1533 Chesapeake Ave Unit A5

Naples, FL 34102

$415,000B-

2 bd · 2.0 ba · 1,080 sqft · Built 1973 · Condo · Active · 14 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $5,490/mo
• Mortgage (P&I): −$2,176
• Tax + insurance: −$909
• HOA: −$948
• Vac / Maint / Mgmt: −$1,153
• Net cashflow: $303/mo
• Annual: $3,640/yr
• Cap rate: 8.40%
• Cash-on-cash: 7.54%
• DSCR: 1.34
• 1% rule: 1.32%
• Cash to close: $116,200

Investor read

• This is a 2-bed/2.0-bath condo listed at $415k.
• At list price, monthly cash flow is $303 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $415k).
• Only 14 days on market — expect competitive offers; lowballing is unlikely to land.
• In year one you build about $20k of equity ($3k loan paydown + $17k appreciation (4.1% local appreciation)).
• Location reads 80/100 on livability (#126 in FL, #1,903 nationally) — a professional / high-income tenant draw. Strengths: crime A+, amenities A+, employment A+; Watch: commute D+, cost of living F.
• 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 fast (+8.8%/yr); 614 active listings in the ZIP; 40 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 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 9y 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 $265k; list at $415k implies a 57% gain — meaningful room to come down on a strong offer.
• At projected returns (4.1% appreciation + 8.0% rent growth), your $116k cash investment doubles in ~4 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$32k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• 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→26/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• At $5,490/mo this rent would consume 50% of the median local household income ($131k/yr) (locally 333% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• Built in 1973 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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?
• 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.
• Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
• This sits on a lake — are riparian / water-frontage rights deeded with the parcel? Any dock permits, shoreline easements, or HOA water-use restrictions?
• What's the documented flood / surge / shoreline-erosion history here (FEMA AND non-FEMA — e.g., storm surge, creek backup, septic-field saturation)?