West of Trail Real Estate

"West of Trail" is one of the 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
  • $952,500
    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 Older homes have been replaced by modern masterpieces.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 1309 VISTA DRIVE, SARASOTA, FL 34239 (MLS # A4491997)
    $17,250,000
    Photo of 1309 VISTA DRIVE, SARASOTA, FL 34239 (MLS # A4491997)
    Photo of 1309 VISTA DRIVE, SARASOTA, FL 34239 (MLS # A4491997)
    1309 VISTA DRIVE, SARASOTA, FL
    1309 VISTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 6 Baths
    • 8,452 Home (sqft)
    • 6 Baths
    • 1.44 Lot (ac)
  2. Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    $9,575,000
    Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    1465 HILLVIEW DRIVE, SARASOTA, FL
    1465 HILLVIEW DRIVE
    SARASOTA, FL
    • 5 Beds
    • 7 Baths
    • 6,654 Home (sqft)
    • 7 Baths
    • 28,753 Lot (sqft)
  3. Photo of 3300 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4520464)
    $8,495,000
    Photo of 3300 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4520464)
    Photo of 3300 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4520464)
    16
     
    3300 OLD OAK DRIVE, SARASOTA, FL
    3300 OLD OAK DRIVE
    SARASOTA, FL
    • 4 Beds
    • 7 Baths
    • 6,428 Home (sqft)
    • 7 Baths
    • 1.43 Lot (ac)
  4. Photo of 2168 SPARROW COURT, SARASOTA, FL 34239 (MLS # A4531141)
    $6,950,000
    Photo of 2168 SPARROW COURT, SARASOTA, FL 34239 (MLS # A4531141)
    Photo of 2168 SPARROW COURT, SARASOTA, FL 34239 (MLS # A4531141)
    2168 SPARROW COURT, SARASOTA, FL
    2168 SPARROW COURT
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,643 Home (sqft)
    • 4 Baths
    • 13,940 Lot (sqft)
  5. Photo of 1393 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4541554)
    $4,699,999
    Photo of 1393 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4541554)
    Photo of 1393 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4541554)
    1393 HARBOR DRIVE, SARASOTA, FL
    1393 HARBOR DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,316 Home (sqft)
    • 5 Baths
    • 15,682 Lot (sqft)
  6. Photo of 1359 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4536349)
    $4,500,000
    Photo of 1359 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4536349)
    Photo of 1359 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4536349)
    1359 HARBOR DRIVE, SARASOTA, FL
    1359 HARBOR DRIVE
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 4,349 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  7. Photo of 1718 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4541870)
    $3,995,000
    Photo of 1718 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4541870)
    Photo of 1718 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4541870)
    1718 PROSPECT STREET, SARASOTA, FL
    1718 PROSPECT STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,282 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  8. Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3366498)
    $3,995,000
    Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3366498)
    Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3366498)
    1558 SANDPIPER LANE, SARASOTA, FL
    1558 SANDPIPER LANE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,942 Home (sqft)
    • 4 Baths
    • 14,375 Lot (sqft)
  9. Photo of 1960 BOYCE STREET, SARASOTA, FL 34239 (MLS # A4519209)
    $3,900,000
    Photo of 1960 BOYCE STREET, SARASOTA, FL 34239 (MLS # A4519209)
    Photo of 1960 BOYCE STREET, SARASOTA, FL 34239 (MLS # A4519209)
    1960 BOYCE STREET, SARASOTA, FL
    1960 BOYCE STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,674 Home (sqft)
    • 5 Baths
    • 10,455 Lot (sqft)
  10. Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534537)
    $3,475,000
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534537)
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534537)
    1537 SIESTA DRIVE, SARASOTA, FL
    1537 SIESTA DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,739 Home (sqft)
    • 6 Baths
    • 12,197 Lot (sqft)
  11. Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4534565)
    $3,350,000
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4534565)
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4534565)
    15
     
    1954 GOLDENROD STREET, SARASOTA, FL
    1954 GOLDENROD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,606 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  12. Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534567)
    $3,350,000
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534567)
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534567)
    3135 S OSPREY AVENUE, SARASOTA, FL
    3135 S OSPREY AVENUE
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 3,595 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  13. Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534568)
    $3,250,000
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534568)
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534568)
    17
     
    3319 S OSPREY AVENUE, SARASOTA, FL
    3319 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,423 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  14. Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4534560)
    $3,150,000
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4534560)
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4534560)
    2171 MCCLELLAN PARKWAY, SARASOTA, FL
    2171 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  15. Photo of 1715 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4540176)
    $2,995,000
    Photo of 1715 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4540176)
    Photo of 1715 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4540176)
    1715 ARLINGTON STREET, SARASOTA, FL
    1715 ARLINGTON STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,732 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  16. Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4534562)
    $2,950,000
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4534562)
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4534562)
    1886 BAHIA VISTA STREET, SARASOTA, FL
    1886 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,153 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  17. Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    $2,950,000
    Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    78
     
    1929 MORRIS STREET, SARASOTA, FL
    1929 MORRIS STREET
    SARASOTA, FL
    • 3 Beds
    • 5 Baths
    • 3,035 Home (sqft)
    • 5 Baths
    • 13,704 Lot (sqft)
  18. Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534540)
    $2,750,000
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534540)
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534540)
    1647 SIESTA DRIVE, SARASOTA, FL
    1647 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  19. Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    $2,600,000
    Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    1844 MAGNOLIA STREET, SARASOTA, FL
    1844 MAGNOLIA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,915 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  20. Photo of 2627 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4531892)
    $2,500,000
    Photo of 2627 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4531892)
    Photo of 2627 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4531892)
    2627 PLEASANT PLACE, SARASOTA, FL
    2627 PLEASANT PLACE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,782 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  21. Photo of 2515 PURITAN TERRACE, SARASOTA, FL 34239 (MLS # A4538961)
    $2,400,000
    Photo of 2515 PURITAN TERRACE, SARASOTA, FL 34239 (MLS # A4538961)
    Photo of 2515 PURITAN TERRACE, SARASOTA, FL 34239 (MLS # A4538961)
    2515 PURITAN TERRACE, SARASOTA, FL
    2515 PURITAN TERRACE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,334 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  22. Photo of 1730 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4524207)
    $2,279,900
    Photo of 1730 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4524207)
    Photo of 1730 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4524207)
    1730 WISCONSIN LANE, SARASOTA, FL
    1730 WISCONSIN LANE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,005 Home (sqft)
    • 5 Baths
    • 6,180 Lot (sqft)
  23. Photo of 2440 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4539511)
    $1,798,888
    Photo of 2440 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4539511)
    Photo of 2440 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4539511)
    71
     
    2440 S OSPREY AVENUE, SARASOTA, FL
    2440 S OSPREY AVENUE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,238 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  24. Photo of 1751 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4542121)
    $1,700,000
    Photo of 1751 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4542121)
    Photo of 1751 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4542121)
    1751 FLOYD STREET, SARASOTA, FL
    1751 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,881 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  25. Photo of 1654 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4538711)
    $1,697,000
    Photo of 1654 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4538711)
    Photo of 1654 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4538711)
    1654 ARLINGTON STREET, SARASOTA, FL
    1654 ARLINGTON STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,514 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  26. Photo of 2504 MULBERRY TERRACE, SARASOTA, FL 34239 (MLS # A4540697)
    $1,400,000
    Photo of 2504 MULBERRY TERRACE, SARASOTA, FL 34239 (MLS # A4540697)
    Photo of 2504 MULBERRY TERRACE, SARASOTA, FL 34239 (MLS # A4540697)
    2504 MULBERRY TERRACE, SARASOTA, FL
    2504 MULBERRY TERRACE
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,665 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  27. Photo of 1872 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4542927)
    $1,100,000
    Photo of 1872 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4542927)
    Photo of 1872 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4542927)
    25
     
    1872 HIBISCUS STREET, SARASOTA, FL
    1872 HIBISCUS STREET
    SARASOTA, FL
    • 4 Beds
    • 2 Baths
    • 1,730 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  28. Photo of 1965 GROVE STREET, SARASOTA, FL 34239 (MLS # A4537304)
    $875,000
    Photo of 1965 GROVE STREET, SARASOTA, FL 34239 (MLS # A4537304)
    Photo of 1965 GROVE STREET, SARASOTA, FL 34239 (MLS # A4537304)
    1965 GROVE STREET, SARASOTA, FL
    1965 GROVE STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,424 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  29. Photo of 850 S TAMIAMI TRAIL #522, SARASOTA, FL 34236 (MLS # A4540881)
    $505,000
    Photo of 850 S TAMIAMI TRAIL #522, SARASOTA, FL 34236 (MLS # A4540881)
    Photo of 850 S TAMIAMI TRAIL #522, SARASOTA, FL 34236 (MLS # A4540881)
    850 S TAMIAMI TRAIL #522, SARASOTA, FL
    850 S TAMIAMI TRAIL #522
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 9.10 Lot (ac)
  30. Photo of 850 S TAMIAMI TRAIL #823, SARASOTA, FL 34236 (MLS # A4539631)
    $450,000
    Photo of 850 S TAMIAMI TRAIL #823, SARASOTA, FL 34236 (MLS # A4539631)
    Photo of 850 S TAMIAMI TRAIL #823, SARASOTA, FL 34236 (MLS # A4539631)
    850 S TAMIAMI TRAIL #823, SARASOTA, FL
    850 S TAMIAMI TRAIL #823
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
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