14165 Winchester Ct #204

Winding Cypress, FL 34114

$370,000B

3 bd · 2.0 ba · 1,368 sqft · Built 2006 · Condo · Active · 9 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $5,463/mo
• Mortgage (P&I): −$1,940
• Tax + insurance: −$272
• HOA: −$701
• Vac / Maint / Mgmt: −$1,147
• Net cashflow: $1,402/mo
• Annual: $16,825/yr
• Cap rate: 10.84%
• Cash-on-cash: 16.24%
• DSCR: 1.72
• 1% rule: 1.48%
• Cash to close: $103,600

Investor read

• This is a 3-bed/2.0-bath condo listed at $370k.
• At list price, monthly cash flow is $1k ($17k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $370k).
• Only 9 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-1.5%/yr); year-one equity from $3k of loan paydown is wiped out by about $5k 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.
• Market conditions: Rents rising (+3.2%/yr); 900 active listings in the ZIP; 38 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); 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.
• 5 sale attempts since 14y 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 $135k; list at $370k implies a 174% gain — meaningful room to come down on a strong offer.
• At projected returns (-1.5% appreciation + 3.2% rent growth), your $104k cash investment doubles in ~6 years — after that, you're playing with house money.
• Climate carrying-cost: major flood risk; severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→29/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• At $5,463/mo this rent would consume 73% of the median local household income ($89k/yr) (locally 550% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
• 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 apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.