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 Older homes have been replaced by modern masterpieces.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 1309 VISTA DRIVE, SARASOTA, FL 34239 (MLS # A4491997)
    $18,000,000
    Photo of 1309 VISTA DRIVE, SARASOTA, FL 34239 (MLS # A4491997)
    Photo of 1309 VISTA DRIVE, SARASOTA, FL 34239 (MLS # A4491997)
    1309 VISTA DRIVE, SARASOTA, FL
    1309 VISTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 6 Baths
    • 8,452 Home (sqft)
    • 6 Baths
    • 1.44 Lot (ac)
  2. Photo of 1486 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4499907)
    $13,950,000
    Photo of 1486 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4499907)
    Photo of 1486 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4499907)
    1486 HILLVIEW DRIVE, SARASOTA, FL
    1486 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 8,433 Home (sqft)
    • 6 Baths
    • 25,070 Lot (sqft)
  3. Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3294850)
    $3,695,000
    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)
  4. 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)
  5. 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)
  6. Photo of 1331 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4503846)
    $2,595,000
    Photo of 1331 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4503846)
    Photo of 1331 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4503846)
    1331 S OSPREY AVENUE, SARASOTA, FL
    1331 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,468 Home (sqft)
    • 4 Baths
    • 8,439 Lot (sqft)
  7. Photo of 1807 GROVE STREET, SARASOTA, FL 34239 (MLS # A4502627)
    $2,184,000
    Photo of 1807 GROVE STREET, SARASOTA, FL 34239 (MLS # A4502627)
    Photo of 1807 GROVE STREET, SARASOTA, FL 34239 (MLS # A4502627)
    25
     
    1807 GROVE STREET, SARASOTA, FL
    1807 GROVE STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,551 Home (sqft)
    • 3 Baths
    • 11,790 Lot (sqft)
  8. Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    $2,050,000
    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)
  9. Photo of 1802 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4492992)
    $1,945,000
    Photo of 1802 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4492992)
    Photo of 1802 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4492992)
    1802 MAGNOLIA STREET, SARASOTA, FL
    1802 MAGNOLIA STREET
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 4,283 Home (sqft)
    • 6 Baths
    • 8,817 Lot (sqft)
  10. Photo of 1655 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4493493)
    $1,500,000
    Photo of 1655 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4493493)
    Photo of 1655 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4493493)
    1655 NORTH DRIVE, SARASOTA, FL
    1655 NORTH DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,694 Home (sqft)
    • 4 Baths
    • 15,001 Lot (sqft)
  11. Photo of 3030 S TAMIAMI TRAIL, SARASOTA, FL 34239 (MLS # A4499341)
    $1,299,000
    Photo of 3030 S TAMIAMI TRAIL, SARASOTA, FL 34239 (MLS # A4499341)
    Photo of 3030 S TAMIAMI TRAIL, SARASOTA, FL 34239 (MLS # A4499341)
    3030 S TAMIAMI TRAIL, SARASOTA, FL
    3030 S TAMIAMI TRAIL
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 1,566 Home (sqft)
    • 0 Baths
    • 14,886 Lot (sqft)
  12. Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4503655)
    $1,025,000
    Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4503655)
    Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4503655)
    1654 PROSPECT STREET, SARASOTA, FL
    1654 PROSPECT STREET
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,998 Home (sqft)
    • 4 Baths
    • 8,070 Lot (sqft)
  13. Photo of 1954 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4501817)
    $899,000
    Photo of 1954 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4501817)
    Photo of 1954 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4501817)
    1954 OLEANDER STREET, SARASOTA, FL
    1954 OLEANDER STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 2,245 Home (sqft)
    • 2 Baths
    • 11,801 Lot (sqft)
  14. Photo of 1912 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4498960)
    $699,000
    Photo of 1912 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4498960)
    Photo of 1912 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4498960)
    1912 WISTERIA STREET, SARASOTA, FL
    1912 WISTERIA STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,426 Home (sqft)
    • 2 Baths
    • 7,441 Lot (sqft)
  15. Photo of 850 S TAMIAMI TRAIL #624, SARASOTA, FL 34236 (MLS # A4503692)
    $279,000
    Photo of 850 S TAMIAMI TRAIL #624, SARASOTA, FL 34236 (MLS # A4503692)
    Photo of 850 S TAMIAMI TRAIL #624, SARASOTA, FL 34236 (MLS # A4503692)
    850 S TAMIAMI TRAIL #624, SARASOTA, FL
    850 S TAMIAMI TRAIL #624
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  16. Photo of 3400 S TAMIAMI TRAIL #302, SARASOTA, FL 34239 (MLS # A4497964)
    $37,800
    Photo of 3400 S TAMIAMI TRAIL #302, SARASOTA, FL 34239 (MLS # A4497964)
    Photo of 3400 S TAMIAMI TRAIL #302, SARASOTA, FL 34239 (MLS # A4497964)
    29
     
    3400 S TAMIAMI TRAIL #302, SARASOTA, FL
    3400 S TAMIAMI TRAIL #302
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 1.33 Lot (ac)
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