lot 8,712 sqft
    MLS 851297
    39 Days on Market
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