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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. 4 Beds,  2.5 Baths
    2,700 sqft   lot 32,670 sqft
    MLS 822706
    99 Days on Market
  2. Price Drop
    3 Beds,  2.5 Baths
    2,200 sqft   lot 40,076 sqft
    MLS 828186
    100 Days on Market
  3. 5 Beds,  4 Baths
    4,200 sqft   lot 1.02 ac
    MLS 828203
    100 Days on Market
  4. 3 Beds,  2.5 Baths
    3,000 sqft   lot 20,909 sqft
    MLS 827576
    100 Days on Market
  5. 3 Beds,  2 Baths
    1,550 sqft   lot 23,087 sqft
    MLS 827612
    102 Days on Market
  6. 3 Beds,  2 Baths
    2,127 sqft   lot 37,026 sqft
    MLS 825390
    104 Days on Market
  7. 3 Beds,  2 Baths
    1,200 sqft   lot 5,228 sqft
    MLS 828349
    105 Days on Market
  8. 1 Bed,  1 Bath
    lot 4.00 ac
    MLS 825742
    106 Days on Market
  9. 4 Beds,  2 Baths
    1,589 sqft   lot 5,228 sqft
    MLS 825421
    108 Days on Market
  10. 4 Beds,  3 Baths
    3,200 sqft   lot 15,246 sqft
    MLS 823903
    113 Days on Market
  11. 5 Beds,  4 Baths
    2,450 sqft   lot 12,197 sqft
    MLS 822831
    114 Days on Market
  12. 4 Beds,  3.5 Baths
    3,000 sqft   lot 14,375 sqft
    MLS 818321
    116 Days on Market
  13. 4 Beds,  3 Baths
    2,000 sqft   lot 39,640 sqft
    MLS 820321
    121 Days on Market
  14. 6 Beds,  6.5 Baths
    9,900 sqft   lot 4.72 ac
    MLS 818952
    124 Days on Market
  15. 7 Beds,  3 Baths
    4,376 sqft   lot 2.84 ac
    MLS 818991
    126 Days on Market
  16. 3 Beds,  2.5 Baths
    1,800 sqft   lot 8,712 sqft
    MLS 817508
    128 Days on Market
  17. 2 Beds,  1 Bath
    1,071 sqft   lot 8,712 sqft
    MLS 812808
    129 Days on Market
  18. 4 Beds,  4.5 Baths
    4,500 sqft   lot 40,250 sqft
    MLS 817670
    129 Days on Market
  19. 2 Beds,  2 Baths
    1,300 sqft   lot 5,228 sqft
    MLS 817817
    130 Days on Market
  20. 4 Beds,  3 Baths
    lot 22,216 sqft
    MLS 816113
    132 Days on Market
  21. 3 Beds,  2.5 Baths
    1,528 sqft  
    MLS 813226
    143 Days on Market
  22. 2 Beds,  2 Baths
    900 sqft   lot 5,228 sqft
    MLS 810184
    153 Days on Market
  23. 2 Beds,  1 Bath
    1,300 sqft  
    MLS 806036
    153 Days on Market
  24. 5 Beds,  3.5 Baths
    3,160 sqft   lot 1.27 ac
    MLS 809216
    155 Days on Market
  25. 3 Beds,  2.5 Baths
    2,048 sqft   lot 17,424 sqft
    MLS 808916
    156 Days on Market
  26. 3 Beds,  2 Baths
    lot 10,455 sqft
    MLS 810223
    156 Days on Market
  27. 2 Beds,  2 Baths
    1,100 sqft  
    MLS 808158
    160 Days on Market
  28. 3 Beds,  1.5 Baths
    2,200 sqft   lot 8,233 sqft
    MLS 807112
    168 Days on Market
  29. 5 Beds,  2 Baths
    1,500 sqft   lot 34,848 sqft
    MLS 804563
    169 Days on Market
  30. 3 Beds,  1 Bath
    960 sqft   lot 6,055 sqft
    MLS 805847
    172 Days on Market
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