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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
    2,127 sqft   lot 37,026 sqft
    MLS 825390
    1 Days on Market
  2. 3 Beds,  2 Baths
    1,650 sqft   lot 12,981 sqft
    MLS 825345
    2 Days on Market
  3. 4 Beds,  4.5 Baths
    3,000 sqft   lot 21,345 sqft
    MLS 826222
    3 Days on Market
  4. 1 Bed,  1 Bath
    lot 4.00 ac
    MLS 825742
    3 Days on Market
  5. 4 Beds,  2 Baths
    1,589 sqft   lot 5,228 sqft
    MLS 825421
    5 Days on Market
  6. 5 Beds,  4.5 Baths
    3,000 sqft   lot 1.70 ac
    MLS 825396
    5 Days on Market
  7. 3 Beds,  2 Baths
    1,800 sqft   lot 6,099 sqft
    MLS 825220
    5 Days on Market
  8. 4 Beds,  3.5 Baths
    3,000 sqft   lot 31,364 sqft
    MLS 824729
    8 Days on Market
  9. 3 Beds,  2 Baths
    1,535 sqft   lot 10,803 sqft
    MLS 816681
    8 Days on Market
  10. 4 Beds,  2.5 Baths
    2,700 sqft   lot 32,670 sqft
    MLS 822706
    8 Days on Market
  11. 3 Beds,  1.5 Baths
    1,999 sqft   lot 21,780 sqft
    MLS 823397
    8 Days on Market
  12. 4 Beds,  4 Baths
    4,000 sqft   lot 5,228 sqft
    MLS 823080
    9 Days on Market
  13. 4 Beds,  3 Baths
    3,200 sqft   lot 15,246 sqft
    MLS 823903
    10 Days on Market
  14. 5 Beds,  4 Baths
    2,450 sqft   lot 12,197 sqft
    MLS 822831
    11 Days on Market
  15. 4 Beds,  3.5 Baths
    3,000 sqft   lot 14,375 sqft
    MLS 818321
    13 Days on Market
  16. 1 Bed,  1 Bath
    1,320 sqft   lot 5,663 sqft
    MLS 822513
    14 Days on Market
  17. 4 Beds,  3 Baths
    2,000 sqft   lot 39,640 sqft
    MLS 820321
    18 Days on Market
  18. 4 Beds,  2 Baths
    2,487 sqft  
    MLS 819108
    18 Days on Market
  19. 3 Beds,  2 Baths
    1,408 sqft   lot 27,879 sqft
    MLS 819503
    19 Days on Market
  20. 2 Beds,  2 Baths
    1,200 sqft   lot 1,438 sqft
    MLS 817798
    20 Days on Market
  21. 6 Beds,  6.5 Baths
    9,900 sqft   lot 4.72 ac
    MLS 818952
    21 Days on Market
  22. 7 Beds,  3 Baths
    4,376 sqft   lot 2.84 ac
    MLS 818991
    23 Days on Market
  23. 4 Beds,  2.5 Baths
    1,840 sqft   lot 7,362 sqft
    MLS 818717
    24 Days on Market
  24. 3 Beds,  2.5 Baths
    1,800 sqft   lot 8,712 sqft
    MLS 817508
    25 Days on Market
  25. 2 Beds,  1 Bath
    1,050 sqft   lot 3,485 sqft
    MLS 817699
    25 Days on Market
  26. 2 Beds,  1 Bath
    1,071 sqft   lot 8,712 sqft
    MLS 812808
    26 Days on Market
  27. 4 Beds,  4.5 Baths
    4,500 sqft   lot 40,250 sqft
    MLS 817670
    26 Days on Market
  28. 2 Beds,  2 Baths
    1,300 sqft   lot 5,228 sqft
    MLS 817817
    27 Days on Market
  29. 4 Beds,  3 Baths
    lot 22,216 sqft
    MLS 816113
    29 Days on Market
  30. 3 Beds,  2.5 Baths
    2,750 sqft   lot 42,254 sqft
    MLS 809533
    30 Days on Market
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