Most lenders see "Monroe County" on the address and panic. I see opportunity. Jumbo, DSCR, STR, second home, conventional — structured around the actual realities of flood zones, wind, and insurance pricing in the Florida Keys.
Insurance availability, flood zone classification, condo questionnaire fights, non-warrantable buildings, and FEMA remap timing all conspire to break deals that look fine on paper. I run the deal the way an experienced Keys broker actually has to.
Key Largo · Tavernier · Plantation Key · Islamorada. Mostly accessible to mainland insurance carriers. Best for second-home jumbos and STR DSCR.
Marathon · Duck Key · Grassy Key · Crawl Key. Hardest market for insurance — Citizens-heavy. STR is regulated; vacation rental income must be documented carefully.
Big Pine · No Name · Cudjoe · Summerland · Sugarloaf · Key West. Strong DSCR and second-home territory. Many properties stilted/elevated — VE zone strategy required.
Pre-1972 builds in Key West and the Lower Keys carry their own quirks — grandfathered flood, ICC payouts, elevation strategies. We've structured these.
Boat slip valuations, pier financing, hatchet marina condo questions — Marina Vale's specialty.
Monroe County STR ordinances are strict. We navigate occupancy proof, T-12 vs projected income, and DSCR lender preferences for vacation rental loans.
If a lender hasn't done a deal in Monroe County in the last 90 days, they don't actually know how to structure one. I do them weekly.
HOI quote came in at $14k? Citizens-only? Surplus lines? I have a network of FL coastal carriers and re-shoppers. Often we get the binder down 30–50% just by re-quoting properly.
Property landed in VE/AE after FIRM remap. Elevation certificate, NFIP vs private flood, Risk Rating 2.0 strategies — all part of the playbook.
HOA litigation, <50% owner-occupied, single-entity ownership over 10% — most lenders walk away. Portfolio jumbo and non-QM carry these.
Need to use STR income to qualify? DSCR with projected income works. Some lenders take T-12 AirDNA. We pick the right one for the property.
Fannie's second-home rules (rate hits, occupancy intent) make Keys second homes tricky. Sometimes investment financing is actually cheaper after rate adjustment.
Old flood policy assumed by buyer = thousands in annual savings. We close pre-FIRM transactions before any rate change is triggered.
Monroe County 2026 conforming limit is $1,209,750 — anything above is jumbo. I write jumbo deals from $1.2M to $5M+ in the Keys regularly.
Jumbo details →No-tax-return investor loans. Qualifying off the rental income — projected or actual. The right product for Airbnb/VRBO operators.
DSCR details →Up to 89.99% LTV with the right structure. Keys second-home buyers — primary in another state, weekend home in the Keys. We do this constantly.
All programs →Self-employed buyers who don't show income on tax returns. 12 or 24 months of business statements, or CPA-prepared P&L.
Non-QM →$0 down, no PMI. Less common than mainland — but I close them. VA appraisal scrutiny on coastal properties demands a broker who knows what to flag.
VA details →Retirees with $$$ in brokerage but limited W-2 income. Asset-based qualification gets the loan done — we use 60-70% of liquid assets / 360 months.
More →Whether you're under contract, pre-shopping, or just exploring — a 30-minute strategy call will save you weeks of back-and-forth with national lenders who don't actually understand the Keys.
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