Winters Landing
Winters Landing Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Winters Landing?
Winters Landing is in the Town of Oakland, FL 34760, in west Orange County, about 0.7 miles from Oakland's historic Town Hall.
What types of homes are in Winters Landing?
Winters Landing is all single-family homes. Based on MLS listings and sales from the past 5 years, homes range from about 2,450 to 3,450 square feet with 3 to 4 bedrooms on lots of roughly 12,600 to 15,700 square feet, built from about 2005 to 2007. MLS listings name David Weekley Homes as the builder.
How much do homes cost in Winters Landing?
Winters Landing is small, so only a few homes sell each year: there were 11 MLS sales over the past 5 years (September 2026), ranging from about $525,000 to $850,000, with a median around $695,000. For today's listings, see this page.
What are the HOA fees in Winters Landing?
Recent MLS listings (September 2026) show HOA fees of about $45 to $75 a month. Ask for the specific home's HOA dues, any CDD amount, and the association rules before making an offer.
What schools serve Winters Landing?
Orange County Public Schools' 2026-27 school zones place Winters Landing in Tildenville Elementary, Lakeview Middle, and West Orange High School.
Who built Winters Landing?
MLS listings name David Weekley Homes as the builder of Winters Landing, with homes built from about 2005 to 2007.
What is nearby?
Oakland's historic town center, the West Orange Trail and the Oakland Nature Preserve are close to Winters Landing, and downtown Winter Garden's shops, restaurants and Saturday farmers market are a short drive.
