Longleaf at Oakland
Longleaf Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Longleaf at Oakland?
Longleaf at Oakland is in the Town of Oakland, FL 34760, in west Orange County, about 0.3 miles from Oakland's historic Town Hall.
Who built Longleaf at Oakland?
MLS listings show Longleaf homes were built by Pulte Homes, from about 2019 to 2021.
What types of homes are in Longleaf at Oakland?
Longleaf has single-family homes and townhomes. Based on MLS listings and sales from the past 24 months, homes range from about 1,470 to 2,470 square feet with 2 to 4 bedrooms.
How much do homes cost in Longleaf at Oakland?
The median sale price in Longleaf over the past 12 months was about $498,000, based on 12 MLS sales (September 2026). Most sales over the past 24 months fell between about $330,000 for townhomes and $700,000 for single-family homes. For today's numbers, see the listings on this page.
What are the HOA fees in Longleaf at Oakland?
Recent MLS listings (September 2026) show Longleaf HOA fees of about $260 to $425 a month, depending on the home type. Ask for the specific home's HOA dues, what they cover, any CDD amount, and the association rules before making an offer.
What schools serve Longleaf at Oakland?
Orange County Public Schools' 2026-27 school zones place Longleaf at Oakland in Tildenville Elementary, Lakeview Middle, and West Orange High School.
What is nearby?
Oakland's historic town center and the West Orange Trail are a short walk away, the Oakland Nature Preserve is nearby, and downtown Winter Garden is a short drive.
