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You are here: Home / Cherokee Park Sarasota Homes for Sale | West of the Trail

Cherokee Park Sarasota Homes for Sale | West of the Trail


Cherokee Park Sarasota Homes for Sale
Located within Sarasota’s highly sought-after West of the Trail neighborhoods, Cherokee Park is one of the city’s most distinguished residential enclaves. Established in the 1920s, this historic neighborhood is known for its stately estates, waterfront setting, and timeless architectural character. Situated north of Spring Creek Drive and west of Osprey Avenue, Cherokee Park extends to Sarasota Bay and includes
a scenic canal that provides direct boating access to the Bay and the Gulf of Mexico.

Cherokee Park functions as both a neighborhood district and a formal subdivision. With fewer than 100 residences, the community offers an exceptional sense of privacy and exclusivity. Homes here reflect a wide range of classic architectural styles, including Southern Plantation, Old Florida, Key West, and Mediterranean estates. Many properties are considered architecturally significant, with several recognized or eligible for historic designation.

Homes in Cherokee Park are typically situated on generously sized lots, many measuring half an acre or more. Mature trees, lush landscaping, and wide sidewalks contribute to the neighborhood’s refined and established atmosphere. Select properties offer deep-water access, private docks, bayfront views, and outdoor living features that take full advantage of Sarasota’s waterfront lifestyle. Latest pricing at Cherokee Park Sarasota Florida will be found below if there is inventory.

The location of Cherokee Park adds to its enduring appeal. Residents enjoy close proximity to Nora Patterson Bay Island Park, downtown Sarasota, and the cultural and dining districts south of Sarasota Memorial Hospital. Siesta Key Beach is just minutes away, making it easy to enjoy Sarasota’s renowned coastline while living in one of the city’s most prestigious neighborhoods.

Homes for Sale at Cherokee Park in Sarasota

3000 SOUTHWEST DRIVE SARASOTA FL 34239
New Listing - 3 weeks on site
1 / 71
$13,250,000
Single Family Residence For Sale
Active
5
BEDS
7
TOTAL BATHS
8,125
SQFT
3000 SOUTHWEST DRIVE
SARASOTA, FL 34239
CHEROKEE PARK Subdivision
2177 SUNNYSIDE PLACE SARASOTA FL 34239
1 / 100
$2,799,000
Single Family Residence For Sale
Active
4
BEDS
6
TOTAL BATHS
4,624
SQFT
2177 SUNNYSIDE PLACE
SARASOTA, FL 34239
HIBISCUS PARK 2 Subdivision
1610 N LODGE DRIVE SARASOTA FL 34239
1 / 30
$11,500,000
Single Family Residence For Sale
Active
5
BEDS
8
TOTAL BATHS
7,110
SQFT
1610 N LODGE DRIVE
SARASOTA, FL 34239
CHEROKEE LODGE Subdivision
1620 N LODGE DRIVE SARASOTA FL 34239
1 / 27
$4,900,000
Single Family Residence For Sale
Active
5
BEDS
4
TOTAL BATHS
4,660
SQFT
1620 N LODGE DRIVE
SARASOTA, FL 34239
CHEROKEE LODGE Subdivision
1740 WISCONSIN LANE SARASOTA FL 34239
1 / 29
$475,000
Land For Sale
Active
0.12
ACRES
SARASOTA
COUNTY
1740 WISCONSIN LANE
SARASOTA, FL 34239
BAYVIEW Subdivision
1740 WISCONSIN LANE SARASOTA FL 34239
1 / 29
$475,000
Single Family Residence For Sale
Active
1
BED
1
TOTAL BATH
576
SQFT
1740 WISCONSIN LANE
SARASOTA, FL 34239
BAYVIEW Subdivision

Frequently Asked Questions About Cherokee Park in Sarasota

Where is Cherokee Park located in Sarasota?

Cherokee Park is located in the highly desirable West of the Trail area of Sarasota, just west of Osprey Avenue and north of Spring Creek Drive. The neighborhood extends to Sarasota Bay and includes canal-front homes with boating access.

Is Cherokee Park a historic neighborhood?

Yes. Cherokee Park dates back to the 1920s and is considered one of Sarasota’s most historic residential districts. Several homes are historically significant, and many properties reflect preserved architectural styles from Sarasota’s early development years.

What types of homes are found in Cherokee Park?

Homes in Cherokee Park include Southern Plantation estates, Old Florida residences, Mediterranean mansions, Key West–style homes, and custom waterfront properties. Each home is unique, and there is no cookie-cutter construction in the neighborhood.

Are there waterfront and boating homes in Cherokee Park?

Yes. Cherokee Park includes both bayfront and canal-front homes. Many properties offer private docks with direct access to Sarasota Bay and the Gulf of Mexico without fixed bridges, making the neighborhood highly appealing to boaters.

How large are the lots in Cherokee Park?

Lot sizes in Cherokee Park are typically generous, with many properties situated on half-acre parcels or larger. Mature trees, landscaped grounds, and wide setbacks contribute to the neighborhood’s private and estate-like feel.

Do homes in Cherokee Park require flood insurance?

Flood insurance requirements vary by property. Some homes are located on elevated ground and may not require flood insurance, while waterfront and canal-front homes typically do. Buyers should review flood zone maps and insurance requirements for individual properties.

What amenities are nearby?

Cherokee Park is close to Nora Patterson Bay Island Park, downtown Sarasota, and the dining and shopping districts near Sarasota Memorial Hospital. Siesta Key Beach is only a short drive or bike ride away.

How often do homes come on the market in Cherokee Park?

Homes in Cherokee Park are rarely available. Many owners hold their properties for long periods, and listings tend to attract strong interest due to the neighborhood’s location, character, and waterfront access.

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