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 Older homes have been replaced by modern masterpieces.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 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # U8097547)
    $899,000
    Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # U8097547)
    Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # U8097547)
    16
     
    1701 HASHAY DRIVE, SARASOTA, FL
    1701 HASHAY DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,510 Home (sqft)
    • 4 Baths
    • 19,138 Lot (sqft)
  2. Photo of 1657 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4450434)
    $895,000
    Photo of 1657 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4450434)
    Photo of 1657 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4450434)
    1657 ALTA VISTA STREET, SARASOTA, FL
    1657 ALTA VISTA STREET
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,455 Home (sqft)
    • 4 Baths
    • 7,500 Lot (sqft)
  3. Photo of 1705 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4468814)
    $849,000
    Photo of 1705 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4468814)
    Photo of 1705 SPRING CREEK DRIVE, SARASOTA, FL 34239 (MLS # A4468814)
    1705 SPRING CREEK DRIVE, SARASOTA, FL
    1705 SPRING CREEK DRIVE
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,001 Home (sqft)
    • 4 Baths
    • 10,315 Lot (sqft)
  4. Photo of 2318 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4478573)
    $840,000
    Photo of 2318 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4478573)
    Photo of 2318 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4478573)
    2318 MCCLELLAN PARKWAY, SARASOTA, FL
    2318 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,314 Home (sqft)
    • 3 Baths
    • 9,883 Lot (sqft)
  5. Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    $829,000
    Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    1705 SHORELAND DRIVE, SARASOTA, FL
    1705 SHORELAND DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,949 Home (sqft)
    • 3 Baths
    • 14,966 Lot (sqft)
  6. Photo of 860 HUDSON AVENUE #860, SARASOTA, FL 34236 (MLS # A4479802)
    $745,000
    Photo of 860 HUDSON AVENUE #860, SARASOTA, FL 34236 (MLS # A4479802)
    Photo of 860 HUDSON AVENUE #860, SARASOTA, FL 34236 (MLS # A4479802)
    860 HUDSON AVENUE #860, SARASOTA, FL
    860 HUDSON AVENUE #860
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,488 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  7. Photo of 1828 GROVE STREET, SARASOTA, FL 34239 (MLS # A4468353)
    $739,900
    Photo of 1828 GROVE STREET, SARASOTA, FL 34239 (MLS # A4468353)
    Photo of 1828 GROVE STREET, SARASOTA, FL 34239 (MLS # A4468353)
    1828 GROVE STREET, SARASOTA, FL
    1828 GROVE STREET
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,559 Home (sqft)
    • 2 Baths
    • 13,870 Lot (sqft)
  8. Photo of 1379 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4480387)
    $715,000
    Photo of 1379 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4480387)
    Photo of 1379 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4480387)
    29
     
    1379 TEAROSE PLACE, SARASOTA, FL
    1379 TEAROSE PLACE
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 2,191 Home (sqft)
    • 3 Baths
    • 7,760 Lot (sqft)
  9. Photo of 1550 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4466863)
    $697,000
    Photo of 1550 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4466863)
    Photo of 1550 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4466863)
    1550 S ORANGE AVENUE, SARASOTA, FL
    1550 S ORANGE AVENUE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,759 Home (sqft)
    • 2 Baths
    • 15,001 Lot (sqft)
  10. 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)
  11. Photo of 862 HUDSON AVENUE #862, SARASOTA, FL 34236 (MLS # A4478919)
    $679,000
    Photo of 862 HUDSON AVENUE #862, SARASOTA, FL 34236 (MLS # A4478919)
    Photo of 862 HUDSON AVENUE #862, SARASOTA, FL 34236 (MLS # A4478919)
    862 HUDSON AVENUE #862, SARASOTA, FL
    862 HUDSON AVENUE #862
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,362 Home (sqft)
    • 2 Baths
    • 37,905 Lot (sqft)
  12. Photo of 1700 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4481213)
    $599,000
    Photo of 1700 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4481213)
    Photo of 1700 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4481213)
    1700 PROSPECT STREET, SARASOTA, FL
    1700 PROSPECT STREET
    SARASOTA, FL
    • 5 Beds
    • 3 Baths
    • 2,272 Home (sqft)
    • 3 Baths
    • 8,551 Lot (sqft)
  13. Photo of 1773 HARMONY LANE, SARASOTA, FL 34239 (MLS # A4476752)
    $550,000
    Photo of 1773 HARMONY LANE, SARASOTA, FL 34239 (MLS # A4476752)
    Photo of 1773 HARMONY LANE, SARASOTA, FL 34239 (MLS # A4476752)
    1773 HARMONY LANE, SARASOTA, FL
    1773 HARMONY LANE
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,098 Home (sqft)
    • 2 Baths
    • 5,250 Lot (sqft)
  14. Photo of 1901 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4469786)
    $439,900
    Photo of 1901 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4469786)
    Photo of 1901 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4469786)
    1901 HIGH POINT DRIVE, SARASOTA, FL
    1901 HIGH POINT DRIVE
    SARASOTA, FL
    • 1 Bed
    • 2 Baths
    • 636 Home (sqft)
    • 2 Baths
    • 3,584 Lot (sqft)
  15. Photo of 1951 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4480894)
    $430,000
    Photo of 1951 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4480894)
    Photo of 1951 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4480894)
    1951 HIGH POINT DRIVE, SARASOTA, FL
    1951 HIGH POINT DRIVE
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,128 Home (sqft)
    • 2 Baths
    • 8,618 Lot (sqft)
  16. Photo of 835 S OSPREY AVENUE #213, SARASOTA, FL 34236 (MLS # A4480802)
    $359,750
    Photo of 835 S OSPREY AVENUE #213, SARASOTA, FL 34236 (MLS # A4480802)
    Photo of 835 S OSPREY AVENUE #213, SARASOTA, FL 34236 (MLS # A4480802)
    835 S OSPREY AVENUE #213, SARASOTA, FL
    835 S OSPREY AVENUE #213
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,320 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  17. Photo of 835 S OSPREY AVENUE #404, SARASOTA, FL 34236 (MLS # U8100711)
    $254,900
    Photo of 835 S OSPREY AVENUE #404, SARASOTA, FL 34236 (MLS # U8100711)
    Photo of 835 S OSPREY AVENUE #404, SARASOTA, FL 34236 (MLS # U8100711)
    835 S OSPREY AVENUE #404, SARASOTA, FL
    835 S OSPREY AVENUE #404
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 940 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  18. Photo of 835 S OSPREY AVENUE #405, SARASOTA, FL 34236 (MLS # A4475699)
    $239,900
    Photo of 835 S OSPREY AVENUE #405, SARASOTA, FL 34236 (MLS # A4475699)
    Photo of 835 S OSPREY AVENUE #405, SARASOTA, FL 34236 (MLS # A4475699)
    835 S OSPREY AVENUE #405, SARASOTA, FL
    835 S OSPREY AVENUE #405
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 721 Home (sqft)
    • 1 Bath
    • 6.06 Lot (ac)
  19. Photo of 850 S TAMIAMI TRL #126, SARASOTA, FL 34236 (MLS # A4463258)
    $235,900
    Photo of 850 S TAMIAMI TRL #126, SARASOTA, FL 34236 (MLS # A4463258)
    Photo of 850 S TAMIAMI TRL #126, SARASOTA, FL 34236 (MLS # A4463258)
    850 S TAMIAMI TRL #126, SARASOTA, FL
    850 S TAMIAMI TRL #126
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  20. Photo of 850 S TAMIAMI TRAIL #502, SARASOTA, FL 34236 (MLS # A4480659)
    $220,000
    Photo of 850 S TAMIAMI TRAIL #502, SARASOTA, FL 34236 (MLS # A4480659)
    Photo of 850 S TAMIAMI TRAIL #502, SARASOTA, FL 34236 (MLS # A4480659)
    850 S TAMIAMI TRAIL #502, SARASOTA, FL
    850 S TAMIAMI TRAIL #502
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 9.10 Lot (ac)
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