REI Lense

REI Lense

Chestertown, MD Mid-Term Rental Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for mid-term rental investments in Chestertown, MD. Based on 10+ datapoints.

Chestertown, MD Mid-Term Rental Investment Snapshot

Based on 10+ mid-term rental datapoints

Median Cap Rate

7.1%

Avg Cash on Cash

-0.8%

Median Cashflow

$202/mo

Avg Rent Estimate

$3,419/mo

Avg Price

$389,367

Price Range

$296,600 - $623,100

Rent to Price

0.88%

okay ratio

Positive Cashflow

67%

of analyzed properties

Recent real estate investor listings analysed as mid-term rental deals in Chestertown, MD

Chestertown, MD is an emerging mid-term rental market gaining attention from investors who want LTR-style stability with stronger furnished-rent premiums. With 10+ analyzed datapoints, early metrics suggest opportunity to enter before MTR inventory matures. Current average cash-on-cash returns sit at -0.8%.

Across 10+ analyzed properties, Chestertown, MD mid-term rental investments show a median monthly cashflow of $202 with average furnished rent estimates of $3,419/month. These figures reflect real property data, not projections.

217 Edmore Rd, Chestertown, MD 21620

Price

$327,200

Rent

$3,602

CachFlow

$432

CoC

5.98

Full Analysis

7464 Shortall St, Chestertown, MD 21620

Price

$296,600

Rent

$2,805

CachFlow

$46

CoC

0.69

Full Analysis

240 Round Top Rd, Chestertown, MD 21620

Price

$324,200

Rent

$3,250

CachFlow

$202

CoC

2.82

Full Analysis

216 Birch Run Rd, Chestertown, MD 21620

Price

$828,400

Rent

$3,554

CachFlow

-$2,928

CoC

-18.3

Full Analysis

109 Parma Rd, Chestertown, MD 21620

Price

$312,200

Rent

$3,297

CachFlow

$298

CoC

4.28

Full Analysis
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Chestertown, MD Mid-Term Rental Market Insights

  • Positive median cashflow of $202/month indicates most investors cover expenses
  • 7.1% median cap rate reflects a balanced risk-return profile
  • 67% positive cashflow rate means roughly half properties are cash-flow positive
  • Mid-to-upper tier market with properties from $296,600 to $623,100
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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