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 Older homes have been replaced by modern masterpieces.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 1964 Datura Street, Sarasota, FL 34239 (MLS # A4600886)
    $2,195,000
    Photo of 1964 Datura Street, Sarasota, FL 34239 (MLS # A4600886)
    Photo of 1964 Datura Street, Sarasota, FL 34239 (MLS # A4600886)
    1964 Datura Street, Sarasota, FL
    1964 Datura Street
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,968 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  2. Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4612901)
    $1,950,000
    Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4612901)
    Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4612901)
    1647 Siesta Drive, Sarasota, FL
    1647 Siesta Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  3. Photo of 1960 Lincoln Drive, Sarasota, FL 34236 (MLS # U8245185)
    $1,575,000
    Photo of 1960 Lincoln Drive, Sarasota, FL 34236 (MLS # U8245185)
    Photo of 1960 Lincoln Drive, Sarasota, FL 34236 (MLS # U8245185)
    1960 Lincoln Drive, Sarasota, FL
    1960 Lincoln Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,611 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  4. Photo of 1600 Wewa Drive, Sarasota, FL 34239 (MLS # A4611024)
    $1,550,000
    Photo of 1600 Wewa Drive, Sarasota, FL 34239 (MLS # A4611024)
    Photo of 1600 Wewa Drive, Sarasota, FL 34239 (MLS # A4611024)
    1600 Wewa Drive, Sarasota, FL
    1600 Wewa Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,933 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  5. Photo of 1127 S Osprey Avenue, Sarasota, FL 34236 (MLS # T3474611)
    $1,499,000
    Photo of 1127 S Osprey Avenue, Sarasota, FL 34236 (MLS # T3474611)
    Photo of 1127 S Osprey Avenue, Sarasota, FL 34236 (MLS # T3474611)
    1127 S Osprey Avenue, Sarasota, FL
    1127 S Osprey Avenue
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 2,200 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  6. Photo of 1789 Loma Linda Street, Sarasota, FL 34239 (MLS # A4585947)
    $1,482,000
    Photo of 1789 Loma Linda Street, Sarasota, FL 34239 (MLS # A4585947)
    Photo of 1789 Loma Linda Street, Sarasota, FL 34239 (MLS # A4585947)
    1789 Loma Linda Street, Sarasota, FL
    1789 Loma Linda Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 3,088 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  7. Photo of 1225 Holly Fern Lane, Sarasota, FL 34239 (MLS # A4603340)
    $1,350,000
    Photo of 1225 Holly Fern Lane, Sarasota, FL 34239 (MLS # A4603340)
    Photo of 1225 Holly Fern Lane, Sarasota, FL 34239 (MLS # A4603340)
    1225 Holly Fern Lane, Sarasota, FL
    1225 Holly Fern Lane
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,909 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  8. Photo of 1723 Bay Street, Sarasota, FL 34236 (MLS # A4605684)
    $1,349,000
    Photo of 1723 Bay Street, Sarasota, FL 34236 (MLS # A4605684)
    Photo of 1723 Bay Street, Sarasota, FL 34236 (MLS # A4605684)
    1723 Bay Street, Sarasota, FL
    1723 Bay Street
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,237 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  9. Photo of 1622 Wisconsin Lane, Sarasota, FL 34239 (MLS # A4616484)
    $1,175,000
    Photo of 1622 Wisconsin Lane, Sarasota, FL 34239 (MLS # A4616484)
    Photo of 1622 Wisconsin Lane, Sarasota, FL 34239 (MLS # A4616484)
    1622 Wisconsin Lane, Sarasota, FL
    1622 Wisconsin Lane
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,486 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  10. Photo of 1917 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4598810)
    $1,150,000
    Photo of 1917 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4598810)
    Photo of 1917 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4598810)
    1917 Bahia Vista Street, Sarasota, FL
    1917 Bahia Vista Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,160 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  11. Photo of 858 Hudson Avenue #858, Sarasota, FL 34236 (MLS # A4589406)
    $1,100,000
    Photo of 858 Hudson Avenue #858, Sarasota, FL 34236 (MLS # A4589406)
    Photo of 858 Hudson Avenue #858, Sarasota, FL 34236 (MLS # A4589406)
    858 Hudson Avenue #858, Sarasota, FL
    858 Hudson Avenue #858
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,533 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  12. Photo of 1681 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4616816)
    $998,000
    Photo of 1681 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4616816)
    Photo of 1681 Bahia Vista Street, Sarasota, FL 34239 (MLS # A4616816)
    1681 Bahia Vista Street, Sarasota, FL
    1681 Bahia Vista Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,568 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  13. Photo of 1773 Harmony Lane, Sarasota, FL 34239 (MLS # A4609513)
    $975,000
    Photo of 1773 Harmony Lane, Sarasota, FL 34239 (MLS # A4609513)
    Photo of 1773 Harmony Lane, Sarasota, FL 34239 (MLS # A4609513)
    1773 Harmony Lane, Sarasota, FL
    1773 Harmony Lane
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,098 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  14. Photo of 1966 Wisteria Street, Sarasota, FL 34239 (MLS # A4605409)
    $799,900
    Photo of 1966 Wisteria Street, Sarasota, FL 34239 (MLS # A4605409)
    Photo of 1966 Wisteria Street, Sarasota, FL 34239 (MLS # A4605409)
    1966 Wisteria Street, Sarasota, FL
    1966 Wisteria Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,524 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  15. Photo of 1958 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4608970)
    $750,000
    Photo of 1958 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4608970)
    Photo of 1958 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4608970)
    1958 Bougainvillea Street, Sarasota, FL
    1958 Bougainvillea Street
    Sarasota, FL
    • 2 Beds
    • 1 Bath
    • 952 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  16. Photo of 1958 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4608749)
    $750,000
    Photo of 1958 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4608749)
    Photo of 1958 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4608749)
    1958 Bougainvillea Street, Sarasota, FL
    1958 Bougainvillea Street
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 8,712 Lot (sqft)
  17. Photo of 1629 Siesta Drive, Sarasota, FL 34239 (MLS # T3522999)
    $749,000
    Photo of 1629 Siesta Drive, Sarasota, FL 34239 (MLS # T3522999)
    Photo of 1629 Siesta Drive, Sarasota, FL 34239 (MLS # T3522999)
    1629 Siesta Drive, Sarasota, FL
    1629 Siesta Drive
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,513 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  18. Photo of 800 Hudson Avenue #108, Sarasota, FL 34236 (MLS # A4614977)
    $629,000
    Photo of 800 Hudson Avenue #108, Sarasota, FL 34236 (MLS # A4614977)
    Photo of 800 Hudson Avenue #108, Sarasota, FL 34236 (MLS # A4614977)
    44
     
    800 Hudson Avenue #108, Sarasota, FL
    800 Hudson Avenue #108
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,252 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  19. Photo of 1740 Wisconsin Lane, Sarasota, FL 34239 (MLS # N6133722)
    $555,000
    Photo of 1740 Wisconsin Lane, Sarasota, FL 34239 (MLS # N6133722)
    Photo of 1740 Wisconsin Lane, Sarasota, FL 34239 (MLS # N6133722)
    1740 Wisconsin Lane, Sarasota, FL
    1740 Wisconsin Lane
    Sarasota, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 5,228 Lot (sqft)
  20. Photo of 1740 Wisconsin Lane, Sarasota, FL 34239 (MLS # N6133623)
    $555,000
    Photo of 1740 Wisconsin Lane, Sarasota, FL 34239 (MLS # N6133623)
    Photo of 1740 Wisconsin Lane, Sarasota, FL 34239 (MLS # N6133623)
    1740 Wisconsin Lane, Sarasota, FL
    1740 Wisconsin Lane
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 5,228 Lot (sqft)
  21. Photo of 825 S Osprey Avenue #302, Sarasota, FL 34236 (MLS # A4618148)
    $549,000
    Photo of 825 S Osprey Avenue #302, Sarasota, FL 34236 (MLS # A4618148)
    Photo of 825 S Osprey Avenue #302, Sarasota, FL 34236 (MLS # A4618148)
    825 S Osprey Avenue #302, Sarasota, FL
    825 S Osprey Avenue #302
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 6.06 Lot (ac)
  22. Photo of 835 S Osprey Avenue #204, Sarasota, FL 34236 (MLS # A4617985)
    $494,000
    Photo of 835 S Osprey Avenue #204, Sarasota, FL 34236 (MLS # A4617985)
    Photo of 835 S Osprey Avenue #204, Sarasota, FL 34236 (MLS # A4617985)
    835 S Osprey Avenue #204, Sarasota, FL
    835 S Osprey Avenue #204
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 940 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  23. Photo of 850 S Tamiami Trail #624, Sarasota, FL 34236 (MLS # A4606550)
    $389,999
    Photo of 850 S Tamiami Trail #624, Sarasota, FL 34236 (MLS # A4606550)
    Photo of 850 S Tamiami Trail #624, Sarasota, FL 34236 (MLS # A4606550)
    44
     
    850 S Tamiami Trail #624, Sarasota, FL
    850 S Tamiami Trail #624
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 9.11 Lot (ac)
  24. Photo of 850 S Tamiami Trail #831, Sarasota, FL 34236 (MLS # A4592498)
    $385,000
    Photo of 850 S Tamiami Trail #831, Sarasota, FL 34236 (MLS # A4592498)
    Photo of 850 S Tamiami Trail #831, Sarasota, FL 34236 (MLS # A4592498)
    850 S Tamiami Trail #831, Sarasota, FL
    850 S Tamiami Trail #831
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  25. Photo of 850 S Tamiami Trail #224, Sarasota, FL 34236 (MLS # C7489011)
    $335,000
    Photo of 850 S Tamiami Trail #224, Sarasota, FL 34236 (MLS # C7489011)
    Photo of 850 S Tamiami Trail #224, Sarasota, FL 34236 (MLS # C7489011)
    850 S Tamiami Trail #224, Sarasota, FL
    850 S Tamiami Trail #224
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,354 Home (sqft)
    • 3 Baths
    • 9.11 Lot (ac)
  26. Photo of 3360 S Osprey Avenue #212B, Sarasota, FL 34239 (MLS # A4581145)
    $290,000
    Photo of 3360 S Osprey Avenue #212B, Sarasota, FL 34239 (MLS # A4581145)
    Photo of 3360 S Osprey Avenue #212B, Sarasota, FL 34239 (MLS # A4581145)
    3360 S Osprey Avenue #212B, Sarasota, FL
    3360 S Osprey Avenue #212B
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,122 Home (sqft)
    • 2 Baths
    • 2.43 Lot (ac)
  27. Photo of 850 S Tamiami Trail #408, Sarasota, FL 34236 (MLS # A4611620)
    $285,000
    Photo of 850 S Tamiami Trail #408, Sarasota, FL 34236 (MLS # A4611620)
    Photo of 850 S Tamiami Trail #408, Sarasota, FL 34236 (MLS # A4611620)
    850 S Tamiami Trail #408, Sarasota, FL
    850 S Tamiami Trail #408
    Sarasota, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  28. Photo of 3360 S Osprey Avenue #102B, Sarasota, FL 34239 (MLS # A4576802)
    $269,000
    Photo of 3360 S Osprey Avenue #102B, Sarasota, FL 34239 (MLS # A4576802)
    Photo of 3360 S Osprey Avenue #102B, Sarasota, FL 34239 (MLS # A4576802)
    3360 S Osprey Avenue #102B, Sarasota, FL
    3360 S Osprey Avenue #102B
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,122 Home (sqft)
    • 2 Baths
    • 2.43 Lot (ac)
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