Cherokee Park

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Cherokee Park Real Estate for Sale – Sarasota, Florida 34239

Cherokee Park

Cherokee Park is a posh residential property with a long and colorful history in the Sarasota Florida real estate market. Many of the ninety-four residences here are durable mansions built during the heydays of the 1950s and the 1960s. The interior features of these homes have been extensively renovated or updated. Notably, the coast of Sarasota Bay is adjacent to the western perimeter of this community, and as such, this particular area counts among the premier Sarasota waterfront real estate properties.

There’s a rich mix of architectural designs among the residences in the community. Some are in Italian, Moorish, and Spanish Mediterranean styles, the theme that the original developer J.C. Brown wanted to strictly adhere to when he set out to develop this property during the 1920s. There are Florida ranch-style houses in the neighborhood, too, as well as tastefully upgraded estates and homes with contemporary architecture.

Cherokee Park

Indisputably upscale, this community is also host to off-the-waterfront properties that are priced just below the million-dollar level. These residences can land in a list of Sarasota homes for sale with price tags from the $800s to the $900s for a home averaging 2,700 square feet and three bedrooms. Beyond the six-figure values, a pool home constructed in 2006 having three bedrooms within its 4,600 square feet can have a starting price around the $2.4 million level.

Among Sarasota waterfront homes for sale, an elite listing at Cherokee Park can have a quoted price around the $5.9 mark. Its basic features of four bedrooms in a total floor area of 7,400 square feet are but for starters. The property’s highlights include a heavily wooded total area of 1.3 acres and an impressive boathouse at its 200-foot direct bay front.

Cherokee Park

The opulence and elegance of these homes are matched by the rich mix of lifestyle possibilities around Cherokee Park’s immediate vicinity. Water-based activities are conveniently accessible with the community’s proximity to the Gulf Coast and its attractions like the famous white-sand beaches of Siesta Key. The land-based points of interest near the neighborhood are as exquisite with its strategic location west of the Tamiami Trail.

These life and leisure offerings are led by the arts and cultural delights of downtown Sarasota to include the Asolo Theater and the Van Wezel Performing Arts Hall. Main Street Merchants and St. Armands Circle, both only a few minutes’ drive north of the property, provide chic venues for dining and shopping. Within a few miles radius from the community too are the life and leisure alternatives of golf and country clubs like Bobby Jones and Prestancia which add up to making Cherokee Park much more than an outstanding Sarasota waterfront real estate property.


Cherokee Park Real Estate for Sale

Below are all of the current real estate listings available for sale at Cherokee Park.

Please contact us 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: $2,460,000
  • 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
  • School day, School day...I want to be in A-rated Southside School...Day!" Location, location, location in the Southside Village neighborhood! This distinctive home is set on a fully fenced 15,000 SF (100 ft X 150 ft) homesite located West of Trail in ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY