Ken Pozek talking about Windermere

Windermere’s Lakeside Luxury & Downtown Charm


Butler Chain living, A-rated schools, and fast access to Orlando.

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Windermere


Windermere blends blue-water mornings with brick-street evenings. Centered on the Butler Chain, it delivers rare lakefront living plus a walkable, shady downtown framed by historic oaks, parks, and community events. Families prize the school options and the easy routine—coffee and market downtown, afternoons on the water, and evenings on Restaurant Row or the golf course. Housing spans thoughtfully updated mid-century homes and townhomes near downtown to guard-gated estates with resort-level outdoor living in enclaves like Lake Butler Sound and Isleworth.

Real Estate Statistics

Average Price $1.4M
Lowest Price $1.9K
Highest Price $18.5M
Total Listings 410
Avg. Days On Market 90
Avg. Price/SQFT $303

Property Types (active listings)

Luxury House in Windermere Neighborhood in Florida

Windermere Highlights


  • 01
    On the Butler Chain of Lakes—true lake lifestyle with docks, boating, and sunset runs.
  • 02
    A-rated schools, boutique brick-street downtown, and a weekly farmers market.
  • 03
    Choose walkable downtown charm or guard-gated grandeur (Isleworth, Lake Butler Sound).
  • 04
    Minutes to Disney/Universal and Restaurant Row; fast reach to I-4/408/Turnpike.
  • 05
    Limited inventory + lifestyle demand—updated or lake-adjacent homes hold value.
  • 06
    Median home value (2025) around ~$1.1M (varies by upgrades and lake access).

Quick Facts

  • Price range: From mid-$400Ks townhomes/entry single-family to $5M–$30M+ trophy lakefront; ~$1.1M median (2025) from our Windermere blog.
  • Home types: Updated non-lake single-family, townhomes/low-maintenance pockets, guard-gated custom estates, and prime lakefront.
  • Commute: Approx. ~20 min to Universal, ~30 min to Disney, ~35 min to Downtown Orlando/MCO (traffic-dependent).
  • Schools: Served by Orange County Public Schools—confirm zoning via the district’s locator.
Windermere restaurant in nice street

Explore Windermere Homes

Browse the newest Windermere homes—from walkable downtown streets to guard-gated estates and Butler Chain lakefront. Create a Save Search to get instant alerts as soon as matching properties hit the market.

Windermere city sign

Properties in Windermere

Windermere Real Estate FAQs

What makes Windermere different from other luxury areas?

The Butler Chain concentrates true lakefront living in a single market, while downtown keeps a small-town pace. You can choose walkable or guard-gated without leaving the area.

For an ultra-luxury lens, see TOR’s Isleworth deep dive; for broader privacy communities, see Best Guard-Gated Communities in Orlando.

Where’s the weekly farmers market and what’s it like?

Right in Town Square Park downtown, typically Fridays late morning to early afternoon, with produce, prepared foods, and local makers—great for meeting neighbors. TOR’s Windermere Farmers Market guide has hours and tips

Which public schools serve my address?

Windermere is served by OCPS. Use OCPS’s Find My School to confirm address-based zoning and programs (magnet/charter options may affect choices).

Where does the West Orange Trail run, and where do I start?

The paved trail runs directly through downtown; the Winter Garden Station trailhead at 455 E. Plant St. offers parking and facilities. Trail hours are generally sunrise to sunset.

How does lake access work on the Butler Chain?

Access varies by waterfront ownership, community/private ramps, and nearby public access points. Docks/lifts and boat size rules depend on HOA and local authorities—your agent will verify per address. TOR’s Community Spotlight: Windermere gives a helpful area orientation.

Do I need permits for renovations, pools, or additions?

Most structural/mechanical/electrical/plumbing work requires permits. Check Orange County/municipal buildingplus any HOA/ARC design standards before starting.

Are short-term rentals allowed?

Many neighborhoods/HOAs restrict short-term leasing. Confirm city/HOA rules and minimum lease terms before purchasing for STR use.

Is Windermere golf-cart friendly?

Some neighborhoods allow carts on designated streets; rules vary. Confirm local allowances and HOA guidance before purchase.

Where can I learn more about specific enclaves?

TOR has detailed pages for Isleworth, Windermere Single-Family/market pages, and the Windermere community spotlight to help you compare lifestyle, price bands, and amenities.

winter garden aerial view

Start searching for your Windermere dream home today.

Explore the beauty and luxury of Windermere living as you search for your perfect home. From serene lakeside views to vibrant neighborhoods, Windermere offers a lifestyle that’s both relaxing and rewarding. Begin your search today and take the first step toward making this sought-after community your new home.

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