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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. 2 Beds,  2 Baths
    lot 10,455 sqft
    MLS 3541346
    19 Days on Market
  2. 4 Beds,  3 Baths
    3,000 sqft   lot 40,076 sqft
    MLS 3541350
    19 Days on Market
  3. 3 Beds,  2 Baths
    1,668 sqft   lot 40,076 sqft
    MLS 3541220
    19 Days on Market
  4. 4 Beds,  3 Baths
    2,662 sqft   lot 1.25 ac
    MLS 3540463
    24 Days on Market
  5. 3 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 3540430
    25 Days on Market
  6. 5 Beds,  3.5 Baths
    3,286 sqft   lot 2.77 ac
    MLS 3540429
    25 Days on Market
  7. 3 Beds,  2 Baths
    1,180 sqft   lot 14,375 sqft
    MLS 3540332
    25 Days on Market
  8. 3 Beds,  1.5 Baths
    1,600 sqft   lot 13,940 sqft
    MLS 3540209
    26 Days on Market
  9. 4 Beds,  5 Baths
    5,465 sqft   lot 3.68 ac
    MLS 3539723
    26 Days on Market
  10. 4 Beds,  2 Baths
    1,500 sqft   lot 17.50 ac
    MLS 3540145
    27 Days on Market
  11. 0 Beds,  1.5 Baths
    1,700 sqft   lot 2,178 sqft
    MLS 3539932
    27 Days on Market
  12. 4 Beds,  4 Baths
    4,700 sqft   lot 1.90 ac
    MLS 3539823
    28 Days on Market
  13. 3 Beds,  2.5 Baths
    lot 9,148 sqft
    MLS 3539796
    29 Days on Market
  14. 4 Beds,  2 Baths
    2,200 sqft   lot 12,197 sqft
    MLS 3539791
    29 Days on Market
  15. 2 Beds,  2 Baths
    1,600 sqft   lot 2,178 sqft
    MLS 3539718
    29 Days on Market
  16. 4 Beds,  3.5 Baths
    lot 14,375 sqft
    MLS 3539656
    29 Days on Market
  17. 7 Beds,  7.5 Baths
    6,500 sqft   lot 32,670 sqft
    MLS 3539573
    30 Days on Market
  18. 5 Beds,  4.5 Baths
    4,000 sqft   lot 1.57 ac
    MLS 3539348
    30 Days on Market
  19. 3 Beds,  1.5 Baths
    lot 17,424 sqft
    MLS 3539127
    31 Days on Market
  20. 4 Beds,  4 Baths
    lot 13,068 sqft
    MLS 3538916
    32 Days on Market
  21. 3 Beds,  2 Baths
    lot 14,811 sqft
    MLS 3538808
    32 Days on Market
  22. 5 Beds,  4.5 Baths
    lot 37,026 sqft
    MLS 3538082
    36 Days on Market
  23. 1 Bed,  2 Baths
    lot 8,712 sqft
    MLS 3537757
    37 Days on Market
  24. 5 Beds,  2 Baths
    2,400 sqft   lot 25,265 sqft
    MLS 3537287
    39 Days on Market
  25. Price Drop
    2 Beds,  2 Baths
    982 sqft   lot 21,780 sqft
    MLS 3537194
    39 Days on Market
  26. 4 Beds,  5.5 Baths
    4,400 sqft   lot 32,670 sqft
    MLS 3537102
    39 Days on Market
  27. 3 Beds,  3.5 Baths
    lot 20,474 sqft
    MLS 3536442
    43 Days on Market
  28. 2 Beds,  1 Bath
    lot 10,890 sqft
    MLS 3536368
    44 Days on Market
  29. 2 Beds,  1 Bath
    MLS 3536111
    45 Days on Market
  30. 4 Beds,  4 Baths
    2,650 sqft   lot 6,970 sqft
    MLS 3536071
    45 Days on Market
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