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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
    3,000 sqft   lot 40,076 sqft
    MLS 3541350
    32 Days on Market
  2. Price Drop
    3 Beds,  2 Baths
    1,668 sqft   lot 40,076 sqft
    MLS 3541220
    32 Days on Market
  3. 4 Beds,  3 Baths
    2,662 sqft   lot 1.25 ac
    MLS 3540463
    37 Days on Market
  4. 3 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 3540430
    38 Days on Market
  5. 5 Beds,  3.5 Baths
    3,286 sqft   lot 2.77 ac
    MLS 3540429
    38 Days on Market
  6. 4 Beds,  5 Baths
    5,465 sqft   lot 3.68 ac
    MLS 3539723
    39 Days on Market
  7. 4 Beds,  2 Baths
    1,500 sqft   lot 17.50 ac
    MLS 3540145
    40 Days on Market
  8. 0 Beds,  1.5 Baths
    1,700 sqft   lot 2,178 sqft
    MLS 3539932
    40 Days on Market
  9. 4 Beds,  4 Baths
    4,700 sqft   lot 1.90 ac
    MLS 3539823
    41 Days on Market
  10. 3 Beds,  2.5 Baths
    lot 9,148 sqft
    MLS 3539796
    42 Days on Market
  11. 4 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 3539791
    42 Days on Market
  12. 4 Beds,  3.5 Baths
    lot 14,375 sqft
    MLS 3539656
    42 Days on Market
  13. 7 Beds,  7.5 Baths
    6,500 sqft   lot 32,670 sqft
    MLS 3539573
    43 Days on Market
  14. 5 Beds,  4.5 Baths
    4,000 sqft   lot 1.57 ac
    MLS 3539348
    43 Days on Market
  15. 3 Beds,  1.5 Baths
    lot 17,424 sqft
    MLS 3539127
    44 Days on Market
  16. 4 Beds,  4 Baths
    lot 13,068 sqft
    MLS 3538916
    45 Days on Market
  17. 5 Beds,  4.5 Baths
    lot 37,026 sqft
    MLS 3538082
    49 Days on Market
  18. 1 Bed,  2 Baths
    lot 8,712 sqft
    MLS 3537757
    50 Days on Market
  19. 2 Beds,  2 Baths
    982 sqft   lot 21,780 sqft
    MLS 3537194
    52 Days on Market
  20. 4 Beds,  5.5 Baths
    4,400 sqft   lot 32,670 sqft
    MLS 3537102
    52 Days on Market
  21. Price Drop
    3 Beds,  3.5 Baths
    lot 20,474 sqft
    MLS 3536442
    56 Days on Market
  22. 2 Beds,  1 Bath
    lot 10,890 sqft
    MLS 3536368
    57 Days on Market
  23. 4 Beds,  4 Baths
    2,650 sqft   lot 6,970 sqft
    MLS 3536071
    58 Days on Market
  24. 4 Beds,  4 Baths
    4,400 sqft   lot 4,356 sqft
    MLS 3535954
    58 Days on Market
  25. 3 Beds,  2.5 Baths
    2,600 sqft   lot 2.46 ac
    MLS 3535810
    59 Days on Market
  26. 2 Beds,  2 Baths
    1,200 sqft   lot 436 sqft
    MLS 3534901
    61 Days on Market
  27. 3 Beds,  3 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 3534990
    63 Days on Market
  28. Price Drop
    3 Beds,  3 Baths
    2,000 sqft   lot 21,780 sqft
    MLS 3534192
    65 Days on Market
  29. 4 Beds,  3.5 Baths
    1,800 sqft   lot 42,254 sqft
    MLS 3531299
    68 Days on Market
  30. 5 Beds,  4 Baths
    4,200 sqft   lot 1.02 ac
    MLS 3533473
    70 Days on Market
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