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 Older homes have been replaced by modern masterpieces.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.

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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 1400 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4483394)
    $7,900,000
    Photo of 1400 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4483394)
    Photo of 1400 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4483394)
    1400 HARBOR DRIVE, SARASOTA, FL
    1400 HARBOR DRIVE
    SARASOTA, FL
    • 5 Beds
    • 6 Baths
    • 5,402 Home (sqft)
    • 6 Baths
    • 14,004 Lot (sqft)
  2. 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)
  3. Photo of 1373 HARBOR DRIVE, SARASOTA, FL 34239 (MLS # A4477187)
    $3,500,000
    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)
  4. Photo of 1590 GULFVIEW DRIVE, SARASOTA, FL 34236 (MLS # A4486913)
    $2,499,500
    Photo of 1590 GULFVIEW DRIVE, SARASOTA, FL 34236 (MLS # A4486913)
    Photo of 1590 GULFVIEW DRIVE, SARASOTA, FL 34236 (MLS # A4486913)
    1590 GULFVIEW DRIVE, SARASOTA, FL
    1590 GULFVIEW DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 3,495 Home (sqft)
    • 4 Baths
    • 22,375 Lot (sqft)
  5. Photo of 2200 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4483149)
    $2,495,000
    Photo of 2200 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4483149)
    Photo of 2200 ORIOLE DRIVE, SARASOTA, FL 34239 (MLS # A4483149)
    2200 ORIOLE DRIVE, SARASOTA, FL
    2200 ORIOLE DRIVE
    SARASOTA, FL
    • 4 Beds
    • 4 Baths
    • 3,753 Home (sqft)
    • 4 Baths
    • 15,328 Lot (sqft)
  6. Photo of 1835 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4485767)
    $2,299,000
    Photo of 1835 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4485767)
    Photo of 1835 WISTERIA STREET, SARASOTA, FL 34239 (MLS # A4485767)
    1835 WISTERIA STREET, SARASOTA, FL
    1835 WISTERIA STREET
    SARASOTA, FL
    • 4 Beds
    • 5 Baths
    • 3,747 Home (sqft)
    • 5 Baths
    • 12,000 Lot (sqft)
  7. Photo of 1722 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4485575)
    $1,895,000
    Photo of 1722 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4485575)
    Photo of 1722 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4485575)
    1722 SHORELAND DRIVE, SARASOTA, FL
    1722 SHORELAND DRIVE
    SARASOTA, FL
    • 5 Beds
    • 4 Baths
    • 3,790 Home (sqft)
    • 4 Baths
    • 6,996 Lot (sqft)
  8. Photo of 1810 GROVE STREET, SARASOTA, FL 34239 (MLS # A4482563)
    $1,895,000
    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)
  9. Photo of 1712 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4487530)
    $1,890,000
    Photo of 1712 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4487530)
    Photo of 1712 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4487530)
    1712 SHORELAND DRIVE, SARASOTA, FL
    1712 SHORELAND DRIVE
    SARASOTA, FL
    • 3 Beds
    • 4 Baths
    • 2,839 Home (sqft)
    • 4 Baths
    • 14,043 Lot (sqft)
  10. Photo of 2146 MCCLELLAN PARKWAY, SARASOTA, FL 34239 (MLS # A4476936)
    $1,805,000
    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)
  11. Photo of 2626 CARDINAL PLACE, SARASOTA, FL 34239 (MLS # A4487121)
    $1,700,000
    Photo of 2626 CARDINAL PLACE, SARASOTA, FL 34239 (MLS # A4487121)
    Photo of 2626 CARDINAL PLACE, SARASOTA, FL 34239 (MLS # A4487121)
    2626 CARDINAL PLACE, SARASOTA, FL
    2626 CARDINAL PLACE
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,866 Home (sqft)
    • 3 Baths
    • 13,144 Lot (sqft)
  12. Photo of 1901 HYDE PARK STREET #1901, SARASOTA, FL 34239 (MLS # A4489029)
    $1,699,000
    Photo of 1901 HYDE PARK STREET #1901, SARASOTA, FL 34239 (MLS # A4489029)
    Photo of 1901 HYDE PARK STREET #1901, SARASOTA, FL 34239 (MLS # A4489029)
    1901 HYDE PARK STREET #1901, SARASOTA, FL
    1901 HYDE PARK STREET #1901
    SARASOTA, FL
    • 8 Beds
    • 8 Baths
    • 4,684 Home (sqft)
    • 8 Baths
    • 13,051 Lot (sqft)
  13. 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)
  14. 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)
  15. Photo of 1666 HILLVIEW STREET, SARASOTA, FL 34239 (MLS # A4459323)
    $1,040,000
    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)
  16. Photo of 1705 SHORELAND DRIVE, SARASOTA, FL 34239 (MLS # A4479185)
    $799,000
    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)
  17. 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)
  18. Photo of 870 HUDSON AVENUE #870, SARASOTA, FL 34236 (MLS # A4488596)
    $725,000
    Photo of 870 HUDSON AVENUE #870, SARASOTA, FL 34236 (MLS # A4488596)
    Photo of 870 HUDSON AVENUE #870, SARASOTA, FL 34236 (MLS # A4488596)
    870 HUDSON AVENUE #870, SARASOTA, FL
    870 HUDSON AVENUE #870
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,362 Home (sqft)
    • 2 Baths
    • 37,905 Lot (sqft)
  19. Photo of 1226 HOLLY FERN LANE, SARASOTA, FL 34239 (MLS # A4486714)
    $710,000
    Photo of 1226 HOLLY FERN LANE, SARASOTA, FL 34239 (MLS # A4486714)
    Photo of 1226 HOLLY FERN LANE, SARASOTA, FL 34239 (MLS # A4486714)
    1226 HOLLY FERN LANE, SARASOTA, FL
    1226 HOLLY FERN LANE
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,872 Home (sqft)
    • 3 Baths
    • 7,751 Lot (sqft)
  20. 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)
    27
     
    1379 TEAROSE PLACE, SARASOTA, FL
    1379 TEAROSE PLACE
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 2,191 Home (sqft)
    • 3 Baths
    • 7,760 Lot (sqft)
  21. 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)
  22. 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)
  23. Photo of 1965 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4485844)
    $675,000
    Photo of 1965 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4485844)
    Photo of 1965 OLEANDER STREET, SARASOTA, FL 34239 (MLS # A4485844)
    1965 OLEANDER STREET, SARASOTA, FL
    1965 OLEANDER STREET
    SARASOTA, FL
    • 3 Beds
    • 2 Baths
    • 1,546 Home (sqft)
    • 2 Baths
    • 11,801 Lot (sqft)
  24. Photo of 835 S OSPREY AVENUE #307, SARASOTA, FL 34236 (MLS # A4487628)
    $379,000
    Photo of 835 S OSPREY AVENUE #307, SARASOTA, FL 34236 (MLS # A4487628)
    Photo of 835 S OSPREY AVENUE #307, SARASOTA, FL 34236 (MLS # A4487628)
    835 S OSPREY AVENUE #307, SARASOTA, FL
    835 S OSPREY AVENUE #307
    SARASOTA, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 6.06 Lot (ac)
  25. Photo of 1901 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4469786)
    $350,000
    Photo of 1901 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4469786)
    Photo of 1901 HIGH POINT DRIVE, SARASOTA, FL 34236 (MLS # A4469786)
    1901 HIGH POINT DRIVE, SARASOTA, FL
    1901 HIGH POINT DRIVE
    SARASOTA, FL
    • 1 Bed
    • 2 Baths
    • 698 Home (sqft)
    • 2 Baths
    • 3,584 Lot (sqft)
  26. Photo of 850 S TAMIAMI TRAIL #135, SARASOTA, FL 34236 (MLS # A4485739)
    $259,000
    Photo of 850 S TAMIAMI TRAIL #135, SARASOTA, FL 34236 (MLS # A4485739)
    Photo of 850 S TAMIAMI TRAIL #135, SARASOTA, FL 34236 (MLS # A4485739)
    850 S TAMIAMI TRAIL #135, SARASOTA, FL
    850 S TAMIAMI TRAIL #135
    SARASOTA, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 9.10 Lot (ac)
  27. Photo of 850 S TAMIAMI TRAIL #502, SARASOTA, FL 34236 (MLS # A4480659)
    $220,000
    Photo of 850 S TAMIAMI TRAIL #502, SARASOTA, FL 34236 (MLS # A4480659)
    Photo of 850 S TAMIAMI TRAIL #502, SARASOTA, FL 34236 (MLS # A4480659)
    850 S TAMIAMI TRAIL #502, SARASOTA, FL
    850 S TAMIAMI TRAIL #502
    SARASOTA, FL
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 9.10 Lot (ac)
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Listing information is deemed reliable, but not guaranteed.

This Real Estate IDX is (c) Diverse Solutions 2021.

 
 

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