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

6.3%

Avg Cash on Cash

-3.1%

Median Cashflow

$144/mo

Avg Rent Estimate

$5,774/mo

Avg Price

$599,278

Price Range

$389,400 - $935,700

Rent to Price

0.96%

okay ratio

Positive Cashflow

56%

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 -3.1%.

Across 10+ analyzed properties, Winter Park, FL mid-term rental investments show a median monthly cashflow of $144 with average furnished rent estimates of $5,774/month. These figures reflect real property data, not projections.

1871 Barker Dr, Winter Park, FL 32789

Price

$744,900

Rent

$7,914

CachFlow

$503

CoC

3.46

Full Analysis

7641 Village Green Drive, Winter Park, FL 32792

Price

$536,600

Rent

$4,686

CachFlow

-$248

CoC

-2.28

Full Analysis

3641 Hawthorne Ln, Winter Park, FL 32792

Price

$428,400

Rent

$4,641

CachFlow

$453

CoC

5.04

Full Analysis

685 Overspin Dr, Winter Park, FL 32789

Price

$606,000

Rent

$6,240

CachFlow

$194

CoC

1.6

Full Analysis

3641 Oak Vista Ln, Winter Park, FL 32792

Price

$475,000

Rent

$4,899

CachFlow

$559

CoC

5.7

Full Analysis
15 of 10
1 / 2

Winter Park, FL Mid-Term Rental Market Insights

  • Positive median cashflow of $144/month indicates most investors cover expenses
  • 6.3% median cap rate reflects a balanced risk-return profile
  • 56% positive cashflow rate means roughly half properties are cash-flow positive
  • Premium market with properties from $389,400 to $935,700
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

Enter a Property Address for Instant Investment Analysis

Fast and accurate real estate investment analysis