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REI Lense

Winchester, KY Mid-Term Rental Analysis

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

Winchester, KY Mid-Term Rental Investment Snapshot

Based on 10+ mid-term rental datapoints

Median Cap Rate

6.2%

Avg Cash on Cash

-0.6%

Median Cashflow

-$54/mo

Avg Rent Estimate

$2,897/mo

Avg Price

$333,482

Price Range

$234,900 - $675,000

Rent to Price

0.87%

okay ratio

Positive Cashflow

40%

of analyzed properties

Recent real estate investor listings analysed as mid-term rental deals in Winchester, KY

Winchester, KY 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 -0.6%.

Across 10+ analyzed properties, Winchester, KY mid-term rental investments show a median monthly cashflow of -$54 with average furnished rent estimates of $2,897/month. These figures reflect real property data, not projections.

178 Hawthorne Dr, Winchester, KY 40391

Price

$383,800

Rent

$3,657

CachFlow

$75

CoC

0.91

Full Analysis

20 Jackson St, Winchester, KY 40391

Price

$281,400

Rent

$2,414

CachFlow

-$117

CoC

-1.82

Full Analysis

4100 Crowe Ridge Rd, Winchester, KY 40391

Price

$309,200

Rent

$3,206

CachFlow

$309

CoC

4.47

Full Analysis

3166 Colby Rd, Winchester, KY 40391

Price

$1,695,000

Rent

$4,304

CachFlow

-$6,839

CoC

-21.95

Full Analysis

316 Maryland Ave, Winchester, KY 40391

Price

$253,300

Rent

$2,097

CachFlow

-$73

CoC

-1.23

Full Analysis
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Winchester, KY Mid-Term Rental Market Insights

  • Median cashflow is -$54/month — careful deal selection is essential here
  • 6.2% median cap rate reflects a balanced risk-return profile
  • 40% positive cashflow rate means roughly two in five properties are cash-flow positive
  • Mid-to-upper tier market with properties from $234,900 to $675,000
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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