Moving from Winston-Salem, NC to Chesapeake, VA
It is a 269 mi drive, roughly 5h 38m, between Winston-Salem, NC and Chesapeake, VA. At mid-range distance you typically see real gaps open up on cost of living, home values, and climate β not just scenery. This page assembles the comparison from federal data sources and Zillow Research for a single-page view of the move.
269 mi Β· 5h 38m by car Β· VA β NC
Distance & route
| Route through | VA β NC |
|---|---|
| Primary highways | I 85, US 58, US 13 |
| Major cities en route | Virginia Beach, Norfolk, Hampton, Newport News, Raleigh |
Route via OSRM driving profile. Actual time varies with traffic and season.
Cost of living
| Winston-Salem | Chesapeake | U.S. avg | |
|---|---|---|---|
| All items (RPP) | 92.043 | 97.941 | 100.0 |
| Rents | 88.421 | 89.579 | 100.0 |
| Goods | 96.621 | 96.767 | 100.0 |
| Services | 71.377 | 99.805 | 100.0 |
Expect roughly 6.4% higher cost of living β rent and services usually drive most of a gap this size.
Source: BEA Regional Price Parities (MSA-level Β· MSA-level); 2024.
Housing prices
Expect roughly 6.4% higher home prices β ZHVI goes from $264,333 to $420,756 moving to Chesapeake.
YoY change: Winston-Salem +0.9%, Chesapeake +2.9%. Snapshot: 2026-03. Data provided by Zillow.
Climate
| 1991β2020 normals | Winston-Salem | Chesapeake |
|---|---|---|
| Annual avg temperature | 60Β°F | 63Β°F |
| January avg low | 31Β°F | 34Β°F |
| July avg high | 88Β°F | 93Β°F |
| Annual snowfall | β | β |
| Annual precipitation | 43.2" | 48.6" |
Annual average temperatures in Winston-Salem (59.5Β°F) and Chesapeake (63.0Β°F) stay within 5Β°F of each other (NOAA normals).
Source: NOAA U.S. Climate Normals 1991β2020 (stations: WINSTON SALEM RYNLDS AP, NC US, FENTRESS NAAS, VA US).
Demographics
| ACS 5-year 2023 | Winston-Salem | Chesapeake |
|---|---|---|
| Population | 250,887 | 251,153 |
| Median household income | $57,673 | $94,189 |
| Median age | 35.6 | 37.7 |
| Bachelor's degree or higher | 21.6% | 22.4% |
| Avg household size | 2.5 | 2.72 |
Chesapeake households earn about 6.4% more than Winston-Salem at the median β $57,673 β $94,189 on ACS 2023.
Source: U.S. Census Bureau, ACS 5-year 2023.
Jobs & wages
Top occupations in Chesapeake MSA
| Occupation | Employment | Median wage |
|---|---|---|
| Office and Administrative Support Occupations | 82,690 | $39,820 |
| Food Preparation and Serving Related Occupations | 71,490 | $29,090 |
| Sales and Related Occupations | 69,500 | $31,880 |
| Transportation and Material Moving Occupations | 59,850 | $38,810 |
| Business and Financial Operations Occupations | 57,140 | $79,090 |
Source: BLS Occupational Employment and Wage Statistics.
Moving between North Carolina and Virginia
State income-tax top marginal rates are from the Tax Foundation, updated annually. Check Virginia's DMV for the current deadline to transfer driver license and vehicle registration after establishing residency. Consult a tax professional for your specific filing situation β state tax treatment depends on residency, sourcing, and reciprocity agreements.
Best time to move
Moving companies typically charge 20β30% more between Memorial Day and Labor Day (peak season). October through April offers the lowest rates and better mover availability.
To avoid mid-semester school transfers, most U.S. families schedule moves between mid-June and mid-August. Public school calendars typically run late August or early September through late May or early June.
Winter driving along this route
- I-64 across Afton Mountain and I-77 at Fancy Gap see chain requirements in winter storms.
- I-40 through Pigeon Gap and I-26 over Saluda Grade can see chain requirements in winter storms.
State DOT 511 phone or web services provide real-time road conditions year-round.
Packing & arrival checklist
- Air conditioning matters: July highs in Chesapeake average 93Β°F on NOAA normals. If the new place has window-unit or no AC, plan that purchase for the first week.
- Arrange utility connection (power, internet, gas, water) two weeks ahead of move-in.
- Update mailing address with USPS change-of-address within the first week post-move.
- Register to vote in Virginia after establishing residency.
Frequently asked
How far is Chesapeake, VA from Winston-Salem, NC?
The driving distance is 269 mi and the route typically takes 5h 38m via I 85 and US 58. The trip crosses 2 state(s). Actual time varies with traffic and season.
How does the job market in Chesapeake compare to Winston-Salem?
BLS Occupational Employment and Wage Statistics show median wages of $46,990 in the Chesapeake MSA vs $43,040 in the Winston-Salem MSA, on total employment of 737,200 and 271,620 respectively. Top occupations on the destination side appear in the Jobs & wages section above.
When is the best time to move from Winston-Salem to Chesapeake?
Moving companies usually charge 20β30% less between October and April (off-peak). Memorial Day through Labor Day is peak pricing. For a 269 mi drive, weather on the route matters too β see the timing section above for state-specific winter warnings.
Is Chesapeake more expensive than Winston-Salem?
Based on BEA Regional Price Parities (2024), overall price level in Chesapeake is 6.4% higher than Winston-Salem (97.941 vs 92.043, U.S. average = 100). Rent and services typically carry most of this gap.
How much do homes cost in Chesapeake compared to Winston-Salem?
Zillow ZHVI (2026-03) puts the typical home value at $420,756 in Chesapeake vs $264,333 in Winston-Salem β a 59.2% higher figure. Data provided by Zillow Research.
How does household income compare in Winston-Salem vs Chesapeake?
Median household income on the Census ACS 5-year (2023) is $94,189 in Chesapeake vs $57,673 in Winston-Salem β a 63.3% higher figure. Compare this against the cost-of-living gap above when budgeting.
Plan the move
Estimate costs with our moving cost calculator, or see where else to move from Winston-Salem.
City profiles: Winston-Salem, NC Β· Chesapeake, VA.