14108 Chesswood Ln

Rotonda, FL 33981

$329,900F

4 bd · 2.0 ba · 1,666 sqft · Built 2024 · Land · Active · 204 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,495/mo
• Mortgage (P&I): −$1,730
• Tax + insurance: −$973
• HOA: −$0
• Vac / Maint / Mgmt: −$524
• Net cashflow: $-732/mo
• Annual: $-8,783/yr
• Cap rate: 5.18%
• Cash-on-cash: -3.97%
• DSCR: 0.82
• 1% rule: 0.76%
• Cash to close: $92,372

Investor read

• This is a 4-bed/2.0-bath land listed at $330k.
• At list price, monthly cash flow is $-732 ($-9k/yr) — negative.
• To cash-flow at today's rent, offer at most $201k (39.2% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $250k (24.4% below list).
• It's been on market 204 days — a 12% lower offer ($290k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $201k (39.2% below list) — sets the bar for cash-flow.
• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $10k of value loss. Plan a longer hold.
• Location reads 67/100 on livability (#548 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A-, cost of living B+; Watch: schools D, amenities F, commute F.
• Charlotte (suburban): math 54% / reading 54% proficiency, ranked #22 of 73 in FL (top 30%) — 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 (+5.3%/yr); 2188 active listings in the ZIP; 26 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 4,585 units permitted in Charlotte County in 2024 (703 in 5+ unit buildings).
• Charlotte County population projected at +24% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• 8 sale attempts since 20y ago; this cycle's ask is 14250% above the opening price — seller raised mid-cycle; expect resistance to lowballs.
• Current owner paid $17k; list at $330k implies a 1841% gain — meaningful room to come down on a strong offer.
• 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→28/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 5.2% vs local median 3.1% in Rotonda — 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.
• This rent runs 36% of the median local income ($84k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

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 204 days. Have you received any prior offers? Is the seller open to a 39% concession, seller financing, or rate buy-down credit?
• 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 D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
• The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
• 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.