Cherokee Park

Listings For SaleSold History and Market Report

Cherokee Park Real Estate for Sale – Sarasota, Florida 34239

Cherokee Park Map

Cherokee Park is another old Sarasota development “West of The Trail”. Cherokee Park is located south of McClellan Park and three blocks north of Siesta Drive. Cherokee Park remains one of Sarasota’s most desirable communities complete with water-front and canal-front residences along Sarasota Bay.

This quiet, Sarasota hallmark community boasts a diversity of architectural styles, ranging from boom time revival to post World War II modern. The stately Florida mansions built here in the 50’s and 60’s on the community’s palm-lined roads add an architectural style that defines the growth years in Sarasota after the Second World War.

Cherokee Gate Post

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.

Cherokee Park Map

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 Big Sugar, Knick’s Tavern and Sam Snead’s on Hyde Park are a two minute drive from Cherokee Park. 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.


Cherokee Park Homes for Sale

Below you will find the current listings of homes and real estate currently for sale in Cherokee Park.

Please contact me if you would like to schedule a tour of any of the listed properties.

MLS# A4588632 - Status: Active View Property Details Add to Favorites View Map

  • 3000 SOUTHWEST DR
  • Price: $14,950,000
  • Zip Code: 34239
  • 8125 Square Feet
  • Subdivision: CHEROKEE PARK 2
  • Bedrooms: 5 Baths: 5+
  • Discover the perfect blend of elegance and privacy on this 1.6-acre estate nestled within Cherokee Park, one of the most sought-after mainland neighborhoods in Sarasota. Tucked away on a small street at the end of Southwest Drive, this double lot est ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4584482 - Status: Active View Property Details Add to Favorites View Map

  • 1655 SOUTH DR
  • Price: $5,985,000
  • Zip Code: 34239
  • 6355 Square Feet
  • Subdivision: CHEROKEE PARK
  • Bedrooms: 5 Baths: 5+
  • Located in one of the most sought-after West of Trail neighborhoods in Sarasota, Cherokee Park, encounter a testament to a bespoke luxury lifestyle, with every detail considered for an exceptional living experience in this extraordinary 5BR/5 full BA ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4597458 - Status: Active View Property Details Add to Favorites View Map

  • 1715 SOUTH DR
  • Price: $3,400,000
  • Zip Code: 34239
  • 3517 Square Feet
  • Subdivision: CHEROKEE PARK 2
  • Bedrooms: 4 Baths: 4
  • Welcome to 1715 South Drive in Cherokee Park, one of the most sought-after "west of Trail" neighborhoods in Sarasota admired for its large lots, boulevard style streets with sidewalks and 100-year-old oak trees. Straight out of the pages of Southern ... Read More
  • Listing courtesy of: COMPASS FLORIDA LLC

MLS# A4597828 - Status: Active View Property Details Add to Favorites View Map

  • 1585 SOUTH DR
  • Price: $2,900,000
  • Zip Code: 34239
  • 2764 Square Feet
  • Subdivision: CHEROKEE PARK 2
  • Bedrooms: 3 Baths: 3+
  • This Cherokee Park home offers an idyllic blend of elegance and comfort. Ideally located just west of Southside Elementary, this neighborhood is a stone's throw from Southside Village, Sarasota Memorial Hospital, and the vibrant heart of downtown Sar ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4584795 - Status: Active View Property Details Add to Favorites View Map

  • 1713 NORTH DR
  • Price: $2,470,000
  • Zip Code: 34239
  • 3227 Square Feet
  • Subdivision: CHEROKEE PARK 2
  • Bedrooms: 4 Baths: 3+
  • Rarely available property in Cherokee Park: In this prime location, this home is fully up to code, meticulously maintained and move-in ready. Situated on a picturesque lot, this home with guest house boasts privacy and tranquility; surrounded by matu ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4596043 - Status: Active View Property Details Add to Favorites View Map

  • 1763 SOUTH DR
  • Price: $2,300,000
  • Zip Code: 34239
  • 2256 Square Feet
  • Subdivision: CHEROKEE PARK 2
  • Bedrooms: 3 Baths: 2
  • Location, location, location! This distinctive home is set on a fully fenced 15,000 SF (100 ft X 150 ft) homesite located West of Trail in picturesque Cherokee Park. Upon entering you will be amazed at how light and bright each room feels. This three ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY