Cherokee Park

Cherokee Park Real Estate for Sale – Sarasota, Florida 34239

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.

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.

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# A4638710 - Status: Active View Property Details Add to Favorites View Map

1686 NORTH DR
Price: $5,450,000
Zip Code: 34239
6128 Square Feet
Subdivision: CHEROKEE PARK 2
Bedrooms: 5 Baths: 5+
Welcome to this stunning 2021-built home in one of Sarasota's most iconic and picturesque historic neighborhoods, Cherokee Park. Offering luxurious living with thoughtful design, this spacious residence of over 6000 square feet features a desirable f ... Read More
Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# TB8358611 - Status: Active View Property Details Add to Favorites View Map

1774 CHEROKEE DR
Price: $4,950,000
Zip Code: 34239
3965 Square Feet
Subdivision: CHEROKEE PARK 2
Bedrooms: 4 Baths: 3+
Don't miss this rarely available Cape Cod style home, full of warmth & character, nestled in the highly desirable Cherokee Park neighborhood. This 4-bedroom, 3 full/2 half bathroom home blends timeless elegance with modern luxury. Situated in a top-r ... Read More
Listing courtesy of: FLAT FEE MLS REALTY

MLS# A4643287 - Status: Active View Property Details Add to Favorites View Map

1744 SOUTH DR
Price: $3,500,000
Zip Code: 34239
4696 Square Feet
Subdivision: CHEROKEE PARK 2
Bedrooms: 5 Baths: 4+
The historic McKaig House built by Sarasota originals Logan and Currin sits on over half an acre and is one of the few remaining crown jewels of Cherokee Park. The home has been impeccably maintained keeping as much of the 1930s character and materia ... Read More
Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4626080 - Status: Active View Property Details Add to Favorites View Map

1585 SOUTH DR
Price: $2,750,000
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: $2,230,000
Zip Code: 34239
3227 Square Feet
Subdivision: CHEROKEE PARK 2
Bedrooms: 4 Baths: 3+
Historic Cherokee Park: This prime, "West of the Trail" property with oak-lined boulevard streets and decorative light posts is located near Southside Village. At 20 feet elevation, this property has NO HISTORY OF FLOODING. Situated on a picturesque ... Read More
Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4629543 - Status: Active View Property Details Add to Favorites View Map

1616 NORTH DR
Price: $2,100,000
Zip Code: 34239
2839 Square Feet
Subdivision: CHEROKEE PARK
Bedrooms: 3 Baths: 3
One or more photo(s) has been virtually staged. Welcome to 1616 North Drive, fourth in from the Bay and the lowest price in coveted CHEROKEE PARK. EXCELLENT LOCATION to build a new home or update the existing home on this 100' x 150' (15,000 Sq. Ft.) ... Read More
Listing courtesy of: RE/MAX ALLIANCE GROUP