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Located on Long Island’s North Shore, along the western edge of Suffolk County, overlooking the Long Island Sound, Smithtown is a large, growing, year-round community with a long, exciting history and even brighter future. First settled in the 1600s, the town has grown into one of Long Island’s most desirable real estate destinations.

According to legend, Richard “Bull” Smith made an agreement with the Native Americans in 1665. As a reward for saving his kidnapped daughter, the chief granted Smith all the land he could encircle in one day riding on a bull. The area established the borders that still define the modern-day hamlet of Smithtown.

Main attractions include the Nissequogue River, the beautiful, 543-acre Caleb Smith State Park Preserve, and historic sites like the Franklin O. Arthur Farm. Smithtown also has a “real” downtown including the Village of Nissequogue, which boasts a coveted area with beautiful luxury homes on the Sound.

Smithtown’s bustling main street offers fine restaurants, small boutiques, retail stores, and a performance arts theater. Attracting young buyers for decades, the town’s child-friendly environment and affordable, high-quality homes make the area ideal for families. Beautiful parks, beaches, and golf clubs add to the charm.

The Long Island Rail Road connects Smithtown residents with a 90-minute commute to New York City. Major highways offer short rides to the famous North Fork vineyards, neighborhoods of central Long Island and the Hamptons, beaches of the South Fork, and the quieter residential communities of Stony Brook, Huntington, and Old Field.

Contact Team Rita today to schedule viewings for homes in Smithtown, New York. Call to schedule a free consultation with one of our real estate agents.


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  1. Price Drop
    4 Beds,  2.5 Baths
    lot 19,167 sqft
    MLS 3581337
    58 Days on Market
  2. 3 Beds,  2.5 Baths
    1,826 sqft   lot 436 sqft
    MLS 3587795
    59 Days on Market
  3. 2 Beds,  1 Bath
    MLS 3581313
    59 Days on Market
  4. Price Drop
    4 Beds,  10 Baths
    MLS 3581301
    59 Days on Market
  5. 5 Beds,  3 Baths
    3,000 sqft   lot 10,455 sqft
    MLS 3581243
    59 Days on Market
  6. 4 Beds,  2.5 Baths
    2,800 sqft   lot 20,038 sqft
    MLS H6329675
    59 Days on Market
  7. 4 Beds,  3.5 Baths
    4,117 sqft   lot 1.09 ac
    MLS 3580977
    60 Days on Market
  8. 5 Beds,  2.5 Baths
    lot 10,455 sqft
    MLS 3579084
    60 Days on Market
  9. 4 Beds,  2.5 Baths
    2,500 sqft   lot 10,019 sqft
    MLS 3579863
    65 Days on Market
  10. 4 Beds,  2.5 Baths
    lot 21,780 sqft
    MLS 3579798
    65 Days on Market
  11. Price Drop
    4 Beds,  2 Baths
    lot 7,841 sqft
    MLS 3579625
    66 Days on Market
  12. 5 Beds,  3 Baths
    lot 43,560 sqft
    MLS 3579158
    66 Days on Market
  13. 4 Beds,  2.5 Baths
    2,900 sqft   lot 15,246 sqft
    MLS 3579334
    67 Days on Market
  14. 5 Beds,  6.5 Baths
    3,100 sqft   lot 1.54 ac
    MLS 3579217
    68 Days on Market
  15. 4 Beds,  1.5 Baths
    lot 13,940 sqft
    MLS 3579177
    68 Days on Market
  16. 5 Beds,  5 Baths
    lot 2.72 ac
    MLS 3578549
    71 Days on Market
  17. 2 Beds,  1 Bath
    lot 21,780 sqft
    MLS 3578474
    72 Days on Market
  18. 3 Beds,  4 Baths
    lot 10,890 sqft
    MLS 3577800
    74 Days on Market
  19. Price Drop
    4 Beds,  4 Baths
    3,700 sqft   lot 2.03 ac
    MLS 3577756
    74 Days on Market
  20. 11 Beds,  6 Baths
    9,411 sqft   lot 4.10 ac
    MLS 3577211
    78 Days on Market
  21. 4 Beds,  2.5 Baths
    lot 24,394 sqft
    MLS 3576611
    79 Days on Market
  22. 5 Beds,  2.5 Baths
    2,865 sqft   lot 10,890 sqft
    MLS 3576581
    79 Days on Market
  23. Price Drop
    5 Beds,  4 Baths
    4,930 sqft   lot 21,780 sqft
    MLS 3576243
    80 Days on Market
  24. 4 Beds,  2.5 Baths
    lot 2.01 ac
    MLS 3585401
    81 Days on Market
  25. Price Drop
    4 Beds,  2.5 Baths
    lot 21,780 sqft
    MLS 3576098
    81 Days on Market
  26. 6 Beds,  3 Baths
    lot 21,780 sqft
    MLS 3575922
    81 Days on Market
  27. 4 Beds,  3.5 Baths
    lot 2.17 ac
    MLS 3574417
    91 Days on Market
  28. 4 Beds,  2.5 Baths
    3,300 sqft   lot 4.08 ac
    MLS 3574321
    92 Days on Market
  29. 7 Beds,  5.5 Baths
    7,500 sqft   lot 2.02 ac
    MLS 3573768
    94 Days on Market
  30. 1 Bed,  1 Bath
    850 sqft   lot 872 sqft
    MLS 3571272
    97 Days on Market
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