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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. 6 Beds,  6.5 Baths
    9,000 sqft   lot 1.19 ac
    MLS L3587632
    57 Days on Market
  2. 2 Beds,  2 Baths
    1,964 sqft   lot 25,962 sqft
    MLS L3587494
    58 Days on Market
  3. 4 Beds,  2 Baths
    lot 14,724 sqft
    MLS L3587176
    59 Days on Market
  4. 2 Beds,  2 Baths
    1,600 sqft   lot 2,309 sqft
    MLS L3587240
    59 Days on Market
  5. 3 Beds,  2.5 Baths
    lot 10,803 sqft
    MLS L3586311
    62 Days on Market
  6. 4 Beds,  3 Baths
    lot 4,966 sqft
    MLS L3586235
    64 Days on Market
  7. 4 Beds,  4 Baths
    4,100 sqft   lot 1.70 ac
    MLS L3586070
    65 Days on Market
  8. 4 Beds,  3.5 Baths
    2,850 sqft   lot 36,373 sqft
    MLS L3585962
    65 Days on Market
  9. 4 Beds,  3 Baths
    lot 26,398 sqft
    MLS L3586003
    65 Days on Market
  10. 4 Beds,  2 Baths
    lot 4.24 ac
    MLS L3584997
    69 Days on Market
  11. 4 Beds,  2.5 Baths
    2,000 sqft   lot 29,011 sqft
    MLS L3584291
    73 Days on Market
  12. 2 Beds,  1 Bath
    lot 2.41 ac
    MLS L3584002
    74 Days on Market
  13. 5 Beds,  4.5 Baths
    4,000 sqft   lot 16,902 sqft
    MLS L3583718
    76 Days on Market
  14. 3 Beds,  3 Baths
    1,800 sqft   lot 31,799 sqft
    MLS L3583141
    79 Days on Market
  15. 4 Beds,  3 Baths
    3,600 sqft   lot 26,398 sqft
    MLS L3582641
    81 Days on Market
  16. 4 Beds,  4 Baths
    3,100 sqft   lot 3.32 ac
    MLS L3582082
    83 Days on Market
  17. 3 Beds,  1 Bath
    1,760 sqft   lot 26,833 sqft
    MLS L3581696
    86 Days on Market
  18. 4 Beds,  3.5 Baths
    3,900 sqft   lot 32,583 sqft
    MLS L3581583
    87 Days on Market
  19. 4 Beds,  3 Baths
    lot 21,650 sqft
    MLS L3587810
    90 Days on Market
  20. 5 Beds,  4.5 Baths
    3,500 sqft   lot 9,540 sqft
    MLS L3579812
    94 Days on Market
  21. 4 Beds,  3 Baths
    2,964 sqft   lot 24,699 sqft
    MLS L3579805
    94 Days on Market
  22. 5 Beds,  3.5 Baths
    lot 1.05 ac
    MLS L3579870
    94 Days on Market
  23. 3 Beds,  1.5 Baths
    2,290 sqft   lot 24,394 sqft
    MLS L3579596
    95 Days on Market
  24. 4 Beds,  2 Baths
    2,286 sqft   lot 1.04 ac
    MLS L3579419
    96 Days on Market
  25. 3 Beds,  1 Bath
    1,550 sqft   lot 20,779 sqft
    MLS L3579185
    98 Days on Market
  26. 3 Beds,  3 Baths
    2,200 sqft   lot 12,110 sqft
    MLS L3578605
    100 Days on Market
  27. Pre-Foreclosure
    or Short Sale
    4 Beds,  2 Baths
    1,800 sqft   lot 5,184 sqft
    MLS L3579053
    100 Days on Market
  28. 5 Beds,  5.5 Baths
    4,000 sqft   lot 1.56 ac
    MLS L3578593
    100 Days on Market
  29. 3 Beds,  1.5 Baths
    1,350 sqft   lot 12,981 sqft
    MLS L3578461
    101 Days on Market
  30. 6 Beds,  5.5 Baths
    5,040 sqft   lot 22,216 sqft
    MLS L3580870
    101 Days on Market
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