50 Best Retirement Towns for the Upper Middle Class

The No. 1 retirement town for members of the upper-middle class, according to results from a new original research study, is not in Florida. 

Before we reveal which town (and state) ranks first for upper-middle class retirees, let’s explain how we determined the nation’s best retirement towns for the upper-middle class.

Using the Pew Research Center’s definition of the middle-class (two-thirds to double the median household income of $51,813 to $155,438), we broke the middle-class income range into thirds. The upper third, $120,896 to $155,438, is upper-middle class.

For the retirement towns, we sourced places with greater than the national average percentage of the population ages 65 and over, which is currently 16.8%. The total cost of living was calculated using each town’s average mortgage and expenditure costs, and the 50/30/20 finance rule was used to double the total cost of living for necessities and find the comfortable cost of living. Each location is ranked by the comfortable cost of living within the upper-middle class income range.

• Dover, New Hampshire, is the best retirement town. New Hampshire recently ranked first in a separate GOBankingRates study on what retirement readiness looks like from coast to coast. The Granite State benefits from no tax on Social Security, and the average retirement savings balance is $512,781, according to GOBankingRates research. The annual cost of living comfortably for the upper-middle class in Dover is $123,246.
• The cost of living is more than $121,000 to live comfortably in the top five towns: Dover, Laguna Woods (CA), Milford (CT), Ashland (OR) and Wheaton (IL).
• Ten Florida towns ranked among the top 50, the most of any state. The annual cost of living comfortably in Coconut Creek (#6), Royal Palm Beach (#10), Delray Beach (#13), Estero (#19), Fort Lauderdale (#23), Pembroke Pines (#27), Hialeah (#38) Bonita Springs (#39) and Aventura (#45) starts at $121,015 in Royal Palm Beach and as much as $142,835 in Naples.
• Illinois surprised with seven towns in the ranking, including two in the top 10: Wheaton (#5), Arlington Heights (#9), Oak Park (#11), Park Ridge (#12), Glen Ellyn (#22), Elmhurst (#25) and Evanston (#33).

Keep reading to see which 50 retirement towns are ideal for upper-middle class retirees.

• Annual cost of living comfortably: $123,246
• Population 65+ (%): 17.2%
• Livability score: 88
• Average home value: $573,860
• Average monthly mortgage: $3,309

• Annual cost of living comfortably: $121,465
• Population 65+ (%): 83%
• Livability score: 73
• Average home value: $536,665
• Average monthly mortgage: $3,094

• Annual cost of living comfortably: $127,612
• Population 65+ (%): 21.3%
• Livability score: 88
• Single family average home value: $530,266
• Average monthly mortgage: $3,057

• Annual cost of living comfortably: $123,252
• Population 65+ (%): 28.6%
• Livability score: 83
• Single family average home value: $567,768
• Average monthly mortgage: $3,274

• Annual cost of living comfortably: $121,798
• Population 65+ (%): 17.4%
• Livability score: 84
• Single family average home value: $538,916
• Average monthly mortgage: $3,107

• Annual cost of living comfortably: $121,656
• Population 65+ (%): 19.3%
• Livability score: 83
• Single family average home value: $524,251
• Average monthly mortgage: $3,023

• Annual cost of living comfortably: $126,027
• Population 65+ (%): 19.9%
• Livability score: 85
• Single family average home value: $599,845
• Average monthly mortgage: $3,459

• Annual cost of living comfortably: $126,074
• Population 65+ (%): 17%
• Livability score: 85
• Single family average home value: $594,932
• Average monthly mortgage: $3,430

• Annual cost of living comfortably: $121,682
• Population 65+ (%): 19.3%
• Livability score: 80
• Single family average home value: $541,936
• Average monthly mortgage: $3,125

• Annual cost of living comfortably: $121,015
• Population 65+ (%): 17.8%
• Livability score: 79
• Single family average home value: $516,569
• Average monthly mortgage: $2,978

• Annual cost of living comfortably: $126,837
• Population 65+ (%): 17.3%
• Livability score: 83
• Single family average home value: $571,481
• Average monthly mortgage: $3,295

• Annual cost of living comfortably: $131,629
• Population 65+ (%): 20.1%
• Livability score: 86
• Single family average home value: $610,055
• Average monthly mortgage: $3,517

• Annual cost of living comfortably: $126,281
• Population 65+ (%): 28%
• Livability score: 80
• Single family average home value: $559,989
• Average monthly mortgage: $3,229

• Annual cost of living comfortably: $125,071
• Population 65+ (%): 17.8%
• Livability score: 81
• Single family average home value: $586,395
• Average monthly mortgage: $3,381

• Annual cost of living comfortably: $126,440
• Population 65+ (%): 17.3%
• Livability score: 82
• Single family average home value: $604,293
• Average monthly mortgage: $3,484

• Annual cost of living comfortably: $124,268
• Population 65+ (%): 17.3%
• Livability score: 80
• Single family average home value: $575,409
• Average monthly mortgage: $3,318

• Annual cost of living comfortably: $129,376
• Population 65+ (%): 19.4%
• Livability score: 83
• Single family average home value: $588,135
• Average monthly mortgage: $3,391

• Annual cost of living comfortably: $138,744
• Population 65+ (%): 18.9%
• Livability score: 90
• Single family average home value: $687,463
• Average monthly mortgage: $3,964

• Annual cost of living comfortably: $132,678
• Population 65+ (%): 50.7%
• Livability score: 79
• Single family average home value: $598,990
• Average monthly mortgage: $3,454

• Annual cost of living comfortably: $123,034
• Population 65+ (%): 39.4%
• Livability score: 73
• Single family average home value: $569,615
• Average monthly mortgage: $3,284

• Annual cost of living comfortably: $123,890
• Population 65+ (%): 19.9%
• Livability score: 77
• Single family average home value: $570,250
• Average monthly mortgage: $3,288

• Annual cost of living comfortably: $131,560
• Population 65+ (%): 18.6%
• Livability score: 83
• Single family average home value: $605,296
• Average monthly mortgage: $3,490

• Annual cost of living comfortably: $129,390 
• Population 65+ (%): 19.6%
• Livability score: 81
• Single family average home value: $580,145
• Average monthly mortgage: $3,345

• Annual cost of living comfortably: $124,969
• Population 65+ (%): 17.8%
• Livability score: 78
• Single family average home value: $593,792
• Average monthly mortgage: $3,424

• Annual cost of living comfortably: $135,013
• Population 65+ (%): 18.5%
• Livability score: 85
• Single family average home value: $631,934
• Average monthly mortgage: $3,644

• Annual cost of living comfortably: $134,747
• Population 65+ (%): 17.1%
• Livability score: 85
• Single family average home value: $643,627
• Average monthly mortgage: $3,711

• Annual cost of living comfortably: $132,944
• Population 65+ (%): 19.5%
• Livability score: 82
• Single family average home value: $600,647
• Average monthly mortgage: $3,463

• Annual cost of living comfortably: $138,023
• Population 65+ (%): 17.9%
• Livability score: 86
• Single family average home value: $681,434
• Average monthly mortgage: $3,929

• Annual cost of living comfortably: $126,094
• Population 65+ (%): 25.8%
• Livability score: 74
• Single family average home value: $612,383
• Average monthly mortgage: $3,531

• Annual cost of living comfortably: $134,412
• Population 65+ (%): 21.7%
• Livability score: 81
• Single family average home value: $614,690
• Average monthly mortgage: $3,544

• Annual cost of living comfortably: $126,569
• Population 65+ (%): 19.8%
• Livability score: 74
• Single family average home value: $568,793
• Average monthly mortgage: $3,280

• Annual cost of living comfortably: $136,453
• Population 65+ (%): 17.1%
• Livability score: 82
• Single family average home value: $610,183
• Average monthly mortgage: $3,518

• Annual cost of living comfortably: $139,457
• Population 65+ (%): 17.8%
• Livability score: 84
• Single family average home value: $667,987
• Average monthly mortgage: $3,851

• Annual cost of living comfortably: $142,835
• Population 65+ (%): 56.2%
• Livability score: 79
• Single family average home value: $694,304
• Average monthly mortgage: $4,003

• Annual cost of living comfortably: $124,606
• Population 65+ (%): 19.6%
• Livability score: 72
• Single family average home value: $574,425
• Average monthly mortgage: $3,312

• Annual cost of living comfortably: $127,353
• Population 65+ (%): 24.6%
• Livability score: 71
• Single family average home value: $598,836
• Average monthly mortgage: $3,453

• Annual cost of living comfortably: $136,647
• Population 65+ (%): 19.3%
• Livability score: 79
• Single family average home value: $666,982
• Average monthly mortgage: $3,846

• Annual cost of living comfortably: $129,324
• Population 65+ (%): 20.4%
• Livability score: 73
• Single family average home value: $569,073
• Average monthly mortgage: $3,281

• Annual cost of living comfortably: $131,780
• Population 65+ (%): 42.9%
• Livability score: 70
• Single family average home value: $599,775
• Average monthly mortgage: $3,458

• Annual cost of living comfortably: $134,307
• Population 65+ (%): 20.9%
• Livability score: 76
• Single family average home value: $642,796
• Average monthly mortgage: $3,706

• Annual cost of living comfortably: $136,593
• Population 65+ (%): 18.3%
• Livability score: 78
• Single family average home value: $614,572
• Average monthly mortgage: $3,543

• Annual cost of living comfortably: $139,973
• Population 65+ (%): 18.2%
• Livability score: 80
• Single family average home value: $680,362
• Average monthly mortgage: $3,923

• Annual cost of living comfortably: $135,222
• Population 65+ (%): 20.1%
• Livability score: 76
• Single family average home value: $574,465
• Average monthly mortgage: $3,312

• Annual cost of living comfortably: $135,376
• Population 65+ (%): 40.5%
• Livability score: 72
• Single family average home value: $625,024
• Average monthly mortgage: $3,604

• Annual cost of living comfortably: $141,445
• Population 65+ (%): 26.3%
• Livability score: 79
• Single family average home value: $655,043
• Average monthly mortgage: $3,777

• Annual cost of living comfortably: $148,244
• Population 65+ (%): 17.9%
• Livability score: 85
• Single family average home value: $694,908
• Average monthly mortgage: $4,007

• Annual cost of living comfortably: $145,460
• Population 65+ (%): 31.1%
• Livability score: 80
• Single family average home value: $740,959
• Average monthly mortgage: $4,272

• Annual cost of living comfortably: $147,938
• Population 65+ (%): 17.4%
• Livability score: 84
• Single family average home value: $755,568
• Average monthly mortgage: $4,356

• Annual cost of living comfortably: $127,228
• Population 65+ (%): 16.9%
• Livability score: 68
• Single family average home value: $549,600
• Average monthly mortgage: $3,169

• Annual cost of living comfortably: $140,934
• Population 65+ (%): 17.2%
• Livability score: 78
• Single family average home value: $664,157
• Average monthly mortgage: $3,829

Find more original studies and surveys in the GOBankingRates original research center.

Editor’s note: Photos are for illustrative purposes only. In many cases, the closest major city outside of the city/county mentioned in the article was used.

Methodology: For this study, GOBankingRates analyzed retirement towns from across the United States to find the best places for the upper middle class. Retirement towns are places with greater than the national average percentage of the population ages 65 and over, currently at 16.8%. Middle class is defined by Pew Research Center as two-thirds to double the median household income ($51,813 to $155,438). To find the upper-middle class, the middle-class income range is broken into thirds, with the upper third being the upper-middle class ($120,896 to $155,438). With the cities identified using data from the U.S. Census American Community Survey, the cost-of-living indexes were sourced from Sperling’s BestPlaces for each location. Using the cost-of-living indexes along with the national average expenditure costs for retirees, as sourced from the Bureau of Labor Statistics Consumer Expenditure Survey for Retired Consumer Units, the average expenditure cost for each location was calculated. The average home value was sourced from Zillow Home Value Index. Assuming a 10% down payment and using the national average 30-year fixed mortgage rate of 6.63%, sourced from the Federal Reserve Economic Data on Aug. 13, the average mortgage cost was calculated for each location. Using the average mortgage and expenditure costs, the total cost of living was calculated. Using the 50/30/20 finance rule that says that needs should not exceed 50% of household income, the total cost of living for necessities was doubled to find the comfortable cost of living. The locations with a comfortable cost of living within the upper-middle class income range were kept. The livability index was sourced from AreaVibes and used to determine the overall quality of life. Using the remaining retirement towns, the percent of the population age 65 and over was scored and weighted at 0.50, the total cost of living for necessities was scored and weighed at 1.00, and the livability index was scored and weighted at 1.50. All scores were summed and sorted to find the best retirement towns for the upper-middle class. All data was collected on and is up to date as of Aug. 13, 2025.