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West of Trail Real Estate

"West of Trail" is one of Sarasota's oldest and most distinctive neighborhoods. Bordering Sarasota Bay, just south of Downtown, and to the west of 41, it is a special urban oasis close to everything. The focal point of the neighborhood is Southside Village, which is within walking distance and offers a gourmet grocery, a local coffee house, shops, and restaurants.

  • 1263
    Homes
  • 386
    Condos
  • $1,514,250
    Median Home Price
  • $150,250
    Median Condo Price
West of Trail home styles are very eclectic. Some homes date back to the 1920s and have been beautifully restored to offer character.

Since the value of the land has dramatically increased in recent years, there has also been tremendous gentrification particularly in the area bordered by Bay Street to the south, and Mound to the north. Older homes have been replaced by modern masterpieces.

The western border hugs Sarasota Bay, resulting in a number of spectacular waterfront there are many waterfront mansions in this stretch of mainland. Southside Elementary School and Sarasota Memorial Hospital are major draws for this neighborhood.

West of Trail
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West of Trail in Sarasota, Florida area map

West of Trail Real Estate

The most sought after West of Trial real estate tends to be bordered by Bee Ridge on the south and Sarasota’s Downtown on the north.

The beauty of these well-established urban streets, with eclectic architectural styles, and great access to downtown, Southside Village and neighborhood schools make this area very desirable. Sarasota Memorial Hospital is also right beyond your doorstep.

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  1. Photo of 3336 Old Oak Drive, Sarasota, FL 34239 (MLS # A4608565)
    $18,000,000
    Photo of 3336 Old Oak Drive, Sarasota, FL 34239 (MLS # A4608565)
    Photo of 3336 Old Oak Drive, Sarasota, FL 34239 (MLS # A4608565)
    3336 Old Oak Drive, Sarasota, FL
    3336 Old Oak Drive
    Sarasota, FL
    • 3 Beds
    • 5 Baths
    • 5,932 Home (sqft)
    • 5 Baths
    • 1.98 Lot (ac)
  2. Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4611675)
    $15,495,000
    Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4611675)
    Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4611675)
    1490 Hillview Drive, Sarasota, FL
    1490 Hillview Drive
    Sarasota, FL
    • 5 Beds
    • 7 Baths
    • 6,587 Home (sqft)
    • 7 Baths
    • 47.00 Lot (ac)
  3. Photo of 1610 N Lodge Drive, Sarasota, FL 34239 (MLS # A4615836)
    $14,800,000
    Photo of 1610 N Lodge Drive, Sarasota, FL 34239 (MLS # A4615836)
    Photo of 1610 N Lodge Drive, Sarasota, FL 34239 (MLS # A4615836)
    1610 N Lodge Drive, Sarasota, FL
    1610 N Lodge Drive
    Sarasota, FL
    • 5 Beds
    • 8 Baths
    • 7,110 Home (sqft)
    • 8 Baths
    • 16,118 Lot (sqft)
  4. Photo of 1500 Bay View Drive, Sarasota, FL 34239 (MLS # A4599458)
    $11,499,000
    Photo of 1500 Bay View Drive, Sarasota, FL 34239 (MLS # A4599458)
    Photo of 1500 Bay View Drive, Sarasota, FL 34239 (MLS # A4599458)
    1500 Bay View Drive, Sarasota, FL
    1500 Bay View Drive
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 4,031 Home (sqft)
    • 5 Baths
    • 23,523 Lot (sqft)
  5. Photo of 1607 Flower Drive, Sarasota, FL 34239 (MLS # A4604898)
    $5,590,000
    Photo of 1607 Flower Drive, Sarasota, FL 34239 (MLS # A4604898)
    Photo of 1607 Flower Drive, Sarasota, FL 34239 (MLS # A4604898)
    1607 Flower Drive, Sarasota, FL
    1607 Flower Drive
    Sarasota, FL
    • 6 Beds
    • 7 Baths
    • 4,769 Home (sqft)
    • 7 Baths
    • 14,811 Lot (sqft)
  6. Photo of 1479 Bay Point Drive, Sarasota, FL 34236 (MLS # A4623431)
    $5,549,000
    Photo of 1479 Bay Point Drive, Sarasota, FL 34236 (MLS # A4623431)
    Photo of 1479 Bay Point Drive, Sarasota, FL 34236 (MLS # A4623431)
    1479 Bay Point Drive, Sarasota, FL
    1479 Bay Point Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 21,345 Lot (sqft)
  7. Photo of 1620 N Lodge Drive, Sarasota, FL 34239 (MLS # A4622195)
    $5,490,000
    Photo of 1620 N Lodge Drive, Sarasota, FL 34239 (MLS # A4622195)
    Photo of 1620 N Lodge Drive, Sarasota, FL 34239 (MLS # A4622195)
    1620 N Lodge Drive, Sarasota, FL
    1620 N Lodge Drive
    Sarasota, FL
    • 5 Beds
    • 4 Baths
    • 4,660 Home (sqft)
    • 4 Baths
    • 20,038 Lot (sqft)
  8. Photo of 1536 Sandpiper Lane, Sarasota, FL 34239 (MLS # A4626396)
    $4,975,000
    Photo of 1536 Sandpiper Lane, Sarasota, FL 34239 (MLS # A4626396)
    Photo of 1536 Sandpiper Lane, Sarasota, FL 34239 (MLS # A4626396)
    1536 Sandpiper Lane, Sarasota, FL
    1536 Sandpiper Lane
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 13,940 Lot (sqft)
  9. Photo of 907 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4626402)
    $4,690,000
    Photo of 907 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4626402)
    Photo of 907 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4626402)
    66
     
    907 Pomelo Avenue, Sarasota, FL
    907 Pomelo Avenue
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 4,289 Home (sqft)
    • 5 Baths
    • 16,989 Lot (sqft)
  10. Photo of 2174 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4622124)
    $4,150,000
    Photo of 2174 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4622124)
    Photo of 2174 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4622124)
    2174 Mcclellan Parkway, Sarasota, FL
    2174 Mcclellan Parkway
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 3,478 Home (sqft)
    • 5 Baths
    • 13,068 Lot (sqft)
  11. Photo of 1908 Irving Street, Sarasota, FL 34236 (MLS # A4597214)
    $3,975,000
    Photo of 1908 Irving Street, Sarasota, FL 34236 (MLS # A4597214)
    Photo of 1908 Irving Street, Sarasota, FL 34236 (MLS # A4597214)
    1908 Irving Street, Sarasota, FL
    1908 Irving Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,503 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  12. Photo of 1805 Goldenrod Street, Sarasota, FL 34239 (MLS # A4612895)
    $3,800,000
    Photo of 1805 Goldenrod Street, Sarasota, FL 34239 (MLS # A4612895)
    Photo of 1805 Goldenrod Street, Sarasota, FL 34239 (MLS # A4612895)
    1805 Goldenrod Street, Sarasota, FL
    1805 Goldenrod Street
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 3,595 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  13. Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4627985)
    $3,775,000
    Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4627985)
    Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4627985)
    1671 Arlington Street, Sarasota, FL
    1671 Arlington Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,250 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  14. Photo of 1919 Irving Street, Sarasota, FL 34236 (MLS # A4624889)
    $3,495,000
    Photo of 1919 Irving Street, Sarasota, FL 34236 (MLS # A4624889)
    Photo of 1919 Irving Street, Sarasota, FL 34236 (MLS # A4624889)
    1919 Irving Street, Sarasota, FL
    1919 Irving Street
    Sarasota, FL
    • 5 Beds
    • 6 Baths
    • 4,956 Home (sqft)
    • 6 Baths
    • 14,811 Lot (sqft)
  15. Photo of 1751 Hawthorne Street, Sarasota, FL 34239 (MLS # A4621900)
    $3,095,000
    Photo of 1751 Hawthorne Street, Sarasota, FL 34239 (MLS # A4621900)
    Photo of 1751 Hawthorne Street, Sarasota, FL 34239 (MLS # A4621900)
    1751 Hawthorne Street, Sarasota, FL
    1751 Hawthorne Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,785 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  16. Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4625429)
    $2,895,000
    Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4625429)
    Photo of 1959 Hibiscus Street, Sarasota, FL 34239 (MLS # A4625429)
    42
     
    1959 Hibiscus Street, Sarasota, FL
    1959 Hibiscus Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,720 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  17. Photo of 1585 South Drive, Sarasota, FL 34239 (MLS # A4626080)
    $2,750,000
    Photo of 1585 South Drive, Sarasota, FL 34239 (MLS # A4626080)
    Photo of 1585 South Drive, Sarasota, FL 34239 (MLS # A4626080)
    41
     
    1585 South Drive, Sarasota, FL
    1585 South Drive
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 2,764 Home (sqft)
    • 4 Baths
    • 16,553 Lot (sqft)
  18. Photo of 1886 Prospect Street, Sarasota, FL 34239 (MLS # A4615714)
    $2,599,000
    Photo of 1886 Prospect Street, Sarasota, FL 34239 (MLS # A4615714)
    Photo of 1886 Prospect Street, Sarasota, FL 34239 (MLS # A4615714)
    1886 Prospect Street, Sarasota, FL
    1886 Prospect Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,444 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  19. Photo of 1734 Wisconsin Lane, Sarasota, FL 34239 (MLS # A4609998)
    $2,550,000
    Photo of 1734 Wisconsin Lane, Sarasota, FL 34239 (MLS # A4609998)
    Photo of 1734 Wisconsin Lane, Sarasota, FL 34239 (MLS # A4609998)
    1734 Wisconsin Lane, Sarasota, FL
    1734 Wisconsin Lane
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,005 Home (sqft)
    • 5 Baths
    • 6,099 Lot (sqft)
  20. Photo of 1389 Harbor Drive, Sarasota, FL 34239 (MLS # A4623196)
    $2,490,000
    Photo of 1389 Harbor Drive, Sarasota, FL 34239 (MLS # A4623196)
    Photo of 1389 Harbor Drive, Sarasota, FL 34239 (MLS # A4623196)
    1389 Harbor Drive, Sarasota, FL
    1389 Harbor Drive
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,376 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  21. Photo of 3464 Camino Real, Sarasota, FL 34239 (MLS # A4621946)
    $2,447,000
    Photo of 3464 Camino Real, Sarasota, FL 34239 (MLS # A4621946)
    Photo of 3464 Camino Real, Sarasota, FL 34239 (MLS # A4621946)
    3464 Camino Real, Sarasota, FL
    3464 Camino Real
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 2,847 Home (sqft)
    • 6 Baths
    • 5,663 Lot (sqft)
  22. Photo of 1826 Boyce Street, Sarasota, FL 34239 (MLS # A4609909)
    $2,350,000
    Photo of 1826 Boyce Street, Sarasota, FL 34239 (MLS # A4609909)
    Photo of 1826 Boyce Street, Sarasota, FL 34239 (MLS # A4609909)
    1826 Boyce Street, Sarasota, FL
    1826 Boyce Street
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 3,270 Home (sqft)
    • 5 Baths
    • 10,455 Lot (sqft)
  23. Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4624670)
    $2,275,000
    Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4624670)
    Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4624670)
    1690 Arlington Street, Sarasota, FL
    1690 Arlington Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 2,965 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  24. Photo of 1964 Datura Street, Sarasota, FL 34239 (MLS # A4600886)
    $2,145,000
    Photo of 1964 Datura Street, Sarasota, FL 34239 (MLS # A4600886)
    Photo of 1964 Datura Street, Sarasota, FL 34239 (MLS # A4600886)
    1964 Datura Street, Sarasota, FL
    1964 Datura Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,272 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  25. Photo of 1519 Harbor Drive, Sarasota, FL 34239 (MLS # A4625720)
    $2,000,000
    Photo of 1519 Harbor Drive, Sarasota, FL 34239 (MLS # A4625720)
    Photo of 1519 Harbor Drive, Sarasota, FL 34239 (MLS # A4625720)
    1519 Harbor Drive, Sarasota, FL
    1519 Harbor Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 13,940 Lot (sqft)
  26. Photo of 1910 Morris Street, Sarasota, FL 34239 (MLS # A4614275)
    $1,975,000
    Photo of 1910 Morris Street, Sarasota, FL 34239 (MLS # A4614275)
    Photo of 1910 Morris Street, Sarasota, FL 34239 (MLS # A4614275)
    1910 Morris Street, Sarasota, FL
    1910 Morris Street
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,695 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  27. Photo of 1884 Grove Street, Sarasota, FL 34239 (MLS # A4625103)
    $1,850,000
    Photo of 1884 Grove Street, Sarasota, FL 34239 (MLS # A4625103)
    Photo of 1884 Grove Street, Sarasota, FL 34239 (MLS # A4625103)
    1884 Grove Street, Sarasota, FL
    1884 Grove Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,714 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  28. Photo of 908 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4627214)
    $1,700,000
    Photo of 908 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4627214)
    Photo of 908 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4627214)
    908 Pomelo Avenue, Sarasota, FL
    908 Pomelo Avenue
    Sarasota, FL
    • 5 Beds
    • 3 Baths
    • 2,358 Home (sqft)
    • 3 Baths
    • 20,909 Lot (sqft)
  29. Photo of 2155 Oriole Drive, Sarasota, FL 34239 (MLS # A4624997)
    $1,595,000
    Photo of 2155 Oriole Drive, Sarasota, FL 34239 (MLS # A4624997)
    Photo of 2155 Oriole Drive, Sarasota, FL 34239 (MLS # A4624997)
    2155 Oriole Drive, Sarasota, FL
    2155 Oriole Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 14,375 Lot (sqft)
  30. Photo of 1960 Lincoln Drive, Sarasota, FL 34236 (MLS # U8245185)
    $1,575,000
    Photo of 1960 Lincoln Drive, Sarasota, FL 34236 (MLS # U8245185)
    Photo of 1960 Lincoln Drive, Sarasota, FL 34236 (MLS # U8245185)
    1960 Lincoln Drive, Sarasota, FL
    1960 Lincoln Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,611 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 11/8/24 12:09 PM PST.

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