2016 Roosevelt Dr

Key West, FL 33040

$1,300,000B

7 bd · 5.0 ba · 2,957 sqft · Built 1950 · MultiFamily · Active · 120 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $16,491/mo
• Mortgage (P&I): −$6,817
• Tax + insurance: −$1,799
• HOA: −$0
• Vac / Maint / Mgmt: −$3,463
• Net cashflow: $4,411/mo
• Annual: $52,936/yr
• Cap rate: 10.76%
• Cash-on-cash: 15.95%
• DSCR: 1.71
• 1% rule: 1.27%
• Cash to close: $364,000

Investor read

• This is a 4 × 7-bed/5.0-bath units multifamily listed at $1.30M.
• At list price, monthly cash flow is $4k ($53k/yr) — positive. Per door: $1k/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($16k rent vs $1.30M).
• It's been on market 120 days — a 9% lower offer ($1.18M) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $1.18M (9.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $9k of loan paydown is wiped out by about $39k of value loss. Plan a longer hold.
• Location reads 82/100 on livability (#65 in FL, #1,123 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, employment A+; Watch: crime D+, cost of living F.
• Monroe (town): math 50% / reading 55% proficiency, ranked #23 of 73 in FL (top 32%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Watch-outs: flood insurance adds $427/mo; built in 1950 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising fast (+4.5%/yr); 496 active listings in the ZIP; solid renter incomes; 332 units permitted in Monroe County in 2024 (42 in 5+ unit buildings).
• Monroe County population projected at +28% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 2 sale attempts since 2y 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 $800k; list at $1.30M implies a 62% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 4.5% rent growth), your $364k 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 — expect insurance premiums to compound above CPI over the hold.
• Cap rate 10.8% vs local median 0.8% in Key West — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.
• At $16,491/mo this rent would consume 229% of the median local household income ($87k/yr) (locally 2502% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Questions for listing agent

• It's been on market 120 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
• Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
• What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
• Built in 1950 — 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?
• Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
• 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?