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REI Lense

Winchester, KY Long-Term Rental Analysis

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

Winchester, KY Long-Term Rental Investment Snapshot

Based on 10+ long-term rental datapoints

Median Cap Rate

4.4%

Avg Cash on Cash

-8.9%

Median Cashflow

-$482/mo

Avg Rent Estimate

$1,931/mo

Avg Price

$333,482

Price Range

$234,900 - $675,000

Rent to Price

0.58%

low ratio

Positive Cashflow

0%

of analyzed properties

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

Winchester, KY is primarily an appreciation-driven market for long-term rental investors. Cap rates average 4.4%, typical of mid-to-upper tier markets where property value growth complements rental income. Investors here build equity through appreciation while rental income covers holding costs.

Based on 10+ analyzed properties, the median monthly cashflow in Winchester, KY is -$482 with average rents of $1,931/month. Properties range from $234,900 to $675,000, offering entry points across multiple investment budgets.

178 Hawthorne Dr, Winchester, KY 40391

Price

$383,800

Rent

$2,438

CachFlow

-$535

CoC

-7.97

Full Analysis

20 Jackson St, Winchester, KY 40391

Price

$281,400

Rent

$1,609

CachFlow

-$518

CoC

-10.52

Full Analysis

4100 Crowe Ridge Rd, Winchester, KY 40391

Price

$309,200

Rent

$2,137

CachFlow

-$226

CoC

-4.18

Full Analysis

3166 Colby Rd, Winchester, KY 40391

Price

$1,695,000

Rent

$2,869

CachFlow

-$7,557

CoC

-25.48

Full Analysis

316 Maryland Ave, Winchester, KY 40391

Price

$253,300

Rent

$1,398

CachFlow

-$422

CoC

-9.52

Full Analysis
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Winchester, KY Rental Market Insights

  • Median cashflow is -$482/month — careful deal selection is essential here
  • 4.4% median cap rate is typical of appreciation-focused markets
  • At 0% positive cashflow rate, Winchester, KY requires selective property picks
  • Mid-to-upper tier market with properties from $234,900 to $675,000
  • Consider this market if your strategy favors equity growth with rental income covering holding costs

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