Moving from Chesapeake, VA to Winston-Salem, NC
It is a 269 mi drive, roughly 5h 38m, between Chesapeake, VA and Winston-Salem, NC. 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
| Chesapeake | Winston-Salem | U.S. avg | |
|---|---|---|---|
| All items (RPP) | 97.941 | 92.043 | 100.0 |
| Rents | 89.579 | 88.421 | 100.0 |
| Goods | 96.767 | 96.621 | 100.0 |
| Services | 99.805 | 71.377 | 100.0 |
Overall cost of living drops 6.0% moving from Chesapeake to Winston-Salem β meaningful on rent but closer to parity on groceries.
Source: BEA Regional Price Parities (MSA-level Β· MSA-level); 2024.
Housing prices
Zillow ZHVI drops from $420,756 in Chesapeake to $264,333 in Winston-Salem, a 6.0% decrease on the typical home value.
YoY change: Chesapeake +2.9%, Winston-Salem +0.9%. Snapshot: 2026-03. Data provided by Zillow.
Climate
| 1991β2020 normals | Chesapeake | Winston-Salem |
|---|---|---|
| Annual avg temperature | 63Β°F | 60Β°F |
| January avg low | 34Β°F | 31Β°F |
| July avg high | 93Β°F | 88Β°F |
| Annual snowfall | β | β |
| Annual precipitation | 48.6" | 43.2" |
Climate is roughly comparable on the annual mean β 63.0Β°F vs 59.5Β°F per NOAA 1991β2020 normals.
Source: NOAA U.S. Climate Normals 1991β2020 (stations: FENTRESS NAAS, VA US, WINSTON SALEM RYNLDS AP, NC US).
Demographics
| ACS 5-year 2023 | Chesapeake | Winston-Salem |
|---|---|---|
| Population | 251,153 | 250,887 |
| Median household income | $94,189 | $57,673 |
| Median age | 37.7 | 35.6 |
| Bachelor's degree or higher | 22.4% | 21.6% |
| Avg household size | 2.72 | 2.5 |
Winston-Salem households earn about 6.0% less than Chesapeake at the median β $94,189 β $57,673 on ACS 2023.
Source: U.S. Census Bureau, ACS 5-year 2023.
Jobs & wages
Top occupations in Winston-Salem MSA
| Occupation | Employment | Median wage |
|---|---|---|
| Office and Administrative Support Occupations | 31,440 | $40,070 |
| Transportation and Material Moving Occupations | 27,960 | $36,300 |
| Sales and Related Occupations | 26,050 | $31,830 |
| Food Preparation and Serving Related Occupations | 24,820 | $27,550 |
| Healthcare Practitioners and Technical Occupations | 24,350 | $78,520 |
Source: BLS Occupational Employment and Wage Statistics.
Moving between Virginia and North Carolina
State income-tax top marginal rates are from the Tax Foundation, updated annually. Check North Carolina'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
- Atlantic hurricane season runs August through October, particularly on the Outer Banks.
- 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 North Carolina after establishing residency.
Frequently asked
How much do homes cost in Winston-Salem compared to Chesapeake?
Zillow ZHVI (2026-03) puts the typical home value at $264,333 in Winston-Salem vs $420,756 in Chesapeake β a 37.2% lower figure. Data provided by Zillow Research.
How far is Winston-Salem, NC from Chesapeake, VA?
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.
When is the best time to move from Chesapeake to Winston-Salem?
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.
How does the job market in Winston-Salem compare to Chesapeake?
BLS Occupational Employment and Wage Statistics show median wages of $43,040 in the Winston-Salem MSA vs $46,990 in the Chesapeake MSA, on total employment of 271,620 and 737,200 respectively. Top occupations on the destination side appear in the Jobs & wages section above.
Is Winston-Salem more expensive than Chesapeake?
Based on BEA Regional Price Parities (2024), overall price level in Winston-Salem is 6.0% lower than Chesapeake (92.043 vs 97.941, U.S. average = 100). Rent and services typically carry most of this gap.
How does household income compare in Chesapeake vs Winston-Salem?
Median household income on the Census ACS 5-year (2023) is $57,673 in Winston-Salem vs $94,189 in Chesapeake β a 38.8% lower 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 Chesapeake.
City profiles: Chesapeake, VA Β· Winston-Salem, NC.