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WYLT Rankings · 2026

Best neighborhoods for retirees
in Florida

Ranked by safety, affordability, and livability — neighborhoods with low crime and manageable costs.

✓ Safety
✓ Affordability
✓ Walkability
25 neighborhoods ranked
👨‍👩‍👧‍👦 Families💻 Remote Workers🌅 Retirees🔑 First-Time Buyers

#1 Pick for Retirees in Florida

Pensacola, Pensacola — Good for now

#1

Pensacola

Good for now

Pensacola, FL

Price

$288K

Schools

8/10

Walk

84/100

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#2

Winter Park

Good for now

Winter Park, FL

Price

$374K

Schools

7.3/10

Walk

80/100

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#3

Englewood

Good for now

Englewood, FL

Price

$408K

Schools

6.3/10

Walk

75/100

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#4

Leesburg

Good for now

Leesburg, FL

Price

$244K

Schools

6.8/10

Walk

61/100

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#5

Longwood

Good for now

Longwood, FL

Price

$383K

Schools

7.1/10

Walk

70/100

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#6

Sebring

Good for now

Sebring, FL

Price

$165K

Schools

7.6/10

Walk

54/100

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#7

Fort Myers

Think twice

Fort Myers, FL

Price

$430K

Schools

7.7/10

Walk

65/100

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#8

Acadia

Good for now

Acadia, FL

Price

$370K

Walk

60/100

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#9

New Smyrna Beach

Settle here

New Smyrna Beach, FL

Price

$359K

Schools

3/10

Walk

56/100

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#10

Jupiter

Good for now

Jupiter, FL

Price

$605K

Schools

7.9/10

Walk

72/100

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#11

Cocoa Beach

Good for now

Cocoa Beach, FL

Price

$532K

Schools

6.2/10

Walk

67/100

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#12

Cape Canaveral

Good for now

Cape Canaveral, FL

Price

$372K

Schools

6.6/10

Walk

89/100

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#13

Gainesville

Good for now

Gainesville, FL

Price

$348K

Schools

8.6/10

Walk

52/100

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#14

Estero

Good for now

Estero, FL

Price

$466K

Schools

8.1/10

Walk

59/100

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#15

Pensacola

Good for now

Pensacola, FL

Price

$318K

Schools

8/10

Walk

47/100

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#16

Brandon

Settle here

Brandon, FL

Price

$350K

Schools

7.6/10

Walk

48/100

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#17

St Pete

Good for now

St Pete, FL

Price

$656K

Schools

8.5/10

Walk

68/100

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#18

Daytona Beach

Good for now

Daytona Beach, FL

Price

$200K

Schools

7/10

Walk

70/100

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#19

Gainesville

Good for now

Gainesville, FL

Price

$179K

Schools

8.7/10

Walk

34/100

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#20

Oviedo

Settle here

Oviedo, FL

Price

$448K

Schools

8.1/10

Walk

51/100

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#21

Orange Park

Settle here

Orange Park, FL

Price

$299K

Schools

8.6/10

Walk

41/100

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#22

Crawfordville

Good for now

Crawfordville, FL

Price

$340K

Schools

7.3/10

Walk

42/100

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#23

Mount Dora

Good for now

Mount Dora, FL

Price

$420K

Schools

7.7/10

Walk

47/100

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#24

Sebastian

Good for now

Sebastian, FL

Price

$314K

Schools

6/10

Walk

39/100

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#25

Inverness

Good for now

Inverness, FL

Price

$224K

Schools

7.6/10

Walk

33/100

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