Chesapeake, VA Rental Market for Investors
An estimated 62% of Chesapeake's active listings could cash-flow as a short-term rental — here's what the numbers say for investors, as of October 2026.
As of October 2026, we analyzed 783 active for-sale homes in Chesapeake, Virginia. The typical listing is priced at $498,000 and is projected to generate about $48,534 a year as a short-term rental.
After setting aside an estimated 20% for operating costs, an estimated 61.6% of those homes could still cover an investor mortgage payment on short-term-rental income — well above the 53.1% median across the 200 major metros we track, ranking Chesapeake #60 of 200 for cash-flow potential.
On market momentum: homes in Chesapeake sit a median of 41 days on the market, and 40% of active listings came on in just the last 30 days — a steadily paced market, which shapes how much room there is to negotiate.
For a DSCR loan — which qualifies on the property's rental income rather than your personal income — that's a relatively healthy setup: in Chesapeake, a meaningful share of listings throw off enough short-term-rental income, after costs, to cover an estimated investor mortgage payment.
What actually works in Chesapeake
Chesapeake works for investors, but the window is specific: 235 of the 637 Chesapeake homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $433,000.
| Price | 2 bed | 3 bed | 4 bed | 5 bed |
|---|---|---|---|---|
| $150k–$250k | 100%2.03 | 100%1.87 | — | — |
| $250k–$350k | 84%1.47 | 88%1.44 | 100%1.68 | — |
| $350k–$500k | — | 40%1.22 | 47%1.23 | 100%1.48 |
| $500k+ | — | 0%0.83 | 1%0.87 | 3%0.83 |
Darker means a larger share of that group cash-flows. “—” means fewer than 8 active listings — too few to draw a conclusion from.
Chesapeake in full
| Active for-sale homes analyzed | 783 |
|---|---|
| Median list price | $498,000 |
| Median projected STR revenue (annual, gross) | $48,534 |
| Median average daily rate (ADR) | $194 |
| Median occupancy | 65% |
| Median beds | 4 |
| Median size | 2,200 sqft |
| Estimated cash-flow-positive share | 61.6% |
| Median days on market | 41 days |
| New listings (last 30 days) | 39.7% of active |
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Estimates for educational purposes. Final terms subject to credit, property & program approval.
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