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retire

Finding the Best Places to Retire Since 2006!

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Windermere, Florida

On an Isthmus in a Chain of Lakes in North Central Florida, Windermere Has a Cozy Downtown, Canopy Lanes and an Understated Atmosphere

Pretty Windermere is just outside of Orlando in north central Florida and sits on an isthmus in the Butler Chain of Lakes, 11 bodies of water recognized for their high water quality and wildlife. The town is known for its tree canopy dirt roads and understated atmosphere.

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Windermere residents are protective of their rural hamlet and work to keep much of the outside world at bay. The town regulates the traffic that travels through it from one side of the lake chain to the other and encourages drivers to use alternate routes. The downtown is cozy and quaint and kept that way through strict building and zoning codes. Residents enjoy several annual festivals, including the Windermere Art Affair and The Festival Among the Lakes, which consists of a wakeboarding competition and boat show. When it comes to dining out, critically acclaimed bistros mingle with fast food chains. A farmers' market operates on Fridays, but most shopping and many services are found in Orlando.

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Housing ranges from fairly average condominiums to extraordinary lakefront mansions, some of which are occupied by celebrities and Orlando Magic basketball players.

Population:  3,500 (city proper)

Age 45 or Better:   41%

Cost of Living:  55% above the national average

Median Home Price:  $710,000

Climate:    The area has a humid subtropical climate. Summers and early fall are hot and rainy with temperatures in the 80s and 90s. Late fall and winter are generally dry and sunny with temperatures in the 50s, 60s and 70s.

At Least One Hospital Accepts Medicare Patients?    No, but Orlando has several hospitals that accept Medicare patients.

At Least One Hospital is Accredited by Joint Commission?  No, but Orlando has several hospitals that are accredited.

Public Transit:  No

Crime Rate: Well below the national average

Public Library:   Yes, and it is located in a Florida cracker-style building with a wraparound porch.

Political Leanings:   Liberal

College Educated:   71%

Is Florida Considered Tax Friendly for Retirement?  Yes

Cons:   The effects of hurricanes are occasionally felt here. In fact, Ian in 2022 brought localized flooding and wind damage.     

Notes:   Windermere has maintained its population during the last decade. The Magic Kingdom's nightly fireworks can be seen from many a Windermere front porch. Home prices have increased 14% since a year ago.

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Recommended as a Retirement Spot?   Yes

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Florida:

Named Pascua Florida by Juan Ponce De Leon, the Sunshine State did not enter the Union until March 3, 1845. Balmy mild winters began attracting snowbirds to the state in the late 19th century. Retirees continue to flock to the state. It's not hard to see why tourism has become the leading industry.

International trade and citrus are also major contributors to the state's economy. Eighty percent of the nation's oranges and grapefruits are grown here, and 40 percent of all U.S. exports to Latin America flow through Florida.

Florida's landscape includes uplands and coastal plains. It contains more than 11,000 miles of waterways and about 4,500 islands spread across 10 acres.

The state has 1,250 golf courses, more than any other state in the Union. The 47 mile Pinellas Trail is the longest urban trail on the east coast. Orlando theme parks attract more visitors than any other theme parks in the U.S. The only place in the world where alligators and crocodiles co-exist is in National Everglades Park.

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