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 Older homes have been replaced by modern masterpieces.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 1378 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4546357)
    $14,000,000
    Photo of 1378 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4546357)
    Photo of 1378 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4546357)
    1378 HARBOR DRIVE, SARASOTA, FL
    1378 HARBOR DRIVE
    SARASOTA, FL
    • 4 Beds
    • 8 Baths
    • 6,238 Home (sqft)
    • 8 Baths
    • 14,375 Lot (sqft)
  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
    • 28,750 Lot (sqft)
  3. Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4525595)
    $8,499,000
    Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4525595)
    Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4525595)
    1507 BAY POINT DRIVE, SARASOTA, FL
    1507 BAY POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 7,350 Home (sqft)
    • 6 Baths
    • 41,818 Lot (sqft)
  4. 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)
    11
     
    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)
  5. Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4522100)
    $8,400,000
    Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4522100)
    Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4522100)
    19
     
    1515 HILLVIEW DRIVE, SARASOTA, FL
    1515 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 5,424 Home (sqft)
    • 6 Baths
    • 21,780 Lot (sqft)
  6. Photo of 1727 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4546473)
    $4,750,000
    Photo of 1727 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4546473)
    Photo of 1727 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4546473)
    1727 BAHIA VISTA STREET, SARASOTA, FL
    1727 BAHIA VISTA STREET
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 4,829 Home (sqft)
    • 5 Baths
    • 14,811 Lot (sqft)
  7. 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)
  8. 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)
  9. Photo of 1785 BAYVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4547713)
    $3,795,000
    Photo of 1785 BAYVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4547713)
    Photo of 1785 BAYVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4547713)
    1785 BAYVIEW DRIVE, SARASOTA, FL
    1785 BAYVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,613 Home (sqft)
    • 6 Baths
    • 11,762 Lot (sqft)
  10. Photo of 1620 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4545760)
    $3,784,000
    Photo of 1620 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4545760)
    Photo of 1620 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4545760)
    1620 N LODGE DRIVE, SARASOTA, FL
    1620 N LODGE DRIVE
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 4,660 Home (sqft)
    • 4 Baths
    • 17,860 Lot (sqft)
  11. Photo of 1718 BAY VIEW DRIVE, SARASOTA, FL 34239 (MLS # A4536016)
    $3,550,000
    Photo of 1718 BAY VIEW DRIVE, SARASOTA, FL 34239 (MLS # A4536016)
    Photo of 1718 BAY VIEW DRIVE, SARASOTA, FL 34239 (MLS # A4536016)
    1718 BAY VIEW DRIVE, SARASOTA, FL
    1718 BAY VIEW DRIVE
    SARASOTA, FL
    • 6 Beds
    • 6 Baths
    • 4,644 Home (sqft)
    • 6 Baths
    • 16,118 Lot (sqft)
  12. Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4547724)
    $3,350,000
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4547724)
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4547724)
    1537 SIESTA DRIVE, SARASOTA, FL
    1537 SIESTA DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,739 Home (sqft)
    • 6 Baths
    • 12,197 Lot (sqft)
  13. Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4547720)
    $3,195,000
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4547720)
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4547720)
    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)
  14. Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4547718)
    $3,195,000
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4547718)
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4547718)
    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)
  15. Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    $3,097,500
    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
    • 13,504 Lot (sqft)
  16. Photo of 1642 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4545879)
    $2,998,000
    Photo of 1642 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4545879)
    Photo of 1642 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4545879)
    10
     
    1642 BAHIA VISTA STREET, SARASOTA, FL
    1642 BAHIA VISTA STREET
    SARASOTA, FL
    • 3 Beds
    • 5 Baths
    • 2,938 Home (sqft)
    • 5 Baths
    • 8,712 Lot (sqft)
  17. Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4547719)
    $2,995,000
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4547719)
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4547719)
    2171 MCCLELLAN PARKWAY, SARASOTA, FL
    2171 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  18. Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4547716)
    $2,995,000
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4547716)
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4547716)
    15
     
    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)
  19. Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4547722)
    $2,795,000
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4547722)
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4547722)
    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)
  20. Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4547723)
    $2,695,000
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4547723)
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4547723)
    1647 SIESTA DRIVE, SARASOTA, FL
    1647 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  21. Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    $2,525,000
    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)
  22. Photo of 0-17 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549875)
    $2,500,000
    Photo of 0-17 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549875)
    Photo of 0-17 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549875)
    0-17 FLOYD STREET, SARASOTA, FL
    0-17 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,356 Home (sqft)
    • 5 Baths
    • 7,841 Lot (sqft)
  23. 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)
  24. Photo of 1944 GROVE STREET, SARASOTA, FL 34239 (MLS # A4550533)
    $2,294,000
    Photo of 1944 GROVE STREET, SARASOTA, FL 34239 (MLS # A4550533)
    Photo of 1944 GROVE STREET, SARASOTA, FL 34239 (MLS # A4550533)
    1944 GROVE STREET, SARASOTA, FL
    1944 GROVE STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,915 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  25. 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
    • 6,099 Lot (sqft)
  26. Photo of 2627 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4531892)
    $2,100,000
    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)
  27. Photo of 0-#13 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549881)
    $2,000,000
    Photo of 0-#13 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549881)
    Photo of 0-#13 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549881)
    0-#13 FLOYD STREET, SARASOTA, FL
    0-#13 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,763 Home (sqft)
    • 5 Baths
    • 1,743 Lot (sqft)
  28. Photo of 0-#11 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549886)
    $2,000,000
    Photo of 0-#11 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549886)
    Photo of 0-#11 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549886)
    0-#11 FLOYD STREET, SARASOTA, FL
    0-#11 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,743 Home (sqft)
    • 5 Baths
    • 1,743 Lot (sqft)
  29. Photo of 0-9 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549839)
    $2,000,000
    Photo of 0-9 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549839)
    Photo of 0-9 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549839)
    0-9 FLOYD STREET, SARASOTA, FL
    0-9 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,743 Home (sqft)
    • 5 Baths
    • 6,099 Lot (sqft)
  30. Photo of 1844 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4551657)
    $1,975,000
    Photo of 1844 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4551657)
    Photo of 1844 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4551657)
    1844 OLEANDER STREET, SARASOTA, FL
    1844 OLEANDER STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,574 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
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