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 Older homes have been replaced by modern masterpieces.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 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 1221 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4434317)
    $7,500,000
    Photo of 1221 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4434317)
    Photo of 1221 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4434317)
    1221 HILLVIEW DRIVE, SARASOTA, FL
    1221 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,187 Home (sqft)
    • 4 Baths
    • 21,780 Lot (sqft)
  2. Photo of 1433 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4442885)
    $4,500,000
    Photo of 1433 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4442885)
    Photo of 1433 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4442885)
    1433 BAY POINT DRIVE, SARASOTA, FL
    1433 BAY POINT DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,915 Home (sqft)
    • 3 Baths
    • 20,038 Lot (sqft)
  3. Photo of 1807 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4414354)
    $4,499,000
    Photo of 1807 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4414354)
    Photo of 1807 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4414354)
    1807 OLEANDER STREET, SARASOTA, FL
    1807 OLEANDER STREET
    SARASOTA, FL
    • 7 Beds
    • 9 Baths
    • 9,492 Home (sqft)
    • 9 Baths
    • 23,087 Lot (sqft)
  4. Photo of 1525 MALLARD LANE, SARASOTA, FL 34239 (MLS # A4443475)
    $4,100,000
    Photo of 1525 MALLARD LANE, SARASOTA, FL 34239 (MLS # A4443475)
    Photo of 1525 MALLARD LANE, SARASOTA, FL 34239 (MLS # A4443475)
    22
     
    1525 MALLARD LANE, SARASOTA, FL
    1525 MALLARD LANE
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 4,781 Home (sqft)
    • 6 Baths
    • 15,246 Lot (sqft)
  5. Photo of 1516 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4442067)
    $3,999,999
    Photo of 1516 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4442067)
    Photo of 1516 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4442067)
    1516 SANDPIPER LANE, SARASOTA, FL
    1516 SANDPIPER LANE
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 5,014 Home (sqft)
    • 6 Baths
    • 13,940 Lot (sqft)
  6. Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    $3,995,000
    Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    23
     
    1575 BAY POINT DRIVE, SARASOTA, FL
    1575 BAY POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 16,988 Lot (sqft)
  7. Photo of 2610 CARDINAL PLACE, SARASOTA, FL 34239 (MLS # A4426055)
    $3,650,000
    Photo of 2610 CARDINAL PLACE, SARASOTA, FL 34239 (MLS # A4426055)
    Photo of 2610 CARDINAL PLACE, SARASOTA, FL 34239 (MLS # A4426055)
    2610 CARDINAL PLACE, SARASOTA, FL
    2610 CARDINAL PLACE
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 4,605 Home (sqft)
    • 6 Baths
    • 25,265 Lot (sqft)
  8. Photo of 1534 HARBOR PLACE, SARASOTA, FL 34239 (MLS # A4424649)
    $2,995,000
    Photo of 1534 HARBOR PLACE, SARASOTA, FL 34239 (MLS # A4424649)
    Photo of 1534 HARBOR PLACE, SARASOTA, FL 34239 (MLS # A4424649)
    1534 HARBOR PLACE, SARASOTA, FL
    1534 HARBOR PLACE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,652 Home (sqft)
    • 6 Baths
    • 14,375 Lot (sqft)
  9. Photo of 1581 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4183577)
    $2,695,000
    Photo of 1581 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4183577)
    Photo of 1581 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4183577)
    38
     
    1581 HILLVIEW DRIVE, SARASOTA, FL
    1581 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,508 Home (sqft)
    • 5 Baths
    • 14,375 Lot (sqft)
  10. Photo of 1502 BLUE HERON DRIVE, SARASOTA, FL 34239 (MLS # A4446276)
    $2,499,000
    Photo of 1502 BLUE HERON DRIVE, SARASOTA, FL 34239 (MLS # A4446276)
    Photo of 1502 BLUE HERON DRIVE, SARASOTA, FL 34239 (MLS # A4446276)
    1502 BLUE HERON DRIVE, SARASOTA, FL
    1502 BLUE HERON DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 2,338 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  11. Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    $2,450,000
    Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    1555 SANDPIPER LANE, SARASOTA, FL
    1555 SANDPIPER LANE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,321 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  12. Photo of 1585 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4440585)
    $2,400,000
    Photo of 1585 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4440585)
    Photo of 1585 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4440585)
    1585 BAY POINT DRIVE, SARASOTA, FL
    1585 BAY POINT DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 2,302 Home (sqft)
    • 2 Baths
    • 20,909 Lot (sqft)
  13. Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4436565)
    $2,300,000
    Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4436565)
    Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4436565)
    1515 HILLVIEW DRIVE, SARASOTA, FL
    1515 HILLVIEW DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,672 Home (sqft)
    • 2 Baths
    • 21,345 Lot (sqft)
  14. Photo of 1606 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4433922)
    $2,199,000
    Photo of 1606 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4433922)
    Photo of 1606 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4433922)
    1606 NORTH DRIVE, SARASOTA, FL
    1606 NORTH DRIVE
    SARASOTA, FL
    • 6 Beds
    • 6 Baths
    • 5,538 Home (sqft)
    • 6 Baths
    • 14,811 Lot (sqft)
  15. Photo of 1757 OVAL DRIVE S, SARASOTA, FL 34239 (MLS # A4438225)
    $2,165,550
    Photo of 1757 OVAL DRIVE S, SARASOTA, FL 34239 (MLS # A4438225)
    Photo of 1757 OVAL DRIVE S, SARASOTA, FL 34239 (MLS # A4438225)
    1757 OVAL DRIVE S, SARASOTA, FL
    1757 OVAL DRIVE S
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,002 Home (sqft)
    • 5 Baths
    • 13,068 Lot (sqft)
  16. Photo of 1734 S OVAL DRIVE, SARASOTA, FL 34239 (MLS # A4436221)
    $2,092,550
    Photo of 1734 S OVAL DRIVE, SARASOTA, FL 34239 (MLS # A4436221)
    Photo of 1734 S OVAL DRIVE, SARASOTA, FL 34239 (MLS # A4436221)
    1734 S OVAL DRIVE, SARASOTA, FL
    1734 S OVAL DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,002 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  17. Photo of 1911 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4406585)
    $1,900,000
    Photo of 1911 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4406585)
    Photo of 1911 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4406585)
    1911 MORRIS STREET, SARASOTA, FL
    1911 MORRIS STREET
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,639 Home (sqft)
    • 6 Baths
    • 13,504 Lot (sqft)
  18. Photo of 1844 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4425625)
    $1,897,000
    Photo of 1844 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4425625)
    Photo of 1844 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4425625)
    1844 WISTERIA STREET, SARASOTA, FL
    1844 WISTERIA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,321 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  19. Photo of 1765 LINCOLN PARK CIRCLE, SARASOTA, FL 34236 (MLS # A4423585)
    $1,895,000
    Photo of 1765 LINCOLN PARK CIRCLE, SARASOTA, FL 34236 (MLS # A4423585)
    Photo of 1765 LINCOLN PARK CIRCLE, SARASOTA, FL 34236 (MLS # A4423585)
    1765 LINCOLN PARK CIRCLE, SARASOTA, FL
    1765 LINCOLN PARK CIRCLE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,378 Home (sqft)
    • 3 Baths
    • 10,018 Lot (sqft)
  20. Photo of 1920 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4419750)
    $1,895,000
    Photo of 1920 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4419750)
    Photo of 1920 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4419750)
    1920 ALTA VISTA STREET, SARASOTA, FL
    1920 ALTA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 3,006 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  21. Photo of 1835 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4439344)
    $1,695,000
    Photo of 1835 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4439344)
    Photo of 1835 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4439344)
    1835 LINCOLN DRIVE, SARASOTA, FL
    1835 LINCOLN DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,476 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  22. Photo of 1570 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4420145)
    $1,625,000
    Photo of 1570 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4420145)
    Photo of 1570 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4420145)
    1570 HILLVIEW DRIVE, SARASOTA, FL
    1570 HILLVIEW DRIVE
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,215 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  23. Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    $1,599,990
    Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    950 S OSPREY AVENUE, SARASOTA, FL
    950 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 2 Baths
    • 1,911 Home (sqft)
    • 2 Baths
    • 37,462 Lot (sqft)
  24. Photo of 1727 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4170368)
    $1,599,900
    Photo of 1727 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4170368)
    Photo of 1727 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4170368)
    1727 SIESTA DRIVE, SARASOTA, FL
    1727 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,464 Home (sqft)
    • 4 Baths
    • 5,662 Lot (sqft)
  25. Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    $1,575,000
    Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    1905 GOLDENROD STREET, SARASOTA, FL
    1905 GOLDENROD STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,048 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  26. Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    $1,524,250
    Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    1959 HIBISCUS STREET, SARASOTA, FL
    1959 HIBISCUS STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,706 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  27. Photo of 1667 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4440133)
    $1,475,000
    Photo of 1667 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4440133)
    Photo of 1667 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4440133)
    1667 HILLVIEW STREET, SARASOTA, FL
    1667 HILLVIEW STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,682 Home (sqft)
    • 5 Baths
    • 11,326 Lot (sqft)
  28. Photo of 2202 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4425734)
    $1,350,000
    Photo of 2202 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4425734)
    Photo of 2202 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4425734)
    2202 MCCLELLAN PARKWAY, SARASOTA, FL
    2202 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,738 Home (sqft)
    • 4 Baths
    • 16,553 Lot (sqft)
  29. Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4446250)
    $1,327,000
    Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4446250)
    Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4446250)
    1690 ARLINGTON STREET, SARASOTA, FL
    1690 ARLINGTON STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,917 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  30. Photo of 974 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4443744)
    $1,325,000
    Photo of 974 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4443744)
    Photo of 974 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4443744)
    974 S OSPREY AVENUE, SARASOTA, FL
    974 S OSPREY AVENUE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,688 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
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