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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
    lot 22,216 sqft
    MLS 816113
    2 Days on Market
  2. 4 Beds,  3.5 Baths
    5,080 sqft   lot 1.60 ac
    MLS 815998
    4 Days on Market
  3. 3 Beds,  2 Baths
    1,600 sqft   lot 21,345 sqft
    MLS 814073
    6 Days on Market
  4. 4 Beds,  3 Baths
    2,400 sqft   lot 12,546 sqft
    MLS 812935
    9 Days on Market
  5. 4 Beds,  2 Baths
    1,900 sqft   lot 39,204 sqft
    MLS 814301
    10 Days on Market
  6. 4 Beds,  2 Baths
    1,589 sqft   lot 5,228 sqft
    MLS 813831
    11 Days on Market
  7. 4 Beds,  4.5 Baths
    3,960 sqft   lot 35,197 sqft
    MLS 814068
    11 Days on Market
  8. 2 Beds,  2 Baths
    2,056 sqft   lot 1.03 ac
    MLS 813250
    11 Days on Market
  9. 2 Beds,  1 Bath
    1,000 sqft   lot 19,167 sqft
    MLS 813272
    12 Days on Market
  10. 4 Beds,  3 Baths
    1,740 sqft   lot 22,216 sqft
    MLS 813518
    12 Days on Market
  11. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS 813226
    13 Days on Market
  12. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS 813208
    13 Days on Market
  13. 4 Beds,  2 Baths
    1,968 sqft   lot 22,652 sqft
    MLS 812921
    13 Days on Market
  14. 6 Beds,  3.5 Baths
    4,000 sqft   lot 14,811 sqft
    MLS 810641
    20 Days on Market
  15. 4 Beds,  2.5 Baths
    2,800 sqft   lot 20,474 sqft
    MLS 810320
    20 Days on Market
  16. 3 Beds,  2 Baths
    1,547 sqft   lot 17,337 sqft
    MLS 810093
    21 Days on Market
  17. 2 Beds,  2 Baths
    900 sqft   lot 5,228 sqft
    MLS 810184
    23 Days on Market
  18. 2 Beds,  1.5 Baths
    1,300 sqft  
    MLS 806036
    23 Days on Market
  19. 5 Beds,  3.5 Baths
    3,160 sqft   lot 1.27 ac
    MLS 809216
    25 Days on Market
  20. 3 Beds,  2.5 Baths
    2,048 sqft   lot 17,424 sqft
    MLS 808916
    26 Days on Market
  21. 3 Beds,  2 Baths
    lot 10,455 sqft
    MLS 810223
    26 Days on Market
  22. 2 Beds,  2 Baths
    1,100 sqft  
    MLS 808158
    30 Days on Market
  23. 5 Beds,  2 Baths
    1,500 sqft  
    MLS 804563
    39 Days on Market
  24. 3 Beds,  2 Baths
    lot 5,663 sqft
    MLS 806303
    40 Days on Market
  25. 2 Beds,  2 Baths
    1,300 sqft  
    MLS 804495
    46 Days on Market
  26. 2 Beds,  1 Bath
    1,400 sqft   lot 9,584 sqft
    MLS 806218
    46 Days on Market
  27. 3 Beds,  3 Baths
    1,100 sqft   lot 43,560 sqft
    MLS 804899
    46 Days on Market
  28. 0 Beds,  3.5 Baths
    1,860 sqft   lot 19,602 sqft
    MLS 804042
    51 Days on Market
  29. 2 Beds,  2 Baths
    1,200 sqft  
    MLS 803610
    52 Days on Market
  30. 4 Beds,  2.5 Baths
    3,400 sqft  
    MLS 802824
    53 Days on Market
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