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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

1359 Tearose Place, Sarasota image
1359 Tearose Place, Sarasota $1,199,000

Welcome to Mandarin Park, one of Sarasota’s most desirable gated communities, where beautiful homes, privacy, and an unbeatable location come together in the heart of the...

  • 2 Beds
  • 2 Baths
  • Mandarin Park SubDv.
  • 34239 Zip Code
1622 Kenilworth Street, Sarasota image
1622 Kenilworth Street, Sarasota $3,595,000

Experience the best of Sarasota living in this exceptional West of Trail residence by Heritage Builders. Ideally positioned in the coveted Oyster Bay area near the histor...

  • 4 Beds
  • 5 Baths
  • Johnson Estates SubDv.
  • 34231 Zip Code
1712 Siesta Drive, Sarasota image
1712 Siesta Drive, Sarasota $549,900

Wonderful home! Was used as an AirBNB/VRBO for years and now it's available for you! Furniture negotiable. Walk to Southside Elementary school! Superior location in S...

  • 2 Beds
  • 1 Baths
  • Granada Park SubDv.
  • 34239 Zip Code
1585 South Drive, Sarasota image
1585 South Drive, Sarasota $2,300,000

Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and ...

  • 3 Beds
  • 4 Baths
  • Cherokee Park SubDv.
  • 34239 Zip Code
1960 Boyce Street, Sarasota image
1960 Boyce Street, Sarasota $3,895,000

Modern architecture, exceptional craftsmanship and resort-style outdoor living define this barely lived-in 2023-built contemporary residence. Offered furnished and immedi...

  • 4 Beds
  • 5 Baths
  • Hartsdale SubDv.
  • 34239 Zip Code
1621 Bay Point Court, Sarasota image
1621 Bay Point Court, Sarasota $5,885,000

Behind a private gate and beneath a canopy of tropical foliage, 1621 Bay Point Court offers a secluded waterfront retreat just moments from downtown Sarasota and the open...

  • 4 Beds
  • 5 Baths
  • Mooring At Bay Pointe The SubDv.
  • 34236 Zip Code
1722 North Drive, Sarasota image
1722 North Drive, Sarasota $2,690,000

Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity...

  • 3 Beds
  • 2 Baths
  • Cherokee Park SubDv.
  • 34239 Zip Code
5166 Kestral Park Terrace, Sarasota image
5166 Kestral Park Terrace, Sarasota $1,650,000

Virtually Staged. Welcome to 5166 Kestrel Park Terrace, an exceptional opportunity in the highly sought-after gated community of The Landings. Privately positioned on an ...

  • 4 Beds
  • 4 Baths
  • The Landings SubDv.
  • 34231 Zip Code
1740 S Orange Avenue, Sarasota image
1740 S Orange Avenue, Sarasota $5,500,000

Pre-Construction. To be built. UNDER CONSTRUCTION — HEMINGWAY LUXURY MODEL BY COURTYARD MODERN HOMES- OR BUILD TO SUIT STARTING AT $4,500,000.00 -- A striking new express...

  • 5 Beds
  • 6 Baths
  • Harbor Acres SubDv.
  • 34239 Zip Code
1907 Magnolia Street, Sarasota image
1907 Magnolia Street, Sarasota $1,495,000

Classic Sarasota charm takes on a fresh, sophisticated spirit in this beautifully updated residence, where relaxed interiors, thoughtful details and lush outdoor spaces c...

  • 3 Beds
  • 3 Baths
  • Poinsettia Park SubDv.
  • 34239 Zip Code
3606 Palonia Court, Sarasota image
3606 Palonia Court, Sarasota $2,299,000

Completely rebuilt from the ground up, this is a rare opportunity to own essentially new construction on one of the largest usable lots in Granada, one of Sarasota's most...

  • 3 Beds
  • 3 Baths
  • Granada SubDv.
  • 34239 Zip Code
2631 Puritan Terrace, Sarasota image
2631 Puritan Terrace, Sarasota $2,150,000

Welcome to this beautifully refreshed, single-story residence in Bay View Heights, one of Sarasota’s most coveted West of Trail neighborhoods. Set on a generous 15,625-sq...

  • 4 Beds
  • 4 Baths
  • Bay View Heights 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

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  • Siesta Key
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  • East of I-75
  • Mid-Town Sarasota

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