The Best Neighborhoods in Windermere, FL (2026)

Q: How were these Windermere neighborhoods ranked?

From MLS data using objective signals: days on market, price per square foot, 1-year appreciation, and a 0-100 Momentum Score.

Looking for the best neighborhoods in Windermere? Instead of opinions, we ranked Windermere’s 82 communities by the numbers that actually matter when you’re choosing where to live — how fast homes sell, price per square foot, and how values are moving. Here’s where Windermere stands, by the data (as of 2026-06-16).

Fastest-selling neighborhoods in Windermere

Where homes sell quickest — a sign of strong buyer demand. (Lowest median days on market, communities with recent closings.)

CHAINE DU LAC — 1 days on market · $3.15M
LAKESIDE/LKS/WINDERMERE — 1 days on market · $311,000
WICKHAM PARK 04 05 06 09 10 11 12 01 — 3 days on market · $390,000
CASABELLA — 6 days on market · $3.08M
BUTLER BAY — 9 days on market · $1.60M

Most affordable neighborhoods in Windermere (price per sq ft)

The lowest median price per square foot in Windermere — where your dollar stretches furthest.

OASIS COVE II/LAKESIDE VILLAGE PH — $193/sq ft · $335,000
LAKES OF WINDERMERE — $216/sq ft · $575,000
LAKESIDE/LKS/WINDERMERE — $222/sq ft · $311,000
LAKES WINDERMERE — $232/sq ft · $550,000
WINDERMERE SOUND — $232/sq ft · $438,000

Top neighborhoods in Windermere by Momentum Score

Momentum’s overall 0-100 market score blends value, demand, and momentum.

LAKESIDE/LKS/WINDERMERE — score 78 · $311,000
Town of Windermere — score 75 · $881,000
PALMS AT WINDERMERE — score 72 · $1.09M
ASHLIN PARK — score 71 · $459,000
WICKHAM PARK 04 05 06 09 10 11 12 01 — score 71 · $390,000

How we ranked these

These lists come from Momentum’s MLS data for Windermere, limited to communities with recent closings so the numbers are meaningful. ‘Fastest-selling’ uses median days on market, ‘most affordable’ uses median price per square foot, ‘fastest-appreciating’ uses the 1-year price change, and the Momentum Score is our overall 0-100 read on each market. The right neighborhood for you also depends on schools, commute, and lifestyle — use these as a data-driven starting point.

Explore Windermere further

Common questions

What are the best neighborhoods in Windermere?

It depends on your priorities. By the data, the fastest-selling, most affordable, and fastest-appreciating Windermere neighborhoods are listed above. The best fit also depends on schools, commute, and budget — a local agent can match you.

What’s the median home price in Windermere?

About $930,000 across the 82 Windermere communities Momentum tracks, though it varies widely by neighborhood.

How were these Windermere neighborhoods ranked?

From Momentum’s MLS data, using objective signals (days on market, price per square foot, 1-year appreciation, and our 0-100 Momentum Score), limited to communities with recent sales.

Rankings are aggregates from Momentum Realty’s MLS data for Windermere, as of 2026-06-16, and change over time. A data-driven starting point, not a guarantee or an endorsement of any community. Equal Housing Opportunity.

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