San Diego vs Madison for Retirees (2026)

Better for retirees: Madison~34% cheaper overall
Median Home Price
$850K
San Diego
$360K
Madison
State Income Tax
9.3%
San Diego
7.7%
Madison
Est. Healthcare / month
$740
San Diego
$485
Madison
Walk Score (0–100)
51
San Diego
55
Madison

Scroll down for retirement income tax breakdown, healthcare estimates, and FAQ.

Full retirement cost breakdown

Metric
San Diego
California
Madison
Wisconsin
1BR rent / month$2,600$1,650Better
Median home price$850K$360KBetter
State income tax9.3%7.7%Better
Sales tax (combined)7.8%5.4%Better
Monthly utilities$130Better$162
Groceries index (US = 100)109101Better
Est. healthcare / month$740$485Better
Walk score (0–100)51 / 10055 / 100Better
Overall COL index (100 = US avg)14897Better

Frequently asked questions

Which city is better for retirement — San Diego or Madison?

Based on home prices, taxes on retirement income, walkability, and overall cost of living, Madison scores better for retirees. Median home prices are $850K in San Diego vs $360K in Madison. Madison is approximately 34% cheaper overall. The best choice still depends on climate, healthcare access, and proximity to family.

Is retirement income taxed in San Diego or Madison?

Madison has the lower state income tax rate (7.7% vs 9.3%). Note that many states exempt Social Security income and some pension income from state taxes even when other income is taxed — check your specific state's retirement tax rules.

What is the estimated monthly healthcare cost in San Diego vs Madison?

Based on national average retiree healthcare spending (~$500/month) scaled by each city's cost-of-living index, estimated monthly healthcare costs are approximately $740 in San Diego and $485 in Madison. That's a difference of ~$255/month, or ~$3,060/year. Actual costs vary based on your Medicare plan, supplements, and health needs.

Can I afford to retire in San Diego on a $50,000 annual income?

On a $50,000/year ($4,167/month) retirement income in San Diego, rent alone would consume approximately 62% of your budget (1BR rent ~$2,600/mo) and healthcare another ~18%. That leaves roughly 20% (~$833/mo) for groceries, transportation, and other expenses. This is tight — a studio apartment or lower-cost neighborhood would help.

Which city is more walkable for retirees?

Madison has a higher walk score (55 vs 51 out of 100). Walkability is increasingly important for retirees who want to reduce car dependence — a score above 70 means most daily errands can be done on foot. Madison offers more independence without a car, which also reduces transportation costs.

Retirement purchasing power

$50K/year in San Diego has the same purchasing power as $33K/year in Madison

Related comparisons

Healthcare estimates based on national avg retiree spending (~$500/mo) scaled by COL index · State income tax rates from Tax Foundation · Data: Zillow, BLS, Numbeo · Q1 2026