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

7.3%

Avg Cash on Cash

0.2%

Median Cashflow

$256/mo

Avg Rent Estimate

$3,577/mo

Avg Price

$409,680

Price Range

$335,800 - $518,000

Rent to Price

0.87%

okay ratio

Positive Cashflow

60%

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 0.2%.

Across 10+ analyzed properties, Chestertown, MD mid-term rental investments show a median monthly cashflow of $256 with average furnished rent estimates of $3,577/month. These figures reflect real property data, not projections.

22481 Goose Hollow Dr, Chestertown, MD 21620

Price

$373,100

Rent

$3,783

CachFlow

$366

CoC

4.56

Full Analysis

25750 Collins Ave, Chestertown, MD 21620

Price

$457,400

Rent

$3,482

CachFlow

-$467

CoC

-4.91

Full Analysis

10572 Watonga Rd, Chestertown, MD 21620

Price

$335,800

Rent

$3,368

CachFlow

$250

CoC

3.39

Full Analysis

118 Grant Ct, Chestertown, MD 21620

Price

$428,200

Rent

$4,386

CachFlow

$322

CoC

3.58

Full Analysis

8629 Airy Hill Rd, Chestertown, MD 21620

Price

$425,000

Rent

$2,934

CachFlow

-$469

CoC

-5.25

Full Analysis
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Chestertown, MD Mid-Term Rental Market Insights

  • Positive median cashflow of $256/month indicates most investors cover expenses
  • 7.3% median cap rate reflects a balanced risk-return profile
  • 60% positive cashflow rate means roughly half properties are cash-flow positive
  • Mid-to-upper tier market with properties from $335,800 to $518,000
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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