221 Grassy Key Ln

Winding Cypress, FL 34114

$138,500B+

2 bd · 1.0 ba · 734 sqft · Built 1989 · SingleFamily · Active · 5 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,315/mo
• Mortgage (P&I): −$726
• Tax + insurance: −$657
• HOA: −$125
• Vac / Maint / Mgmt: −$486
• Net cashflow: $320/mo
• Annual: $3,840/yr
• Cap rate: 12.76%
• Cash-on-cash: 23.10%
• DSCR: 2.03
• 1% rule: 1.67%
• Cash to close: $38,780

Investor read

• This is a 2-bed/1.0-bath single-family listed at $138k.
• At list price, monthly cash flow is $320 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $138k).
• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-1.5%/yr); year-one equity from $958 of loan paydown is wiped out by about $2k of value loss. Plan a longer hold.
• Location reads: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Collier (suburban): math 60% / reading 56% proficiency, ranked #16 of 73 in FL (top 22%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Watch-outs: flood insurance adds $427/mo.
• Market conditions: Rents rising (+3.2%/yr); 900 active listings in the ZIP; solid renter incomes; 3,520 units permitted in Collier County in 2024 (959 in 5+ unit buildings).
• Collier County population projected at +30% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 4 sale attempts since 18y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $40k; list at $138k implies a 246% gain — meaningful room to come down on a strong offer.
• At projected returns (-1.5% appreciation + 3.2% rent growth), your $39k cash investment doubles in ~8 years — after that, you're playing with house money.
• Climate carrying-cost: in FEMA flood zone AE (mandatory federal flood insurance); severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→30/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• This rent runs 31% of the median local income ($89k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Questions for listing agent

• What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
• What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
• How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.