Buying or selling? Call (904) 351-6461

The Best Neighborhoods in Windermere, FL (2026)

By , Co-Founder, Momentum Realty · Updated June 16, 2026

Windermere is in Orange County, Florida (ZIP codes 34786). Not Windermere, England. · Homes for sale in Windermere · Orange County

Buying in Windermere? Get matched with a local agent →Selling? Get your Windermere home value →or call (904) 351-6461

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.)

  1. CHAINE DU LAC — 1 days on market · $3.15M
  2. LAKESIDE/LKS/WINDERMERE — 1 days on market · $311,000
  3. WICKHAM PARK 04 05 06 09 10 11 12 01 — 3 days on market · $390,000
  4. CASABELLA — 6 days on market · $3.08M
  5. 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.

  1. OASIS COVE II/LAKESIDE VILLAGE PH — $193/sq ft · $335,000
  2. LAKES OF WINDERMERE — $216/sq ft · $575,000
  3. LAKESIDE/LKS/WINDERMERE — $222/sq ft · $311,000
  4. LAKES WINDERMERE — $232/sq ft · $550,000
  5. 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.

  1. LAKESIDE/LKS/WINDERMERE — score 78 · $311,000
  2. Town of Windermere — score 75 · $881,000
  3. PALMS AT WINDERMERE — score 72 · $1.09M
  4. ASHLIN PARK — score 71 · $459,000
  5. 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

Windermere guides & data

Everything we publish about Windermere: live listings by type, prices and market data, taxes, insurance and what it costs to live here.

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.

Budgeting your move? Cost of living in Windermere: taxes, insurance & the real cost to own.
New to the area? Moving to Windermere? The full relocation guide.

Everything we publish about Windermere

Florida statewide

Moving to Windermere?

Find the right Windermere neighborhood for you.

Tell us what matters — budget, schools, commute, lifestyle — and a local Momentum expert will match you to the Windermere neighborhoods that fit. No pressure, no obligation.

Prefer to talk now? Call (904) 351-6461.

Find your Windermere neighborhood

A local specialist will send matches that fit your life, usually within one business day.

By submitting, you agree that EAB RE INVESTMENTS LLC (Momentum Realty) and its agents may call, email, and text you about your inquiry, which may involve automated means and prerecorded or artificial voices. You do not need to consent as a condition of buying any property, goods, or services. To opt out, reply STOP at any time or reply HELP for assistance. You can also click the unsubscribe link in emails. Message and data rates may apply. Message frequency may vary. See our Privacy Policy and SMS Terms.or call (904) 351-6461

Common questions

What's the median home price in Windermere?

About $930,000 across the 82 Windermere communities Momentum tracks.