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REI Lense

Winter Garden, FL Mid-Term Rental Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for mid-term rental investments in Winter Garden, FL. Based on 15+ datapoints.

Winter Garden, FL Mid-Term Rental Investment Snapshot

Based on 15+ mid-term rental datapoints

Median Cap Rate

5.1%

Avg Cash on Cash

-4.3%

Median Cashflow

-$551/mo

Avg Rent Estimate

$4,476/mo

Avg Price

$530,379

Price Range

$419,000 - $639,990

Rent to Price

0.84%

okay ratio

Positive Cashflow

18%

of analyzed properties

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

Winter Garden, FL is an emerging mid-term rental market gaining attention from investors who want LTR-style stability with stronger furnished-rent premiums. With 15+ analyzed datapoints, early metrics suggest opportunity to enter before MTR inventory matures. Current average cash-on-cash returns sit at -4.3%.

Across 15+ analyzed properties, Winter Garden, FL mid-term rental investments show a median monthly cashflow of -$551 with average furnished rent estimates of $4,476/month. These figures reflect real property data, not projections.

2202 Romanum Dr, Winter Garden, FL 34787

Price

$543,500

Rent

$4,422

CachFlow

-$551

CoC

-5

Full Analysis

6587 Old Carriage Rd, Winter Garden, FL 34787

Price

$621,300

Rent

$4,446

CachFlow

-$1,020

CoC

-8.24

Full Analysis

15183 Bridgewater Crossings Blvd, Winter Garden, FL 34787

Price

$505,900

Rent

$5,412

CachFlow

$99

CoC

0.96

Full Analysis

17056 Red Bird Rd, Winter Garden, FL 34787

Price

$795,000

Rent

$4,383

CachFlow

-$1,446

CoC

-9.38

Full Analysis

1645 E Spring Ridge Cir, Winter Garden, FL 34787

Price

$380,600

Rent

$3,530

CachFlow

-$41

CoC

-0.5

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

  • Median cashflow is -$551/month — careful deal selection is essential here
  • 5.1% median cap rate reflects a balanced risk-return profile
  • At 18% positive cashflow rate, Winter Garden, FL requires selective property picks
  • Premium market with properties from $419,000 to $639,990
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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