4350 Chatham Dr #106

Longboat Key, FL 34228

$399,000D+

2 bd · 2.0 ba · 1,072 sqft · Built 1969 · Condo · Active · 84 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $4,647/mo
• Mortgage (P&I): −$2,092
• Tax + insurance: −$782
• HOA: −$1,351
• Vac / Maint / Mgmt: −$976
• Net cashflow: $-554/mo
• Annual: $-6,652/yr
• Cap rate: 5.91%
• Cash-on-cash: -1.37%
• DSCR: 0.94
• 1% rule: 1.16%
• Cash to close: $111,720

Investor read

• This is a 2-bed/2.0-bath condo listed at $399k.
• At list price, monthly cash flow is $-554 ($-7k/yr) — negative.
• To cash-flow at today's rent, offer at most $301k (24.5% below list).
• Meets the 1% rule at list price ($5k rent vs $399k).
• It's been on market 84 days — a 6% lower offer ($375k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $301k (24.5% below list) — sets the bar for cash-flow.
• In year one you build about $6k of equity ($3k loan paydown + $3k appreciation (0.7% local appreciation)).
• Location reads 64/100 on livability (#693 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: housing C-, amenities F, commute F.
• Manatee (suburban): math 54% / reading 50% proficiency, ranked #26 of 73 in FL (top 36%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Anna Maria Elementary School (math 77% / reading 77%, grade A, #170 of 2,144 statewide, top 9%, 190 students, 36% FRL); Manatee High School (math 32% / reading 47%, grade F, #304 of 667 statewide, top 47%, 1,983 students, 59% FRL) — zoned schools at 48% FRL track the district average.
• Watch-outs: flood insurance adds $427/mo; HOA is 29% of rent.
• Market conditions: 539 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals at typical pace (median 25d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 7,472 units permitted in Manatee County in 2024 (1,782 in 5+ unit buildings).
• Manatee County population projected at +43% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 4 sale attempts since 19y 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 $270k; 48% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• By year 6, paydown + projected appreciation supports a ~$33k 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→27/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 5.9% vs local median 0.5% in Longboat Key — 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.

Questions for listing agent

• What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
• It's been on market 84 days. Have you received any prior offers? Is the seller open to a 25% concession, seller financing, or rate buy-down credit?
• Built in 1969 — 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?
• 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.