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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 Baths
    1,690 sqft   lot 8,277 sqft
    MLS 832086
    26 Days on Market
  2. 3 Beds,  1 Bath
    1,200 sqft  
    MLS 830199
    26 Days on Market
  3. 3 Beds,  1 Bath
    1,300 sqft   lot 13,504 sqft
    MLS 830795
    28 Days on Market
  4. 3 Beds,  1 Bath
    900 sqft   lot 9,584 sqft
    MLS 820656
    28 Days on Market
  5. 6 Beds,  6 Baths
    6,800 sqft   lot 3.50 ac
    MLS 829935
    29 Days on Market
  6. 4 Beds,  5.5 Baths
    5,500 sqft   lot 1.94 ac
    MLS 830269
    29 Days on Market
  7. 3 Beds,  1 Bath
    1,000 sqft   lot 14,811 sqft
    MLS 830215
    30 Days on Market
  8. 4 Beds,  3.5 Baths
    2,480 sqft   lot 18,731 sqft
    MLS 829795
    33 Days on Market
  9. 5 Beds,  4.5 Baths
    3,000 sqft   lot 1.70 ac
    MLS 829743
    33 Days on Market
  10. 4 Beds,  2 Baths
    1,456 sqft   lot 6,099 sqft
    MLS 828785
    33 Days on Market
  11. 2 Beds,  2 Baths
    1,100 sqft   lot 2,614 sqft
    MLS 827962
    34 Days on Market
  12. 4 Beds,  2.5 Baths
    1,800 sqft  
    MLS 828693
    34 Days on Market
  13. 3 Beds,  2 Baths
    2,306 sqft   lot 18,296 sqft
    MLS 826980
    34 Days on Market
  14. Price Drop
    2 Beds,  2 Baths
    1,100 sqft   lot 1,024 sqft
    MLS 828475
    34 Days on Market
  15. 5 Beds,  3.5 Baths
    2,500 sqft   lot 1.06 ac
    MLS 819860
    34 Days on Market
  16. 5 Beds,  2.5 Baths
    3,175 sqft   lot 43,560 sqft
    MLS 826956
    34 Days on Market
  17. 4 Beds,  2.5 Baths
    2,700 sqft   lot 32,670 sqft
    MLS 822706
    34 Days on Market
  18. 3 Beds,  2.5 Baths
    2,200 sqft   lot 40,076 sqft
    MLS 828186
    35 Days on Market
  19. 5 Beds,  4 Baths
    4,200 sqft   lot 1.02 ac
    MLS 828203
    35 Days on Market
  20. 3 Beds,  2.5 Baths
    3,000 sqft   lot 20,909 sqft
    MLS 827576
    35 Days on Market
  21. 5 Beds,  6 Baths
    7,000 sqft   lot 1.29 ac
    MLS 827737
    36 Days on Market
  22. 3 Beds,  2 Baths
    2,127 sqft   lot 37,026 sqft
    MLS 825390
    39 Days on Market
  23. 3 Beds,  2 Baths
    1,200 sqft   lot 5,228 sqft
    MLS 828349
    40 Days on Market
  24. 3 Beds,  2 Baths
    1,650 sqft   lot 12,981 sqft
    MLS 825345
    40 Days on Market
  25. 4 Beds,  1.5 Baths
    1,200 sqft   lot 11,326 sqft
    MLS 825933
    41 Days on Market
  26. 1 Bed,  1 Bath
    lot 4.00 ac
    MLS 825742
    41 Days on Market
  27. 3 Beds,  2 Baths
    1,500 sqft   lot 1.84 ac
    MLS 825540
    42 Days on Market
  28. Price Drop
    4 Beds,  2 Baths
    1,589 sqft   lot 5,228 sqft
    MLS 825421
    43 Days on Market
  29. 3 Beds,  1.5 Baths
    1,999 sqft   lot 21,780 sqft
    MLS 823397
    46 Days on Market
  30. 4 Beds,  4 Baths
    4,000 sqft   lot 5,228 sqft
    MLS 823080
    47 Days on Market
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