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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. 2 Beds,  2 Baths
    960 sqft   lot 2,614 sqft
    MLS 863727
    1 Days on Market
  2. 3 Beds,  2 Baths
    1,425 sqft   lot 8,712 sqft
    MLS 843099
    2 Days on Market
  3. 3 Beds,  3 Baths
    2,250 sqft   lot 14,811 sqft
    MLS 862258
    2 Days on Market
  4. 3 Beds,  2.5 Baths
    2,026 sqft   lot 13,068 sqft
    MLS 861571
    2 Days on Market
  5. 4 Beds,  4 Baths
    2,600 sqft   lot 18,296 sqft
    MLS 863961
    2 Days on Market
  6. 5 Beds,  5.5 Baths
    3,350 sqft   lot 30,492 sqft
    MLS 863916
    3 Days on Market
  7. 4 Beds,  2 Baths
    2,235 sqft   lot 26,136 sqft
    MLS 863970
    3 Days on Market
  8. 2 Beds,  1.5 Baths
    2,300 sqft   lot 21,780 sqft
    MLS 861585
    5 Days on Market
  9. 3 Beds,  2.5 Baths
    3,735 sqft   lot 10,890 sqft
    MLS 862942
    6 Days on Market
  10. 3 Beds,  2.5 Baths
    2,045 sqft   lot 10,890 sqft
    MLS 861090
    6 Days on Market
  11. 3 Beds,  2.5 Baths
    2,238 sqft   lot 436 sqft
    MLS 862399
    6 Days on Market
  12. 3 Beds,  3.5 Baths
    2,000 sqft   lot 5,228 sqft
    MLS 861088
    6 Days on Market
  13. 3 Beds,  3 Baths
    2,500 sqft   lot 25,265 sqft
    MLS 861882
    7 Days on Market
  14. 4 Beds,  3 Baths
    2,150 sqft   lot 21,780 sqft
    MLS 861719
    8 Days on Market
  15. 5 Beds,  4.5 Baths
    3,500 sqft   lot 1.20 ac
    MLS 857922
    8 Days on Market
  16. 4 Beds,  3 Baths
    1,800 sqft   lot 17,337 sqft
    MLS 862801
    9 Days on Market
  17. 3 Beds,  1 Bath
    1,100 sqft   lot 11,762 sqft
    MLS 856542
    9 Days on Market
  18. 4 Beds,  4.5 Baths
    2,842 sqft   lot 20,038 sqft
    MLS 862752
    10 Days on Market
  19. 4 Beds,  2.5 Baths
    2,100 sqft   lot 43,560 sqft
    MLS 860121
    12 Days on Market
  20. 3 Beds,  3 Baths
    3,000 sqft   lot 15,246 sqft
    MLS 858803
    13 Days on Market
  21. 3 Beds,  2 Baths
    1,500 sqft   lot 16,989 sqft
    MLS 859237
    14 Days on Market
  22. 8 Beds,  7 Baths
    5,600 sqft   lot 2.28 ac
    MLS 859020
    14 Days on Market
  23. 3 Beds,  2 Baths
    2,100 sqft   lot 27,443 sqft
    MLS 857773
    14 Days on Market
  24. 3 Beds,  2 Baths
    1,584 sqft   lot 3,877 sqft
    MLS 854289
    15 Days on Market
  25. 4 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 858113
    15 Days on Market
  26. 4 Beds,  1.5 Baths
    1,600 sqft   lot 7,406 sqft
    MLS 857635
    16 Days on Market
  27. 4 Beds,  2.5 Baths
    2,400 sqft   lot 20,909 sqft
    MLS 857324
    16 Days on Market
  28. 3 Beds,  2 Baths
    2,000 sqft   lot 28,750 sqft
    MLS 855331
    17 Days on Market
  29. 3 Beds,  3 Baths
    2,300 sqft   lot 33,542 sqft
    MLS 857115
    18 Days on Market
  30. 3 Beds,  3 Baths
    1,599 sqft   lot 17,424 sqft
    MLS 856972
    19 Days on Market
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