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

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 Older homes have been replaced by modern masterpieces.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)
    $14,995,000
    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
    • 24,830 Lot (sqft)
  3. Photo of 3000 Southwest Drive, Sarasota, FL 34239 (MLS # A4588632)
    $12,950,000
    Photo of 3000 Southwest Drive, Sarasota, FL 34239 (MLS # A4588632)
    Photo of 3000 Southwest Drive, Sarasota, FL 34239 (MLS # A4588632)
    3000 Southwest Drive, Sarasota, FL
    3000 Southwest Drive
    Sarasota, FL
    • 5 Beds
    • 7 Baths
    • 8,125 Home (sqft)
    • 7 Baths
    • 1.61 Lot (ac)
  4. Photo of 3350 Old Oak Drive, Sarasota, FL 34239 (MLS # A4595100)
    $11,500,000
    Photo of 3350 Old Oak Drive, Sarasota, FL 34239 (MLS # A4595100)
    Photo of 3350 Old Oak Drive, Sarasota, FL 34239 (MLS # A4595100)
    3350 Old Oak Drive, Sarasota, FL
    3350 Old Oak Drive
    Sarasota, FL
    • 7 Beds
    • 8 Baths
    • 7,181 Home (sqft)
    • 8 Baths
    • 2.10 Lot (ac)
  5. 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)
  6. Photo of 1378 Harbor Drive, Sarasota, FL 34239 (MLS # A4590940)
    $11,350,000
    Photo of 1378 Harbor Drive, Sarasota, FL 34239 (MLS # A4590940)
    Photo of 1378 Harbor Drive, Sarasota, FL 34239 (MLS # A4590940)
    1378 Harbor Drive, Sarasota, FL
    1378 Harbor Drive
    Sarasota, FL
    • 4 Beds
    • 8 Baths
    • 6,238 Home (sqft)
    • 8 Baths
    • 14,375 Lot (sqft)
  7. Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4546764)
    $7,500,000
    Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4546764)
    Photo of 1490 Hillview Drive, Sarasota, FL 34239 (MLS # A4546764)
    11
     
    1490 Hillview Drive, Sarasota, FL
    1490 Hillview Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,474 Lot (sqft)
  8. Photo of 2100 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4610921)
    $7,000,000
    Photo of 2100 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4610921)
    Photo of 2100 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4610921)
    2100 Mcclellan Parkway, Sarasota, FL
    2100 Mcclellan Parkway
    Sarasota, FL
    • 5 Beds
    • 9 Baths
    • 4,450 Home (sqft)
    • 9 Baths
    • 19,602 Lot (sqft)
  9. Photo of 1479 Bay Point Drive, Sarasota, FL 34236 (MLS # A4561284)
    $5,875,000
    Photo of 1479 Bay Point Drive, Sarasota, FL 34236 (MLS # A4561284)
    Photo of 1479 Bay Point Drive, Sarasota, FL 34236 (MLS # A4561284)
    1479 Bay Point Drive, Sarasota, FL
    1479 Bay Point Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,783 Home (sqft)
    • 3 Baths
    • 21,345 Lot (sqft)
  10. Photo of 1640 Waldemere Street, Sarasota, FL 34239 (MLS # A4610108)
    $5,775,000
    Photo of 1640 Waldemere Street, Sarasota, FL 34239 (MLS # A4610108)
    Photo of 1640 Waldemere Street, Sarasota, FL 34239 (MLS # A4610108)
    1640 Waldemere Street, Sarasota, FL
    1640 Waldemere Street
    Sarasota, FL
    • 7 Beds
    • 8 Baths
    • 5,500 Home (sqft)
    • 8 Baths
    • 10,890 Lot (sqft)
  11. Photo of 1655 South Drive, Sarasota, FL 34239 (MLS # A4584482)
    $5,695,000
    Photo of 1655 South Drive, Sarasota, FL 34239 (MLS # A4584482)
    Photo of 1655 South Drive, Sarasota, FL 34239 (MLS # A4584482)
    1655 South Drive, Sarasota, FL
    1655 South Drive
    Sarasota, FL
    • 5 Beds
    • 9 Baths
    • 6,355 Home (sqft)
    • 9 Baths
    • 14,811 Lot (sqft)
  12. 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)
  13. Photo of 907 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4597533)
    $4,995,000
    Photo of 907 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4597533)
    Photo of 907 Pomelo Avenue, Sarasota, FL 34236 (MLS # A4597533)
    907 Pomelo Avenue, Sarasota, FL
    907 Pomelo Avenue
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 4,289 Home (sqft)
    • 5 Baths
    • 16,989 Lot (sqft)
  14. Photo of 1521 Bay Point Drive, Sarasota, FL 34236 (MLS # A4604073)
    $4,950,000
    Photo of 1521 Bay Point Drive, Sarasota, FL 34236 (MLS # A4604073)
    Photo of 1521 Bay Point Drive, Sarasota, FL 34236 (MLS # A4604073)
    1521 Bay Point Drive, Sarasota, FL
    1521 Bay Point Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,474 Lot (sqft)
  15. Photo of 1507 Bay Point Drive, Sarasota, FL 34236 (MLS # A4564576)
    $4,950,000
    Photo of 1507 Bay Point Drive, Sarasota, FL 34236 (MLS # A4564576)
    Photo of 1507 Bay Point Drive, Sarasota, FL 34236 (MLS # A4564576)
    1507 Bay Point Drive, Sarasota, FL
    1507 Bay Point Drive
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,909 Lot (sqft)
  16. Photo of 1718 Bay Street, Sarasota, FL 34236 (MLS # A4586511)
    $4,735,000
    Photo of 1718 Bay Street, Sarasota, FL 34236 (MLS # A4586511)
    Photo of 1718 Bay Street, Sarasota, FL 34236 (MLS # A4586511)
    1718 Bay Street, Sarasota, FL
    1718 Bay Street
    Sarasota, FL
    • 5 Beds
    • 4 Baths
    • 4,015 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  17. Photo of 1550 S Orange Avenue, Sarasota, FL 34239 (MLS # A4566256)
    $4,438,000
    Photo of 1550 S Orange Avenue, Sarasota, FL 34239 (MLS # A4566256)
    Photo of 1550 S Orange Avenue, Sarasota, FL 34239 (MLS # A4566256)
    15
     
    1550 S Orange Avenue, Sarasota, FL
    1550 S Orange Avenue
    Sarasota, FL
    • 4 Beds
    • 6 Baths
    • 4,189 Home (sqft)
    • 6 Baths
    • 14,811 Lot (sqft)
  18. Photo of 1639 S Orange Avenue, Sarasota, FL 34239 (MLS # A4610395)
    $4,100,000
    Photo of 1639 S Orange Avenue, Sarasota, FL 34239 (MLS # A4610395)
    Photo of 1639 S Orange Avenue, Sarasota, FL 34239 (MLS # A4610395)
    1639 S Orange Avenue, Sarasota, FL
    1639 S Orange Avenue
    Sarasota, FL
    • 5 Beds
    • 7 Baths
    • 4,670 Home (sqft)
    • 7 Baths
    • 12,633 Lot (sqft)
  19. Photo of 1631 Hawthorne Street, Sarasota, FL 34239 (MLS # A4586973)
    $3,990,000
    Photo of 1631 Hawthorne Street, Sarasota, FL 34239 (MLS # A4586973)
    Photo of 1631 Hawthorne Street, Sarasota, FL 34239 (MLS # A4586973)
    49
     
    1631 Hawthorne Street, Sarasota, FL
    1631 Hawthorne Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,430 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  20. 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)
  21. Photo of 1050 Bay Point Place, Sarasota, FL 34236 (MLS # A4609345)
    $3,950,000
    Photo of 1050 Bay Point Place, Sarasota, FL 34236 (MLS # A4609345)
    Photo of 1050 Bay Point Place, Sarasota, FL 34236 (MLS # A4609345)
    1050 Bay Point Place, Sarasota, FL
    1050 Bay Point Place
    Sarasota, FL
    • 5 Beds
    • 5 Baths
    • 3,930 Home (sqft)
    • 5 Baths
    • 14,375 Lot (sqft)
  22. Photo of 1924 Lincoln Drive, Sarasota, FL 34236 (MLS # A4570095)
    $3,950,000
    Photo of 1924 Lincoln Drive, Sarasota, FL 34236 (MLS # A4570095)
    Photo of 1924 Lincoln Drive, Sarasota, FL 34236 (MLS # A4570095)
    1924 Lincoln Drive, Sarasota, FL
    1924 Lincoln Drive
    Sarasota, FL
    • 4 Beds
    • 7 Baths
    • 5,434 Home (sqft)
    • 7 Baths
    • 17,860 Lot (sqft)
  23. Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4609222)
    $3,775,000
    Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4609222)
    Photo of 1671 Arlington Street, Sarasota, FL 34239 (MLS # A4609222)
    1671 Arlington Street, Sarasota, FL
    1671 Arlington Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,250 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  24. Photo of 1426 S Osprey Avenue, Sarasota, FL 34239 (MLS # A4595174)
    $3,489,000
    Photo of 1426 S Osprey Avenue, Sarasota, FL 34239 (MLS # A4595174)
    Photo of 1426 S Osprey Avenue, Sarasota, FL 34239 (MLS # A4595174)
    1426 S Osprey Avenue, Sarasota, FL
    1426 S Osprey Avenue
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,000 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
  25. Photo of 1886 Prospect Street, Sarasota, FL 34239 (MLS # A4594315)
    $2,995,000
    Photo of 1886 Prospect Street, Sarasota, FL 34239 (MLS # A4594315)
    Photo of 1886 Prospect Street, Sarasota, FL 34239 (MLS # A4594315)
    22
     
    1886 Prospect Street, Sarasota, FL
    1886 Prospect Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,444 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  26. Photo of 1912 Wisteria Street, Sarasota, FL 34239 (MLS # A4563784)
    $2,950,000
    Photo of 1912 Wisteria Street, Sarasota, FL 34239 (MLS # A4563784)
    Photo of 1912 Wisteria Street, Sarasota, FL 34239 (MLS # A4563784)
    1912 Wisteria Street, Sarasota, FL
    1912 Wisteria Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,547 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
  27. Photo of 1632 Floyd Street, Sarasota, FL 34239 (MLS # A4593582)
    $2,850,000
    Photo of 1632 Floyd Street, Sarasota, FL 34239 (MLS # A4593582)
    Photo of 1632 Floyd Street, Sarasota, FL 34239 (MLS # A4593582)
    1632 Floyd Street, Sarasota, FL
    1632 Floyd Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 4,338 Home (sqft)
    • 5 Baths
    • 14,375 Lot (sqft)
  28. Photo of 1859 Magnolia Street, Sarasota, FL 34239 (MLS # A4564854)
    $2,697,500
    Photo of 1859 Magnolia Street, Sarasota, FL 34239 (MLS # A4564854)
    Photo of 1859 Magnolia Street, Sarasota, FL 34239 (MLS # A4564854)
    1859 Magnolia Street, Sarasota, FL
    1859 Magnolia Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,220 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  29. 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)
  30. Photo of 2171 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4597297)
    $2,499,000
    Photo of 2171 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4597297)
    Photo of 2171 Mcclellan Parkway, Sarasota, FL 34239 (MLS # A4597297)
    28
     
    2171 Mcclellan Parkway, Sarasota, FL
    2171 Mcclellan Parkway
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 7,406 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 5/27/24 3:11 AM PDT.

This MLS IDX is (c) Diverse Solutions 2024.

 
 

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