Moving to Windermere, FL: The 2026 Relocation Guide

Q: What are the best neighborhoods in Windermere?

We rank Windermere's neighborhoods by demand, value, and appreciation on the best-neighborhoods page; a local agent can match you to the right fit.

Q: Is Windermere a good place to move?

For many, yes: no state income tax, a protected property-tax cap once homesteaded, and varied neighborhoods. Plan for insurance costs.

Thinking about moving to Windermere, Florida? This guide pulls together everything you need to plan the move — the housing market, what it really costs to live here, the best neighborhoods, new construction, and Florida’s tax advantages — using Momentum’s MLS data (as of 2026-06-16).

Windermere at a glance

$930,000

Median home price

61 days

Median days on market

$6,290

Est. monthly cost to own

Communities

Why people move to Windermere

Florida’s draw is simple: no state income tax, year-round sunshine, and no income tax on retirement income. In Windermere specifically, the median home runs about $930,000, and homes sell in a median of 61 days. Once you buy and homestead, Florida’s Save Our Homes cap limits how fast your property taxes can rise. The trade-off to plan for is home insurance, which runs above the national average — we break that down in the cost-of-living guide below.

Best neighborhoods in Windermere

A few of Windermere’s strongest communities by the data: LAKESIDE/LKS/WINDERMERE, Town of Windermere, PALMS AT WINDERMERE. See the full, ranked list → best neighborhoods in Windermere.

What it costs to live in Windermere

For a typical Windermere home, the estimated monthly cost to own is about $6,290 (principal, interest, Orange County property tax, and insurance). Full breakdown → cost of living in Windermere.

Your Windermere relocation toolkit

Common questions

Does Florida have a state income tax?

No. Florida has no state income tax, including on retirement income, which is one of the biggest reasons people relocate here.

How much does it cost to live in Windermere?

A typical Windermere home is about $930,000, with an estimated monthly cost to own around $6,290. See the cost-of-living guide for the full breakdown including taxes and insurance.

What are the best neighborhoods in Windermere?

It depends on your budget, schools, and commute. We rank Windermere's neighborhoods by the data (demand, value, appreciation) on the best-neighborhoods page, and a local agent can match you.

Is Windermere a good place to move?

For many people, yes — no state income tax, a protected property-tax cap once you homestead, and a range of neighborhoods and new construction. The variable to plan for is insurance.

Figures are estimates from Momentum Realty’s MLS data and Orange County tax/insurance data, as of 2026-06-16, and change over time. General relocation guidance, not financial advice. Equal Housing Opportunity.