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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. 5 Beds,  5 Baths
    lot 1.44 ac
    MLS 3519606
    1 Days on Market
  2. 3 Beds,  3 Baths
    2,500 sqft   lot 24,830 sqft
    MLS 3519194
    5 Days on Market
  3. 4 Beds,  3 Baths
    lot 1.05 ac
    MLS 3519113
    5 Days on Market
  4. 3 Beds,  2 Baths
    1,300 sqft   lot 4,356 sqft
    MLS 3519106
    5 Days on Market
  5. 6 Beds,  7.5 Baths
    16,000 sqft   lot 13.37 ac
    MLS 3519056
    5 Days on Market
  6. 3 Beds,  3 Baths
    2,300 sqft   lot 16,118 sqft
    MLS 3518853
    6 Days on Market
  7. 4 Beds,  1.5 Baths
    1,500 sqft   lot 26,136 sqft
    MLS 3518600
    8 Days on Market
  8. 3 Beds,  1.5 Baths
    lot 8,277 sqft
    MLS 3518187
    9 Days on Market
  9. 2 Beds,  1.5 Baths
    1,300 sqft   lot 31,799 sqft
    MLS 3517354
    12 Days on Market
  10. 4 Beds,  4 Baths
    lot 43,560 sqft
    MLS 3517609
    17 Days on Market
  11. 4 Beds,  3 Baths
    lot 41,818 sqft
    MLS 3517170
    19 Days on Market
  12. 3 Beds,  2 Baths
    lot 7,406 sqft
    MLS 3517085
    19 Days on Market
  13. 2 Beds,  1 Bath
    800 sqft   lot 3,050 sqft
    MLS 3516734
    21 Days on Market
  14. 3 Beds,  2 Baths
    lot 40,947 sqft
    MLS 3516722
    21 Days on Market
  15. 5 Beds,  4.5 Baths
    4,857 sqft   lot 37,026 sqft
    MLS 3516644
    21 Days on Market
  16. 3 Beds,  2 Baths
    2,250 sqft   lot 20,474 sqft
    MLS 3516309
    23 Days on Market
  17. 0 Beds,  3 Baths
    lot 2.00 ac
    MLS 3516181
    23 Days on Market
  18. 3 Beds,  2 Baths
    1,449 sqft   lot 6,970 sqft
    MLS 3515761
    27 Days on Market
  19. 2 Beds,  1.5 Baths
    MLS 3515730
    27 Days on Market
  20. 4 Beds,  3 Baths
    1,640 sqft   lot 2.00 ac
    MLS 3515681
    27 Days on Market
  21. 5 Beds,  4.5 Baths
    4,051 sqft   lot 2.44 ac
    MLS 3515679
    27 Days on Market
  22. 3 Beds,  2 Baths
    1,920 sqft   lot 29,621 sqft
    MLS 3515677
    27 Days on Market
  23. 2 Beds,  2 Baths
    lot 27,008 sqft
    MLS 3515604
    27 Days on Market
  24. 4 Beds,  3 Baths
    lot 43,125 sqft
    MLS 3515195
    29 Days on Market
  25. 2 Beds,  1.5 Baths
    800 sqft   lot 10,890 sqft
    MLS 3515140
    29 Days on Market
  26. Price Drop
    3 Beds,  2 Baths
    lot 42,254 sqft
    MLS 3514764
    30 Days on Market
  27. 3 Beds,  1.5 Baths
    1,500 sqft   lot 1.01 ac
    MLS 3514065
    35 Days on Market
  28. 5 Beds,  4 Baths
    4,835 sqft   lot 56.00 ac
    MLS 3513901
    35 Days on Market
  29. 3 Beds,  2 Baths
    1,400 sqft   lot 25,701 sqft
    MLS 3513710
    36 Days on Market
  30. 3 Beds,  2 Baths
    lot 10,890 sqft
    MLS 3513554
    37 Days on Market
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