9556 Buccaneer Trl · Rotonda, FL 33946

$640,000

3 bd · 2.0 ba · 1,144 sqft · SingleFamily public records · 307 Days on market

Built 2001 7,700 sqft lot Est $754k · 15% under $54/mo HOA · 1% of rent

---

Why this score? — see what drove the B grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +25.6/30.0
• ARV discount +14.3/15.0
• DSCR +8.5/10.0
• 1% rule +6.3/10.0
• Schools +4.6/10.0
• Appreciation +4.0/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Island life awaits you! This charming 3 bed/2.5 bath stilt-style home offers the perfect blend of modern comfort and seaside living. Home features various upgrades including a new air conditioner (12/21) water heater, all new doors, all new exterior hardie board, all new wooden marine decking/railings, screen porch, plus much more! This gem is just a short walk away from the pristine beach and convenient boat docks where space is plentiful with 3 community docks to choose from, this property is a haven for those who love the ocean and outdoor adventures. Don't miss this rare opportunity to own a piece of beachside paradise. Whether you're looking for a permanent residence, a vacation home,

Key facts

• New doors
• New air conditioner
• New water heater

Tags

• STILT-STYLE HOME
• NEW AIR CONDITIONER
• NEW WATER HEATER
• NEW DOORS
• NEW EXTERIOR HARDIE BOARD
• NEW WOODEN MARINE DECKING

Property features AI

Finance

• Other: Property located on Little Gasparilla Island — accessible by boat only
• HOA & community: Homeowners association required; Annual association fee $650 (about $54.17/month); Pets allowed

Exterior

• Parking: Attached garage with 1 garage space; Golf cart garage
• Utilities: Public water; Septic tank; Electricity connected; Water connected
• Home design: Single-family residence; Stilt / on pilings foundation; Two levels (listed as 1 story total); Northwest-facing
• Construction: Vinyl siding; Shingle roof
• Exterior features: Balcony; French doors; Beach access (deeded) to Gulf/Ocean; Gravel road access; Lot dimensions approximately 70 x 110

Interior

• Kitchen: Convection oven; Dishwasher; Microwave; Refrigerator
• Bedrooms: 3 bedrooms
• Flooring: Tile flooring
• Bathrooms: 2 full bathrooms; 1 half bathroom
• Heating & cooling: Central heating; Central air conditioning
• Interior features: Open living/dining combo; Split bedroom layout; Wet bar
• Laundry & utility: Indoor laundry in a closet

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $640k.

Deal economics

• At list price, monthly cash flow is $1k ($13k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($7k rent vs $640k).
• Recommended offer: $563k (12.0% below list) — sets the bar for market timing.
• Cap rate 9.1% 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.

Location & tenants

• 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.
• Market conditions: 915 active listings in the ZIP; 7 comparable units currently listed for rent nearby; rentals at typical pace (median 23d on market — plan ~3-4 weeks tenant-placement turnaround); 4,585 units permitted in Charlotte County in 2024 (703 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-1.9%/yr); year-one equity from $4k of loan paydown is wiped out by about $12k of value loss. Plan a longer hold.
• Charlotte County population projected at +24% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 307 days — a 12% lower offer ($563k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 4y ago; this cycle's ask has dropped $80k (11%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $300k; list at $640k implies a 113% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $427/mo.
• 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→24/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $563,200 (12.0% below list)

Questions for the listing agent

1. It's been on market 307 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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.
8. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
9. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 1.13% ✓
• Cap rate: 9.12%
• Cash-on-cash: 10.10%
• DSCR: 1.45
• GRM: 7.4

CMA / ARV

• ARV (on-the-fly): $753,896
• Comps found: 2

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
9444 Rum Runner Rd	0.07mi	3/2.0	1,260 (+10%)	15mo	$522,000	$414	68
9752 Little Gasparilla Is	0.21mi	3/2.0	1,060 (-7%)	13mo	$699,000	$659	67

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-1.9% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -0.6%
• Equity multiple: 0.97×
• Total profit: $-4,764
• Equity at exit: $127,170

10-year hold

• IRR: 7.2%
• Equity multiple: 1.63×
• Total profit: $112,201
• Equity at exit: $111,429

Cash invested: $179,200 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Florida: 87 Strongly Landlord-Friendly · R+3
• County: — inherits STATE
• City: — inherits STATE

3-day pay-or-quit; preempts local rent control; landlord-friendly statutes. Court speed varies by county.

Methodology + full state rankings →

ZIP-level market 33946

• Home prices YoY: -0.7%
• Active inventory: 915
• Price-to-rent: 7.4×

Monthly cashflow live

• Estimated rent: $7,205 medium
• Mortgage (P&I): −$3,356
• Tax from tax record: −$507 /mo · $6,089/yr
• Insurance: −$267
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$54
• Vacancy / Maint / Mgmt: −$1,513
• Net cashflow: $1,081

Break-even live

Break-even rent $5,837

Max offer price $640,000

Occupancy floor 80%

Sensitivity live

Price	-10% $1,444	-5% $1,263	+0% $1,081	+5% $900	+10% $719
Rent	-10% $512	-5% $797	+0% $1,081	+5% $1,366	+10% $1,651
Rate	-1.0pp $1,404	-0.5pp $1,244	base $1,081	+0.5pp $916	+1.0pp $747

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $160,000
• Closing costs: $19,200
• Reserves months: —
• Total cash needed: —

Rent comps 7 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
9400 Little Gasparilla Unit G9 Placida, FL	2.0	2.0	946	$6,900	$7.29	22d	1	0.11mi
9400 Little Gasparilla Unit F9 Placida, FL	2.0	2.0	946	$6,500	$6.87	22d	1	0.17mi
9400 Little Gasparilla Unit H8 Placida, FL	2.0	2.0	946	$5,850	$6.18	22d	1	0.17mi
9750 Little Gasparilla Placida, FL	3.0	1.5	957	$10,000	$10.45	22d	1	0.19mi
6021 Boca Grande Cswy Unit G80 Boca Grande, FL	2.0	2.0	1248	$3,500	$2.80	22d	1	1.06mi
6001 Boca Grande Cswy Unit E58 Boca Grande, FL	2.0	2.0	1248	$3,150	$2.52	22d	1	1.12mi
6010 Boca Grande Cswy Unit C26 Boca Grande, FL	2.0	2.0	1248	$3,200	$2.56	22d	1	1.14mi

HOA detail

• Monthly dues: $54 · $648/yr
• Likely covers: water

Listing history 26 events

1. 2026-06-18
   days on market $640,000 Active 307 DOM
2. 2026-06-17
   days on market $640,000 Active 306 DOM
3. 2026-06-16
   days on market $640,000 Active 305 DOM
4. 2026-06-15
   days on market $640,000 Active 304 DOM
5. 2026-06-14
   days on market $640,000 Active 302 DOM
6. 2026-06-13
   days on market $640,000 Active 301 DOM
7. 2026-06-10
   days on market $640,000 Active 299 DOM
8. 2026-06-09
   days on market $640,000 Active 298 DOM
9. 2026-06-08
   days on market $640,000 Active 297 DOM
10. 2026-06-05
    days on market $640,000 Active 293 DOM
11. 2026-06-02
    days on market $640,000 Active 291 DOM
12. 2026-06-01
    days on market $640,000 Active 290 DOM
13. 2026-05-31
    days on market $640,000 Active 289 DOM
14. 2026-05-30
    days on market $640,000 Active 288 DOM
15. 2026-02-11
    price $640,000
16. 2025-08-15
    listed $720,000 Active
17. 2024-11-30
    historical
18. 2024-05-15
    listed $795,000 Active
19. 2024-05-15
    listed $795,000 Active
20. 2022-08-19
    status Active
21. 2022-08-17
    historical
22. 2022-05-18
    price $720,000
23. 2022-03-01
    listed $750,000 Active
24. 2003-05-28
    soldstatus $300,000
25. 1999-01-26
    soldstatus $14,900
26. 1997-10-01
    soldstatus $10,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast FL · Resets to sale price

• Current annual tax: $6,089 · $507/mo
• Projected year-2 tax: $6,089 · $507/mo
• Expected delta: $0/yr ($0/mo · -0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 10/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 10/10 Extreme 7 d/yr ≥107°F today · 24 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $86,466
• − Mortgage interest: −$35,850
• − Property taxes: −$6,089
• − Insurance: −$8,318
• − Repairs & maintenance: −$6,917
• − Management: −$6,917
• − HOA: −$648
• − Depreciation: −$18,618
• Taxable income: $3,108
• Est. tax owed @ 24.0%: −$746
• After-tax cash flow: $12,232/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Charlotte
• NCES district ID: 1200240
• Math proficiency: 54% ▼ -6.00%
• Reading proficiency: 54% ▼ -1.00%
• Median HH income: $44,864
• Composite: 45.62/100
• National rank: #2586
• State rank: #22 of 73 in FL

Livability — Rotonda

• Score: 67/100
• State rank: #548
• US rank: #10359

Category grades

Amenities F Commute F Cost of living B+ Crime A+ Employment C+ Housing A- Health & safety D- User ratings A+

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 10,490
• Population (ZIP): 2,745

Population outlook (Charlotte County) Hauer SSP2

• Today (2025): 198,646 people
• By 2030: 210,507 · +6.0%
• By 2040: 230,857 · +16.2%
• By 2050: 247,148 · +24.4%
• By 2075: 281,777 · +41.8%
• By 2100: 293,609 · +47.8%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (95%)
• Race & ethnicity: White 95% Hispanic / Latino 2% Asian 1% Two or more races 1%
• Common ancestry: Italian 3% Romanian 2% Russian 2%
• Foreign-born: 6% · Canada
• Languages at home: 91% English-only · Russian/Polish/Slavic 5% Spanish 1% French/Haitian/Cajun 1%

Political lean MEDSL · Charlotte

• 2024 margin: Solid R (+34.0) · D 32.7% · R 66.7%
• 2008→2024 swing: -26.7pp toward R · 2008: -7.2pp · 2024: -34.0pp
• All cycles: 2024: R+34.0 2020: R+26.6 2016: R+27.8 2012: R+14.3 2008: R+7.2

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -1.90%
• Current HPI: 288.559
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 3.28%
• F500 in state: 36

Industry mix (Fortune 500 HQ in FL)

Industry	F500 HQs	Revenue
▸Industrial Technology	2	$29B
▸Insurance	2	$17B
▸Retail	1	$60B
▸Technology Distribution	1	$58B
▸Homebuilding	1	$35B
▸Technology Manufacturing	1	$35B

Price history

+6300.0% since first listed

12 events — show timeline

• 2026-02-11 Price Changed $640,000 Stellar MLS as Distributed by MLS Grid
• 2025-08-15 Listed $720,000 Stellar MLS as Distributed by MLS Grid
• 2024-11-30 Listing Removed — FORTMLS
• 2024-05-15 Listed $795,000 FORTMLS
• 2024-05-15 Listed $795,000 Stellar MLS as Distributed by MLS Grid
• 2022-08-19 Relisted — Stellar MLS as Distributed by MLS Grid
• 2022-08-17 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2022-05-18 Price Changed $720,000 Stellar MLS as Distributed by MLS Grid
• 2022-03-01 Listed $750,000 Stellar MLS as Distributed by MLS Grid
• 2003-05-28 Sold (Public Records) $300,000 Public Records
• 1999-01-26 Sold (Public Records) $14,900 Public Records
• 1997-10-01 Sold (Public Records) $10,000 Public Records

Property tax history

+2.8%/yr

Latest (2025): $6,089 · -10.1% YoY. Source: county tax records.