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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. 1 Bed,  1.5 Baths
    2,000 sqft   lot 5,184 sqft
    MLS 848840
    1 Days on Market
  2. 2 Beds,  1.5 Baths
    1,425 sqft   lot 16,118 sqft
    MLS 840741
    2 Days on Market
  3. 2 Beds,  1 Bath
    900 sqft  
    MLS 848766
    3 Days on Market
  4. 3 Beds,  2.5 Baths
    2,000 sqft   lot 21,780 sqft
    MLS 849430
    4 Days on Market
  5. 5 Beds,  4.5 Baths
    5,283 sqft  
    MLS 843944
    4 Days on Market
  6. 3 Beds,  2 Baths
    1,568 sqft   lot 17,424 sqft
    MLS 850205
    5 Days on Market
  7. 2 Beds,  1 Bath
    1,300 sqft   lot 19,602 sqft
    MLS 849006
    5 Days on Market
  8. 3 Beds,  3.5 Baths
    2,000 sqft   lot 10,890 sqft
    MLS 848378
    7 Days on Market
  9. 6 Beds,  5 Baths
    5,466 sqft   lot 2.50 ac
    MLS 848155
    8 Days on Market
  10. 4 Beds,  5 Baths
    3,500 sqft   lot 30,928 sqft
    MLS 847672
    9 Days on Market
  11. 2 Beds,  2 Baths
    1,200 sqft   lot 1,124 sqft
    MLS 845006
    9 Days on Market
  12. 4 Beds,  1.5 Baths
    2,106 sqft   lot 43,560 sqft
    MLS 846684
    10 Days on Market
  13. 4 Beds,  2.5 Baths
    2,264 sqft   lot 16,118 sqft
    MLS 844387
    10 Days on Market
  14. 3 Beds,  1 Bath
    940 sqft   lot 10,455 sqft
    MLS 847097
    11 Days on Market
  15. 4 Beds,  2 Baths
    1,629 sqft   lot 17,424 sqft
    MLS 845954
    12 Days on Market
  16. 3 Beds,  1.5 Baths
    1,700 sqft   lot 5,228 sqft
    MLS 845400
    12 Days on Market
  17. 3 Beds,  2 Baths
    1,196 sqft   lot 14,811 sqft
    MLS 845624
    12 Days on Market
  18. 3 Beds,  3 Baths
    2,851 sqft   lot 10,890 sqft
    MLS 843233
    13 Days on Market
  19. 2 Beds,  1 Bath
    1,000 sqft   lot 5.70 ac
    MLS 844761
    15 Days on Market
  20. 4 Beds,  2 Baths
    1,874 sqft   lot 20,038 sqft
    MLS 844282
    15 Days on Market
  21. 3 Beds,  2 Baths
    1,650 sqft   lot 40,076 sqft
    MLS 841740
    15 Days on Market
  22. 2 Beds,  2 Baths
    800 sqft  
    MLS 842585
    16 Days on Market
  23. 3 Beds,  2 Baths
    1,599 sqft   lot 13,504 sqft
    MLS 842986
    16 Days on Market
  24. 2 Beds,  1 Bath
    1,100 sqft   lot 6,534 sqft
    MLS 843897
    17 Days on Market
  25. 4 Beds,  1.5 Baths
    1,600 sqft   lot 26,572 sqft
    MLS 842442
    17 Days on Market
  26. 4 Beds,  3.5 Baths
    3,000 sqft   lot 1.06 ac
    MLS 842796
    18 Days on Market
  27. 5 Beds,  2.5 Baths
    2,726 sqft   lot 1.09 ac
    MLS 843095
    18 Days on Market
  28. 3 Beds,  2 Baths
    1,575 sqft   lot 28,314 sqft
    MLS 842408
    18 Days on Market
  29. 4 Beds,  2 Baths
    1,911 sqft   lot 30,492 sqft
    MLS 842341
    18 Days on Market
  30. 4 Beds,  3.5 Baths
    3,300 sqft   lot 1.25 ac
    MLS 842464
    18 Days on Market
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