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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. 2 Beds,  1 Bath
    lot 8,233 sqft
    MLS L3577803
    207 Days on Market
  2. 4 Beds,  3 Baths
    2,800 sqft   lot 40,250 sqft
    MLS L3576725
    212 Days on Market
  3. 4 Beds,  4.5 Baths
    lot 6,491 sqft
    MLS L3577146
    213 Days on Market
  4. 4 Beds,  2 Baths
    lot 30,318 sqft
    MLS L3575647
    217 Days on Market
  5. 3 Beds,  3 Baths
    2,100 sqft   lot 21,127 sqft
    MLS L3574281
    225 Days on Market
  6. 5 Beds,  4.5 Baths
    4,122 sqft   lot 1.00 ac
    MLS L3574213
    226 Days on Market
  7. 6 Beds,  4.5 Baths
    lot 1.32 ac
    MLS L3573568
    228 Days on Market
  8. 3 Beds,  3.5 Baths
    lot 5,228 sqft
    MLS L3572634
    233 Days on Market
  9. 3 Beds,  2.5 Baths
    1,572 sqft   lot 20,779 sqft
    MLS L3572625
    233 Days on Market
  10. 3 Beds,  1.5 Baths
    1,500 sqft   lot 7,362 sqft
    MLS L3571743
    236 Days on Market
  11. 3 Beds,  1.5 Baths
    2,086 sqft   lot 19.40 ac
    MLS L3570534
    243 Days on Market
  12. 2 Beds,  1 Bath
    lot 5,184 sqft
    MLS L3570090
    245 Days on Market
  13. 3 Beds,  1 Bath
    lot 5,184 sqft
    MLS L3565361
    267 Days on Market
  14. 5 Beds,  3.5 Baths
    4,419 sqft   lot 1.34 ac
    MLS L3562280
    281 Days on Market
  15. 1 Bed,  2.5 Baths
    4,744 sqft   lot 3.13 ac
    MLS L3561587
    284 Days on Market
  16. 4 Beds,  3 Baths
    lot 32,453 sqft
    MLS L3556934
    303 Days on Market
  17. 4 Beds,  3 Baths
    2,300 sqft  
    MLS L3556148
    306 Days on Market
  18. 4 Beds,  5.5 Baths
    6,366 sqft   lot 30,492 sqft
    MLS L3555160
    310 Days on Market
  19. 3 Beds,  2.5 Baths
    1,900 sqft   lot 1.94 ac
    MLS L3555058
    311 Days on Market
  20. 4 Beds,  2 Baths
    1,845 sqft   lot 10,803 sqft
    MLS L3552341
    324 Days on Market
  21. 5 Beds,  7.5 Baths
    lot 19,907 sqft
    MLS L3550261
    332 Days on Market
  22. 7 Beds,  8 Baths
    lot 8.85 ac
    MLS L3549432
    335 Days on Market
  23. 4 Beds,  2 Baths
    2,000 sqft   lot 1.74 ac
    MLS L3548646
    339 Days on Market
  24. Price Drop
    4 Beds,  3.5 Baths
    4,000 sqft   lot 41,818 sqft
    MLS H6303191
    345 Days on Market
  25. 4 Beds,  3 Baths
    lot 2.22 ac
    MLS L3569738
    346 Days on Market
  26. Price Drop
    3 Beds,  2.5 Baths
    lot 18,165 sqft
    MLS L3546094
    350 Days on Market
  27. 3 Beds,  1.5 Baths
    1,504 sqft   lot 21,650 sqft
    MLS L3544978
    354 Days on Market
  28. 4 Beds,  3.5 Baths
    lot 14,375 sqft
    MLS L3539656
    379 Days on Market
  29. 1 Bed,  1 Bath
    850 sqft   lot 8,669 sqft
    MLS L3532660
    410 Days on Market
  30. 5 Beds,  4.5 Baths
    4,900 sqft   lot 39,814 sqft
    MLS L3528746
    430 Days on Market
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