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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,  1 Bath
    885 sqft   lot 8,712 sqft
    MLS 851297
    41 Days on Market
  2. 3 Beds,  2 Baths
    1,150 sqft   lot 10,890 sqft
    MLS 850659
    42 Days on Market
  3. 4 Beds,  3.5 Baths
    3,205 sqft   lot 1.20 ac
    MLS 846275
    42 Days on Market
  4. 1 Bed,  1.5 Baths
    1,596 sqft   lot 5,184 sqft
    MLS 848840
    45 Days on Market
  5. 3 Beds,  1.5 Baths
    1,425 sqft   lot 16,118 sqft
    MLS 840741
    46 Days on Market
  6. 4 Beds,  2.5 Baths
    2,300 sqft   lot 14,811 sqft
    MLS 849500
    47 Days on Market
  7. 2 Beds,  1 Bath
    900 sqft  
    MLS 848766
    47 Days on Market
  8. 3 Beds,  3 Baths
    2,000 sqft   lot 21,780 sqft
    MLS 849430
    48 Days on Market
  9. 5 Beds,  4.5 Baths
    5,283 sqft  
    MLS 843944
    48 Days on Market
  10. 3 Beds,  2 Baths
    1,568 sqft   lot 17,424 sqft
    MLS 850205
    49 Days on Market
  11. 3 Beds,  3.5 Baths
    2,000 sqft   lot 10,890 sqft
    MLS 848378
    51 Days on Market
  12. 4 Beds,  5 Baths
    3,500 sqft   lot 30,928 sqft
    MLS 847672
    53 Days on Market
  13. 4 Beds,  2.5 Baths
    2,264 sqft   lot 16,118 sqft
    MLS 844387
    54 Days on Market
  14. 3 Beds,  1 Bath
    940 sqft   lot 10,455 sqft
    MLS 847097
    55 Days on Market
  15. 4 Beds,  2 Baths
    1,629 sqft   lot 17,424 sqft
    MLS 845954
    56 Days on Market
  16. 3 Beds,  1.5 Baths
    1,700 sqft   lot 5,228 sqft
    MLS 845400
    56 Days on Market
  17. Price Drop
    3 Beds,  2 Baths
    1,196 sqft   lot 14,811 sqft
    MLS 845624
    56 Days on Market
  18. 4 Beds,  2 Baths
    1,874 sqft   lot 20,038 sqft
    MLS 844282
    59 Days on Market
  19. 3 Beds,  2 Baths
    1,650 sqft   lot 40,076 sqft
    MLS 841740
    59 Days on Market
  20. 2 Beds,  2 Baths
    1,250 sqft  
    MLS 842585
    60 Days on Market
  21. 4 Beds,  1.5 Baths
    1,600 sqft   lot 26,572 sqft
    MLS 842442
    61 Days on Market
  22. 4 Beds,  3.5 Baths
    3,000 sqft   lot 1.06 ac
    MLS 842796
    62 Days on Market
  23. 5 Beds,  2.5 Baths
    2,726 sqft   lot 1.09 ac
    MLS 843095
    62 Days on Market
  24. 4 Beds,  5.5 Baths
    3,000 sqft   lot 25,265 sqft
    MLS 806509
    63 Days on Market
  25. 3 Beds,  2.5 Baths
    1,500 sqft   lot 14,375 sqft
    MLS 839291
    67 Days on Market
  26. 3 Beds,  1 Bath
    1,150 sqft   lot 1.11 ac
    MLS 840484
    68 Days on Market
  27. 5 Beds,  3 Baths
    2,300 sqft   lot 13,504 sqft
    MLS 840724
    68 Days on Market
  28. 5 Beds,  4 Baths
    4,455 sqft   lot 1.38 ac
    MLS 839800
    69 Days on Market
  29. 4 Beds,  5 Baths
    3,000 sqft   lot 4.18 ac
    MLS 835584
    70 Days on Market
  30. 4 Beds,  4 Baths
    3,400 sqft   lot 17,424 sqft
    MLS 835289
    71 Days on Market
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