Cherokee Park, Sarasota

cherokee-park-homes-for-saleCherokee Park is an original old “West of the Trail” Sarasota neighborhoods. An enchanted area of Sarasota with its tree lined streets is complete with waterfront and canal-front residences along Sarasota Bay.

Have you dreamed of looking out your window and seeing the sparkling waters of the Sarasota Bay? If so, Cherokee Park homes might be the perfect oasis for you to call home. Located just north of Siesta Drive, Cherokee Park is one of the oldest neighborhoods in Sarasota. While it was established in the roaring 20s, most of the homes were built after WWII, and almost all of them have been updated to fit with today’s busy and luxurious lifestyles.

Browse listings below or read more about homes for sale in Cherokee Park, Sarasota.

Cherokee Park Real Estate Listings

All Listings Over $1,000,000
1 – 2 of 2 Listings
Price, High to Low

6 Bed • 6 Bath • 5,944 Sf • 1 Acres


1562 South Drive, SARASOTA

Arguably, One Of The Most Classic And Unique Homes To Come On The Market In Sarasota County In Years. Located On A Double Lot (almost 3/4 Of An Acr...

View Listing

4 Bed • 4 Bath • 3,224 Sf


1723 South Drive, SARASOTA

Beautiful, Sprawling Ranch In The Much Sought-after Cherokee Park Neighborhood, West Of The Trail. This Charming Four-bedroom, Three-and-a-half-bat...

View Listing


Register with to get unlimited access to listings in sunny Sarasota, mark your favorite listings, save custom searches, request showings, and get the latest listings that fit your criteria emailed to you.

Register Now

More on Cherokee Park, Sarasota, FL

Cherokee Park homes for sale offer quiet and historic surroundings boasting a diversity of architectural styles, ranging from boom time revival to post World War II modern. The stately Florida mansions that were built here in the 1950’s and 1960’s on the community’s palm-lined roads add an architectural style that defines the growth years in Sarasota after the Second World War.

Offered starting in the $800Ks and extending up into the millions, the homes in Cherokee Bay range from Old World to more modern styles. Many are situated right on the Bay, so you will be able to hop on your boat and head into the Gulf without ever getting in your car. Amenities vary, but many homes have private pools, upgraded kitchens, Spanish tile, crown molding and other special touches that today’s discerning buyer is looking for.

While every home in Cherokee Park is unique, here are some amenities that you might enjoy:

  • You’ll be close to the beach; Siesta Key, Lido Key and Bird Key are all just minutes away via bridges across the Bay.
  • Proximity to the downtown area, where you can take advantage of a variety of dining, shopping and entertainment options.
  • Special touches that make your home feel like a haven. From upgrades in the kitchens and bathrooms, to high-quality flooring and molding, your home is teeming with luxury.
  • An eclectic neighborhood packed with historical charm.

Amenities Near Cherokee Park Homes For Sale

When you live in Cherokee Park, you’ll be close to the action of downtown Sarasota, but not so close that you’ll be bothered by traffic or city noise. Grab lunch at the very nearby and aptly named Oasis Cafe, catch a show at the Van Wezel, and be back in plenty of time to watch the sunset from your own private lanai. Excellent medical facilities and a good school system are also within easy reach. If you’re ready to explore neighboring areas, you’ll be happy to know that you can get to Tampa in about an hour, and the high-excitement attractions of Orlando are only about two hours away by car.

A History of Cherokee Park Real Estate

The history of Cherokee Park real estate, which is separated from Osprey Avenue by a stucco wall and gate posts with decorative tile work depicting a Cherokee rose, the subdivision was originally platted in 1926. Developer J.C. Brown’s vision for Cherokee Park was a neighborhood filled with homes designed in the Spanish, Moorish, or Italian styles of architecture. Due to the magnitude of the real estate bust of the late 1920’s, his dream was never realized. As of 1937, there were only 3 homes built in the community. Browns original home named Cherokee Lodge was demolished in 1962 to make way for the bay front properties that exist today.

In 1940, the western portion of the Cherokee Park development was re-platted in order to include South, West and North West drives and a strip of land was set aside for a park along the bay front. Later, this bay front park was sold and subdivided, along with the 12 acres occupied by J.C Browns original home.

Southside Village restaurants such as Libby’s, Sam Snead’s on Hyde Park are within walking distance This favorite “hang out” of the locals also boasts Morton’s Gourmet Market as well as many trendy watering holes well suited to the atmosphere and generation living in the area.

Want to Learn More About Real Estate In Sarasota?

Tamara Berryman can help you find your dream home in Sarasota, Florida.
Call 941.954.0900 or contact Tamara online for a free consultation.

Contact Tamara

Back to communities

^ Back to top of Cherokee Park, FL real estate

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on January 17th, 2021 at 2:35am CST.

Have a Question?

Contact Us

Follow Us