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 Older homes have been replaced by modern masterpieces.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 1486 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4514185)
    $10,800,000
    Photo of 1486 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4514185)
    Photo of 1486 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4514185)
    1486 HILLVIEW DRIVE, SARASOTA, FL
    1486 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 8,433 Home (sqft)
    • 6 Baths
    • 25,070 Lot (sqft)
  2. Photo of 1610 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4520219)
    $9,874,000
    Photo of 1610 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4520219)
    Photo of 1610 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4520219)
    1610 N LODGE DRIVE, SARASOTA, FL
    1610 N LODGE DRIVE
    SARASOTA, FL
    • 6 Beds
    • 8 Baths
    • 6,800 Home (sqft)
    • 8 Baths
    • 16,136 Lot (sqft)
  3. Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    $8,650,000
    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)
  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)
    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)
  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)
    1515 HILLVIEW DRIVE, SARASOTA, FL
    1515 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 5,424 Home (sqft)
    • 6 Baths
    • 21,491 Lot (sqft)
  6. Photo of 1506 MALLARD LANE, SARASOTA, FL 34239 (MLS # A4508637)
    $4,100,000
    Photo of 1506 MALLARD LANE, SARASOTA, FL 34239 (MLS # A4508637)
    Photo of 1506 MALLARD LANE, SARASOTA, FL 34239 (MLS # A4508637)
    1506 MALLARD LANE, SARASOTA, FL
    1506 MALLARD LANE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 5,777 Home (sqft)
    • 5 Baths
    • 13,297 Lot (sqft)
  7. Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3294850)
    $3,995,000
    Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3294850)
    Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3294850)
    1558 SANDPIPER LANE, SARASOTA, FL
    1558 SANDPIPER LANE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,942 Home (sqft)
    • 4 Baths
    • 14,357 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
    • 10,276 Lot (sqft)
  9. Photo of 2141 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4522413)
    $3,199,000
    Photo of 2141 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4522413)
    Photo of 2141 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4522413)
    2141 MCCLELLAN PARKWAY, SARASOTA, FL
    2141 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,253 Home (sqft)
    • 5 Baths
    • 12,346 Lot (sqft)
  10. Photo of 1653 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4522690)
    $2,995,000
    Photo of 1653 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4522690)
    Photo of 1653 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4522690)
    1653 PROSPECT STREET, SARASOTA, FL
    1653 PROSPECT STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,142 Home (sqft)
    • 5 Baths
    • 12,907 Lot (sqft)
  11. Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    $2,850,000
    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)
  12. Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4516724)
    $2,795,000
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4516724)
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4516724)
    1537 SIESTA DRIVE, SARASOTA, FL
    1537 SIESTA DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,739 Home (sqft)
    • 6 Baths
    • 12,432 Lot (sqft)
  13. Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4516728)
    $2,795,000
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4516728)
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4516728)
    2171 MCCLELLAN PARKWAY, SARASOTA, FL
    2171 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 7,475 Lot (sqft)
  14. Photo of 1925 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4521280)
    $2,650,000
    Photo of 1925 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4521280)
    Photo of 1925 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4521280)
    35
     
    1925 OLEANDER STREET, SARASOTA, FL
    1925 OLEANDER STREET
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,851 Home (sqft)
    • 4 Baths
    • 11,801 Lot (sqft)
  15. Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4516584)
    $2,495,000
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4516584)
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4516584)
    15
     
    1954 GOLDENROD STREET, SARASOTA, FL
    1954 GOLDENROD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,606 Home (sqft)
    • 5 Baths
    • 10,029 Lot (sqft)
  16. Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516571)
    $2,495,000
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516571)
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516571)
    3135 S OSPREY AVENUE, SARASOTA, FL
    3135 S OSPREY AVENUE
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 3,595 Home (sqft)
    • 5 Baths
    • 8,354 Lot (sqft)
  17. Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4510517)
    $2,495,000
    Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4510517)
    Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4510517)
    2330 MIETAW DRIVE, SARASOTA, FL
    2330 MIETAW DRIVE
    SARASOTA, FL
    • 5 Beds
    • 3 Baths
    • 3,267 Home (sqft)
    • 3 Baths
    • 7,076 Lot (sqft)
  18. Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    $2,380,000
    Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    2146 MCCLELLAN PARKWAY, SARASOTA, FL
    2146 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,538 Home (sqft)
    • 4 Baths
    • 12,376 Lot (sqft)
  19. Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4517079)
    $2,295,000
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4517079)
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4517079)
    1886 BAHIA VISTA STREET, SARASOTA, FL
    1886 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,153 Home (sqft)
    • 4 Baths
    • 10,613 Lot (sqft)
  20. Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516579)
    $2,295,000
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516579)
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516579)
    15
     
    3319 S OSPREY AVENUE, SARASOTA, FL
    3319 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,423 Home (sqft)
    • 5 Baths
    • 8,121 Lot (sqft)
  21. Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4517352)
    $2,095,000
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4517352)
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4517352)
    1647 SIESTA DRIVE, SARASOTA, FL
    1647 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,851 Lot (sqft)
  22. Photo of 1734 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4509418)
    $1,959,900
    Photo of 1734 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4509418)
    Photo of 1734 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4509418)
    1734 WISCONSIN LANE, SARASOTA, FL
    1734 WISCONSIN LANE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,005 Home (sqft)
    • 5 Baths
    • 6,180 Lot (sqft)
  23. Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4518467)
    $1,759,900
    Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4518467)
    Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4518467)
    1654 PROSPECT STREET, SARASOTA, FL
    1654 PROSPECT STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,998 Home (sqft)
    • 3 Baths
    • 8,070 Lot (sqft)
  24. Photo of 1720 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4523200)
    $1,700,000
    Photo of 1720 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4523200)
    Photo of 1720 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4523200)
    1720 SPRING CREEK DRIVE, SARASOTA, FL
    1720 SPRING CREEK DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,104 Home (sqft)
    • 4 Baths
    • 15,430 Lot (sqft)
  25. Photo of 1917 ROSE STREET, SARASOTA, FL 34239 (MLS # A4521547)
    $1,150,000
    Photo of 1917 ROSE STREET, SARASOTA, FL 34239 (MLS # A4521547)
    Photo of 1917 ROSE STREET, SARASOTA, FL 34239 (MLS # A4521547)
    1917 ROSE STREET, SARASOTA, FL
    1917 ROSE STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,839 Home (sqft)
    • 2 Baths
    • 8,850 Lot (sqft)
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