Oakland Park
Oakland Park Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Oakland Park located?
Oakland Park is a master-planned community on the south shore of Lake Apopka, with part of the community in the City of Winter Garden and part in the Town of Oakland (both in Orange County), with addresses in Winter Garden, FL 34787, off Tildenville School Road and Oakland Avenue just north of SR 50. The West Orange Trail runs along the community, historic downtown Winter Garden is only a few minutes away, and Walt Disney World is roughly 25–30 minutes.
Who built the homes in Oakland Park?
Oakland Park has been built out since about 2012 by several builders, including David Weekley Homes, Ashton Woods, Dream Finders Homes, and J&J Building, with more recent homes from RCB Homes and others.
What types of homes are in Oakland Park?
Oakland Park is made up of single-family homes. Based on MLS listings and sales from the past 12 months, homes typically range from about 1,770 to 4,100 square feet with 3 to 6 bedrooms, on lots of roughly 0.08 to 0.24 acres. It is a certified green community covering about 258 acres.
How much do homes cost in Oakland Park?
The median sale price in Oakland Park over the past 12 months was about $905,000 (MLS data, September 2026), with more than 40 homes sold in that period. For today's numbers, see the live stats and current listings at the top of this page.
Is Oakland Park a gated community?
No. Oakland Park is not gated. It is an open, walkable community connected to the West Orange Trail.
What are the HOA fees in Oakland Park?
Recent MLS listings show Oakland Park HOA dues of roughly $200 to $355 per month (median about $210) as of September 2026. Ask for the specific home's HOA and any CDD amounts before making an offer.
What is the Oakland Park HOA?
The association is Oakland Park Association, Inc. Ask for the current management company and contact details in the resale documents, since management can change.
What schools serve Oakland Park?
Oakland Park homes are zoned for Tildenville Elementary and West Orange High School, based on recent listings. Most homes are zoned for Lakeview Middle, and some for SunRidge Middle.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
What amenities does Oakland Park have?
Oakland Park amenities include a clubhouse with a catering kitchen, two pools (including a zero-entry pool), a playground, a pavilion, a fire pit, parks, and walking trails, plus direct access to the West Orange Trail.
