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 Older homes have been replaced by modern masterpieces.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 2430 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549881)
    $2,100,000
    Photo of 2430 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549881)
    Photo of 2430 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549881)
    2430 FLOYD STREET, SARASOTA, FL
    2430 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,763 Home (sqft)
    • 5 Baths
    • 1,743 Lot (sqft)
  2. Photo of 2446 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549839)
    $2,100,000
    Photo of 2446 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549839)
    Photo of 2446 FLOYD STREET, SARASOTA, FL 34239 (MLS # A4549839)
    2446 FLOYD STREET, SARASOTA, FL
    2446 FLOYD STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 2,743 Home (sqft)
    • 5 Baths
    • 6,099 Lot (sqft)
  3. Photo of 1719 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4558823)
    $1,899,000
    Photo of 1719 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4558823)
    Photo of 1719 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4558823)
    1719 SHORELAND DRIVE, SARASOTA, FL
    1719 SHORELAND DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,568 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
  4. Photo of 866 HUDSON AVENUE #866, SARASOTA, FL 34236 (MLS # A4563127)
    $1,895,000
    Photo of 866 HUDSON AVENUE #866, SARASOTA, FL 34236 (MLS # A4563127)
    Photo of 866 HUDSON AVENUE #866, SARASOTA, FL 34236 (MLS # A4563127)
    866 HUDSON AVENUE #866, SARASOTA, FL
    866 HUDSON AVENUE #866
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,293 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  5. Photo of 1723 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4564155)
    $1,725,000
    Photo of 1723 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4564155)
    Photo of 1723 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4564155)
    1723 HILLVIEW STREET, SARASOTA, FL
    1723 HILLVIEW STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 2,030 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  6. Photo of 2440 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4545991)
    $1,599,900
    Photo of 2440 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4545991)
    Photo of 2440 S OSPREY AVENUE, SARASOTA, FL 34239 (MLS # A4545991)
    62
     
    2440 S OSPREY AVENUE, SARASOTA, FL
    2440 S OSPREY AVENUE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,238 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  7. Photo of 1737 BAY STREET, SARASOTA, FL 34236 (MLS # A4553541)
    $1,500,000
    Photo of 1737 BAY STREET, SARASOTA, FL 34236 (MLS # A4553541)
    Photo of 1737 BAY STREET, SARASOTA, FL 34236 (MLS # A4553541)
    1737 BAY STREET, SARASOTA, FL
    1737 BAY STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,896 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  8. Photo of 1960 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4563796)
    $1,450,000
    Photo of 1960 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4563796)
    Photo of 1960 LINCOLN DRIVE, SARASOTA, FL 34236 (MLS # A4563796)
    1960 LINCOLN DRIVE, SARASOTA, FL
    1960 LINCOLN DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,611 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  9. Photo of 1348 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4563484)
    $1,350,000
    Photo of 1348 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4563484)
    Photo of 1348 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4563484)
    1348 TEAROSE PLACE, SARASOTA, FL
    1348 TEAROSE PLACE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,257 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  10. Photo of 1854 BAHIA VISTA, SARASOTA, FL 34239 (MLS # A4549872)
    $1,285,000
    Photo of 1854 BAHIA VISTA, SARASOTA, FL 34239 (MLS # A4549872)
    Photo of 1854 BAHIA VISTA, SARASOTA, FL 34239 (MLS # A4549872)
    33
     
    1854 BAHIA VISTA, SARASOTA, FL
    1854 BAHIA VISTA
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,587 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  11. Photo of 1630 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4560809)
    $1,100,000
    Photo of 1630 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4560809)
    Photo of 1630 HYDE PARK STREET, SARASOTA, FL 34239 (MLS # A4560809)
    1630 HYDE PARK STREET, SARASOTA, FL
    1630 HYDE PARK STREET
    SARASOTA, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 6,099 Lot (sqft)
  12. Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4555121)
    $1,100,000
    Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4555121)
    Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4555121)
    1622 WISCONSIN LANE, SARASOTA, FL
    1622 WISCONSIN LANE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,486 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  13. Photo of 1741 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4560544)
    $999,999
    Photo of 1741 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4560544)
    Photo of 1741 SIESTA DRIVE, SARASOTA, FL 34239 (MLS # A4560544)
    1741 SIESTA DRIVE, SARASOTA, FL
    1741 SIESTA DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,468 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  14. Photo of 1644 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # T3427890)
    $990,000
    Photo of 1644 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # T3427890)
    Photo of 1644 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # T3427890)
    40
     
    1644 HILLVIEW STREET, SARASOTA, FL
    1644 HILLVIEW STREET
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,620 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  15. Photo of 850 S TAMIAMI TRAIL #722, SARASOTA, FL 34236 (MLS # A4563817)
    $439,000
    Photo of 850 S TAMIAMI TRAIL #722, SARASOTA, FL 34236 (MLS # A4563817)
    Photo of 850 S TAMIAMI TRAIL #722, SARASOTA, FL 34236 (MLS # A4563817)
    850 S TAMIAMI TRAIL #722, SARASOTA, FL
    850 S TAMIAMI TRAIL #722
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  16. Photo of 3350 S OSPREY AVENUE #109A, SARASOTA, FL 34239 (MLS # T3413519)
    $435,000
    Photo of 3350 S OSPREY AVENUE #109A, SARASOTA, FL 34239 (MLS # T3413519)
    Photo of 3350 S OSPREY AVENUE #109A, SARASOTA, FL 34239 (MLS # T3413519)
    3350 S OSPREY AVENUE #109A, SARASOTA, FL
    3350 S OSPREY AVENUE #109A
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,122 Home (sqft)
    • 2 Baths
    • 2.43 Lot (ac)
  17. Photo of 835 S OSPREY AVENUE #211, SARASOTA, FL 34236 (MLS # A4564426)
    $409,900
    Photo of 835 S OSPREY AVENUE #211, SARASOTA, FL 34236 (MLS # A4564426)
    Photo of 835 S OSPREY AVENUE #211, SARASOTA, FL 34236 (MLS # A4564426)
    835 S OSPREY AVENUE #211, SARASOTA, FL
    835 S OSPREY AVENUE #211
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 721 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  18. Photo of 850 S TAMIAMI TRAIL #326, SARASOTA, FL 34236 (MLS # A4562995)
    $379,000
    Photo of 850 S TAMIAMI TRAIL #326, SARASOTA, FL 34236 (MLS # A4562995)
    Photo of 850 S TAMIAMI TRAIL #326, SARASOTA, FL 34236 (MLS # A4562995)
    850 S TAMIAMI TRAIL #326, SARASOTA, FL
    850 S TAMIAMI TRAIL #326
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  19. Photo of 850 S TAMIAMI TRAIL #822, SARASOTA, FL 34236 (MLS # A4557317)
    $375,000
    Photo of 850 S TAMIAMI TRAIL #822, SARASOTA, FL 34236 (MLS # A4557317)
    Photo of 850 S TAMIAMI TRAIL #822, SARASOTA, FL 34236 (MLS # A4557317)
    850 S TAMIAMI TRAIL #822, SARASOTA, FL
    850 S TAMIAMI TRAIL #822
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  20. Photo of 850 S TAMIAMI TRAIL #823, SARASOTA, FL 34236 (MLS # A4539631)
    $349,000
    Photo of 850 S TAMIAMI TRAIL #823, SARASOTA, FL 34236 (MLS # A4539631)
    Photo of 850 S TAMIAMI TRAIL #823, SARASOTA, FL 34236 (MLS # A4539631)
    850 S TAMIAMI TRAIL #823, SARASOTA, FL
    850 S TAMIAMI TRAIL #823
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  21. Photo of 3360 S OSPREY AVENUE #110B, SARASOTA, FL 34239 (MLS # A4556081)
    $339,950
    Photo of 3360 S OSPREY AVENUE #110B, SARASOTA, FL 34239 (MLS # A4556081)
    Photo of 3360 S OSPREY AVENUE #110B, SARASOTA, FL 34239 (MLS # A4556081)
    33
     
    3360 S OSPREY AVENUE #110B, SARASOTA, FL
    3360 S OSPREY AVENUE #110B
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,122 Home (sqft)
    • 2 Baths
    • 2.43 Lot (ac)
  22. Photo of 850 S TAMIAMI TRAIL #706, SARASOTA, FL 34236 (MLS # A4560596)
    $325,000
    Photo of 850 S TAMIAMI TRAIL #706, SARASOTA, FL 34236 (MLS # A4560596)
    Photo of 850 S TAMIAMI TRAIL #706, SARASOTA, FL 34236 (MLS # A4560596)
    850 S TAMIAMI TRAIL #706, SARASOTA, FL
    850 S TAMIAMI TRAIL #706
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 9.10 Lot (ac)
  23. Photo of 850 S TAMIAMI TRAIL #707, SARASOTA, FL 34236 (MLS # A4558981)
    $305,000
    Photo of 850 S TAMIAMI TRAIL #707, SARASOTA, FL 34236 (MLS # A4558981)
    Photo of 850 S TAMIAMI TRAIL #707, SARASOTA, FL 34236 (MLS # A4558981)
    850 S TAMIAMI TRAIL #707, SARASOTA, FL
    850 S TAMIAMI TRAIL #707
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 9.10 Lot (ac)
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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 3/22/23 12:03 PM PDT.

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

 
 

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