"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 Older homes have been replaced by modern masterpieces.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 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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$2,100,0002430 FLOYD STREET, SARASOTA, FL2430 FLOYD STREET
SARASOTA, FL- 4 Beds
- 5 Baths
- 2,763 Home (sqft)
- 5 Baths
- 1,743 Lot (sqft)
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$2,100,0002446 FLOYD STREET, SARASOTA, FL2446 FLOYD STREET
SARASOTA, FL- 4 Beds
- 5 Baths
- 2,743 Home (sqft)
- 5 Baths
- 6,099 Lot (sqft)
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$1,899,0001719 SHORELAND DRIVE, SARASOTA, FL1719 SHORELAND DRIVE
SARASOTA, FL- 3 Beds
- 3 Baths
- 2,568 Home (sqft)
- 3 Baths
- 14,811 Lot (sqft)
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$1,895,000866 HUDSON AVENUE #866, SARASOTA, FL866 HUDSON AVENUE #866
SARASOTA, FL- 3 Beds
- 3 Baths
- 2,293 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$1,725,0001723 HILLVIEW STREET, SARASOTA, FL1723 HILLVIEW STREET
SARASOTA, FL- 3 Beds
- 2 Baths
- 2,030 Home (sqft)
- 2 Baths
- 6,970 Lot (sqft)
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$1,599,9002440 S OSPREY AVENUE, SARASOTA, FL2440 S OSPREY AVENUE
SARASOTA, FL- 3 Beds
- 4 Baths
- 2,238 Home (sqft)
- 4 Baths
- 13,068 Lot (sqft)
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$1,500,0001737 BAY STREET, SARASOTA, FL1737 BAY STREET
SARASOTA, FL- 3 Beds
- 3 Baths
- 1,896 Home (sqft)
- 3 Baths
- 5,663 Lot (sqft)
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$1,450,0001960 LINCOLN DRIVE, SARASOTA, FL1960 LINCOLN DRIVE
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,611 Home (sqft)
- 2 Baths
- 11,326 Lot (sqft)
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$1,350,0001348 TEAROSE PLACE, SARASOTA, FL1348 TEAROSE PLACE
SARASOTA, FL- 3 Beds
- 4 Baths
- 2,257 Home (sqft)
- 4 Baths
- 6,534 Lot (sqft)
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$1,285,0001854 BAHIA VISTA, SARASOTA, FL1854 BAHIA VISTA
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,587 Home (sqft)
- 2 Baths
- 10,890 Lot (sqft)
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$1,100,0001630 HYDE PARK STREET, SARASOTA, FL1630 HYDE PARK STREET
SARASOTA, FL- 0 Beds
- 0 Baths
- 0 Home (sqft)
- 0 Baths
- 6,099 Lot (sqft)
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$1,100,0001622 WISCONSIN LANE, SARASOTA, FL1622 WISCONSIN LANE
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,486 Home (sqft)
- 2 Baths
- 5,228 Lot (sqft)
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$999,9991741 SIESTA DRIVE, SARASOTA, FL1741 SIESTA DRIVE
SARASOTA, FL- 3 Beds
- 2 Baths
- 1,468 Home (sqft)
- 2 Baths
- 5,663 Lot (sqft)
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$990,0001644 HILLVIEW STREET, SARASOTA, FL1644 HILLVIEW STREET
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,620 Home (sqft)
- 2 Baths
- 8,712 Lot (sqft)
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$439,000850 S TAMIAMI TRAIL #722, SARASOTA, FL850 S TAMIAMI TRAIL #722
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,224 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$435,0003350 S OSPREY AVENUE #109A, SARASOTA, FL3350 S OSPREY AVENUE #109A
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,122 Home (sqft)
- 2 Baths
- 2.43 Lot (ac)
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$409,900835 S OSPREY AVENUE #211, SARASOTA, FL835 S OSPREY AVENUE #211
SARASOTA, FL- 1 Bed
- 1 Bath
- 721 Home (sqft)
- 1 Bath
- 0 Lot (sqft)
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$379,000850 S TAMIAMI TRAIL #326, SARASOTA, FL850 S TAMIAMI TRAIL #326
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,224 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$375,000850 S TAMIAMI TRAIL #822, SARASOTA, FL850 S TAMIAMI TRAIL #822
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,224 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$349,000850 S TAMIAMI TRAIL #823, SARASOTA, FL850 S TAMIAMI TRAIL #823
SARASOTA, FL- 2 Beds
- 3 Baths
- 1,224 Home (sqft)
- 3 Baths
- 0 Lot (sqft)
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$339,9503360 S OSPREY AVENUE #110B, SARASOTA, FL3360 S OSPREY AVENUE #110B
SARASOTA, FL- 2 Beds
- 2 Baths
- 1,122 Home (sqft)
- 2 Baths
- 2.43 Lot (ac)
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$325,000850 S TAMIAMI TRAIL #706, SARASOTA, FL850 S TAMIAMI TRAIL #706
SARASOTA, FL- 1 Bed
- 1 Bath
- 576 Home (sqft)
- 1 Bath
- 9.10 Lot (ac)
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$305,000850 S TAMIAMI TRAIL #707, SARASOTA, FL850 S TAMIAMI TRAIL #707
SARASOTA, FL- 1 Bed
- 1 Bath
- 576 Home (sqft)
- 1 Bath
- 9.10 Lot (ac)
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