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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
    3,175 sqft   lot 43,560 sqft
    MLS 3552755
    3 Days on Market
  2. 2 Beds,  1 Bath
    lot 5,228 sqft
    MLS 3552745
    3 Days on Market
  3. 3 Beds,  3 Baths
    lot 10,890 sqft
    MLS 3552746
    4 Days on Market
  4. 2 Beds,  1 Bath
    lot 10,890 sqft
    MLS 3552615
    4 Days on Market
  5. 4 Beds,  2 Baths
    1,700 sqft   lot 13,068 sqft
    MLS 3552105
    4 Days on Market
  6. 4 Beds,  2 Baths
    lot 21,780 sqft
    MLS 3549972
    4 Days on Market
  7. 4 Beds,  2.5 Baths
    lot 35,284 sqft
    MLS 3552374
    5 Days on Market
  8. 4 Beds,  2 Baths
    1,845 sqft   lot 10,890 sqft
    MLS 3552341
    5 Days on Market
  9. 4 Beds,  4.5 Baths
    4,300 sqft   lot 1.27 ac
    MLS 3551748
    6 Days on Market
  10. 1 Bed,  1 Bath
    700 sqft  
    MLS 3549829
    6 Days on Market
  11. 3 Beds,  2 Baths
    1,530 sqft   lot 1.96 ac
    MLS 3551085
    9 Days on Market
  12. 3 Beds,  2 Baths
    lot 17,424 sqft
    MLS 3549473
    9 Days on Market
  13. 3 Beds,  2 Baths
    2,000 sqft   lot 18,296 sqft
    MLS 3548854
    9 Days on Market
  14. 2 Beds,  1 Bath
    lot 19,602 sqft
    MLS 3550862
    11 Days on Market
  15. 3 Beds,  2 Baths
    1,600 sqft   lot 1.15 ac
    MLS 3550645
    12 Days on Market
  16. 6 Beds,  5.5 Baths
    6,250 sqft   lot 1.08 ac
    MLS 3550414
    12 Days on Market
  17. 3 Beds,  3 Baths
    2,175 sqft   lot 16,118 sqft
    MLS 3550403
    12 Days on Market
  18. 5 Beds,  7.5 Baths
    lot 20,038 sqft
    MLS 3550261
    13 Days on Market
  19. 4 Beds,  2.5 Baths
    lot 1.20 ac
    MLS 3550018
    14 Days on Market
  20. 3 Beds,  1.5 Baths
    1,364 sqft   lot 1.60 ac
    MLS 3549934
    14 Days on Market
  21. 3 Beds,  1 Bath
    lot 12,633 sqft
    MLS 3549777
    14 Days on Market
  22. 7 Beds,  8 Baths
    lot 8.90 ac
    MLS 3549432
    14 Days on Market
  23. 3 Beds,  1.5 Baths
    lot 11,326 sqft
    MLS 3549500
    15 Days on Market
  24. 2 Beds,  2 Baths
    2,700 sqft   lot 38,769 sqft
    MLS 3546866
    15 Days on Market
  25. 5 Beds,  3 Baths
    3,316 sqft   lot 27,008 sqft
    MLS 3549427
    16 Days on Market
  26. 4 Beds,  3.5 Baths
    3,770 sqft   lot 27,443 sqft
    MLS 3549424
    16 Days on Market
  27. 4 Beds,  3.5 Baths
    3,770 sqft   lot 27,008 sqft
    MLS 3549423
    16 Days on Market
  28. 5 Beds,  3 Baths
    lot 1.13 ac
    MLS 3549163
    18 Days on Market
  29. 3 Beds,  3 Baths
    lot 20,909 sqft
    MLS 3549139
    18 Days on Market
  30. 5 Beds,  4 Baths
    lot 1.38 ac
    MLS 3548818
    18 Days on Market
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