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Chesapeake, VA Short-Term Rental / Airbnb Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for short-term rental / airbnb investments in Chesapeake, VA. Based on 10+ datapoints.

Chesapeake, VA Short-Term Rental / Airbnb Investment Snapshot

Based on 10+ short-term rental / airbnb datapoints

Median Cap Rate

3.1%

Avg Cash on Cash

-11.2%

Median Cashflow

-$982/mo

Avg Rent Estimate

$2,904/mo

Avg Price

$420,164

Price Range

$305,000 - $635,000

Rent to Price

0.69%

low ratio

Positive Cashflow

0%

of analyzed properties

Recent real estate investor listings analysed as short-term rental / airbnb deals in Chesapeake, VA

Chesapeake, VA is a premium short-term rental market where property values drive long-term wealth. While cap rates are modest at 3.1%, the mid-to-upper tier property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 10+ analyzed properties, Chesapeake, VA STR investments show a median monthly cashflow of -$982 with an average estimated nightly-rate-adjusted revenue of $2,904/month. These figures reflect real property data, not projections.

429 Clemson Ave, Chesapeake, VA 23324

Price

$360,000

Rent

$1,789

CachFlow

-$1,268

CoC

-16.26

Full Analysis

312 Sawmill Arch, Chesapeake, VA 23323

Price

$485,000

Rent

$5,395

CachFlow

-$240

CoC

-2.4

Full Analysis

357 Dexter St E, Chesapeake, VA 23324

Price

$415,000

Rent

$513

CachFlow

-$2,271

CoC

-25.92

Full Analysis

4313 Portsmouth Blvd, Chesapeake, VA 23321

Price

$335,000

Rent

$3,110

CachFlow

-$412

CoC

-5.6

Full Analysis

927 Thatcher Way, Chesapeake, VA 23320

Price

$445,000

Rent

$2,580

CachFlow

-$1,070

CoC

-11.52

Full Analysis
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Chesapeake, VA Airbnb Market Insights

  • Median cashflow is -$982/month — careful deal selection is essential here
  • 3.1% median cap rate is typical of appreciation-focused markets
  • At 0% positive cashflow rate, Chesapeake, VA requires selective property picks
  • Mid-to-upper tier market with properties from $305,000 to $635,000
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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