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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

6.8%

Avg Cash on Cash

0.3%

Median Cashflow

$260/mo

Avg Rent Estimate

$6,317/mo

Avg Price

$668,389

Price Range

$344,400 - $1,407,000

Rent to Price

0.95%

okay ratio

Positive Cashflow

62%

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 0.3%.

Across 10+ analyzed properties, Winter Park, FL mid-term rental investments show a median monthly cashflow of $260 with average furnished rent estimates of $6,317/month. These figures reflect real property data, not projections.

150 E READING WAY, Winter Park, FL 32789

Price

$1,407,000

Rent

$7,413

CachFlow

-$2,986

CoC

-11.43

Full Analysis

1420 ALOMA AVENUE, Winter Park, FL 32789

Price

$970,500

Rent

$8,836

CachFlow

-$681

CoC

-3.68

Full Analysis

7261 ABBEY LANE, Winter Park, FL 32792

Price

$344,400

Rent

$3,894

CachFlow

$327

CoC

4.34

Full Analysis

2781 ABBEY ROAD, Winter Park, FL 32792

Price

$502,700

Rent

$4,464

CachFlow

-$52

CoC

-0.5

Full Analysis

1871 Barker Dr, Winter Park, FL 32789

Price

$744,900

Rent

$7,914

CachFlow

$503

CoC

3.46

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

  • Positive median cashflow of $260/month indicates most investors cover expenses
  • 6.8% median cap rate reflects a balanced risk-return profile
  • 62% positive cashflow rate means roughly half properties are cash-flow positive
  • Premium market with properties from $344,400 to $1,407,000
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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