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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
    2,048 sqft   lot 17,424 sqft
    MLS 808916
    95 Days on Market
  2. 3 Beds,  2 Baths
    lot 10,455 sqft
    MLS 810223
    95 Days on Market
  3. 2 Beds,  2 Baths
    1,100 sqft  
    MLS 808158
    99 Days on Market
  4. 3 Beds,  1.5 Baths
    2,200 sqft   lot 8,233 sqft
    MLS 807112
    107 Days on Market
  5. 4 Beds,  2 Baths
    1,500 sqft   lot 34,848 sqft
    MLS 804563
    108 Days on Market
  6. 3 Beds,  1 Bath
    960 sqft   lot 6,055 sqft
    MLS 805847
    111 Days on Market
  7. 2 Beds,  2 Baths
    1,325 sqft  
    MLS 804495
    115 Days on Market
  8. 2 Beds,  1 Bath
    1,400 sqft   lot 9,584 sqft
    MLS 806218
    115 Days on Market
  9. 3 Beds,  3 Baths
    1,100 sqft   lot 43,560 sqft
    MLS 804899
    115 Days on Market
  10. 0 Beds,  2 Baths
    1,860 sqft   lot 19,602 sqft
    MLS 804042
    120 Days on Market
  11. 6 Beds,  5.5 Baths
    3,630 sqft   lot 21,780 sqft
    MLS LP1439478
    130 Days on Market
  12. 4 Beds,  5.5 Baths
    4,671 sqft   lot 43,299 sqft
    MLS L3592723
    134 Days on Market
  13. 4 Beds,  3 Baths
    1,800 sqft   lot 39,814 sqft
    MLS L3592550
    135 Days on Market
  14. 4 Beds,  2 Baths
    2,200 sqft   lot 3.19 ac
    MLS L3592218
    136 Days on Market
  15. 5 Beds,  4.5 Baths
    2,950 sqft  
    MLS H6335251
    147 Days on Market
  16. 4 Beds,  6 Baths
    5,220 sqft   lot 14,811 sqft
    MLS L3590145
    148 Days on Market
  17. 11 Beds,  13 Baths
    lot 131 sqft
    MLS L3590171
    148 Days on Market
  18. 2 Beds,  1 Bath
    MLS L3589570
    150 Days on Market
  19. 3 Beds,  2.5 Baths
    lot 2.03 ac
    MLS L3588159
    159 Days on Market
  20. 3 Beds,  2 Baths
    1,300 sqft   lot 5,925 sqft
    MLS L3587738
    160 Days on Market
  21. 5 Beds,  4.5 Baths
    4,627 sqft   lot 42,864 sqft
    MLS L3587614
    161 Days on Market
  22. 4 Beds,  2 Baths
    lot 14,724 sqft
    MLS L3587176
    163 Days on Market
  23. 3 Beds,  1.5 Baths
    1,300 sqft   lot 5,663 sqft
    MLS H6333877
    164 Days on Market
  24. 3 Beds,  2.5 Baths
    lot 10,803 sqft
    MLS L3586311
    166 Days on Market
  25. 4 Beds,  3 Baths
    lot 4,966 sqft
    MLS L3586235
    168 Days on Market
  26. 4 Beds,  2 Baths
    lot 4.24 ac
    MLS L3584997
    173 Days on Market
  27. 2 Beds,  1 Bath
    lot 2.41 ac
    MLS L3584002
    178 Days on Market
  28. 4 Beds,  3 Baths
    lot 21,650 sqft
    MLS L3587810
    194 Days on Market
  29. 5 Beds,  4.5 Baths
    3,500 sqft   lot 9,540 sqft
    MLS L3579812
    198 Days on Market
  30. 3 Beds,  1.5 Baths
    2,290 sqft   lot 24,394 sqft
    MLS L3579596
    199 Days on Market
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