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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. 3 Beds,  2.5 Baths
    2,200 sqft   lot 1.56 ac
    MLS L3577749
    103 Days on Market
  2. 2 Beds,  1 Bath
    lot 8,233 sqft
    MLS L3577803
    103 Days on Market
  3. 6 Beds,  4 Baths
    4,000 sqft   lot 2.28 ac
    MLS L3577500
    104 Days on Market
  4. 3 Beds,  2.5 Baths
    lot 21,650 sqft
    MLS L3577576
    104 Days on Market
  5. 3 Beds,  2.5 Baths
    3,700 sqft   lot 3.80 ac
    MLS L3576752
    108 Days on Market
  6. 4 Beds,  3 Baths
    2,800 sqft   lot 40,250 sqft
    MLS L3576725
    108 Days on Market
  7. 4 Beds,  4.5 Baths
    lot 6,491 sqft
    MLS L3577146
    109 Days on Market
  8. 4 Beds,  2 Baths
    lot 30,318 sqft
    MLS L3575647
    113 Days on Market
  9. 2 Beds,  1 Bath
    lot 21,214 sqft
    MLS L3575479
    114 Days on Market
  10. 3 Beds,  3 Baths
    2,100 sqft   lot 21,127 sqft
    MLS L3574281
    121 Days on Market
  11. 4 Beds,  2.5 Baths
    lot 20,779 sqft
    MLS L3573918
    122 Days on Market
  12. 5 Beds,  4.5 Baths
    4,122 sqft   lot 1.00 ac
    MLS L3574213
    122 Days on Market
  13. 3 Beds,  2 Baths
    1,422 sqft   lot 2.34 ac
    MLS L3572823
    129 Days on Market
  14. 3 Beds,  3.5 Baths
    lot 5,228 sqft
    MLS L3572634
    129 Days on Market
  15. 3 Beds,  2.5 Baths
    1,572 sqft   lot 20,779 sqft
    MLS L3572625
    129 Days on Market
  16. 3 Beds,  2 Baths
    2,100 sqft   lot 27,269 sqft
    MLS L3580174
    130 Days on Market
  17. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS L3571920
    132 Days on Market
  18. 3 Beds,  2 Baths
    1,650 sqft   lot 12,981 sqft
    MLS L3585163
    132 Days on Market
  19. 3 Beds,  1.5 Baths
    1,500 sqft   lot 7,362 sqft
    MLS L3571743
    132 Days on Market
  20. 5 Beds,  6 Baths
    lot 1.28 ac
    MLS L3570923
    137 Days on Market
  21. 3 Beds,  1.5 Baths
    2,086 sqft   lot 19.40 ac
    MLS L3570534
    139 Days on Market
  22. 2 Beds,  1 Bath
    lot 5,184 sqft
    MLS L3570090
    141 Days on Market
  23. 8 Beds,  7 Baths
    5,600 sqft   lot 2.28 ac
    MLS L3569381
    144 Days on Market
  24. 4 Beds,  2 Baths
    1,968 sqft   lot 22,521 sqft
    MLS L3580526
    146 Days on Market
  25. 4 Beds,  3 Baths
    2,150 sqft   lot 21,650 sqft
    MLS L3568549
    149 Days on Market
  26. 4 Beds,  2.5 Baths
    2,450 sqft   lot 41,121 sqft
    MLS L3568309
    150 Days on Market
  27. 4 Beds,  4 Baths
    3,100 sqft   lot 40,729 sqft
    MLS L3567805
    151 Days on Market
  28. 4 Beds,  4.5 Baths
    3,400 sqft   lot 40,729 sqft
    MLS L3567804
    151 Days on Market
  29. 3 Beds,  1.5 Baths
    lot 12,981 sqft
    MLS L3565566
    162 Days on Market
  30. 3 Beds,  1 Bath
    lot 5,184 sqft
    MLS L3565361
    163 Days on Market
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