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 Older homes have been replaced by modern masterpieces.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 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 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)
  2. Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    $3,849,000
    Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    Photo of 1575 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4425602)
    1575 BAY POINT DRIVE, SARASOTA, FL
    1575 BAY POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 16,971 Lot (sqft)
  3. Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4477187)
    $3,750,000
    Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4477187)
    Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4477187)
    1373 HARBOR DRIVE, SARASOTA, FL
    1373 HARBOR DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 5,950 Home (sqft)
    • 5 Baths
    • 20,148 Lot (sqft)
  4. Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    $3,350,000
    Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    Photo of 1545 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4449105)
    1545 HILLVIEW DRIVE, SARASOTA, FL
    1545 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,625 Home (sqft)
    • 5 Baths
    • 36,296 Lot (sqft)
  5. Photo of 2231 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4449326)
    $3,295,000
    Photo of 2231 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4449326)
    Photo of 2231 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4449326)
    2231 ORIOLE DRIVE, SARASOTA, FL
    2231 ORIOLE DRIVE
    SARASOTA, FL
    • 5 Beds
    • 8 Baths
    • 8,162 Home (sqft)
    • 8 Baths
    • 17,289 Lot (sqft)
  6. Photo of 1534 HARBOR PLACE, SARASOTA, FL 34239 (MLS # A4476964)
    $3,195,000
    Photo of 1534 HARBOR PLACE, SARASOTA, FL 34239 (MLS # A4476964)
    Photo of 1534 HARBOR PLACE, SARASOTA, FL 34239 (MLS # A4476964)
    1534 HARBOR PLACE, SARASOTA, FL
    1534 HARBOR PLACE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,074 Home (sqft)
    • 5 Baths
    • 14,587 Lot (sqft)
  7. Photo of 1658 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4451948)
    $2,395,000
    Photo of 1658 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4451948)
    Photo of 1658 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4451948)
    1658 HAWTHORNE STREET, SARASOTA, FL
    1658 HAWTHORNE STREET
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,939 Home (sqft)
    • 4 Baths
    • 14,058 Lot (sqft)
  8. Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    $2,297,000
    Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    1555 SANDPIPER LANE, SARASOTA, FL
    1555 SANDPIPER LANE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,498 Home (sqft)
    • 4 Baths
    • 14,785 Lot (sqft)
  9. Photo of 1589 GULFVIEW DRIVE, SARASOTA, FL 34236 (MLS # A4476264)
    $2,250,000
    Photo of 1589 GULFVIEW DRIVE, SARASOTA, FL 34236 (MLS # A4476264)
    Photo of 1589 GULFVIEW DRIVE, SARASOTA, FL 34236 (MLS # A4476264)
    1589 GULFVIEW DRIVE, SARASOTA, FL
    1589 GULFVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,114 Home (sqft)
    • 4 Baths
    • 13,500 Lot (sqft)
  10. Photo of 1753 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4477754)
    $2,200,000
    Photo of 1753 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4477754)
    Photo of 1753 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4477754)
    1753 NORTH DRIVE, SARASOTA, FL
    1753 NORTH DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,702 Home (sqft)
    • 4 Baths
    • 15,001 Lot (sqft)
  11. Photo of 1826 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4478329)
    $2,028,000
    Photo of 1826 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4478329)
    Photo of 1826 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4478329)
    12
     
    1826 CLEMATIS STREET, SARASOTA, FL
    1826 CLEMATIS STREET
    SARASOTA, FL
    • 3 Beds
    • 5 Baths
    • 3,093 Home (sqft)
    • 5 Baths
    • 12,000 Lot (sqft)
  12. Photo of 1547 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4476267)
    $1,950,000
    Photo of 1547 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4476267)
    Photo of 1547 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4476267)
    1547 SANDPIPER LANE, SARASOTA, FL
    1547 SANDPIPER LANE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,135 Home (sqft)
    • 4 Baths
    • 15,140 Lot (sqft)
  13. Photo of 1700 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4469068)
    $1,900,000
    Photo of 1700 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4469068)
    Photo of 1700 NORTH DRIVE, SARASOTA, FL 34239 (MLS # A4469068)
    1700 NORTH DRIVE, SARASOTA, FL
    1700 NORTH DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,382 Home (sqft)
    • 4 Baths
    • 22,501 Lot (sqft)
  14. Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    $1,875,000
    Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    Photo of 1905 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4403697)
    1905 GOLDENROD STREET, SARASOTA, FL
    1905 GOLDENROD STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,048 Home (sqft)
    • 4 Baths
    • 8,850 Lot (sqft)
  15. Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    $1,800,000
    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)
  16. Photo of 1943 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4475565)
    $1,799,000
    Photo of 1943 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4475565)
    Photo of 1943 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4475565)
    1943 MORRIS STREET, SARASOTA, FL
    1943 MORRIS STREET
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,855 Home (sqft)
    • 4 Baths
    • 13,703 Lot (sqft)
  17. Photo of 1800 LOMA LINDA STREET, SARASOTA, FL 34239 (MLS # A4474193)
    $1,749,000
    Photo of 1800 LOMA LINDA STREET, SARASOTA, FL 34239 (MLS # A4474193)
    Photo of 1800 LOMA LINDA STREET, SARASOTA, FL 34239 (MLS # A4474193)
    1800 LOMA LINDA STREET, SARASOTA, FL
    1800 LOMA LINDA STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,256 Home (sqft)
    • 5 Baths
    • 9,213 Lot (sqft)
  18. Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4474860)
    $1,695,000
    Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4474860)
    Photo of 2330 MIETAW DRIVE, SARASOTA, FL 34239 (MLS # A4474860)
    2330 MIETAW DRIVE, SARASOTA, FL
    2330 MIETAW DRIVE
    SARASOTA, FL
    • 5 Beds
    • 3 Baths
    • 3,267 Home (sqft)
    • 3 Baths
    • 7,076 Lot (sqft)
  19. Photo of 1907 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4474600)
    $1,675,000
    Photo of 1907 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4474600)
    Photo of 1907 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4474600)
    1907 CLEMATIS STREET, SARASOTA, FL
    1907 CLEMATIS STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 3,223 Home (sqft)
    • 3 Baths
    • 9,120 Lot (sqft)
  20. Photo of 1727 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4170368)
    $1,599,900
    Photo of 1727 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4170368)
    Photo of 1727 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4170368)
    1727 SIESTA DRIVE, SARASOTA, FL
    1727 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,464 Home (sqft)
    • 4 Baths
    • 5,851 Lot (sqft)
  21. Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    $1,499,000
    Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    Photo of 1886 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4450957)
    1886 PROSPECT STREET, SARASOTA, FL
    1886 PROSPECT STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,444 Home (sqft)
    • 4 Baths
    • 9,720 Lot (sqft)
  22. Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    $1,497,000
    Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    Photo of 1959 HIBISCUS STREET, SARASOTA, FL 34239 (MLS # A4434816)
    1959 HIBISCUS STREET, SARASOTA, FL
    1959 HIBISCUS STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,706 Home (sqft)
    • 3 Baths
    • 10,321 Lot (sqft)
  23. Photo of 1701 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4477002)
    $1,479,000
    Photo of 1701 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4477002)
    Photo of 1701 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4477002)
    1701 HILLVIEW STREET, SARASOTA, FL
    1701 HILLVIEW STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,545 Home (sqft)
    • 3 Baths
    • 12,355 Lot (sqft)
  24. Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    $1,349,990
    Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    Photo of 950 S OSPREY AVENUE, SARASOTA, FL 34236 (MLS # A4410905)
    950 S OSPREY AVENUE, SARASOTA, FL
    950 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 2 Baths
    • 1,911 Home (sqft)
    • 2 Baths
    • 37,550 Lot (sqft)
  25. Photo of 3347 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4475650)
    $1,199,000
    Photo of 3347 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4475650)
    Photo of 3347 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4475650)
    49
     
    3347 OLD OAK DRIVE, SARASOTA, FL
    3347 OLD OAK DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,133 Home (sqft)
    • 4 Baths
    • 14,420 Lot (sqft)
  26. Photo of 1840 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4475259)
    $1,149,000
    Photo of 1840 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4475259)
    Photo of 1840 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4475259)
    1840 HYDE PARK STREET, SARASOTA, FL
    1840 HYDE PARK STREET
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,363 Home (sqft)
    • 4 Baths
    • 6,000 Lot (sqft)
  27. Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    $1,045,000
    Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    1666 HILLVIEW STREET, SARASOTA, FL
    1666 HILLVIEW STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,232 Home (sqft)
    • 3 Baths
    • 18,318 Lot (sqft)
  28. Photo of 1715 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4449499)
    $999,900
    Photo of 1715 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4449499)
    Photo of 1715 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4449499)
    1715 HYDE PARK STREET, SARASOTA, FL
    1715 HYDE PARK STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,809 Home (sqft)
    • 4 Baths
    • 12,780 Lot (sqft)
  29. Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # U8097547)
    $969,000
    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)
  30. Photo of 1122 POMELO AVENUE, SARASOTA, FL 34236 (MLS # A4478101)
    $899,000
    Photo of 1122 POMELO AVENUE, SARASOTA, FL 34236 (MLS # A4478101)
    Photo of 1122 POMELO AVENUE, SARASOTA, FL 34236 (MLS # A4478101)
    1122 POMELO AVENUE, SARASOTA, FL
    1122 POMELO AVENUE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,878 Home (sqft)
    • 3 Baths
    • 7,001 Lot (sqft)
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Listing information is deemed reliable, but not guaranteed.

This IDX Solution is (c) Diverse Solutions 2020.

 
 

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