Cherokee Park
Old Sarasota Character, Tree-Lined Streets, and Timeless Neighborhood Appeal.
Sarasota West of Trail Neighborhood Guide - Updated October 2026
Cherokee Park is an established West of Trail neighborhood in Sarasota, Florida (zip code 34239)[cite: 1]. Located south of downtown and west of Tamiami Trail (US-41), single-family homes range from $1,200,000 to over $3,500,000[cite: 1]. The community feeds into Southside Elementary School and features mature oak canopies minutes from Siesta Key[cite: 1].
Compare active West of Trail single-family listings, Southside Elementary school boundary zoning, and lot values with luxury specialist Kim Ogilvie.
West of Trail Residential Heritage
Cherokee Park stands as one of Sarasota's most beloved residential enclaves within the broader West of Trail corridor[cite: 1]. Positioned south of downtown Sarasota and west of Tamiami Trail (US-41), the neighborhood preserves an authentic residential feel defined by mature banyan and oak trees, generous lot setbacks, and quiet, walkable streets[cite: 1].
The housing stock blends post-war Florida ranch homes, solid concrete block construction, and tastefully renovated coastal bungalows alongside bespoke modern luxury infill residences[cite: 1]. Its location provides direct convenience to Morton's Gourmet Market, Sarasota Memorial Hospital, downtown cultural arts venues, and Siesta Key beaches[cite: 1].
Submarket Architecture
Real estate options in Cherokee Park encompass varied architectural eras and lot configurations across the West of Trail market[cite: 1]:
1950s and 1960s single-story concrete block homes and Florida ranch layouts set on shaded 1/4 to 1/3-acre parcels[cite: 1]. Highly sought after for extensive interior modernization or lot redevelopment[cite: 1]. View Original Home Options →
Expanded mid-century homes featuring open floor plans, updated gourmet kitchens, custom swimming pools, and modernized hurricane-impact glass while preserving exterior canopy charm[cite: 1]. View Renovated Properties →
Bespoke custom homes built to modern elevation and hurricane standards[cite: 1]. Incorporates coastal transitional and West Indies architecture tailored to human-scale neighborhood proportions[cite: 1]. Explore High-End Deal Process →
Substantial lot dimensions featuring deep setbacks and mature canopy foliage, supporting extensive outdoor living spaces and detached guest suites[cite: 1]. View Lot Availability →
Market Intelligence
A multi-variable comparison of valuation figures, location logistics, and district zoning across Cherokee Park[cite: 1]:
Category / Benchmark | Cherokee Park Data Metric | Sarasota West of Trail Context |
|---|---|---|
Single-Family Price Range | $1,200,000 – $3,500,000+[cite: 1] | Accessible entry point relative to bayfront Harbor Acres ($5M+)[cite: 1] |
Primary Zip Code | 34239[cite: 1] | Core South Sarasota West of Trail residential zip code[cite: 1] |
Primary Elementary School | Southside Elementary School[cite: 1] | Highly rated FLDOE "A" rated neighborhood elementary school[cite: 1] |
Drive Time to Downtown Sarasota | 5–10 Minutes[cite: 1] | Direct access to Ringling Museum, Opera House, and Bayfront Park[cite: 1] |
Drive Time to Siesta Key Beach | 10–15 Minutes[cite: 1] | Immediate access via Siesta Drive or Stickney Point bridges[cite: 1] |
Nearby Specialty Retail | Morton's Gourmet Market[cite: 1] | Historic Southside Village commercial and dining core[cite: 1] |
Sources: Realtor Association of Sarasota and Manatee (RASM) MLS, Sarasota County GIS, Kim Ogilvie Group Intelligence 2026[cite: 1].
Key neighborhood logistics and municipal details for prospective Cherokee Park buyers[cite: 1]:
Internal Navigation
Frequently Asked Questions
Cherokee Park is located in south Sarasota, west of Tamiami Trail (US-41) within the West of Trail designation[cite: 1]. It sits between downtown Sarasota to the north and Siesta Key to the south[cite: 1].
Yes, Cherokee Park is located entirely west of Tamiami Trail (US-41), placing it inside Sarasota's West of Trail real estate corridor alongside Oyster Bay Estates and Harbor Acres[cite: 1].
Single-family home prices in Cherokee Park generally range from $1,200,000 for original ranch homes on generous lots to over $3,500,000 for expanded or newly built custom residences[cite: 1].
Cherokee Park is zoned for Southside Elementary School, Booker Middle School, and Sarasota High School[cite: 1]. Students also have access to Pine View School for the Gifted[cite: 1].
Cherokee Park is located approximately 10 to 15 minutes north of Siesta Key Beach via the Siesta Drive bridge[cite: 1].
Kim Ogilvie | Kim Ogilvie Group at Michael Saunders & Company
Sarasota Luxury Real Estate Specialist | License #SL418491
Kim Ogilvie is a premier Sarasota luxury real estate advisor with over 35 years of experience, representing buyers and sellers across West of Trail, Casey Key, Siesta Key, Bird Key, and Downtown Sarasota. Office: 1605 Main St, Sarasota, FL 34236[cite: 1].
Private Advisory
Planning to buy or sell in Cherokee Park or neighboring West of Trail communities? Contact the Kim Ogilvie Group for expert market guidance[cite: 1].
383 people live in Cherokee Park, where the median age is 59 and the average individual income is $133,959. Data provided by the U.S. Census Bureau.
Total Population
Median Age
Population Density
Average individual Income
There's plenty to do around Cherokee Park, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.
Explore popular things to do in the area, including Vino Vino, Publix Super Markets, and Libby's Neighborhood Brasserie.
| Name | Category | Distance | Reviews |
Ratings by
Yelp
|
|---|---|---|---|---|
| Dining | 0.59 miles | 139 reviews | 4.9/5 stars | |
| Dining · $$ | 0.6 miles | 20 reviews | 2.7/5 stars | |
| Dining · $$ | 0.62 miles | 727 reviews | 3.9/5 stars | |
| Dining · $ | 0.64 miles | 40 reviews | 4.6/5 stars | |
| Dining · $ | 0.69 miles | 4 reviews | 3/5 stars | |
| Dining | 0.71 miles | 5 reviews | 4/5 stars | |
| Shopping | 0.6 miles | 3 reviews | 5/5 stars | |
| Shopping | 0.62 miles | 13 reviews | 4.3/5 stars | |
| Shopping | 0.64 miles | 16 reviews | 4.8/5 stars | |
| Shopping | 0.7 miles | 27 reviews | 2.9/5 stars | |
| Active | 0.38 miles | 0 reviews | 0/5 stars | |
| Active | 0.59 miles | 6 reviews | 4.3/5 stars | |
| Active | 0.61 miles | 1 review | 3/5 stars | |
| Active | 0.69 miles | 0 reviews | 0/5 stars | |
| Active | 0.74 miles | 0 reviews | 0/5 stars | |
| Active | 0.81 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.53 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.59 miles | 1 review | 5/5 stars | |
| Beauty | 0.61 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.62 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.71 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.81 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.81 miles | 0 reviews | 0/5 stars | |
| Beauty | 0.81 miles | 0 reviews | 0/5 stars | |
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Cherokee Park has 166 households, with an average household size of 2. Data provided by the U.S. Census Bureau. Here’s what the people living in Cherokee Park do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau.
Total Population
Population Density Population Density This is the number of people per square mile in a neighborhood.
Median Age
Men vs Women
Population by Age Group
0-9 Years
10-17 Years
18-24 Years
25-64 Years
65-74 Years
75+ Years
Education Level
Total Households
Average Household Size
Average individual Income
Households with Children
With Children:
Without Children:
Blue vs White Collar Workers
Blue Collar:
White Collar:
With more than four decades of experience in Sarasota’s luxury real estate market, the Kim Ogilvie Group has built a reputation for unmatched expertise, market knowledge, and results. Their proven success and deep understanding of Sarasota’s premier neighborhoods make them the trusted choice for buyers and sellers seeking exceptional representation in today’s competitive market. Connect with the Kim Ogilvie Group to put this experience to work for you.
1605 MAIN STREET SARASOTA, FL 34236
1605 MAIN STREET SARASOTA, FL 34236
