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Home  >  Sarasota  >  Central Sarasota  >  West of Trail

Sarasota Real Estate for Sale

West of Trail in Sarasota

The "West of Trail" area of Sarasota is named for the homes located west of Tamiami Trail in Sarasota to Sarasota Bay. From Mound Street south to Siesta Key Drive. Some even extend the area into The Landings and south to Stickly Point Road. Some of the most spectacular Bayfront homes in Sarasota are located here and all homes have the convenience of Southside Village, Sarasota Memorial Hospital, and the downtown Sarasota area including the waterfront surrounding Marina Jack. Of course, it is just a few minutes to one of the top beaches in the US, Siesta Key beach. Head the other direction across the John Ringling bridge, past Bird Key and the Sarasota Yacht Club and you find the internationally acclaimed St. Armand’s Circle.

West of Trail in Sarasota, Florida
West of Trail Sarasota Map Search
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The prime locations within the west of the trail area are the homes located west of Osprey Avenue which include subdivision names like Harbor Acres, McClellan Park, San Remo Estates, and Cherokee Park. Many of the homes are older and have been maintained and updated. Established landscaping and canopy lined streets are throughout.

From Osprey Avenue east to Tamiami Trail are homes that feature the same highly desirable area without the higher prices found in homes located on or near the water. There is a mix of older homes of character and residences are the results of recycling of home sites as found throughout the area. 

There are no large tracts of land to build on so the redevelopment tends to track as the older homes are brought to market. Gated communities, like Mandarin Park are rare here. Many of the higher priced homes on larger lots may also have their own gate and security.

Find Similar West of Trail Sarasota Homes for Sale
The latest Sarasota real estate sales west of trail
The latest market report for the west of the trail area of Sarasota, FL

Be sure to take a look at our similar home search to the right to get started or check back here for updates. We keep our MLS data within 15 minutes of changes so you are always assured the timeliest and complete listing information available. Registered buyers and sellers have the added benefit of receiving property updates, based on their specific criteria, of the newest listings, price changes, and recent sales.

We have been selling Sarasota real estate for nearly two decades. Our local knowledge and continued emphasis on professionalism is unmatched in the local market. We are always eager to answer your questions and look forward to your email or call. Objective #1 is for you to have both a smooth and rewarding transaction.

The Latest Sarasota West of Trail MLS Listings

1711 Kenilworth Street, Sarasota image
1711 Kenilworth Street, Sarasota $1,699,000

Welcome to 1711 Kenilworth Street, an exceptional opportunity to own a move-in-ready home in one of Sarasota’s most desirable West of the Trail neighborhoods. Located wit...

  • 4 Beds
  • 3 Baths
  • Kenilworth Estates SubDv.
  • 34231 Zip Code
1675 Landings Lane, Sarasota image
1675 Landings Lane, Sarasota $1,930,000

Virtually Staged. Tucked beneath a canopy of sweeping mature oaks in one of Sarasota's most coveted gated communities, this gracious two-story home strikes the perfect ba...

  • 5 Beds
  • 6 Baths
  • Landings SubDv.
  • 34231 Zip Code
1440 Kimlira Lane, Sarasota image
1440 Kimlira Lane, Sarasota $7,350,000

Located on approximately 200 feet of open Bay frontage in one of Sarasota's most prestigious neighborhoods, this remarkable property enjoys a postcard-worthy setting on m...

  • 4 Beds
  • 4 Baths
  • 34231 Zip Code
1555 Eastbrook Drive, Sarasota image
1555 Eastbrook Drive, Sarasota $4,250,000

Modern architecture reaches an extraordinary new level at 1555 Eastbrook Drive, a newly completed 2025 estate offering nearly 4,000 square feet of sophisticated single-le...

  • 5 Beds
  • 6 Baths
  • Kentwood Estates SubDv.
  • 34231 Zip Code
1386 Tangier Way, Sarasota image
1386 Tangier Way, Sarasota $16,000,000

Pre-Construction. To be built. Situated in San Remo Estates, one of Sarasota's most exclusive waterfront communities, this upcoming new construction home, designed and bu...

  • 4 Beds
  • 6 Baths
  • San Remo Estates SubDv.
  • 34239 Zip Code
3727 Tangier Terrace, Sarasota image
3727 Tangier Terrace, Sarasota $2,490,000

Welcome to a rare opportunity to own a spacious residence in the highly sought-after San Remo Estates, one of Sarasota's most desirable West of the Trail neighborhoods, i...

  • 4 Beds
  • 3 Baths
  • San Remo SubDv.
  • 34239 Zip Code
1838 Oleander Street, Sarasota image
1838 Oleander Street, Sarasota $3,295,000

Poised on one of the prettiest tree-lined West of Trail streets, this modern coastal residence offers the ideal blend of casual elegance, thoughtful design, and everyday ...

  • 4 Beds
  • 3 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1647 Siesta Drive, Sarasota image
1647 Siesta Drive, Sarasota $1,690,000

Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms w...

  • 5 Beds
  • 3 Baths
  • Bayview SubDv.
  • 34239 Zip Code
1372 Harbor Drive, Sarasota image
1372 Harbor Drive, Sarasota $14,950,000

This immaculate Sarasota Bay front estate is prominently positioned on the point of Harbor Drive. It embodies the pinnacle of luxury waterfront living, where timeless ar...

  • 4 Beds
  • 7 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
3921 Maravic Place, Sarasota image
3921 Maravic Place, Sarasota $2,100,000

Virtually Staged. Exceptional West of Trail location! Nestled on a quiet cul-de-sac, this beautifully updated home offers the perfect blend of modern style and everyday c...

  • 4 Beds
  • 3 Baths
  • Moller Sub SubDv.
  • 34231 Zip Code
1805 Goldenrod Street, Sarasota image
1805 Goldenrod Street, Sarasota $3,790,000

Welcome to this exceptional new construction, upgraded residence located West of Trail, featuring 5 bedrooms, 5 full bathrooms, and 3,640 square feet of thoughtfully cura...

  • 5 Beds
  • 5 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
1800 Webber Street, Sarasota image
1800 Webber Street, Sarasota $4,490,000

Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 b...

  • 4 Beds
  • 6 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code

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Central Sarasota West - 34239

  • Bay View Heights
  • Cherokee Park
  • Desota Park
  • Forest Lakes
  • Granada
  • Harbor Acres
  • Hartsdale
  • Hyde Park
  • La Linda Terrace
  • Loma Linda
  • Mandarin Park
  • McClellan Park
  • Orange Park
  • Poinsettia Park
  • San Remo Estates
  • South Gate
  • Village Green
  • West of Trail

Central Sarasota North - 34232

  • Bearded Oaks
  • Beechwood Estates
  • Brentwood
  • Colonial Oaks
  • Enclave at Forest Lakes
  • Forest Lakes
  • Hidden Oaks
  • Lakes Estates
  • Oak Vistas
  • Phillippi Pines
  • Ridgewood Estates
  • Sarasota Springs
  • Sherwood Forest
  • Tamaron
  • Whispering Oaks
  • Woodland Park

Central Sarasota South - 34233

  • Amberlea
  • Ashton Glen
  • Ashton Oaks
  • Ashton Palms
  • Casa del Sol
  • Center Gate
  • Country Manor
  • Country Place
  • Crestwood Villas
  • Emerald Gardens
  • Grove Pointe
  • Luna Bay
  • Magnolia Pond
  • McIntosh Lake
  • Oakleaf
  • Parkstone
  • Silver Leaf
  • Southfield
  • South Gate Ridge
  • Strathmore Villa
  • Stonehaven
  • Three Oaks
  • Villa Rosa

Nearby Sarasota Real Estate

  • Siesta Key
  • Downtown Sarasota
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  • Palmer Ranch
  • East of I-75
  • Mid-Town Sarasota

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