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 Older homes have been replaced by modern masterpieces.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 1423 & 1435 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4525534)
    $21,600,000
    Photo of 1423 & 1435 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4525534)
    Photo of 1423 & 1435 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4525534)
    1423 & 1435 HILLVIEW DRIVE, SARASOTA, FL
    1423 & 1435 HILLVIEW DRIVE
    SARASOTA, FL
    • 6 Beds
    • 9 Baths
    • 21,492 Home (sqft)
    • 9 Baths
    • 1.80 Lot (ac)
  2. 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)
  3. Photo of N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4520219)
    $9,874,000
    Photo of N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4520219)
    Photo of N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4520219)
    N LODGE DRIVE, SARASOTA, FL
    N LODGE DRIVE
    SARASOTA, FL
    • 6 Beds
    • 8 Baths
    • 12,000 Home (sqft)
    • 8 Baths
    • 16,118 Lot (sqft)
  4. Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    $9,575,000
    Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    Photo of 1465 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4515981)
    1465 HILLVIEW DRIVE, SARASOTA, FL
    1465 HILLVIEW DRIVE
    SARASOTA, FL
    • 5 Beds
    • 7 Baths
    • 6,654 Home (sqft)
    • 7 Baths
    • 28,753 Lot (sqft)
  5. Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4525595)
    $9,499,000
    Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4525595)
    Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4525595)
    1507 BAY POINT DRIVE, SARASOTA, FL
    1507 BAY POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 7,350 Home (sqft)
    • 6 Baths
    • 41,818 Lot (sqft)
  6. Photo of OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4520464)
    $8,495,000
    Photo of OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4520464)
    Photo of OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4520464)
    16
     
    OLD OAK DRIVE, SARASOTA, FL
    OLD OAK DRIVE
    SARASOTA, FL
    • 4 Beds
    • 7 Baths
    • 6,428 Home (sqft)
    • 7 Baths
    • 1.43 Lot (ac)
  7. Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4522100)
    $8,400,000
    Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4522100)
    Photo of 1515 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4522100)
    16
     
    1515 HILLVIEW DRIVE, SARASOTA, FL
    1515 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 5,424 Home (sqft)
    • 6 Baths
    • 21,780 Lot (sqft)
  8. Photo of 2168 SPARROW COURT, SARASOTA, FL 34239 (MLS # A4531141)
    $7,490,000
    Photo of 2168 SPARROW COURT, SARASOTA, FL 34239 (MLS # A4531141)
    Photo of 2168 SPARROW COURT, SARASOTA, FL 34239 (MLS # A4531141)
    2168 SPARROW COURT, SARASOTA, FL
    2168 SPARROW COURT
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 8,906 Home (sqft)
    • 4 Baths
    • 13,940 Lot (sqft)
  9. Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4526939)
    $6,000,000
    Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4526939)
    Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4526939)
    1373 HARBOR DRIVE, SARASOTA, FL
    1373 HARBOR DRIVE
    SARASOTA, FL
    • 6 Beds
    • 5 Baths
    • 11,400 Home (sqft)
    • 5 Baths
    • 20,038 Lot (sqft)
  10. Photo of 1785 BAYVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4534325)
    $4,495,000
    Photo of 1785 BAYVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4534325)
    Photo of 1785 BAYVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4534325)
    1785 BAYVIEW DRIVE, SARASOTA, FL
    1785 BAYVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 5,697 Home (sqft)
    • 6 Baths
    • 11,762 Lot (sqft)
  11. Photo of 1960 BOYCE STREET, SARASOTA, FL 34239 (MLS # A4519209)
    $3,900,000
    Photo of 1960 BOYCE STREET, SARASOTA, FL 34239 (MLS # A4519209)
    Photo of 1960 BOYCE STREET, SARASOTA, FL 34239 (MLS # A4519209)
    1960 BOYCE STREET, SARASOTA, FL
    1960 BOYCE STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,674 Home (sqft)
    • 5 Baths
    • 10,276 Lot (sqft)
  12. Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3366498)
    $3,875,000
    Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3366498)
    Photo of 1558 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # T3366498)
    1558 SANDPIPER LANE, SARASOTA, FL
    1558 SANDPIPER LANE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,942 Home (sqft)
    • 4 Baths
    • 14,357 Lot (sqft)
  13. Photo of 1682 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4527476)
    $3,850,000
    Photo of 1682 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4527476)
    Photo of 1682 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4527476)
    61
     
    1682 HAWTHORNE STREET, SARASOTA, FL
    1682 HAWTHORNE STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,471 Home (sqft)
    • 5 Baths
    • 19,602 Lot (sqft)
  14. Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534537)
    $3,195,000
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534537)
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534537)
    1537 SIESTA DRIVE, SARASOTA, FL
    1537 SIESTA DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 5,663 Home (sqft)
    • 6 Baths
    • 12,197 Lot (sqft)
  15. Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4534565)
    $2,995,000
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4534565)
    Photo of 1954 GOLDENROD STREET, SARASOTA, FL 34239 (MLS # A4534565)
    15
     
    1954 GOLDENROD STREET, SARASOTA, FL
    1954 GOLDENROD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,882 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  16. Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534567)
    $2,995,000
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534567)
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534567)
    3135 S OSPREY AVENUE, SARASOTA, FL
    3135 S OSPREY AVENUE
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 4,660 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  17. Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    $2,950,000
    Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    Photo of 1929 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4521281)
    78
     
    1929 MORRIS STREET, SARASOTA, FL
    1929 MORRIS STREET
    SARASOTA, FL
    • 3 Beds
    • 5 Baths
    • 3,035 Home (sqft)
    • 5 Baths
    • 13,704 Lot (sqft)
  18. Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4534560)
    $2,895,000
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4534560)
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4534560)
    2171 MCCLELLAN PARKWAY, SARASOTA, FL
    2171 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 4,147 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  19. Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534568)
    $2,895,000
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534568)
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4534568)
    17
     
    3319 S OSPREY AVENUE, SARASOTA, FL
    3319 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,377 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  20. Photo of 1659 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4531202)
    $2,799,000
    Photo of 1659 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4531202)
    Photo of 1659 HAWTHORNE STREET, SARASOTA, FL 34239 (MLS # A4531202)
    1659 HAWTHORNE STREET, SARASOTA, FL
    1659 HAWTHORNE STREET
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 2,967 Home (sqft)
    • 4 Baths
    • 14,375 Lot (sqft)
  21. Photo of 1547 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4531554)
    $2,699,000
    Photo of 1547 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4531554)
    Photo of 1547 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4531554)
    1547 SANDPIPER LANE, SARASOTA, FL
    1547 SANDPIPER LANE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 4,540 Home (sqft)
    • 4 Baths
    • 15,246 Lot (sqft)
  22. Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4534562)
    $2,695,000
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4534562)
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4534562)
    1886 BAHIA VISTA STREET, SARASOTA, FL
    1886 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,713 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  23. Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534540)
    $2,595,000
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534540)
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4534540)
    1647 SIESTA DRIVE, SARASOTA, FL
    1647 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 4,039 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  24. Photo of 1730 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4524207)
    $2,279,900
    Photo of 1730 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4524207)
    Photo of 1730 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4524207)
    1730 WISCONSIN LANE, SARASOTA, FL
    1730 WISCONSIN LANE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,005 Home (sqft)
    • 5 Baths
    • 6,180 Lot (sqft)
  25. Photo of 1704 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4529406)
    $2,100,000
    Photo of 1704 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4529406)
    Photo of 1704 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4529406)
    1704 ARLINGTON STREET, SARASOTA, FL
    1704 ARLINGTON STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,786 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  26. Photo of 1743 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4535435)
    $1,355,000
    Photo of 1743 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4535435)
    Photo of 1743 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4535435)
    1743 ALTA VISTA STREET, SARASOTA, FL
    1743 ALTA VISTA STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,140 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  27. Photo of 1694 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4533919)
    $1,350,000
    Photo of 1694 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4533919)
    Photo of 1694 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4533919)
    1694 FLOYD STREET, SARASOTA, FL
    1694 FLOYD STREET
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 2,974 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  28. Photo of 1703 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4535182)
    $1,140,000
    Photo of 1703 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4535182)
    Photo of 1703 ALTA VISTA STREET, SARASOTA, FL 34236 (MLS # A4535182)
    1703 ALTA VISTA STREET, SARASOTA, FL
    1703 ALTA VISTA STREET
    SARASOTA, FL
    • 2 Beds
    • 1 Bath
    • 1,451 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  29. Photo of GROVE STREET, SARASOTA, FL 34239 (MLS # A4532266)
    $1,095,000
    Photo of GROVE STREET, SARASOTA, FL 34239 (MLS # A4532266)
    Photo of GROVE STREET, SARASOTA, FL 34239 (MLS # A4532266)
    GROVE STREET, SARASOTA, FL
    GROVE STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,512 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
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