There are 94 houses in the exclusive west of the trail neighborhood of Cherokee Park. Its location, just south of downtown Sarasota and close to the hospital district, makes this bayfront neighborhood popular with doctors and professionals.
Most of the houses in this historic community have been renovated or rebuilt. Wide, quiet streets and sidewalks are lined with mature oak trees and tropical vegetation. The rich history dates back to 1926 when the neighborhood was platted.
There are a wide range of architectural styles - traditional, Mediterranean and even a few contemporary. Homes range in size from 1800 to over 8000 square feet. Prices range from the $700,000s for interior properties to over $8,000,000 for luxurious bayfront estates.
To learn more about any of these listings or receive email updates when new properties hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!
… Read More| Total Listings: | 7 |
| Average Price: | $4,983,571 |
| Highest Price: | $11,500,000 |
| Lowest Price: | $2,000,000 |
| Average Size: | 5,233 ft² |
| Average Price Per Square Foot: | $1,115 per ft² |
Neighborhoods
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Stunning Waterfront Three Story, Coastal Modern, Single-family Waterfront Home Is The Perfect Blend Of Comfort And Luxury Located In The Treasured Cherokee Park Neighborhood. Nestled On A Street Adorned With Majestic Oak And Canopy Trees, This Exc...
First Time Available In 40 Years! "tween Bridges" Is A Rare Bayfront Property Located In Highly Sought-after Cherokee Park, West Of Trail. This 4-bedroom,3.5 Bath Residence Offers Unobstructed Panoramic Views Of Sarasota Bay. The Breathtaking Su...
One Or More Photo(s) Has Been Virtually Staged. In Sarasota's Desired West Of Trail Enclave Of Cherokee Park, 1655 South Drive, Masterfully Designed Three-story Estate Where Thoughtful Architecture Meets Effortless Luxury. Positioned On A Homesite...
A Timeless Expression Of Spanish Mediterranean Elegance Set Along Tranquil Waterfront. Welcome To 1634 N Lodge Drive. Perfectly Positioned In One Of Sarasota’s Most Coveted Neighborhoods, This Exceptional Canal-front Estate Blends Old-world Archi...
One Or More Photo(s) Has Been Virtually Staged. Tucked Beneath A Canopy Of Mature Trees In One Of Sarasota’s Most Coveted Neighborhoods, 1714 South Drive Presents A Rare Opportunity To Secure A Prime Homesite In Cherokee Park, West Of The Trail An...
This Exceptional 100x200 Lot In Historic Cherokee Park Awaits Your Dream Home, With Fergeson Brothers Design/construction As The Designated Builder; This West-of-the-trail Neighborhood Is Located On Sarasota Bay In The City Of Sarasota; The Adjo...
An Exceptional 100x200 Lot In Historic Cherokee Park Awaits Your Dream Home, With Fergeson Brothers Design/construction As The Designated Builder; This West-of-the-trail Neighborhood Is Located On Sarasota Bay In The City Of Sarasota; The Adjoini...
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Listing data comes from My Florida Regional MLS DBA Stellar MLS.
Listing information last updated on May 16th, 2026 at 1:53pm EDT.
Neighborhood Information
There are 94 houses in the exclusive west of the trail neighborhood of Cherokee Park. Its location, just south of downtown Sarasota and close to the hospital district, makes this bayfront neighborhood popular with doctors and professionals.
Most of the homes in this historic community have been renovated or rebuilt. Wide, quiet streets and sidewalks are lined with mature oak trees and tropical vegetation. The rich history dates back to 1926 when the neighborhood was platted.
There are a wide range of architectural styles - traditional, Mediterranean and even a few contemporary. Homes range in size from 1800 to over 8000 square feet. Prices range from the $700,000s for interior houses to over $8,000,000 for luxurious bayfront estates.
Do you have any questions or need more information? Contact me today at 941-544-6467 or use the form at the bottom of the page so we can talk about your real estate needs.
