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 Older homes have been replaced by modern masterpieces.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 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)
  2. Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    $3,849,000
    Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    1575 BAY POINT DRIVE, SARASOTA, FL
    1575 BAY POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 16,971 Lot (sqft)
  3. Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    $3,499,000
    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)
  4. 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)
  5. Photo of 1352 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4447026)
    $3,295,000
    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
    • 15,405 Lot (sqft)
  6. Photo of 1718 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4464923)
    $2,600,000
    Photo of 1718 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4464923)
    Photo of 1718 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4464923)
    1718 PROSPECT STREET, SARASOTA, FL
    1718 PROSPECT STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,224 Home (sqft)
    • 5 Baths
    • 10,689 Lot (sqft)
  7. 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)
  8. Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    $2,374,000
    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
    • 14,785 Lot (sqft)
  9. Photo of 1608 HUDSON POINTE DRIVE, SARASOTA, FL 34236 (MLS # A4462875)
    $2,350,000
    Photo of 1608 HUDSON POINTE DRIVE, SARASOTA, FL 34236 (MLS # A4462875)
    Photo of 1608 HUDSON POINTE DRIVE, SARASOTA, FL 34236 (MLS # A4462875)
    1608 HUDSON POINTE DRIVE, SARASOTA, FL
    1608 HUDSON POINTE DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,600 Home (sqft)
    • 5 Baths
    • 14,660 Lot (sqft)
  10. Photo of 1734 S OVAL DRIVE, SARASOTA, FL 34239 (MLS # A4436221)
    $2,085,000
    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
    • 15,774 Lot (sqft)
  11. Photo of 2229 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4463211)
    $1,995,000
    Photo of 2229 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4463211)
    Photo of 2229 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4463211)
    2229 MCCLELLAN PARKWAY, SARASOTA, FL
    2229 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 4,831 Home (sqft)
    • 6 Baths
    • 1.09 Lot (ac)
  12. Photo of 1934 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4469554)
    $1,950,000
    Photo of 1934 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4469554)
    Photo of 1934 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4469554)
    1934 CLEMATIS STREET, SARASOTA, FL
    1934 CLEMATIS STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,731 Home (sqft)
    • 3 Baths
    • 12,841 Lot (sqft)
  13. Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4463334)
    $1,950,000
    Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4463334)
    Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4463334)
    1810 GROVE STREET, SARASOTA, FL
    1810 GROVE STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,281 Home (sqft)
    • 4 Baths
    • 9,679 Lot (sqft)
  14. Photo of 1700 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4469068)
    $1,900,000
    Photo of 1700 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4469068)
    Photo of 1700 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4469068)
    1700 NORTH DRIVE, SARASOTA, FL
    1700 NORTH DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,382 Home (sqft)
    • 4 Baths
    • 22,501 Lot (sqft)
  15. Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    $1,875,000
    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)
  16. Photo of 1560 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4470005)
    $1,795,000
    Photo of 1560 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4470005)
    Photo of 1560 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4470005)
    1560 HILLVIEW DRIVE, SARASOTA, FL
    1560 HILLVIEW DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,338 Home (sqft)
    • 4 Baths
    • 14,378 Lot (sqft)
  17. Photo of 1351 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4458735)
    $1,795,000
    Photo of 1351 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4458735)
    Photo of 1351 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4458735)
    1351 HARBOR DRIVE, SARASOTA, FL
    1351 HARBOR DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,206 Home (sqft)
    • 4 Baths
    • 14,564 Lot (sqft)
  18. 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
    • 5,851 Lot (sqft)
  19. Photo of 1924 BOUGAINVILLEA STREET, SARASOTA, FL 34239 (MLS # A4452994)
    $1,595,000
    Photo of 1924 BOUGAINVILLEA STREET, SARASOTA, FL 34239 (MLS # A4452994)
    Photo of 1924 BOUGAINVILLEA STREET, SARASOTA, FL 34239 (MLS # A4452994)
    1924 BOUGAINVILLEA STREET, SARASOTA, FL
    1924 BOUGAINVILLEA STREET
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,889 Home (sqft)
    • 4 Baths
    • 7,671 Lot (sqft)
  20. Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    $1,594,000
    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)
  21. Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    $1,534,000
    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)
  22. Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    $1,399,990
    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)
  23. Photo of 1664 WALDEMERE STREET, SARASOTA, FL 34239 (MLS # A4468691)
    $1,394,000
    Photo of 1664 WALDEMERE STREET, SARASOTA, FL 34239 (MLS # A4468691)
    Photo of 1664 WALDEMERE STREET, SARASOTA, FL 34239 (MLS # A4468691)
    1664 WALDEMERE STREET, SARASOTA, FL
    1664 WALDEMERE STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,124 Home (sqft)
    • 4 Baths
    • 14,304 Lot (sqft)
  24. Photo of 1803 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4455724)
    $1,250,000
    Photo of 1803 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4455724)
    Photo of 1803 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4455724)
    1803 MORRIS STREET, SARASOTA, FL
    1803 MORRIS STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,367 Home (sqft)
    • 4 Baths
    • 11,210 Lot (sqft)
  25. Photo of 1605 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4454103)
    $1,249,000
    Photo of 1605 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4454103)
    Photo of 1605 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4454103)
    1605 S ORANGE AVENUE, SARASOTA, FL
    1605 S ORANGE AVENUE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,372 Home (sqft)
    • 5 Baths
    • 11,364 Lot (sqft)
  26. Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4446250)
    $1,149,000
    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
    • 8,112 Lot (sqft)
  27. Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    $1,100,000
    Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    1666 HILLVIEW STREET, SARASOTA, FL
    1666 HILLVIEW STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,232 Home (sqft)
    • 3 Baths
    • 18,318 Lot (sqft)
  28. Photo of 1840 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4461053)
    $1,094,000
    Photo of 1840 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4461053)
    Photo of 1840 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4461053)
    1840 HYDE PARK STREET, SARASOTA, FL
    1840 HYDE PARK STREET
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,363 Home (sqft)
    • 4 Baths
    • 6,000 Lot (sqft)
  29. Photo of 1656 BLUE HERON DRIVE, SARASOTA, FL 34239 (MLS # A4460616)
    $1,019,000
    Photo of 1656 BLUE HERON DRIVE, SARASOTA, FL 34239 (MLS # A4460616)
    Photo of 1656 BLUE HERON DRIVE, SARASOTA, FL 34239 (MLS # A4460616)
    1656 BLUE HERON DRIVE, SARASOTA, FL
    1656 BLUE HERON DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,346 Home (sqft)
    • 4 Baths
    • 7,780 Lot (sqft)
  30. Photo of 1741 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4447949)
    $1,015,000
    Photo of 1741 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4447949)
    Photo of 1741 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4447949)
    1741 ALTA VISTA STREET, SARASOTA, FL
    1741 ALTA VISTA STREET
    SARASOTA, FL
    • 5 Beds
    • 3 Baths
    • 3,178 Home (sqft)
    • 3 Baths
    • 8,554 Lot (sqft)
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