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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,  2.5 Baths
    2,650 sqft   lot 16,684 sqft
    MLS 868031
    1 Days on Market
  2. 4 Beds,  2.5 Baths
    2,800 sqft   lot 20,474 sqft
    MLS 868314
    1 Days on Market
  3. 4 Beds,  2.5 Baths
    2,652 sqft   lot 28,750 sqft
    MLS 865497
    1 Days on Market
  4. 4 Beds,  3.5 Baths
    3,500 sqft   lot 27,008 sqft
    MLS 866393
    4 Days on Market
  5. 3 Beds,  2 Baths
    1,620 sqft   lot 6,970 sqft
    MLS 866253
    7 Days on Market
  6. 4 Beds,  4.5 Baths
    2,842 sqft   lot 20,038 sqft
    MLS 862752
    7 Days on Market
  7. 2 Beds,  1.5 Baths
    lot 10,890 sqft
    MLS 865793
    8 Days on Market
  8. 4 Beds,  2.5 Baths
    2,246 sqft   lot 41,382 sqft
    MLS 864398
    8 Days on Market
  9. 3 Beds,  2 Baths
    1,800 sqft   lot 25,265 sqft
    MLS 865734
    8 Days on Market
  10. 4 Beds,  2.5 Baths
    2,100 sqft   lot 43,560 sqft
    MLS 860121
    8 Days on Market
  11. 3 Beds,  2 Baths
    1,500 sqft   lot 24,394 sqft
    MLS 864984
    9 Days on Market
  12. 3 Beds,  2 Baths
    1,500 sqft   lot 21,345 sqft
    MLS 864533
    9 Days on Market
  13. 3 Beds,  2 Baths
    1,632 sqft   lot 18,731 sqft
    MLS 864961
    10 Days on Market
  14. 4 Beds,  2.5 Baths
    3,234 sqft   lot 1.05 ac
    MLS 865319
    10 Days on Market
  15. 2 Beds,  2 Baths
    1,040 sqft   lot 2,614 sqft
    MLS 863727
    10 Days on Market
  16. 3 Beds,  2 Baths
    1,425 sqft   lot 8,712 sqft
    MLS 843099
    11 Days on Market
  17. 3 Beds,  3 Baths
    2,250 sqft   lot 14,811 sqft
    MLS 862258
    11 Days on Market
  18. 3 Beds,  2.5 Baths
    2,026 sqft   lot 13,068 sqft
    MLS 861571
    11 Days on Market
  19. 4 Beds,  4 Baths
    2,600 sqft   lot 18,296 sqft
    MLS 863961
    11 Days on Market
  20. 5 Beds,  5.5 Baths
    3,350 sqft   lot 30,492 sqft
    MLS 863916
    12 Days on Market
  21. 4 Beds,  2 Baths
    2,235 sqft   lot 26,136 sqft
    MLS 863970
    12 Days on Market
  22. 4 Beds,  3 Baths
    1,595 sqft   lot 31,799 sqft
    MLS 862263
    14 Days on Market
  23. Price Drop
    3 Beds,  1 Bath
    1,500 sqft   lot 9.05 ac
    MLS 863319
    14 Days on Market
  24. Price Drop
    3 Beds,  1 Bath
    1,500 sqft   lot 7.22 ac
    MLS 863292
    14 Days on Market
  25. 2 Beds,  1.5 Baths
    2,300 sqft   lot 21,780 sqft
    MLS 861585
    14 Days on Market
  26. 3 Beds,  2.5 Baths
    3,735 sqft   lot 10,890 sqft
    MLS 862942
    15 Days on Market
  27. 3 Beds,  2.5 Baths
    2,045 sqft   lot 10,890 sqft
    MLS 861090
    15 Days on Market
  28. 3 Beds,  2.5 Baths
    2,238 sqft   lot 436 sqft
    MLS 862399
    15 Days on Market
  29. 3 Beds,  3.5 Baths
    2,000 sqft   lot 5,228 sqft
    MLS 861088
    15 Days on Market
  30. 4 Beds,  3 Baths
    2,150 sqft   lot 21,780 sqft
    MLS 861719
    17 Days on Market
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