Investor market data · Virginia

Chesapeake, VA Rental Market for Investors

An estimated 61% of Chesapeake's active listings could cash-flow as a short-term rental — here's what the numbers say for investors, as of August 2026.

See what pencils →Run a DSCR

$499,900Median list price816 active listings

$49,410Median STR revenue / yrprojected, gross

Homes in Chesapeake that pencil right now

A sample of active Chesapeake listings whose DSCR clears 1.25 using short-term rental income projections we accept as a direct lender. These are spread across the price range, not ranked, and current as of August 2026.

$220,000DSCR 1.92
4 bed · 2 bath · 1,928 sqft
House in 23324 · built 1908
STR revenue
$40,641/yr
Est. interest-only payment
$1,409/mo
On the market 127 days · Listed by AtCoastal Realty
Scout this home & market: 4-bed house in Chesapeake
$240,000DSCR 2.02
2 bed · 2.5 bath · 1,168 sqft
Condo in 23320 · built 2019
STR revenue
$44,390/yr
Est. interest-only payment
$1,465/mo
On the market 36 days · Listed by BHHS RW Towne Realty
Scout this home & market: 2-bed condo in Chesapeake
$268,999DSCR 1.96
2 bed · 2.5 bath · 1,255 sqft
Condo in 23320 · built 2000
STR revenue
$48,347/yr
Est. interest-only payment
$1,646/mo
On the market 125 days · Listed by Redfin Corporation
Scout this home & market: 2-bed condo in Chesapeake
$292,000DSCR 1.37
2 bed · 2 bath · 1,150 sqft
House in 23324 · built 1979
STR revenue
$35,658/yr
Est. interest-only payment
$1,732/mo
On the market 22 days · Listed by Swell Real Estate Co.
Scout this home & market: 2-bed house in Chesapeake
$324,900DSCR 1.56
4 bed · 1 bath · 1,500 sqft
House in 23324 · built 1965
STR revenue
$45,809/yr
Est. interest-only payment
$1,956/mo
On the market 23 days · Listed by A Better Way Realty Inc.
Scout this home & market: 4-bed house in Chesapeake
$335,000DSCR 1.53
3 bed · 2.5 bath · 1,635 sqft
Townhouse in 23320 · built 1992
STR revenue
$47,044/yr
Est. interest-only payment
$2,054/mo
On the market 8 days · Listed by The Real Estate Group, LLC
Scout this home & market: 3-bed townhouse in Chesapeake
$375,000DSCR 1.42
3 bed · 2.5 bath · 1,894 sqft
Condo in 23320 · built 1990
STR revenue
$48,306/yr
Est. interest-only payment
$2,260/mo
On the market 22 days · Listed by Long & Foster Oceanfront
Scout this home & market: 3-bed condo in Chesapeake
$420,000DSCR 1.31
4 bed · 2.5 bath · 1,710 sqft
House in 23322 · built 1986
STR revenue
$49,886/yr
Est. interest-only payment
$2,546/mo
On the market 34 days · Listed by BHHS RW Towne Realty
Scout this home & market: 4-bed house in Chesapeake

Ask about Chesapeake deals →Run any address yourself

As of August 2026, we analyzed 816 active for-sale homes in Chesapeake, Virginia. The typical listing is priced at $499,900 and is projected to generate about $49,410 a year as a short-term rental.

After setting aside an estimated 20% for operating costs, an estimated 61.4% of those homes could still cover an investor mortgage payment on short-term-rental income — well above the 52.5% median across the 200 major metros we track, ranking Chesapeake #64 of 200 for cash-flow potential.

On market momentum: homes in Chesapeake sit a median of 27 days on the market, and 54% of active listings came on in just the last 30 days — a fast-moving 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: 281 of the 710 Chesapeake homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $435,000.

Share of those listings clearing an DSCR of 1.25, by price and bedroom count. The smaller figure is the median DSCR for that group.
Price	2 bed	3 bed	4 bed	5 bed
$150k–$250k	97%2.05	100%2.26	—	—
$250k–$350k	91%1.56	97%1.56	100%1.68	—
$350k–$500k	—	49%1.25	51%1.26	82%1.43
$500k+	—	0%0.86	1%0.88	6%0.84

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	816
Median list price	$499,900
Median projected STR revenue (annual, gross)	$49,410
Median average daily rate (ADR)	$194
Median occupancy	66%
Median beds	4
Median size	2,200 sqft
Estimated cash-flow-positive share	61.4%
Median days on market	27 days
New listings (last 30 days)	54.0% of active