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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
    1,650 sqft   lot 12,981 sqft
    MLS 825345
    41 Days on Market
  2. 4 Beds,  1.5 Baths
    1,200 sqft   lot 11,326 sqft
    MLS 825933
    42 Days on Market
  3. 1 Bed,  1 Bath
    lot 4.00 ac
    MLS 825742
    42 Days on Market
  4. 3 Beds,  2 Baths
    1,500 sqft   lot 1.84 ac
    MLS 825540
    43 Days on Market
  5. Price Drop
    4 Beds,  2 Baths
    1,589 sqft   lot 5,228 sqft
    MLS 825421
    44 Days on Market
  6. 3 Beds,  1.5 Baths
    1,999 sqft   lot 21,780 sqft
    MLS 823397
    47 Days on Market
  7. 4 Beds,  4 Baths
    4,000 sqft   lot 5,228 sqft
    MLS 823080
    48 Days on Market
  8. 4 Beds,  3 Baths
    3,200 sqft   lot 15,246 sqft
    MLS 823903
    49 Days on Market
  9. 5 Beds,  4 Baths
    2,450 sqft   lot 12,197 sqft
    MLS 822831
    50 Days on Market
  10. 4 Beds,  3.5 Baths
    3,000 sqft   lot 14,375 sqft
    MLS 818321
    52 Days on Market
  11. 1 Bed,  1 Bath
    800 sqft   lot 5,663 sqft
    MLS 822513
    53 Days on Market
  12. Price Drop
    4 Beds,  3 Baths
    2,000 sqft   lot 39,640 sqft
    MLS 820321
    57 Days on Market
  13. 4 Beds,  2 Baths
    2,487 sqft  
    MLS 819108
    57 Days on Market
  14. 6 Beds,  6.5 Baths
    9,900 sqft   lot 4.72 ac
    MLS 818952
    60 Days on Market
  15. 7 Beds,  3 Baths
    4,376 sqft   lot 2.84 ac
    MLS 818991
    62 Days on Market
  16. 3 Beds,  2.5 Baths
    1,800 sqft   lot 8,712 sqft
    MLS 817508
    64 Days on Market
  17. 2 Beds,  1 Bath
    1,071 sqft   lot 8,712 sqft
    MLS 812808
    65 Days on Market
  18. Price Drop
    4 Beds,  4.5 Baths
    4,500 sqft   lot 40,250 sqft
    MLS 817670
    65 Days on Market
  19. 2 Beds,  2 Baths
    1,300 sqft   lot 5,228 sqft
    MLS 817817
    66 Days on Market
  20. 4 Beds,  3 Baths
    lot 22,216 sqft
    MLS 816113
    68 Days on Market
  21. 4 Beds,  4.5 Baths
    3,960 sqft   lot 35,197 sqft
    MLS 814068
    77 Days on Market
  22. 4 Beds,  3 Baths
    1,740 sqft   lot 22,216 sqft
    MLS 813518
    78 Days on Market
  23. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS 813226
    79 Days on Market
  24. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS 813208
    79 Days on Market
  25. 6 Beds,  3.5 Baths
    3,000 sqft   lot 14,811 sqft
    MLS 810641
    86 Days on Market
  26. 4 Beds,  2.5 Baths
    2,800 sqft   lot 20,474 sqft
    MLS 810320
    86 Days on Market
  27. 3 Beds,  2 Baths
    1,547 sqft   lot 17,337 sqft
    MLS 810093
    87 Days on Market
  28. Price Drop
    2 Beds,  2 Baths
    900 sqft   lot 5,228 sqft
    MLS 810184
    89 Days on Market
  29. 2 Beds,  1 Bath
    1,300 sqft  
    MLS 806036
    89 Days on Market
  30. 5 Beds,  3.5 Baths
    3,160 sqft   lot 1.27 ac
    MLS 809216
    91 Days on Market
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