Winston-Salem vs Montgomery for Retirees (2026)

Median Home Price
$260K
Winston-Salem
$195K
Montgomery
State Income Tax
4.5%
Winston-Salem
5%
Montgomery
Est. Healthcare / month
$435
Winston-Salem
$405
Montgomery
Walk Score (0–100)
26
Winston-Salem
24
Montgomery

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

Full retirement cost breakdown

Metric
Winston-Salem
North Carolina
Montgomery
Alabama
1BR rent / month$1,300$1,050Better
Median home price$260K$195KBetter
State income tax4.5%Better5%
Sales tax (combined)7%Better9.2%
Monthly utilities$150Better$170
Groceries index (US = 100)9593Better
Est. healthcare / month$435$405Better
Walk score (0–100)26 / 100Better24 / 100
Overall COL index (100 = US avg)8781Better

Frequently asked questions

Which city is better for retirement — Winston-Salem or Montgomery?

Winston-Salem and Montgomery are closely matched for retirees. Housing costs, tax burden, and overall affordability are similar. Your specific priorities — climate, walkability, family proximity — should guide the decision.

Is retirement income taxed in Winston-Salem or Montgomery?

Winston-Salem has the lower state income tax rate (4.5% vs 5%). 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 Winston-Salem vs Montgomery?

Based on national average retiree healthcare spending (~$500/month) scaled by each city's cost-of-living index, estimated monthly healthcare costs are approximately $435 in Winston-Salem and $405 in Montgomery. That's a difference of ~$30/month, or ~$360/year. Actual costs vary based on your Medicare plan, supplements, and health needs.

Can I afford to retire in Winston-Salem on a $50,000 annual income?

On a $50,000/year ($4,167/month) retirement income in Winston-Salem, rent alone would consume approximately 31% of your budget (1BR rent ~$1,300/mo) and healthcare another ~10%. That leaves roughly 59% (~$2,458/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?

Winston-Salem has a higher walk score (26 vs 24 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. Winston-Salem offers more independence without a car, which also reduces transportation costs.

Retirement purchasing power

$50K/year in Winston-Salem has the same purchasing power as $47K/year in Montgomery

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