REI Lense

REI Lense

Winter Park, FL Mid-Term Rental Analysis

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

Winter Park, FL Mid-Term Rental Investment Snapshot

Based on 10+ mid-term rental datapoints

Median Cap Rate

5.6%

Avg Cash on Cash

-3.4%

Median Cashflow

-$234/mo

Avg Rent Estimate

$3,899/mo

Avg Price

$576,920

Price Range

$389,400 - $950,000

Rent to Price

0.68%

low ratio

Positive Cashflow

30%

of analyzed properties

Recent real estate investor listings analysed as mid-term rental deals in Winter Park, FL

Winter Park, FL 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 -3.4%.

Across 10+ analyzed properties, Winter Park, FL mid-term rental investments show a median monthly cashflow of -$234 with average furnished rent estimates of $3,899/month. These figures reflect real property data, not projections.

241 W Lake Sue Ave, Winter Park, FL 32789

Price

$935,700

Rent

$7,576

CachFlow

-$1,350

CoC

-7.55

Full Analysis

2940 De Brocy Way, Winter Park, FL 32792

Price

$752,500

Rent

$4,074

CachFlow

-$2,078

CoC

-14.17

Full Analysis

1433 Aster Ct, Winter Park, FL 32792

Price

$389,400

Rent

$3,496

CachFlow

$144

CoC

1.73

Full Analysis

1438 Tierra Cir, Winter Park, FL 32792

Price

$525,000

Rent

$4,032

CachFlow

-$211

CoC

-1.97

Full Analysis

7761 Fox Knoll Pl, Winter Park, FL 32792

Price

$414,900

Rent

$3,458

CachFlow

-$256

CoC

-2.92

Full Analysis
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Winter Park, FL Mid-Term Rental Market Insights

  • Median cashflow is -$234/month — careful deal selection is essential here
  • 5.6% median cap rate reflects a balanced risk-return profile
  • At 30% positive cashflow rate, Winter Park, FL requires selective property picks
  • Premium market with properties from $389,400 to $950,000
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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