Orange County · Central Florida
Windermere Real Estate
The Butler Chain Address. Homes for sale, what living here is really like, and the local intel Evolve Estates uses to help buyers and sellers here.
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Why people choose Windermere
Windermere is the address on the Butler Chain, thirteen connected lakes the state designates Outstanding Florida Waters, its highest water-quality protection. The little town at the center keeps its original streets as graded dirt by choice, a preservation move that sets the tone: quiet, canopied, and deliberately unhurried. Around the incorporated town, the broader Windermere area carries some of Orange County's most established lakefront and golf communities. Buyers here are usually chasing water, and this is the water worth chasing: skiing, fishing, and sunset cruises across a chain you can boat for hours.
The essentials
What to know before you buy here
County & tax district
Windermere sits in Orange County. The base unincorporated rate is 16.0858 mills, of which 6.449 mills funds schools. City limits and CDD communities pay more than this.
What a buyer actually pays
Florida reassesses at just value when a home sells, and on a recent arm's length sale that tracks closely to the price paid. On a $400,000 purchase in Orange County, first-year tax runs about $6,434, or roughly $5,778 once homestead is filed.
Schools
Florida is a school-choice state and assignment is by address, not by community. Verify the schools zoned to a specific Windermere address through Orange County Schools before you write an offer.
Insurance
Statewide average on a $300,000 dwelling is about $5,100 a year, commonly quoted between $4,400 and $5,800. Roof age moves this more than any other factor. Flood coverage is separate.
First-year property tax in Orange County
| Purchase price | Before homestead | With homestead | Annual difference |
|---|---|---|---|
| $300,000 | $4,826 | $4,169 | $657 |
| $400,000 | $6,434 | $5,778 | $657 |
| $600,000 | $9,651 | $8,995 | $657 |
Above an assessed value of $76,411 the homestead saving is the same dollar figure at every price, because the exemption reduces assessed value by a fixed amount rather than by a percentage. That makes it worth proportionally more on a lower-priced home. Below $76,411 the second $26,411 exemption phases in and the saving is smaller. Calculated from Orange County 2025 final millage of 16.0858 mills (Unincorporated Orange (base mill code 11)) and the Florida homestead structure: the first $25,000 of assessed value is exempt from all levies, and a second $26,411 above $50,000 is exempt from everything except school levies. Figures are the base unincorporated district and exclude municipal, CDD, and non-ad-valorem assessments. Verify your parcel with the Orange County Property Appraiser.
Moving in from another state? The tax reset above catches Northeast buyers hardest, because the figure advertised on a listing is the prior owner's capped bill and not yours. The New York to Florida guide runs this same math against what you pay today, alongside closing costs, insurance, and the homestead timeline.
Compare the area
Other communities we serve
Buyers who start with Windermere usually shortlist two or three of these. Tax district, HOA and CDD structure, and commute differ across them, and those move the monthly payment more than the sticker price does.
Search homes
Homes for sale in Windermere
Filter by beds, baths, price, and property type. Sample listings are shown while our MLS connection is being finalized.
Sample data notice. The listings shown above are fictional sample listings for demonstration while our MLS connection is being finalized. They do not represent real properties or real inventory. This view shows Windermere results only, not the full market. Required MLS attribution, the data-as-of disclaimer, and the filtered-display disclosure will appear here once live listing data is enabled.
Local resources
Official Windermere links
Direct links to local government, schools, and community organizations. Evolve Estates is an independent real estate resource and is not affiliated with these entities.
Good to know
Windermere questions
What county is Windermere in, and what are the property taxes?
What schools serve Windermere?
What is Windermere known for?
What does homeowners insurance cost near Windermere?
What are the closing costs when buying in Windermere?
What other communities should I look at near Windermere?
Talk to a local Realtor
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Tell us your priorities and we will tell you what Windermere looks like for you, whether you are buying, selling, or investing.
Disclosure. This page is a real estate resource by Evolve Estates Group, brokered by eXp Realty. It is not affiliated with, endorsed by, or an official publication of the City of Windermere, Orange County, or any government agency, community development district, or homeowners association. All information is provided for general informational purposes and is deemed reliable but not guaranteed; verify all details independently. Equal Housing Opportunity.