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

-4.4%

Median Cashflow

-$294/mo

Avg Rent Estimate

$4,432/mo

Avg Price

$626,250

Price Range

$294,300 - $1,407,000

Rent to Price

0.71%

low ratio

Positive Cashflow

27%

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 -4.4%.

Across 10+ analyzed properties, Winter Park, FL mid-term rental investments show a median monthly cashflow of -$294 with average furnished rent estimates of $4,432/month. These figures reflect real property data, not projections.

1320 BUCKINGHAM ROAD, Winter Park, FL 32789

Price

$449,000

Rent

$4,282

CachFlow

$16

CoC

0.17

Full Analysis

112 BELL PLACE, Winter Park, FL 32792

Price

$556,900

Rent

$4,088

CachFlow

-$1,097

CoC

-9.75

Full Analysis

4910 SEMINOLE AVENUE, Winter Park, FL 32792

Price

$325,600

Rent

$3,354

CachFlow

-$82

CoC

-1.14

Full Analysis

5080 SEMINOLE AVENUE, Winter Park, FL 32792

Price

$294,300

Rent

$3,471

CachFlow

$334

CoC

5.02

Full Analysis

2136 LINDEN ROAD, Winter Park, FL 32792

Price

$365,000

Rent

$3,012

CachFlow

-$294

CoC

-3.73

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

  • •Median cashflow is -$294/month — careful deal selection is essential here
  • •5.6% median cap rate reflects a balanced risk-return profile
  • •At 27% positive cashflow rate, Winter Park, FL requires selective property picks
  • •Premium market with properties from $294,300 to $1,407,000
  • •Early-stage market data — revisit as more properties are analyzed for stronger signals

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