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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
    lot 7,841 sqft
    MLS 3583290
    1 Days on Market
  2. 3 Beds,  3 Baths
    lot 31,799 sqft
    MLS 3583141
    1 Days on Market
  3. 3 Beds,  1 Bath
    1,200 sqft   lot 8,277 sqft
    MLS 3582904
    2 Days on Market
  4. 3 Beds,  2 Baths
    lot 15,246 sqft
    MLS 3582712
    3 Days on Market
  5. 4 Beds,  3 Baths
    3,600 sqft   lot 26,572 sqft
    MLS 3582641
    3 Days on Market
  6. 5 Beds,  4.5 Baths
    4,240 sqft   lot 13.08 ac
    MLS 3582528
    3 Days on Market
  7. 3 Beds,  3 Baths
    lot 2,614 sqft
    MLS 3582452
    4 Days on Market
  8. 4 Beds,  4 Baths
    3,100 sqft   lot 3.34 ac
    MLS 3582082
    5 Days on Market
  9. 4 Beds,  2.5 Baths
    2,700 sqft   lot 1.52 ac
    MLS 3581835
    7 Days on Market
  10. 3 Beds,  1 Bath
    1,760 sqft   lot 27,008 sqft
    MLS 3581696
    8 Days on Market
  11. 4 Beds,  3.5 Baths
    3,900 sqft   lot 32,670 sqft
    MLS 3581583
    9 Days on Market
  12. 5 Beds,  4.5 Baths
    6,510 sqft   lot 40,511 sqft
    MLS 3581461
    9 Days on Market
  13. 3 Beds,  2 Baths
    1,425 sqft   lot 8,712 sqft
    MLS 3581372
    9 Days on Market
  14. 4 Beds,  3 Baths
    lot 40,076 sqft
    MLS 3581269
    10 Days on Market
  15. 3 Beds,  2 Baths
    1,800 sqft   lot 1.27 ac
    MLS 3581057
    10 Days on Market
  16. 4 Beds,  3 Baths
    lot 21,780 sqft
    MLS 3580571
    12 Days on Market
  17. 5 Beds,  3.5 Baths
    3,235 sqft   lot 18,296 sqft
    MLS H6328682
    13 Days on Market
  18. 4 Beds,  2 Baths
    2,100 sqft   lot 20,909 sqft
    MLS 3580219
    15 Days on Market
  19. 3 Beds,  2 Baths
    2,100 sqft   lot 27,443 sqft
    MLS 3580174
    15 Days on Market
  20. 5 Beds,  3.5 Baths
    lot 1.06 ac
    MLS 3579870
    16 Days on Market
  21. 3 Beds,  3 Baths
    lot 10,890 sqft
    MLS 3579841
    16 Days on Market
  22. 5 Beds,  4.5 Baths
    3,500 sqft   lot 9,584 sqft
    MLS 3579812
    16 Days on Market
  23. 2 Beds,  2 Baths
    lot 8,277 sqft
    MLS 3579813
    16 Days on Market
  24. 4 Beds,  3 Baths
    2,964 sqft   lot 24,830 sqft
    MLS 3579805
    16 Days on Market
  25. 3 Beds,  2 Baths
    lot 4,792 sqft
    MLS 3579650
    17 Days on Market
  26. 3 Beds,  1.5 Baths
    2,290 sqft   lot 24,394 sqft
    MLS 3579596
    17 Days on Market
  27. 3 Beds,  1 Bath
    1,028 sqft   lot 10,019 sqft
    MLS H6328114
    18 Days on Market
  28. 4 Beds,  2 Baths
    2,286 sqft   lot 1.05 ac
    MLS 3579419
    18 Days on Market
  29. 3 Beds,  3 Baths
    lot 21,345 sqft
    MLS 3579226
    19 Days on Market
  30. 6 Beds,  8.5 Baths
    7,000 sqft   lot 5.81 ac
    MLS 3579087
    19 Days on Market
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