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 Older homes have been replaced by modern masterpieces.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.

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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 1807 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4475067)
    $4,399,000
    Photo of 1807 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4475067)
    Photo of 1807 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4475067)
    1807 OLEANDER STREET, SARASOTA, FL
    1807 OLEANDER STREET
    SARASOTA, FL
    • 5 Beds
    • 9 Baths
    • 9,492 Home (sqft)
    • 9 Baths
    • 23,081 Lot (sqft)
  3. Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3294850)
    $4,100,000
    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 1347 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4497689)
    $3,500,000
    Photo of 1347 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4497689)
    Photo of 1347 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4497689)
    1347 HARBOR DRIVE, SARASOTA, FL
    1347 HARBOR DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,834 Home (sqft)
    • 4 Baths
    • 15,643 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 2524 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4490046)
    $2,795,000
    Photo of 2524 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4490046)
    Photo of 2524 PLEASANT PLACE, SARASOTA, FL 34239 (MLS # A4490046)
    2524 PLEASANT PLACE, SARASOTA, FL
    2524 PLEASANT PLACE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,399 Home (sqft)
    • 4 Baths
    • 12,501 Lot (sqft)
  7. Photo of 1749 LINCOLN PARK CIRCLE, SARASOTA, FL 34236 (MLS # A4492531)
    $2,395,000
    Photo of 1749 LINCOLN PARK CIRCLE, SARASOTA, FL 34236 (MLS # A4492531)
    Photo of 1749 LINCOLN PARK CIRCLE, SARASOTA, FL 34236 (MLS # A4492531)
    1749 LINCOLN PARK CIRCLE, SARASOTA, FL
    1749 LINCOLN PARK CIRCLE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,020 Home (sqft)
    • 4 Baths
    • 10,021 Lot (sqft)
  8. Photo of 1802 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4492992)
    $2,241,000
    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)
  9. Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4494479)
    $2,195,000
    Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4494479)
    Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4494479)
    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 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    $1,975,000
    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)
  11. Photo of 1643 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4494096)
    $1,850,000
    Photo of 1643 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4494096)
    Photo of 1643 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4494096)
    1643 SPRING CREEK DRIVE, SARASOTA, FL
    1643 SPRING CREEK DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,623 Home (sqft)
    • 4 Baths
    • 10,234 Lot (sqft)
  12. Photo of 1846 DATURA STREET, SARASOTA, FL 34239 (MLS # A4494289)
    $1,699,000
    Photo of 1846 DATURA STREET, SARASOTA, FL 34239 (MLS # A4494289)
    Photo of 1846 DATURA STREET, SARASOTA, FL 34239 (MLS # A4494289)
    1846 DATURA STREET, SARASOTA, FL
    1846 DATURA STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,332 Home (sqft)
    • 5 Baths
    • 9,001 Lot (sqft)
  13. Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4495615)
    $1,600,000
    Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4495615)
    Photo of 1690 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4495615)
    1690 ARLINGTON STREET, SARASOTA, FL
    1690 ARLINGTON STREET
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 2,965 Home (sqft)
    • 5 Baths
    • 8,112 Lot (sqft)
  14. Photo of 3223 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4495325)
    $1,585,000
    Photo of 3223 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4495325)
    Photo of 3223 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4495325)
    51
     
    3223 OLD OAK DRIVE, SARASOTA, FL
    3223 OLD OAK DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,090 Home (sqft)
    • 4 Baths
    • 17,645 Lot (sqft)
  15. 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)
  16. Photo of 1958 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4497656)
    $1,100,000
    Photo of 1958 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4497656)
    Photo of 1958 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4497656)
    1958 PROSPECT STREET, SARASOTA, FL
    1958 PROSPECT STREET
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 3,619 Home (sqft)
    • 0 Baths
    • 22,125 Lot (sqft)
  17. Photo of 1743 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4496927)
    $1,035,600
    Photo of 1743 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4496927)
    Photo of 1743 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4496927)
    1743 SPRING CREEK DRIVE, SARASOTA, FL
    1743 SPRING CREEK DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,589 Home (sqft)
    • 3 Baths
    • 14,001 Lot (sqft)
  18. Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4481303)
    $688,000
    Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4481303)
    Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4481303)
    1622 WISCONSIN LANE, SARASOTA, FL
    1622 WISCONSIN LANE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,486 Home (sqft)
    • 2 Baths
    • 5,373 Lot (sqft)
  19. Photo of 1226 HOLLY FERN LANE, SARASOTA, FL 34239 (MLS # A4486714)
    $675,000
    Photo of 1226 HOLLY FERN LANE, SARASOTA, FL 34239 (MLS # A4486714)
    Photo of 1226 HOLLY FERN LANE, SARASOTA, FL 34239 (MLS # A4486714)
    1226 HOLLY FERN LANE, SARASOTA, FL
    1226 HOLLY FERN LANE
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,872 Home (sqft)
    • 3 Baths
    • 7,751 Lot (sqft)
  20. Photo of 850 S TAMIAMI TRAIL #422, SARASOTA, FL 34236 (MLS # A4494895)
    $400,000
    Photo of 850 S TAMIAMI TRAIL #422, SARASOTA, FL 34236 (MLS # A4494895)
    Photo of 850 S TAMIAMI TRAIL #422, SARASOTA, FL 34236 (MLS # A4494895)
    850 S TAMIAMI TRAIL #422, SARASOTA, FL
    850 S TAMIAMI TRAIL #422
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  21. Photo of 825 S OSPREY AVENUE #102, SARASOTA, FL 34236 (MLS # A4495252)
    $359,000
    Photo of 825 S OSPREY AVENUE #102, SARASOTA, FL 34236 (MLS # A4495252)
    Photo of 825 S OSPREY AVENUE #102, SARASOTA, FL 34236 (MLS # A4495252)
    825 S OSPREY AVENUE #102, SARASOTA, FL
    825 S OSPREY AVENUE #102
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 6.06 Lot (ac)
  22. Photo of 850 S TAMIAMI TRAIL #523, SARASOTA, FL 34236 (MLS # A4496441)
    $260,000
    Photo of 850 S TAMIAMI TRAIL #523, SARASOTA, FL 34236 (MLS # A4496441)
    Photo of 850 S TAMIAMI TRAIL #523, SARASOTA, FL 34236 (MLS # A4496441)
    850 S TAMIAMI TRAIL #523, SARASOTA, FL
    850 S TAMIAMI TRAIL #523
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
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Listing information is deemed reliable, but not guaranteed.

This Real Estate IDX is (c) Diverse Solutions 2021.

 
 

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