01 - Taxes
Retirement Tax Treatment
Virginia does not tax Social Security benefits, though other retirement income is subject to state income tax.
Source · Tax Foundation
8
Fact text
- Chesapeake is home to the international headquarters of Dollar Tree, so yes, every bargain you've ever scored there traces back here.
- Chesapeake contains a substantial chunk of the Great Dismal Swamp National Wildlife Refuge, which has arguably the best name of any wildlife refuge in America.
- Despite being the 92nd most populous city in the U.S., Chesapeake ranks 17th largest by land area, it's basically a giant city pretending to be countryside.
Your
Chesapeake
Retirement Outlook — in 90 seconds
Hosted by Michael McMillan, President of Annuities.net
Every figure mentioned is drawn from the same sourced public data shown below — and the video updates as the data does.
242,647
+
Total Population
$
81,261
Median Income
$
286,000
Median Home
13
%
Age 65+
Retirement Suitability
How
Chesapeake
ranks for retirees?
35
/ 100
A blended, sourced view of how this city ranks for retirees across tax, affordability, healthcare, and climate.
Tax
8
Affordability
57
Healthcare
50
Climate
24
Results
Chesapeake
Suitability Breakdown
02 - Income
Annuity Rates Available Here
Fixed annuity rates reach up to
7
% on 5-year terms, with most landing between
5
% and
5
%.
Source · Cannex
57
03 - Healthcare
Hospital Access & Quality
The area has
Medicare-certified hospitals, averaging a
/5 CMS quality rating.
Source · CMS Hospital Compare
04 - Climate
Weather & Comfort
A
Cold / Snowy
climate — summers peak near
88
°F, winters dip to about
25
°F, with roughly
″ of snow a year.
Source · NOAA Climate Normals
Cold / Snowy
05 - Risk
Natural Disaster Risk
FEMA's overall natural-disaster risk rating for this county on the National Risk Index.
Source · FEMA National Risk Index
Relatively Low
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Frequently Asked Questions
Does Virginia tax Social Security income for retirees in Chesapeake?
Virginia does not tax Social Security benefits, which can meaningfully stretch retirement income for Chesapeake residents. However, other retirement income such as withdrawals from IRAs or pensions may still be subject to Virginia state income tax. Retirees should review their full income picture with a tax professional to understand how state taxes apply to their specific situation.
How do annuities fit into a Chesapeake retiree’s Virginia tax picture?
Virginia does not tax Social Security benefits, but other retirement income — including annuity payouts — is subject to state income tax, so Chesapeake retirees often look closely at how guaranteed income fits their overall tax picture. A multi-year guaranteed annuity locks in a fixed interest rate for a set term, letting you plan around predictable growth rather than market swings. That certainty can matter when covering essential expenses. Current rates change often, so check our current annuity rates page for today’s figures.
How much does a home typically cost in Chesapeake, Virginia?
The median home value in Chesapeake is approximately $286,000, and the median household income is around $81,261. These figures suggest a relatively accessible housing market compared to many mid-Atlantic cities. For retirees evaluating whether to downsize or relocate, understanding local home values helps in estimating how housing equity might support a broader retirement income plan.
What is the natural disaster risk like for retirees living in Chesapeake?
FEMA’s National Risk Index rates Chesapeake’s county overall natural-disaster risk as Relatively Low. That said, Chesapeake experiences warm summers with average highs near 88 degrees Fahrenheit and cold winters with lows around 24 to 25 degrees Fahrenheit. Retirees should factor seasonal weather into decisions about housing, insurance, and emergency preparedness planning.
How large is the retiree population in Chesapeake and what does that mean for retirement services?
About 13.2 percent of Chesapeake’s roughly 242,647 residents are aged 65 or older, reflecting a growing but not yet peaked retirement population. With a substantial pre-retiree group also present, demand for retirement planning resources and services is likely to increase in coming years, which may influence the availability of financial and community support options locally.