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 Older homes have been replaced by modern masterpieces.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 1954 Goldenrod Street W, Sarasota, FL 34239 (MLS # A4597295)
    $2,499,000
    Photo of 1954 Goldenrod Street W, Sarasota, FL 34239 (MLS # A4597295)
    Photo of 1954 Goldenrod Street W, Sarasota, FL 34239 (MLS # A4597295)
    31
     
    1954 Goldenrod Street W, Sarasota, FL
    1954 Goldenrod Street W
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 3,606 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  2. Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4606798)
    $2,495,000
    Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4606798)
    Photo of 1690 Arlington Street, Sarasota, FL 34239 (MLS # A4606798)
    1690 Arlington Street, Sarasota, FL
    1690 Arlington Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 2,965 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  3. Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4597473)
    $2,199,000
    Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4597473)
    Photo of 1647 Siesta Drive, Sarasota, FL 34239 (MLS # A4597473)
    1647 Siesta Drive, Sarasota, FL
    1647 Siesta Drive
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  4. 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
    • 3,272 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  5. Photo of 1713 North Drive, Sarasota, FL 34239 (MLS # A4584795)
    $2,100,000
    Photo of 1713 North Drive, Sarasota, FL 34239 (MLS # A4584795)
    Photo of 1713 North Drive, Sarasota, FL 34239 (MLS # A4584795)
    1713 North Drive, Sarasota, FL
    1713 North Drive
    Sarasota, FL
    • 4 Beds
    • 4 Baths
    • 3,227 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  6. Photo of 1912 High Point Drive, Sarasota, FL 34236 (MLS # D6136333)
    $1,975,000
    Photo of 1912 High Point Drive, Sarasota, FL 34236 (MLS # D6136333)
    Photo of 1912 High Point Drive, Sarasota, FL 34236 (MLS # D6136333)
    1912 High Point Drive, Sarasota, FL
    1912 High Point Drive
    Sarasota, FL
    • 3 Beds
    • 4 Baths
    • 1,941 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  7. Photo of 1954 Datura Street, Sarasota, FL 34239 (MLS # A4571231)
    $1,899,000
    Photo of 1954 Datura Street, Sarasota, FL 34239 (MLS # A4571231)
    Photo of 1954 Datura Street, Sarasota, FL 34239 (MLS # A4571231)
    1954 Datura Street, Sarasota, FL
    1954 Datura Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,763 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  8. Photo of 1919 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4610040)
    $1,875,000
    Photo of 1919 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4610040)
    Photo of 1919 Bougainvillea Street, Sarasota, FL 34239 (MLS # A4610040)
    1919 Bougainvillea Street, Sarasota, FL
    1919 Bougainvillea Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 2,556 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  9. Photo of 866 Hudson Avenue #866, Sarasota, FL 34236 (MLS # D6135650)
    $1,849,000
    Photo of 866 Hudson Avenue #866, Sarasota, FL 34236 (MLS # D6135650)
    Photo of 866 Hudson Avenue #866, Sarasota, FL 34236 (MLS # D6135650)
    866 Hudson Avenue #866, Sarasota, FL
    866 Hudson Avenue #866
    Sarasota, FL
    • 4 Beds
    • 3 Baths
    • 2,293 Home (sqft)
    • 3 Baths
    • 37,898 Lot (sqft)
  10. Photo of 1966 Hyde Park Street, Sarasota, FL 34239 (MLS # A4595835)
    $1,749,000
    Photo of 1966 Hyde Park Street, Sarasota, FL 34239 (MLS # A4595835)
    Photo of 1966 Hyde Park Street, Sarasota, FL 34239 (MLS # A4595835)
    1966 Hyde Park Street, Sarasota, FL
    1966 Hyde Park Street
    Sarasota, FL
    • 5 Beds
    • 4 Baths
    • 3,321 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  11. Photo of 1723 Bay Street, Sarasota, FL 34236 (MLS # A4605684)
    $1,699,000
    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)
  12. Photo of 1751 Floyd Street, Sarasota, FL 34239 (MLS # A4598261)
    $1,600,000
    Photo of 1751 Floyd Street, Sarasota, FL 34239 (MLS # A4598261)
    Photo of 1751 Floyd Street, Sarasota, FL 34239 (MLS # A4598261)
    1751 Floyd Street, Sarasota, FL
    1751 Floyd Street
    Sarasota, FL
    • 4 Beds
    • 5 Baths
    • 2,881 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  13. 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)
  14. 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
    • 2,560 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  15. Photo of 1737 Bay Street, Sarasota, FL 34236 (MLS # A4581318)
    $1,375,000
    Photo of 1737 Bay Street, Sarasota, FL 34236 (MLS # A4581318)
    Photo of 1737 Bay Street, Sarasota, FL 34236 (MLS # A4581318)
    1737 Bay Street, Sarasota, FL
    1737 Bay Street
    Sarasota, FL
    • 3 Beds
    • 3 Baths
    • 1,896 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  16. 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)
  17. Photo of 858 Hudson Avenue #858, Sarasota, FL 34236 (MLS # A4589406)
    $1,200,000
    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)
  18. Photo of 1938 High Point Drive, Sarasota, FL 34236 (MLS # A4566910)
    $1,200,000
    Photo of 1938 High Point Drive, Sarasota, FL 34236 (MLS # A4566910)
    Photo of 1938 High Point Drive, Sarasota, FL 34236 (MLS # A4566910)
    1938 High Point Drive, Sarasota, FL
    1938 High Point Drive
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,164 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  19. Photo of 1881 Orchid Street, Sarasota, FL 34239 (MLS # A4600271)
    $999,999
    Photo of 1881 Orchid Street, Sarasota, FL 34239 (MLS # A4600271)
    Photo of 1881 Orchid Street, Sarasota, FL 34239 (MLS # A4600271)
    1881 Orchid Street, Sarasota, FL
    1881 Orchid Street
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,710 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  20. 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)
  21. Photo of 1368 Tearose Place, Sarasota, FL 34239 (MLS # A4604753)
    $950,000
    Photo of 1368 Tearose Place, Sarasota, FL 34239 (MLS # A4604753)
    Photo of 1368 Tearose Place, Sarasota, FL 34239 (MLS # A4604753)
    1368 Tearose Place, Sarasota, FL
    1368 Tearose Place
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 1,542 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  22. Photo of 1966 Wisteria Street, Sarasota, FL 34239 (MLS # A4605409)
    $849,900
    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)
  23. Photo of 1629 Siesta Drive, Sarasota, FL 34239 (MLS # T3522999)
    $799,000
    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)
  24. Photo of 852 Hudson Avenue #852, Sarasota, FL 34236 (MLS # A4597488)
    $799,000
    Photo of 852 Hudson Avenue #852, Sarasota, FL 34236 (MLS # A4597488)
    Photo of 852 Hudson Avenue #852, Sarasota, FL 34236 (MLS # A4597488)
    852 Hudson Avenue #852, Sarasota, FL
    852 Hudson Avenue #852
    Sarasota, FL
    • 3 Beds
    • 2 Baths
    • 1,579 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. 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)
  26. 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)
  27. Photo of 850 S Tamiami Trail #801, Sarasota, FL 34236 (MLS # A4606628)
    $399,900
    Photo of 850 S Tamiami Trail #801, Sarasota, FL 34236 (MLS # A4606628)
    Photo of 850 S Tamiami Trail #801, Sarasota, FL 34236 (MLS # A4606628)
    850 S Tamiami Trail #801, Sarasota, FL
    850 S Tamiami Trail #801
    Sarasota, FL
    • 2 Beds
    • 2 Baths
    • 980 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  28. Photo of 850 S Tamiami Trail #624, Sarasota, FL 34236 (MLS # A4606550)
    $399,900
    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)
  29. Photo of 850 S Tamiami Trail #424, Sarasota, FL 34236 (MLS # T3505304)
    $399,500
    Photo of 850 S Tamiami Trail #424, Sarasota, FL 34236 (MLS # T3505304)
    Photo of 850 S Tamiami Trail #424, Sarasota, FL 34236 (MLS # T3505304)
    850 S Tamiami Trail #424, Sarasota, FL
    850 S Tamiami Trail #424
    Sarasota, FL
    • 2 Beds
    • 3 Baths
    • 1,224 Home (sqft)
    • 3 Baths
    • 9.11 Lot (ac)
  30. Photo of 850 S Tamiami Trail #831, Sarasota, FL 34236 (MLS # A4592498)
    $399,000
    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)
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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 5/27/24 11:11 AM PDT.

This MLS IDX is (c) Diverse Solutions 2024.

 
 

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