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 Older homes have been replaced by modern masterpieces.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.

previous arrow
next arrow
previous arrownext arrow
Slider
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.


Show Map
  • List View
  • Grid View
Sorted by
1 - 30 of 42 | Previous Page 1 of 2 Next
  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 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4477187)
    $3,600,000
    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)
  3. 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)
  4. Photo of 1595 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4479218)
    $2,490,000
    Photo of 1595 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4479218)
    Photo of 1595 BAY POINT DRIVE, SARASOTA, FL 34236 (MLS # A4479218)
    1595 BAY POINT DRIVE, SARASOTA, FL
    1595 BAY POINT DRIVE
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 2,749 Home (sqft)
    • 4 Baths
    • 21,658 Lot (sqft)
  5. Photo of 1555 SANDPIPER LANE, SARASOTA, FL 34239 (MLS # A4436047)
    $2,292,000
    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)
  6. 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)
  7. Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4482563)
    $1,950,000
    Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4482563)
    Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4482563)
    1810 GROVE STREET, SARASOTA, FL
    1810 GROVE STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,281 Home (sqft)
    • 4 Baths
    • 9,679 Lot (sqft)
  8. 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)
  9. 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)
  10. Photo of 1767 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4480476)
    $1,650,000
    Photo of 1767 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4480476)
    Photo of 1767 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4480476)
    1767 ARLINGTON STREET, SARASOTA, FL
    1767 ARLINGTON STREET
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,150 Home (sqft)
    • 4 Baths
    • 7,745 Lot (sqft)
  11. Photo of 1950 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4481769)
    $1,595,000
    Photo of 1950 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4481769)
    Photo of 1950 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4481769)
    1950 HIGH POINT DRIVE, SARASOTA, FL
    1950 HIGH POINT DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,472 Home (sqft)
    • 4 Baths
    • 12,772 Lot (sqft)
  12. Photo of 1570 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4481664)
    $1,595,000
    Photo of 1570 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4481664)
    Photo of 1570 HILLVIEW DRIVE, SARASOTA, FL 34239 (MLS # A4481664)
    1570 HILLVIEW DRIVE, SARASOTA, FL
    1570 HILLVIEW DRIVE
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,215 Home (sqft)
    • 2 Baths
    • 13,207 Lot (sqft)
  13. Photo of 1115 CITRUS AVENUE, SARASOTA, FL 34236 (MLS # A4484615)
    $1,545,000
    Photo of 1115 CITRUS AVENUE, SARASOTA, FL 34236 (MLS # A4484615)
    Photo of 1115 CITRUS AVENUE, SARASOTA, FL 34236 (MLS # A4484615)
    1115 CITRUS AVENUE, SARASOTA, FL
    1115 CITRUS AVENUE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,183 Home (sqft)
    • 4 Baths
    • 14,001 Lot (sqft)
  14. Photo of 1701 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4477002)
    $1,439,000
    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)
  15. 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)
  16. Photo of 1723 SOUTH DRIVE, SARASOTA, FL 34239 (MLS # A4483701)
    $1,269,000
    Photo of 1723 SOUTH DRIVE, SARASOTA, FL 34239 (MLS # A4483701)
    Photo of 1723 SOUTH DRIVE, SARASOTA, FL 34239 (MLS # A4483701)
    1723 SOUTH DRIVE, SARASOTA, FL
    1723 SOUTH DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,224 Home (sqft)
    • 4 Baths
    • 15,001 Lot (sqft)
  17. 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)
  18. 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)
  19. Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4473738)
    $899,999
    Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4473738)
    Photo of 1654 PROSPECT STREET, SARASOTA, FL 34239 (MLS # A4473738)
    24
     
    1654 PROSPECT STREET, SARASOTA, FL
    1654 PROSPECT STREET
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 2,667 Home (sqft)
    • 3 Baths
    • 8,070 Lot (sqft)
  20. Photo of 1701 HASHAY DRIVE, SARASOTA, FL 34239 (MLS # U8097547)
    $874,900
    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)
  21. Photo of 1695 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4484769)
    $825,000
    Photo of 1695 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4484769)
    Photo of 1695 ARLINGTON STREET, SARASOTA, FL 34239 (MLS # A4484769)
    1695 ARLINGTON STREET, SARASOTA, FL
    1695 ARLINGTON STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 3,120 Home (sqft)
    • 2 Baths
    • 13,345 Lot (sqft)
  22. Photo of 2318 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4478573)
    $825,000
    Photo of 2318 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4478573)
    Photo of 2318 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4478573)
    2318 MCCLELLAN PARKWAY, SARASOTA, FL
    2318 MCCLELLAN PARKWAY
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,314 Home (sqft)
    • 3 Baths
    • 9,883 Lot (sqft)
  23. Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    $824,900
    Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    1705 SHORELAND DRIVE, SARASOTA, FL
    1705 SHORELAND DRIVE
    SARASOTA, FL
    • 3 Beds
    • 3 Baths
    • 1,949 Home (sqft)
    • 3 Baths
    • 14,966 Lot (sqft)
  24. Photo of 860 HUDSON AVENUE #860, SARASOTA, FL 34236 (MLS # A4479802)
    $745,000
    Photo of 860 HUDSON AVENUE #860, SARASOTA, FL 34236 (MLS # A4479802)
    Photo of 860 HUDSON AVENUE #860, SARASOTA, FL 34236 (MLS # A4479802)
    860 HUDSON AVENUE #860, SARASOTA, FL
    860 HUDSON AVENUE #860
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,488 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 1828 GROVE STREET, SARASOTA, FL 34239 (MLS # A4468353)
    $739,900
    Photo of 1828 GROVE STREET, SARASOTA, FL 34239 (MLS # A4468353)
    Photo of 1828 GROVE STREET, SARASOTA, FL 34239 (MLS # A4468353)
    1828 GROVE STREET, SARASOTA, FL
    1828 GROVE STREET
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,559 Home (sqft)
    • 2 Baths
    • 13,870 Lot (sqft)
  26. Photo of 3424 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4484722)
    $725,000
    Photo of 3424 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4484722)
    Photo of 3424 OLD OAK DRIVE, SARASOTA, FL 34239 (MLS # A4484722)
    3424 OLD OAK DRIVE, SARASOTA, FL
    3424 OLD OAK DRIVE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,368 Home (sqft)
    • 2 Baths
    • 9,773 Lot (sqft)
  27. Photo of 1379 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4480387)
    $699,000
    Photo of 1379 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4480387)
    Photo of 1379 TEAROSE PLACE, SARASOTA, FL 34239 (MLS # A4480387)
    29
     
    1379 TEAROSE PLACE, SARASOTA, FL
    1379 TEAROSE PLACE
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 2,191 Home (sqft)
    • 3 Baths
    • 7,760 Lot (sqft)
  28. Photo of 1723 BAY STREET, SARASOTA, FL 34236 (MLS # A4453885)
    $699,000
    Photo of 1723 BAY STREET, SARASOTA, FL 34236 (MLS # A4453885)
    Photo of 1723 BAY STREET, SARASOTA, FL 34236 (MLS # A4453885)
    1723 BAY STREET, SARASOTA, FL
    1723 BAY STREET
    SARASOTA, FL
    • 4 Beds
    • 3 Baths
    • 2,237 Home (sqft)
    • 3 Baths
    • 9,836 Lot (sqft)
  29. Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4481303)
    $688,000
    Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4481303)
    Photo of 1622 WISCONSIN LANE, SARASOTA, FL 34239 (MLS # A4481303)
    1622 WISCONSIN LANE, SARASOTA, FL
    1622 WISCONSIN LANE
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,486 Home (sqft)
    • 2 Baths
    • 5,373 Lot (sqft)
  30. Photo of 862 HUDSON AVENUE #862, SARASOTA, FL 34236 (MLS # A4478919)
    $679,000
    Photo of 862 HUDSON AVENUE #862, SARASOTA, FL 34236 (MLS # A4478919)
    Photo of 862 HUDSON AVENUE #862, SARASOTA, FL 34236 (MLS # A4478919)
    862 HUDSON AVENUE #862, SARASOTA, FL
    862 HUDSON AVENUE #862
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,362 Home (sqft)
    • 2 Baths
    • 37,905 Lot (sqft)
Previous Page 1 of 2 Next
Listing information is deemed reliable, but not guaranteed.

This Real Estate IDX is (c) Diverse Solutions 2020.

 
 

Sharing is caring!

Ask us any question or schedule a free consult

We will be pleased to answer any question, without obligation.

941.587.0740

×
Let’s Talk Sarasota Real Estate
[contact-form-7 404 "Not Found"]
×
Ask us Any Question or Schedule a Free Tour

We will be pleased to answer any question, without obligation.





    ×