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Investing in Winter Haven, FL Real Estate

A data-driven snapshot of the Winter Haven, FL rental-property market, built from recently sold homes and CashFlowRE's per-listing investment modeling — median price, cap rate, monthly cash flow, appreciation and inventory — so you can judge the market before you ever open a listing.

$277,700Median sold price
$163Median $/sqft
4.7%Median cap rate
$-387Modeled cash flow / mo
—Appreciation YoY
54.6Months of supply
2,082Active listings
458Sold (last 12 mo)

What the Winter Haven numbers say

In Winter Haven, FL, the median home sold for $277,700 (about $163 per square foot), and the typical deal models out to a 4.7% cap rate with a median $-387 of monthly cash flow. Inventory sits at about 54.6 months of supply — a looser, buyer-friendly market. These are medians across recorded sales; individual properties vary widely, which is exactly what CashFlowRE scores listing by listing.

🔨 See 6 fix-and-flip deals in Winter Haven — listings where the estimated after-repair value beats list price + rehab.

Other Florida markets to compare

See Winter Haven cash-flowing listings

CashFlowRE ranks every for-sale home in Winter Haven, FL by cap rate, cash-on-cash return, DSCR and monthly cash flow — so the best rental deals rise to the top. Create a free account to screen Winter Haven deals, or browse the national market data.