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Cherokee Park Homes for Sale

For those looking “West of Trail”, finding a home in Cherokee Park says that yes, you have arrived!  Cherokee Park offers a diverse example of the finest architecture and construction in spirit of the old Florida lifestyle.  It is located from west of Osprey Avenue to Sarasota Bay. The streets include North Drive, Cherokee Drive, South Drive, Old Oak Drive and North and South Lodge Drives. A drive down Cherokee Drive reveals a wide divided tree lined street with homes situated on large lots and mature old oaks. The development was originally established in the mid 1920’s. Homes are set back quite a bit from the road by Florida’s standards.  Upon turning off of Osprey Avenue, you instantly know this is one of Sarasota’s Grand Neighborhoods.

You may notice that out of the seventy-five homes that might be for sale, homes were built as early as 1925 or as new as 2009.  Be assured the affluent owners here have kept these homes to the highest of standards. Some of the older homes are preserved with integrity and can have all the current upgrades completed to the exacting standards you would expect.   Home sizes range from under 2,000 square feet to almost 9,000 square feet.  A select few homeowners with the resources will enjoy breathtaking full bay views including Siesta Key and Bird Key to the west.

Lot sizes are generally rectangular and vary from 15,000 to 30,000+ square feet.  The few irregular bay front lots can be an acre or more.

The schools for Cherokee Park are Southside Elementary, Brookside Middle and Sarasota High School.

If Cherokee Park is on your radar, we suggest getting informed about recent sales and take a look at our real estate analysis for the neighborhood. Tight knit, smaller communities can require a working knowledge of the local market. Age and proximity to the bay or major routes can play a large role when it comes to value. 

We have been selling Sarasota real estate for nearly two decades and are the local experts in the Sarasota Real Estate Market.  If Cherokee Park or West of Trail Real Estate and the surrounding area is for you, we know the Sarasota Real Estate market and welcome the opportunity to work for you. Real estate success requires knowledge and our name says it all.