3240 Gulf OF Mexico Dr Unit B104 · Longboat Key, FL 34228

$450,000

2 bd · 2.0 ba · 1,260 sqft · Condo public records · 72 Days on market

Built 1975 $357/sqft · 44% below area Est $811k · 44% under $1625/mo HOA · 35% of rent ↓ 10% since listing

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Why this score? — see what drove the D 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).

• ARV discount +15.0/15.0
• Cash flow +5.7/30.0
• Appreciation +5.4/10.0
• Schools +5.4/10.0
• 1% rule +5.2/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +0.1/10.0

Listing remarks MLS

Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from sliding glass doors that span the width of the residence. The large screened-in lanai is accessible from the living area and both bedrooms—seamlessly blending indoor and outdoor living while overlooking a generous grassy yard space and peaceful bayou, perfect for canoeing and kayaking right from your backyard. The kitchen features granite countertops and stainless steel appliances. Offered turn-key and fully furnished, this residence is move-in ready and ideal for seasonal or full-time living. Portobello is a sought-after Beach-to-Bay community ideally located mid-Key, offering an exceptional array of amenities including 600 feet of private beach frontage and 260 feet along the bay. Residents enjoy a heated community pool, tennis courts, clubhouse, BBQ and picnic areas, fishing pier, and kayak launch. Just minutes from the world-class shopping and dining of St. Armands Circle and everything Sarasota has to offer, this exceptional residence invites you to experience the pinnacle of Longboat Key living—where every day feels like a vacation.

Key facts

• Private serene views
• Generous grassy yard
• Lush mangroves

Tags

• PRIVATE SERENE VIEWS
• EXPANSIVE GROUNDS
• LUSH MANGROVES
• LARGE SCREENED-IN LANAI
• GENEROUS GRASSY YARD
• PEACEFUL BAYOU

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath condo listed at $450k.

Deal economics

• At list price, monthly cash flow is $-1k ($-16k/yr) — negative.
• To cash-flow at today's rent, offer at most $211k (53.1% below list).
• Meets the 1% rule at list price ($5k rent vs $450k).
• Recommended offer: $211k (53.1% below list) — sets the bar for cash-flow.
• Cap rate 3.8% 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.

Location & tenants

• 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.
• Sarasota (urban): math 63% / reading 63% proficiency, ranked #7 of 73 in FL (top 10%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Southside Elementary School (math 79% / reading 81%, grade A+, #110 of 2,144 statewide, top 5%, 687 students, 26% FRL); Booker Middle School (math 45% / reading 41%, grade D-, #331 of 571 statewide, top 59%, 950 students, 76% FRL); Booker High School (math 26% / reading 43%, grade F, #386 of 667 statewide, top 59%, 1,309 students, 68% FRL).
• Market conditions: 543 active listings in the ZIP; 1 comparable units currently listed for rent nearby; high-income renter base; 7,466 units permitted in Sarasota County in 2024 (2,138 in 5+ unit buildings).

Forward outlook

• In year one you build about $6k of equity ($3k loan paydown + $3k appreciation (0.7% local appreciation)).
• Sarasota County population projected at +20% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• By year 5, paydown + projected appreciation supports a ~$31k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 72 days — a 6% lower offer ($423k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 21y ago; this cycle's ask has dropped $45k (9%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $260k; list at $450k implies a 73% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $427/mo; HOA is 35% of rent.
• 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→30/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $210,835 (53.1% below list)

Questions for the listing agent

1. 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?
2. It's been on market 72 days. Have you received any prior offers? Is the seller open to a 53% concession, seller financing, or rate buy-down credit?
3. Built in 1975 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
5. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
6. 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?
7. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
8. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
9. 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?
10. 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.
11. 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.
12. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 1.02% ✓
• Cap rate: 3.82%
• Cash-on-cash: -8.83%
• DSCR: 0.61
• GRM: 8.2

CMA / ARV

• ARV (median comp): $810,693
• List price: $450,000
• Delta: -44.49%
• Verdict: UNDERPRICED
• Comps: 20 within 2.0 mi

Projected returns pro-forma

0.73% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -13.3%
• Equity multiple: 0.34×
• Total profit: $-82,556
• Equity at exit: $147,282

10-year hold

• IRR: -6.7%
• Equity multiple: 0.20×
• Total profit: $-100,729
• Equity at exit: $190,912

Cash invested: $126,000 (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 34228

• Home prices YoY: 0.3%
• Active inventory: 543
• Price-to-rent: 8.2×

Monthly cashflow live

• Estimated rent: $4,586 medium
• Mortgage (P&I): −$2,360
• Tax from tax record: −$378 /mo · $4,538/yr
• Insurance: −$188
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$1,625
• Vacancy / Maint / Mgmt: −$963
• Net cashflow: $-1,354

Break-even live

Break-even rent $6,300

Max offer price $210,835

Occupancy floor —

Sensitivity live

Price	-10% $-1,099	-5% $-1,226	+0% $-1,354	+5% $-1,481	+10% $-1,609
Rent	-10% $-1,716	-5% $-1,535	+0% $-1,354	+5% $-1,173	+10% $-992
Rate	-1.0pp $-1,127	-0.5pp $-1,239	base $-1,354	+0.5pp $-1,470	+1.0pp $-1,589

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: $112,500
• Closing costs: $13,500
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
4325 Gulf of Mexico Dr Longboat Key, FL	2.0–3.0	2.0–2.5	1373	$5,500	$4.00	17d	3	1.40mi

HOA detail condo

• Monthly dues: $1,625 · $19,500/yr
• Likely covers: waterlandscapingpool
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 28 events

1. 2026-06-21
   days on market $450,000 Active 72 DOM
2. 2026-06-18
   days on market $450,000 Active 69 DOM
3. 2026-06-17
   days on market $450,000 Active 68 DOM
4. 2026-06-16
   days on market $450,000 Active 67 DOM
5. 2026-06-15
   days on market $450,000 Active 66 DOM
6. 2026-06-13
   days on market $450,000 Active 64 DOM
7. 2026-06-13
   days on market $450,000 Active 63 DOM
8. 2026-06-10
   days on market $450,000 Active 61 DOM
9. 2026-06-09
   days on market $450,000 Active 60 DOM
10. 2026-06-08
    days on market $450,000 Active 59 DOM
11. 2026-06-08
    pricedays on market $450,000 Active 58 DOM
12. 2026-06-05
    days on market $475,000 Active 55 DOM
13. 2026-06-03
    days on market $475,000 Active 54 DOM
14. 2026-06-02
    days on market $475,000 Active 53 DOM
15. 2026-06-01
    days on market $475,000 Active 52 DOM
16. 2026-05-31
    days on market $475,000 Active 51 DOM
17. 2026-04-22
    price $475,000 1464-char remark

    Show marketing remark (1464 chars)

    Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from sliding glass doors that span the width of the residence. The large screened-in lanai is accessible from the living area and both bedrooms—seamlessly blending indoor and outdoor living while overlooking a generous grassy yard space and peaceful bayou, perfect for canoeing and kayaking right from your backyard. The kitchen features granite countertops and stainless steel appliances. Offered turn-key and fully furnished, this residence is move-in ready and ideal for seasonal or full-time living. Portobello is a sought-after Beach-to-Bay community ideally located mid-Key, offering an exceptional array of amenities including 600 feet of private beach frontage and 260 feet along the bay. Residents enjoy a heated community pool, tennis courts, clubhouse, BBQ and picnic areas, fishing pier, and kayak launch. Just minutes from the world-class shopping and dining of St. Armands Circle and everything Sarasota has to offer, this exceptional residence invites you to experience the pinnacle of Longboat Key living—where every day feels like a vacation.

18. 2026-04-10
    listed $495,000 Active 1464-char remark

    Show marketing remark (1464 chars)

    Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from sliding glass doors that span the width of the residence. The large screened-in lanai is accessible from the living area and both bedrooms—seamlessly blending indoor and outdoor living while overlooking a generous grassy yard space and peaceful bayou, perfect for canoeing and kayaking right from your backyard. The kitchen features granite countertops and stainless steel appliances. Offered turn-key and fully furnished, this residence is move-in ready and ideal for seasonal or full-time living. Portobello is a sought-after Beach-to-Bay community ideally located mid-Key, offering an exceptional array of amenities including 600 feet of private beach frontage and 260 feet along the bay. Residents enjoy a heated community pool, tennis courts, clubhouse, BBQ and picnic areas, fishing pier, and kayak launch. Just minutes from the world-class shopping and dining of St. Armands Circle and everything Sarasota has to offer, this exceptional residence invites you to experience the pinnacle of Longboat Key living—where every day feels like a vacation.

19. 2025-12-31
    historical
20. 2025-07-03
    price $499,900
21. 2025-03-28
    price $584,900
22. 2025-01-22
    listed $599,900 Active
23. 2011-06-07
    soldstatus $260,000
24. 2008-04-04
    soldstatus $255,000
25. 2008-03-27
    soldstatus $255,000
26. 2007-09-28
    listed $324,900
27. 2006-02-01
    listed $429,000
28. 2005-08-01
    listed $529,000

ⓘ 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: $4,538 · $378/mo
• Projected year-2 tax: $4,538 · $378/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 6/10 Major FEMA zone AE · 72% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 10/10 Extreme 7 d/yr ≥106°F today · 30 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $55,036
• − Mortgage interest: −$25,207
• − Property taxes: −$4,538
• − Insurance: −$7,369
• − Repairs & maintenance: −$4,403
• − Management: −$4,403
• − HOA: −$19,500
• − Depreciation: −$13,091
• Taxable loss: −$23,474
• Est. tax savings @ 24.0%: +$5,634
• After-tax cash flow: $-10,612/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: Sarasota
• NCES district ID: 1201680
• Math proficiency: 63% ▼ -8.00%
• Reading proficiency: 63% ▼ -3.00%
• Median HH income: $51,167
• Composite: 53.68/100
• National rank: #1428
• State rank: #7 of 73 in FL

Livability — Longboat Key

• Score: 64/100
• State rank: #693
• US rank: #14452

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Longboat Key, FL
• County: Sarasota County · 448,376 people
• City population: 7,539
• Metro: North Port-Sarasota-Bradenton, FL
• Population (ZIP): 7,539
• Household income: $158,030
• Rent vs Own: 6.4% rent · 93.6% own
• Severe rent burden: 98.0

Population outlook (Sarasota County) Hauer SSP2

• Today (2025): 452,380 people
• By 2030: 474,175 · +4.8%
• By 2040: 511,577 · +13.1%
• By 2050: 541,467 · +19.7%
• By 2075: 604,947 · +33.7%
• By 2100: 621,965 · +37.5%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (93%)
• Race & ethnicity: White 93% Hispanic / Latino 4% Two or more races 3% Asian 1%
• Common ancestry: Scotch-Irish 7% Romanian 6% Lithuanian 4%
• Foreign-born: 14% · Canada, China
• Languages at home: 92% English-only · Spanish 2% Other Indo-European 2% German/W. Germanic 2%

Political lean MEDSL · Sarasota

• 2024 margin: R (+18.2) · D 40.5% · R 58.7%
• 2008→2024 swing: -18.1pp toward R · 2008: -0.1pp · 2024: -18.2pp
• All cycles: 2024: R+18.2 2020: R+10.4 2016: R+11.6 2012: R+7.4 2008: R+0.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 0.73%
• Current HPI: 234.5017
• Rent YoY: —
• Metro: North Port-Sarasota-Bradenton, FL
• 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

-10.2% since first listed

12 events — show timeline

• 2026-04-22 Price Changed $475,000 Stellar MLS as Distributed by MLS Grid
• 2026-04-10 Listed $495,000 Stellar MLS as Distributed by MLS Grid
• 2025-12-31 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2025-07-03 Price Changed $499,900 Stellar MLS as Distributed by MLS Grid
• 2025-03-28 Price Changed $584,900 Stellar MLS as Distributed by MLS Grid
• 2025-01-22 Listed $599,900 Stellar MLS as Distributed by MLS Grid
• 2011-06-07 Sold (Public Records) $260,000 Public Records
• 2008-04-04 Sold (Public Records) $255,000 Public Records
• 2008-03-27 Sold (MLS) $255,000 Stellar MLS as Distributed by MLS Grid
• 2007-09-28 Listed $324,900 Stellar MLS as Distributed by MLS Grid
• 2006-02-01 Listed $429,000 Stellar MLS as Distributed by MLS Grid
• 2005-08-01 Listed $529,000 Stellar MLS as Distributed by MLS Grid

Property tax history

+3.0%/yr

Latest (2025): $4,538 · +0.2% YoY. Source: county tax records.