Rentals that pay for themselves in Winter Haven.
There are 201 rentals in Winter Haven, Florida where the rent currently covers the full mortgage, taxes, and insurance. The median cashflowing listing lists at $245,000, with most homes priced between $115,000 and $289,500. They pencil at about a 1.03 DSCR — roughly $111/mo left over after the payment on a typical 3-bedroom home. The most active ZIPs right now are 33884, 33881, 33880. Every listing below shows the full math up front — and only the ones our partners can fund.
- Cashflowing listings
- 201
- Median price
- $245,000
- Median DSCR
- 1.03
- Avg. monthly cashflow
- +$111
Top cashflow ratios in Winter Haven today
Full FL catalog3bd · 1ba · 1,016 sqft
- Est. rent
- $1,895/mo
- All-in
- $1,109/mo
- Cash to start
- $20,250
- Cashflow
- +$786/mo
3bd · 1ba · 1,141 sqft
- Est. rent
- $1,895/mo
- All-in
- $1,150/mo
- Cash to start
- $20,998
- Cashflow
- +$745/mo
1bd · 1ba · 826 sqft
- Est. rent
- $1,300/mo
- All-in
- $819/mo
- Cash to start
- $14,000
- Cashflow
- +$481/mo
2bd · 2ba · 1,024 sqft
- Est. rent
- $1,573/mo
- All-in
- $1,059/mo
- Cash to start
- $18,950
- Cashflow
- +$514/mo
4bd · 2ba · 1,304 sqft
- Est. rent
- $2,195/mo
- All-in
- $1,520/mo
- Cash to start
- $27,750
- Cashflow
- +$675/mo
3bd · 2ba · 2,182 sqft
- Est. rent
- $1,895/mo
- All-in
- $1,314/mo
- Cash to start
- $24,000
- Cashflow
- +$581/mo
3bd · 2ba · 1,226 sqft
- Est. rent
- $1,803/mo
- All-in
- $1,265/mo
- Cash to start
- $19,800
- Cashflow
- +$538/mo
2bd · 1ba · 840 sqft
- Est. rent
- $1,400/mo
- All-in
- $979/mo
- Cash to start
- $15,960
- Cashflow
- +$421/mo
1bd · 1ba · 1,078 sqft
- Est. rent
- $1,300/mo
- All-in
- $955/mo
- Cash to start
- $19,000
- Cashflow
- +$345/mo
Showing the top 9 of 201 cashflowing Winter Haven listings — browse the rest →
Every listing is pre-screened
We score live listings against real DSCR lending criteria — only the ones whose rent covers the full payment make this page.
The math is shown in full
Rent estimate, all-in payment, cash to start, cashflow ratio. Open any property for the complete breakdown.
Financing is attached
These loans qualify on the property's rent, not your W-2. One click gets you to a loan officer with real terms.
Common questions
How do I know these Winter Haven rentals actually cashflow?+
Every property is scored against current DSCR lending criteria using a rent estimate built from local market comps — the median asking rent for similar homes in the same zip. “Pays for itself” means the estimated rent covers the full monthly payment: mortgage, taxes, and insurance. Final numbers are always confirmed by a loan officer and appraisal.
Can I qualify without a W-2 or tax returns?+
Yes — that's the point of a DSCR loan. It qualifies on whether the property's rent covers the payment, not your personal income. You need a down payment (typically 20–25%), decent credit, and to already own or have recently owned a home.
I don't own a home yet. Can I still invest here?+
Not with a DSCR loan — but you can house-hack: buy a 2–4 unit property with a regular consumer loan at as little as ~3.5–5% down, live in one unit, and rent the rest. A year later, the listings on this page become your shopping list.
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