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 Older homes have been replaced by modern masterpieces.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 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)
  3. Photo of 1765 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4500630)
    $3,600,000
    Photo of 1765 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4500630)
    Photo of 1765 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4500630)
    1765 FLOYD STREET, SARASOTA, FL
    1765 FLOYD STREET
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 4,067 Home (sqft)
    • 6 Baths
    • 10,689 Lot (sqft)
  4. Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # A4508192)
    $3,499,900
    Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # A4508192)
    Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # A4508192)
    1701 HASHAY DRIVE, SARASOTA, FL
    1701 HASHAY DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,894 Home (sqft)
    • 4 Baths
    • 19,138 Lot (sqft)
  5. Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3294850)
    $3,495,000
    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)
  6. Photo of 1865 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4494732)
    $2,900,000
    Photo of 1865 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4494732)
    Photo of 1865 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4494732)
    59
     
    1865 CLEMATIS STREET, SARASOTA, FL
    1865 CLEMATIS STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,990 Home (sqft)
    • 5 Baths
    • 12,000 Lot (sqft)
  7. Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4516724)
    $2,695,000
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4516724)
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4516724)
    15
     
    1537 SIESTA DRIVE, SARASOTA, FL
    1537 SIESTA DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,739 Home (sqft)
    • 6 Baths
    • 12,432 Lot (sqft)
  8. Photo of 1739 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4514239)
    $2,695,000
    Photo of 1739 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4514239)
    Photo of 1739 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4514239)
    1739 S ORANGE AVENUE, SARASOTA, FL
    1739 S ORANGE AVENUE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,270 Home (sqft)
    • 5 Baths
    • 11,712 Lot (sqft)
  9. 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)
  10. Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4516728)
    $2,395,000
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4516728)
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4516728)
    10
     
    2171 MCCLELLAN PARKWAY, SARASOTA, FL
    2171 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,157 Home (sqft)
    • 4 Baths
    • 7,475 Lot (sqft)
  11. Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4516584)
    $2,395,000
    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)
  12. Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516571)
    $2,395,000
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516571)
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516571)
    15
     
    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)
  13. Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    $2,325,000
    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)
  14. Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4517079)
    $2,195,000
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4517079)
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4517079)
    15
     
    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)
  15. Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4516579)
    $2,195,000
    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)
  16. Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4518467)
    $1,995,000
    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)
  17. Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4517352)
    $1,995,000
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4517352)
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4517352)
    16
     
    1647 SIESTA DRIVE, SARASOTA, FL
    1647 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,851 Lot (sqft)
  18. Photo of 1734 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4509418)
    $1,799,000
    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)
  19. Photo of 1762 BAY STREET #401, SARASOTA, FL 34236 (MLS # A4515327)
    $1,245,000
    Photo of 1762 BAY STREET #401, SARASOTA, FL 34236 (MLS # A4515327)
    Photo of 1762 BAY STREET #401, SARASOTA, FL 34236 (MLS # A4515327)
    1762 BAY STREET #401, SARASOTA, FL
    1762 BAY STREET #401
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,183 Home (sqft)
    • 3 Baths
    • 29,197 Lot (sqft)
  20. Photo of 1965 GROVE STREET, SARASOTA, FL 34239 (MLS # A4510893)
    $699,000
    Photo of 1965 GROVE STREET, SARASOTA, FL 34239 (MLS # A4510893)
    Photo of 1965 GROVE STREET, SARASOTA, FL 34239 (MLS # A4510893)
    1965 GROVE STREET, SARASOTA, FL
    1965 GROVE STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,360 Home (sqft)
    • 2 Baths
    • 10,403 Lot (sqft)
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