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

5.9%

Avg Cash on Cash

-1.7%

Median Cashflow

-$102/mo

Avg Rent Estimate

$4,694/mo

Avg Price

$559,892

Price Range

$389,400 - $950,000

Rent to Price

0.84%

okay ratio

Positive Cashflow

46%

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 -1.7%.

Across 10+ analyzed properties, Winter Park, FL mid-term rental investments show a median monthly cashflow of -$102 with average furnished rent estimates of $4,694/month. These figures reflect real property data, not projections.

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

1724 Pine Ave, Winter Park, FL 32789

Price

$2,877,800

Rent

$10,179

CachFlow

-$11,837

CoC

-22.82

Full Analysis

241 W Lake Sue Ave, Winter Park, FL 32789

Price

$935,700

Rent

$7,576

CachFlow

-$1,350

CoC

-7.55

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

  • Median cashflow is -$102/month — careful deal selection is essential here
  • 5.9% median cap rate reflects a balanced risk-return profile
  • 46% positive cashflow rate means roughly two in five properties are cash-flow positive
  • 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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