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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
    2,020 sqft   lot 21,780 sqft
    MLS 3546580
    1 Days on Market
  2. 4 Beds,  2 Baths
    lot 5,228 sqft
    MLS 3546300
    2 Days on Market
  3. 3 Beds,  2.5 Baths
    2,000 sqft   lot 16,553 sqft
    MLS 3546245
    2 Days on Market
  4. 3 Beds,  2.5 Baths
    lot 42,254 sqft
    MLS 3546200
    3 Days on Market
  5. 3 Beds,  2.5 Baths
    lot 18,296 sqft
    MLS 3546094
    4 Days on Market
  6. 3 Beds,  1 Bath
    lot 19,602 sqft
    MLS 3545928
    5 Days on Market
  7. 2 Beds,  1 Bath
    lot 20,909 sqft
    MLS 3545848
    5 Days on Market
  8. 4 Beds,  2 Baths
    lot 31,364 sqft
    MLS 3545423
    5 Days on Market
  9. 3 Beds,  4 Baths
    3,187 sqft   lot 11,326 sqft
    MLS 3545783
    6 Days on Market
  10. 4 Beds,  4 Baths
    2,450 sqft   lot 12,197 sqft
    MLS 3545167
    6 Days on Market
  11. 3 Beds,  3 Baths
    lot 16,989 sqft
    MLS 3545379
    7 Days on Market
  12. 2 Beds,  1 Bath
    lot 9,148 sqft
    MLS 3545362
    7 Days on Market
  13. 4 Beds,  2.5 Baths
    2,000 sqft   lot 30,057 sqft
    MLS 3545350
    7 Days on Market
  14. 4 Beds,  2.5 Baths
    lot 18,731 sqft
    MLS 3545223
    7 Days on Market
  15. 3 Beds,  3 Baths
    3,000 sqft   lot 1.10 ac
    MLS 3545214
    8 Days on Market
  16. 3 Beds,  1.5 Baths
    1,504 sqft   lot 21,780 sqft
    MLS 3544978
    8 Days on Market
  17. 3 Beds,  3 Baths
    2,492 sqft   lot 33,542 sqft
    MLS 3544899
    8 Days on Market
  18. 1 Bed,  1 Bath
    MLS 3544755
    9 Days on Market
  19. 3 Beds,  2.5 Baths
    1,400 sqft   lot 39,640 sqft
    MLS 3543307
    10 Days on Market
  20. 5 Beds,  7 Baths
    6,000 sqft   lot 1.90 ac
    MLS 3544128
    11 Days on Market
  21. 4 Beds,  3 Baths
    1,856 sqft   lot 39,640 sqft
    MLS 3544314
    12 Days on Market
  22. 4 Beds,  4 Baths
    2,900 sqft   lot 16,553 sqft
    MLS 3543518
    14 Days on Market
  23. 2 Beds,  1.5 Baths
    lot 6,970 sqft
    MLS 3543258
    15 Days on Market
  24. 3 Beds,  1.5 Baths
    lot 21,780 sqft
    MLS 3543065
    16 Days on Market
  25. 3 Beds,  2 Baths
    lot 21,780 sqft
    MLS 3542993
    16 Days on Market
  26. 3 Beds,  2.5 Baths
    2,492 sqft   lot 17,424 sqft
    MLS 3542205
    20 Days on Market
  27. 4 Beds,  3 Baths
    2,750 sqft   lot 1.23 ac
    MLS 3542098
    21 Days on Market
  28. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS 3541853
    22 Days on Market
  29. 3 Beds,  3.5 Baths
    lot 27,008 sqft
    MLS 3541721
    22 Days on Market
  30. 4 Beds,  2.5 Baths
    2,700 sqft   lot 32,670 sqft
    MLS 3541573
    22 Days on Market
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