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 Older homes have been replaced by modern masterpieces.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 1364 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4450162)
    $6,995,000
    Photo of 1364 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4450162)
    Photo of 1364 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4450162)
    1364 HARBOR DRIVE, SARASOTA, FL
    1364 HARBOR DRIVE
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 5,244 Home (sqft)
    • 6 Baths
    • 16,577 Lot (sqft)
  3. 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)
  4. 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)
  5. 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)
  6. 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
    • 13,910 Lot (sqft)
  7. 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
    • 16,989 Lot (sqft)
  8. Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    $3,650,000
    Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    1545 HILLVIEW DRIVE, SARASOTA, FL
    1545 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,625 Home (sqft)
    • 5 Baths
    • 36,296 Lot (sqft)
  9. 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
    • 25,085 Lot (sqft)
  10. Photo of 1352 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4447026)
    $3,449,000
    Photo of 1352 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4447026)
    Photo of 1352 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4447026)
    1352 HARBOR DRIVE, SARASOTA, FL
    1352 HARBOR DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,373 Home (sqft)
    • 4 Baths
    • 15,246 Lot (sqft)
  11. Photo of 2231 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4449326)
    $3,295,000
    Photo of 2231 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4449326)
    Photo of 2231 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4449326)
    2231 ORIOLE DRIVE, SARASOTA, FL
    2231 ORIOLE DRIVE
    SARASOTA, FL
    • 5 Beds
    • 8 Baths
    • 8,162 Home (sqft)
    • 8 Baths
    • 17,289 Lot (sqft)
  12. 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
    • 14,587 Lot (sqft)
  13. Photo of 1658 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4451948)
    $2,495,000
    Photo of 1658 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4451948)
    Photo of 1658 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4451948)
    1658 HAWTHORNE STREET, SARASOTA, FL
    1658 HAWTHORNE STREET
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,939 Home (sqft)
    • 4 Baths
    • 14,058 Lot (sqft)
  14. Photo of 1581 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4183577)
    $2,495,000
    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
    • 14,225 Lot (sqft)
  15. 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
    • 3,498 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  16. 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
    • 22,216 Lot (sqft)
  17. Photo of 1898 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4446722)
    $2,390,000
    Photo of 1898 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4446722)
    Photo of 1898 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4446722)
    1898 HIGH POINT DRIVE, SARASOTA, FL
    1898 HIGH POINT DRIVE
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 4,106 Home (sqft)
    • 6 Baths
    • 10,100 Lot (sqft)
  18. 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)
  19. 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)
  20. 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)
  21. 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
    • 13,706 Lot (sqft)
  22. 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
    • 10,325 Lot (sqft)
  23. Photo of 1706 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4450069)
    $1,700,000
    Photo of 1706 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4450069)
    Photo of 1706 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4450069)
    1706 SPRING CREEK DRIVE, SARASOTA, FL
    1706 SPRING CREEK DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,353 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  24. Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    $1,675,000
    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
    • 8,850 Lot (sqft)
  25. 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
    • 5,663 Lot (sqft)
  26. Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    $1,599,000
    Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    1886 PROSPECT STREET, SARASOTA, FL
    1886 PROSPECT STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,444 Home (sqft)
    • 4 Baths
    • 9,720 Lot (sqft)
  27. Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    $1,549,000
    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
    • 10,321 Lot (sqft)
  28. Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    $1,499,990
    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
    • 37,550 Lot (sqft)
  29. Photo of 1667 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4440133)
    $1,439,000
    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
    • 11,517 Lot (sqft)
  30. Photo of 1620 HUDSON POINTE DRIVE, SARASOTA, FL 34236 (MLS # A4448579)
    $1,399,000
    Photo of 1620 HUDSON POINTE DRIVE, SARASOTA, FL 34236 (MLS # A4448579)
    Photo of 1620 HUDSON POINTE DRIVE, SARASOTA, FL 34236 (MLS # A4448579)
    1620 HUDSON POINTE DRIVE, SARASOTA, FL
    1620 HUDSON POINTE DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,195 Home (sqft)
    • 4 Baths
    • 16,259 Lot (sqft)
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