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Chesapeake, VA Mid-Term Rental Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for mid-term rental investments in Chesapeake, VA. Based on 40+ datapoints.

Chesapeake, VA Mid-Term Rental Investment Snapshot

Based on 40+ mid-term rental datapoints

Median Cap Rate

6.1%

Avg Cash on Cash

-1%

Median Cashflow

-$48/mo

Avg Rent Estimate

$3,638/mo

Avg Price

$390,007

Price Range

$274,990 - $595,000

Rent to Price

0.93%

okay ratio

Positive Cashflow

44%

of analyzed properties

Recent real estate investor listings analysed as mid-term rental deals in Chesapeake, VA

Chesapeake, VA presents a balanced mid-term rental profile across 40+ analyzed datapoints. A median 6.1% cap rate combined with -1% average cash-on-cash returns make this a solid market for investors blending furnished-rental yield with the operational simplicity of monthly stays at a mid-to-upper tier price point.

Across 40+ analyzed properties, Chesapeake, VA mid-term rental investments show a median monthly cashflow of -$48 with average furnished rent estimates of $3,638/month. These figures reflect real property data, not projections.

2423 Herring Ditch Rd, Chesapeake, VA 23323

Price

$300,000

Rent

$3,236

CachFlow

$254

CoC

3.76

Full Analysis

2749 Meadow Dr E, Chesapeake, VA 23321

Price

$399,900

Rent

$4,056

CachFlow

$243

CoC

2.86

Full Analysis

1323 Oleander Ave, Chesapeake, VA 23325

Price

$345,000

Rent

$3,232

CachFlow

$122

CoC

1.62

Full Analysis

4313 Portsmouth Blvd, Chesapeake, VA 23321

Price

$335,000

Rent

$3,040

CachFlow

-$24

CoC

-0.33

Full Analysis

1212 Santeetlah Ave, Chesapeake, VA 23325

Price

$425,000

Rent

$3,342

CachFlow

-$336

CoC

-3.76

Full Analysis
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Chesapeake, VA Mid-Term Rental Market Insights

  • Median cashflow is -$48/month — careful deal selection is essential here
  • 6.1% median cap rate reflects a balanced risk-return profile
  • 44% positive cashflow rate means roughly two in five properties are cash-flow positive
  • Mid-to-upper tier market with properties from $274,990 to $595,000

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