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REI Lense

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 20+ datapoints.

Chesapeake, VA Short-Term Rental / Airbnb Investment Snapshot

Based on 20+ short-term rental / airbnb datapoints

Median Cap Rate

4.4%

Avg Cash on Cash

-8.8%

Median Cashflow

-$873/mo

Avg Rent Estimate

$3,934/mo

Avg Price

$515,255

Price Range

$250,000 - $824,500

Rent to Price

0.76%

okay ratio

Positive Cashflow

4%

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 4.4%, the premium property prices reflect strong underlying demand. STR investors here typically benefit from appreciation alongside rental income.

Across 20+ analyzed properties, Chesapeake, VA STR investments show a median monthly cashflow of -$873 with an average estimated nightly-rate-adjusted revenue of $3,934/month. These figures reflect real property data, not projections.

3136 Woodbaugh Dr, Chesapeake, VA 23321

Price

$334,900

Rent

$2,989

CachFlow

-$504

CoC

-6.85

Full Analysis

109 Edgeware Ct, Chesapeake, VA 23322

Price

$644,900

Rent

$5,106

CachFlow

-$1,234

CoC

-9.65

Full Analysis

3017 Bill Reid Ct, Chesapeake, VA 23324

Price

$295,000

Rent

$3,364

CachFlow

-$108

CoC

-1.62

Full Analysis

715 Wimbley Ln, Chesapeake, VA 23322

Price

$540,000

Rent

$4,037

CachFlow

-$1,105

CoC

-10.09

Full Analysis

660 Margaret Dr, Chesapeake, VA 23322

Price

$649,900

Rent

$3,155

CachFlow

-$2,212

CoC

-17.18

Full Analysis
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Chesapeake, VA Airbnb Market Insights

  • Median cashflow is -$873/month — careful deal selection is essential here
  • 4.4% median cap rate is typical of appreciation-focused markets
  • At 4% positive cashflow rate, Chesapeake, VA requires selective property picks
  • Premium market with properties from $250,000 to $824,500
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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