West of Trail Real Estate

"West of Trail" is one of 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
  • $1,514,250
    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 Older homes have been replaced by modern masterpieces.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 1610 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4558525)
    $11,700,000
    Photo of 1610 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4558525)
    Photo of 1610 N LODGE DRIVE, SARASOTA, FL 34239 (MLS # A4558525)
    1610 N LODGE DRIVE, SARASOTA, FL
    1610 N LODGE DRIVE
    SARASOTA, FL
    • 6 Beds
    • 8 Baths
    • 6,800 Home (sqft)
    • 8 Baths
    • 16,118 Lot (sqft)
  2. 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)
    18
     
    1515 HILLVIEW DRIVE, SARASOTA, FL
    1515 HILLVIEW DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 5,424 Home (sqft)
    • 6 Baths
    • 21,780 Lot (sqft)
  3. Photo of 1490 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4546764)
    $7,600,000
    Photo of 1490 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4546764)
    Photo of 1490 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4546764)
    1490 HILLVIEW DRIVE, SARASOTA, FL
    1490 HILLVIEW DRIVE
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,474 Lot (sqft)
  4. Photo of 1479 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4561284)
    $6,850,000
    Photo of 1479 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4561284)
    Photo of 1479 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4561284)
    1479 BAY POINT DRIVE, SARASOTA, FL
    1479 BAY POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 3,783 Home (sqft)
    • 3 Baths
    • 21,345 Lot (sqft)
  5. Photo of 1718 BAY STREET, SARASOTA, FL 34236 (MLS # A4570776)
    $6,150,000
    Photo of 1718 BAY STREET, SARASOTA, FL 34236 (MLS # A4570776)
    Photo of 1718 BAY STREET, SARASOTA, FL 34236 (MLS # A4570776)
    43
     
    1718 BAY STREET, SARASOTA, FL
    1718 BAY STREET
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 4,016 Home (sqft)
    • 4 Baths
    • 17,860 Lot (sqft)
  6. Photo of 1630 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4564634)
    $4,995,000
    Photo of 1630 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4564634)
    Photo of 1630 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4564634)
    1630 S ORANGE AVENUE, SARASOTA, FL
    1630 S ORANGE AVENUE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 4,692 Home (sqft)
    • 6 Baths
    • 14,811 Lot (sqft)
  7. Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4564576)
    $4,950,000
    Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4564576)
    Photo of 1507 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4564576)
    1507 BAY POINT DRIVE, SARASOTA, FL
    1507 BAY POINT DRIVE
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,909 Lot (sqft)
  8. Photo of 1739 CHEROKEE DRIVE, SARASOTA, FL 34239 (MLS # A4565142)
    $4,885,000
    Photo of 1739 CHEROKEE DRIVE, SARASOTA, FL 34239 (MLS # A4565142)
    Photo of 1739 CHEROKEE DRIVE, SARASOTA, FL 34239 (MLS # A4565142)
    1739 CHEROKEE DRIVE, SARASOTA, FL
    1739 CHEROKEE DRIVE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 4,538 Home (sqft)
    • 5 Baths
    • 20,038 Lot (sqft)
  9. Photo of 1924 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4570095)
    $4,750,000
    Photo of 1924 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4570095)
    Photo of 1924 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4570095)
    49
     
    1924 LINCOLN DRIVE, SARASOTA, FL
    1924 LINCOLN DRIVE
    SARASOTA, FL
    • 4 Beds
    • 7 Baths
    • 5,434 Home (sqft)
    • 7 Baths
    • 17,860 Lot (sqft)
  10. Photo of 1550 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4566256)
    $4,438,000
    Photo of 1550 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4566256)
    Photo of 1550 S ORANGE AVENUE, SARASOTA, FL 34239 (MLS # A4566256)
    1550 S ORANGE AVENUE, SARASOTA, FL
    1550 S ORANGE AVENUE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 4,189 Home (sqft)
    • 6 Baths
    • 14,811 Lot (sqft)
  11. Photo of 2540 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570774)
    $4,100,000
    Photo of 2540 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570774)
    Photo of 2540 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570774)
    21
     
    2540 S OSPREY AVENUE, SARASOTA, FL
    2540 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,613 Home (sqft)
    • 6 Baths
    • 11,762 Lot (sqft)
  12. 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
    • 10,455 Lot (sqft)
  13. Photo of 2624 MULBERRY TERRACE, SARASOTA, FL 34239 (MLS # A4565137)
    $3,750,000
    Photo of 2624 MULBERRY TERRACE, SARASOTA, FL 34239 (MLS # A4565137)
    Photo of 2624 MULBERRY TERRACE, SARASOTA, FL 34239 (MLS # A4565137)
    2624 MULBERRY TERRACE, SARASOTA, FL
    2624 MULBERRY TERRACE
    SARASOTA, FL
    • 3 Beds
    • 5 Baths
    • 3,744 Home (sqft)
    • 5 Baths
    • 9,584 Lot (sqft)
  14. Photo of 1727 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4546473)
    $3,650,000
    Photo of 1727 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4546473)
    Photo of 1727 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4546473)
    1727 BAHIA VISTA STREET, SARASOTA, FL
    1727 BAHIA VISTA STREET
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 4,829 Home (sqft)
    • 5 Baths
    • 14,811 Lot (sqft)
  15. Photo of 1843 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4553636)
    $3,575,000
    Photo of 1843 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4553636)
    Photo of 1843 MORRIS STREET, SARASOTA, FL 34239 (MLS # A4553636)
    1843 MORRIS STREET, SARASOTA, FL
    1843 MORRIS STREET
    SARASOTA, FL
    • 3 Beds
    • 5 Baths
    • 3,183 Home (sqft)
    • 5 Baths
    • 13,504 Lot (sqft)
  16. Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570879)
    $3,350,000
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570879)
    Photo of 1537 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570879)
    1537 SIESTA DRIVE, SARASOTA, FL
    1537 SIESTA DRIVE
    SARASOTA, FL
    • 4 Beds
    • 6 Baths
    • 3,736 Home (sqft)
    • 6 Baths
    • 12,197 Lot (sqft)
  17. Photo of 1718 BAY VIEW DRIVE, SARASOTA, FL 34239 (MLS # A4536016)
    $3,295,000
    Photo of 1718 BAY VIEW DRIVE, SARASOTA, FL 34239 (MLS # A4536016)
    Photo of 1718 BAY VIEW DRIVE, SARASOTA, FL 34239 (MLS # A4536016)
    1718 BAY VIEW DRIVE, SARASOTA, FL
    1718 BAY VIEW DRIVE
    SARASOTA, FL
    • 6 Beds
    • 6 Baths
    • 4,644 Home (sqft)
    • 6 Baths
    • 16,118 Lot (sqft)
  18. Photo of 2131 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4566296)
    $3,250,000
    Photo of 2131 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4566296)
    Photo of 2131 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4566296)
    2131 MCCLELLAN PARKWAY, SARASOTA, FL
    2131 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 6 Beds
    • 4 Baths
    • 4,358 Home (sqft)
    • 4 Baths
    • 14,375 Lot (sqft)
  19. Photo of 1912 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4563784)
    $3,200,000
    Photo of 1912 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4563784)
    Photo of 1912 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4563784)
    1912 WISTERIA STREET, SARASOTA, FL
    1912 WISTERIA STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,547 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
  20. Photo of 1915 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4571582)
    $3,150,000
    Photo of 1915 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4571582)
    Photo of 1915 CLEMATIS STREET, SARASOTA, FL 34239 (MLS # A4571582)
    1915 CLEMATIS STREET, SARASOTA, FL
    1915 CLEMATIS STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,161 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  21. Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570911)
    $3,150,000
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570911)
    Photo of 3135 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570911)
    3135 S OSPREY AVENUE, SARASOTA, FL
    3135 S OSPREY AVENUE
    SARASOTA, FL
    • 5 Beds
    • 5 Baths
    • 3,595 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  22. Photo of 1954 GOLDENROD STREET W, SARASOTA, FL 34239 (MLS # A4570836)
    $3,150,000
    Photo of 1954 GOLDENROD STREET W, SARASOTA, FL 34239 (MLS # A4570836)
    Photo of 1954 GOLDENROD STREET W, SARASOTA, FL 34239 (MLS # A4570836)
    1954 GOLDENROD STREET W, SARASOTA, FL
    1954 GOLDENROD STREET W
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,606 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  23. Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4570754)
    $3,150,000
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4570754)
    Photo of 2171 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4570754)
    22
     
    2171 MCCLELLAN PARKWAY, SARASOTA, FL
    2171 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  24. Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4570821)
    $2,950,000
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4570821)
    Photo of 1886 BAHIA VISTA STREET, SARASOTA, FL 34239 (MLS # A4570821)
    20
     
    1886 BAHIA VISTA STREET, SARASOTA, FL
    1886 BAHIA VISTA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,153 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  25. Photo of 1957 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4554010)
    $2,900,000
    Photo of 1957 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4554010)
    Photo of 1957 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4554010)
    67
     
    1957 LINCOLN DRIVE, SARASOTA, FL
    1957 LINCOLN DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,483 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  26. Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570920)
    $2,895,000
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570920)
    Photo of 3319 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4570920)
    3319 S OSPREY AVENUE, SARASOTA, FL
    3319 S OSPREY AVENUE
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,423 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  27. Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570917)
    $2,795,000
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570917)
    Photo of 1647 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4570917)
    1647 SIESTA DRIVE, SARASOTA, FL
    1647 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  28. Photo of 1859 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4564854)
    $2,710,612
    Photo of 1859 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4564854)
    Photo of 1859 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4564854)
    1859 MAGNOLIA STREET, SARASOTA, FL
    1859 MAGNOLIA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,220 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  29. Photo of 1912 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4563196)
    $2,335,000
    Photo of 1912 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4563196)
    Photo of 1912 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4563196)
    1912 HIGH POINT DRIVE, SARASOTA, FL
    1912 HIGH POINT DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,941 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  30. Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    $2,289,000
    Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    Photo of 1844 MAGNOLIA STREET, SARASOTA, FL 34239 (MLS # A4544297)
    1844 MAGNOLIA STREET, SARASOTA, FL
    1844 MAGNOLIA STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 2,915 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 6/3/23 10:32 AM PDT.

This MLS IDX is (c) Diverse Solutions 2023. Privacy | Terms & Conditions

 
 

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