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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,  1.5 Baths
    2,200 sqft   lot 8,233 sqft
    MLS 807112
    170 Days on Market
  2. 5 Beds,  2 Baths
    1,500 sqft   lot 34,848 sqft
    MLS 804563
    171 Days on Market
  3. 3 Beds,  1 Bath
    960 sqft   lot 6,055 sqft
    MLS 805847
    174 Days on Market
  4. 3 Beds,  3 Baths
    1,100 sqft   lot 43,560 sqft
    MLS 804899
    178 Days on Market
  5. Price Drop
    0 Beds,  2 Baths
    1,860 sqft   lot 26,572 sqft
    MLS 804042
    183 Days on Market
  6. 6 Beds,  5.5 Baths
    3,630 sqft   lot 21,780 sqft
    MLS LP1439478
    193 Days on Market
  7. 4 Beds,  3 Baths
    1,800 sqft   lot 39,814 sqft
    MLS L3592550
    198 Days on Market
  8. 4 Beds,  2 Baths
    2,200 sqft   lot 3.19 ac
    MLS L3592218
    199 Days on Market
  9. 5 Beds,  4.5 Baths
    2,950 sqft  
    MLS H6335251
    210 Days on Market
  10. 4 Beds,  6 Baths
    5,220 sqft   lot 14,811 sqft
    MLS L3590145
    211 Days on Market
  11. 3 Beds,  1.5 Baths
    2,000 sqft   lot 1.74 ac
    MLS L3590177
    211 Days on Market
  12. 11 Beds,  13 Baths
    lot 131 sqft
    MLS L3590171
    211 Days on Market
  13. 2 Beds,  1 Bath
    MLS L3589570
    213 Days on Market
  14. 3 Beds,  2 Baths
    1,300 sqft   lot 5,925 sqft
    MLS L3587738
    223 Days on Market
  15. 5 Beds,  4.5 Baths
    4,627 sqft   lot 42,864 sqft
    MLS L3587614
    224 Days on Market
  16. 3 Beds,  2.5 Baths
    lot 10,803 sqft
    MLS L3586311
    229 Days on Market
  17. 2 Beds,  1 Bath
    lot 2.41 ac
    MLS L3584002
    241 Days on Market
  18. 5 Beds,  4.5 Baths
    3,500 sqft   lot 9,540 sqft
    MLS L3579812
    261 Days on Market
  19. 3 Beds,  1.5 Baths
    2,290 sqft   lot 24,394 sqft
    MLS L3579596
    262 Days on Market
  20. 4 Beds,  4.5 Baths
    lot 6,491 sqft
    MLS L3577146
    276 Days on Market
  21. 4 Beds,  2 Baths
    lot 30,318 sqft
    MLS L3575647
    280 Days on Market
  22. 5 Beds,  4.5 Baths
    4,122 sqft   lot 1.00 ac
    MLS L3574213
    289 Days on Market
  23. 6 Beds,  4.5 Baths
    lot 1.32 ac
    MLS L3573568
    291 Days on Market
  24. 3 Beds,  3.5 Baths
    lot 5,228 sqft
    MLS L3572634
    296 Days on Market
  25. Price Drop
    3 Beds,  2.5 Baths
    1,572 sqft   lot 20,779 sqft
    MLS L3572625
    296 Days on Market
  26. 3 Beds,  1.5 Baths
    2,086 sqft   lot 19.40 ac
    MLS L3570534
    306 Days on Market
  27. 2 Beds,  1 Bath
    lot 5,184 sqft
    MLS L3570090
    308 Days on Market
  28. 5 Beds,  3.5 Baths
    4,419 sqft   lot 1.34 ac
    MLS L3562280
    344 Days on Market
  29. 3 Beds,  2.5 Baths
    1,900 sqft   lot 1.94 ac
    MLS L3555058
    374 Days on Market
  30. 4 Beds,  2 Baths
    1,845 sqft   lot 10,803 sqft
    MLS L3552341
    387 Days on Market
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