4350 Chatham Dr #106 · Longboat Key, FL 34228

$399,000

2 bd · 2.0 ba · 1,072 sqft · Condo public records · 84 Days on market

Built 1969 $1351/mo HOA · 29% of rent

---

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).

• Cash flow +11.5/30.0
• ARV discount +7.5/15.0
• 1% rule +6.6/10.0
• Appreciation +5.4/10.0
• Schools +4.4/10.0
• DSCR +3.4/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Price reduced!Investment Opportunity! Flora & Fauna abound inside & outside of this charming ground floor walk out unit, with picturesque water views, just steps to the pool, boat docks, & directly across the street from the private pavilion beach access. "Delightful lanai looks out over deep lawn to widest part of the lagoon where manatees make their winter home. " "Building faces E-W so all rooms are bright and cheery with lighter, Florida-colored furnishings and light tile floors to make you feel as thoyou are in the tropics, updated kitchen & baths, all new windows, sliders. It shows beautifully! Amenities include boat docks, 4 pools, kayak launch, tennis, active clubhouse, exercise, billiards, sauna, new cards lounge & much more. .. .

Key facts

• Heated pools
• Deeded beach access
• Community center

Tags

• ENCLOSED LANAI
• WATER VIEW
• DEEDED BEACH ACCESS
• HEATED POOLS
• FULL EQUIPPED GYM
• COMMUNITY CENTER

Property features AI

Finance

• Other: Unfurnished; Irrigation equipment
• Financial info: Total annual association fees: $16,212; Lease restrictions apply
• HOA & community: Has HOA (monthly fees required); Monthly condo/association fee: $1,351; Association amenities include elevator, fitness center, pool, sauna, recreation facilities, laundry, maintenance, storage, tennis, pickleball and shuffleboard courts; Association fee includes pool, sewer, water, trash, pest control, maintenance (grounds & structure), escrow reserves and fidelity bond; Association approval required; Full-time community management; Community features: deed restrictions, community mailbox, buyer approval required, association-owned recreation

Exterior

• Parking: Assigned parking; Driveway; Ground level parking; Guest parking; Off-street parking; Reserved spaces; Has 1-car carport
• Security: Gated community
• Utilities: Public water; Public sewer; Cable available; Electricity connected; Sewer connected; Water connected; Kayak dock/launch
• Home design: Condominium; Residential property; One-level unit; Faces west; On waterfront with full bay/harbor views; Water access with deeded beach access, gulf/ocean, intracoastal and marina access; Water extras include assigned boat slip, lift, fishing pier, seawall, sailboat water and no-wake zone
• Construction: Block and stucco construction; Other roof type; Slab foundation; Building identified as E
• Exterior features: Enclosed patio/porch and rear porch; Porch; Sliding doors; Outdoor lighting; Private mailbox; Rain gutters; Shade shutters; Sidewalk; Storage; Tennis court(s); Mature landscaping with trees; Near marina; Paved surfaces; Asphalt road surface; Flood zone (flood insurance required)

Interior

• Kitchen: Dishwasher; Range; Refrigerator; Disposal
• Bedrooms: 2 bedrooms
• Flooring: Carpet; Tile
• Bathrooms: 2 full bathrooms
• Heating & cooling: Electric heating; Central air conditioning
• Interior features: Ceiling fans; Open floorplan; Living room/dining room combo; Solid surface counters; Thermostat; Walk-in closet(s); Window treatments; Shades; Exhaust fan; Building elevator access
• Laundry & utility: Common area laundry room; Electric water heater

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath condo listed at $399k.

Deal economics

• 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).
• Recommended offer: $301k (24.5% below list) — sets the bar for cash-flow.
• 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.

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.
• 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.
• Market conditions: 539 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals at typical pace (median 24d 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).

Forward outlook

• In year one you build about $6k of equity ($3k loan paydown + $3k appreciation (0.7% local appreciation)).
• Manatee County population projected at +43% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• By year 6, paydown + projected appreciation supports a ~$33k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 84 days — a 6% lower offer ($375k) is reasonable based on typical stale-listing flexibility.
• 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.

Risks & watch-outs

• Watch-outs: flood insurance adds $427/mo; HOA is 29% 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→27/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $301,070 (24.5% 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 84 days. Have you received any prior offers? Is the seller open to a 25% concession, seller financing, or rate buy-down credit?
3. Built in 1969 — 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: 1.16% ✓
• Cap rate: 5.91%
• Cash-on-cash: -1.37%
• DSCR: 0.94
• GRM: 7.2

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: -5.8%
• Equity multiple: 0.71×
• Total profit: $-32,158
• Equity at exit: $130,590

10-year hold

• IRR: -0.1%
• Equity multiple: 0.99×
• Total profit: $-1,023
• Equity at exit: $169,275

Cash invested: $111,720 (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: 539
• Price-to-rent: 7.2×

Monthly cashflow live

• Estimated rent: $4,647 high
• Mortgage (P&I): −$2,092
• Tax from tax record: −$189 /mo · $2,272/yr
• Insurance: −$166
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$1,351
• Vacancy / Maint / Mgmt: −$976
• Net cashflow: $-554

Break-even live

Break-even rent $5,349

Max offer price $301,070

Occupancy floor —

Sensitivity live

Price	-10% $-328	-5% $-441	+0% $-554	+5% $-667	+10% $-780
Rent	-10% $-921	-5% $-738	+0% $-554	+5% $-371	+10% $-187
Rate	-1.0pp $-353	-0.5pp $-453	base $-554	+0.5pp $-658	+1.0pp $-763

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: $99,750
• Closing costs: $11,970
• Reserves months: —
• Total cash needed: —

Rent comps 5 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
4340 Falmouth Dr Longboat Key, FL	2.0	2.0	1330	$3,000	$2.26	24d	1	0.12mi
4420 Exeter Dr #208 Longboat Key, FL	2.0	2.0	1168	$4,900	$4.20	24d	1	0.12mi
4325 Gulf of Mexico Dr Longboat Key, FL	2.0–3.0	2.0–2.5	1373	$5,500	$4.00	16d	3	0.18mi
600 Sutton Pl #201 Longboat Key, FL	1.0	1.0	836	$3,200	$3.83	24d	1	0.20mi
4825 Gulf of Mexico Dr #201 Longboat Key, FL	2.0	2.0	1393	$7,800	$5.60	24d	1	0.61mi

HOA detail condo

• Monthly dues: $1,351 · $16,212/yr
• Likely covers: waterpool
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 24 events

1. 2026-06-18
   days on market $399,000 Active 84 DOM
2. 2026-06-17
   days on market $399,000 Active 83 DOM
3. 2026-06-16
   days on market $399,000 Active 82 DOM
4. 2026-06-15
   days on market $399,000 Active 81 DOM
5. 2026-06-13
   days on market $399,000 Active 79 DOM
6. 2026-06-13
   days on market $399,000 Active 78 DOM
7. 2026-06-10
   days on market $399,000 Active 76 DOM
8. 2026-06-09
   days on market $399,000 Active 75 DOM
9. 2026-06-08
   days on market $399,000 Active 74 DOM
10. 2026-06-08
    days on market $399,000 Active 73 DOM
11. 2026-06-03
    days on market $399,000 Active 69 DOM
12. 2026-06-02
    days on market $399,000 Active 68 DOM
13. 2026-06-01
    days on market $399,000 Active 67 DOM
14. 2026-05-31
    days on market $399,000 Active 66 DOM
15. 2026-05-05
    price $399,000
16. 2026-03-26
    listed $409,000 Active
17. 2014-08-01
    historical
18. 2014-06-14
    status Active
19. 2014-06-10
    historical
20. 2014-01-30
    listed $289,900 Active
21. 2009-05-06
    soldstatus $270,000
22. 2009-04-30
    soldstatus $270,000 793-char remark

    Show marketing remark (793 chars)

    Price reduced!Investment Opportunity! Flora & Fauna abound inside & outside of this charming ground floor walk out unit, with picturesque water views, just steps to the pool, boat docks, & directly across the street from the private pavilion beach access. "Delightful lanai looks out over deep lawn to widest part of the lagoon where manatees make their winter home. " "Building faces E-W so all rooms are bright and cheery with lighter, Florida-colored furnishings and light tile floors to make you feel as thoyou are in the tropics, updated kitchen & baths, all new windows, sliders. It shows beautifully! Amenities include boat docks, 4 pools, kayak launch, tennis, active clubhouse, exercise, billiards, sauna, new cards lounge & much more. .. .

23. 2007-11-09
    listed $285,000 793-char remark

    Show marketing remark (793 chars)

    Price reduced!Investment Opportunity! Flora & Fauna abound inside & outside of this charming ground floor walk out unit, with picturesque water views, just steps to the pool, boat docks, & directly across the street from the private pavilion beach access. "Delightful lanai looks out over deep lawn to widest part of the lagoon where manatees make their winter home. " "Building faces E-W so all rooms are bright and cheery with lighter, Florida-colored furnishings and light tile floors to make you feel as thoyou are in the tropics, updated kitchen & baths, all new windows, sliders. It shows beautifully! Amenities include boat docks, 4 pools, kayak launch, tennis, active clubhouse, exercise, billiards, sauna, new cards lounge & much more. .. .

24. 1998-03-11
    soldstatus $118,600

ⓘ 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: $2,272 · $189/mo
• Projected year-2 tax: $3,312 · $276/mo
• Expected delta: +$1,040/yr (+$87/mo · 45.8%)

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

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 10/10 Extreme 7 d/yr ≥106°F today · 27 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: $55,764
• − Mortgage interest: −$22,350
• − Property taxes: −$2,272
• − Insurance: −$7,114
• − Repairs & maintenance: −$4,461
• − Management: −$4,461
• − HOA: −$16,212
• − Depreciation: −$11,607
• Taxable loss: −$12,713
• Est. tax savings @ 24.0%: +$3,051
• After-tax cash flow: $-3,601/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: Manatee
• NCES district ID: 1201230
• Math proficiency: 54% ▼ -6.00%
• Reading proficiency: 50% ▼ -2.00%
• Median HH income: $49,607
• Composite: 44.43/100
• National rank: #2806
• State rank: #26 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 (Manatee County) Hauer SSP2

• Today (2025): 447,342 people
• By 2030: 488,911 · +9.3%
• By 2040: 567,934 · +27.0%
• By 2050: 637,995 · +42.6%
• By 2075: 781,970 · +74.8%
• By 2100: 848,272 · +89.6%

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 · Manatee

• 2024 margin: Strong R (+23.5) · D 37.9% · R 61.4%
• 2008→2024 swing: -16.5pp toward R · 2008: -7.0pp · 2024: -23.5pp
• All cycles: 2024: R+23.5 2020: R+16.1 2016: R+17.1 2012: R+12.5 2008: R+7.0

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

+236.4% since first listed

10 events — show timeline

• 2026-05-05 Price Changed $399,000 Stellar MLS as Distributed by MLS Grid
• 2026-03-26 Listed $409,000 Stellar MLS as Distributed by MLS Grid
• 2014-08-01 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2014-06-14 Relisted — Stellar MLS as Distributed by MLS Grid
• 2014-06-10 Listing Removed — Stellar MLS as Distributed by MLS Grid
• 2014-01-30 Listed $289,900 Stellar MLS as Distributed by MLS Grid
• 2009-05-06 Sold (Public Records) $270,000 Public Records
• 2009-04-30 Sold (MLS) $270,000 Stellar MLS as Distributed by MLS Grid
• 2007-11-09 Listed $285,000 Stellar MLS as Distributed by MLS Grid
• 1998-03-11 Sold (Public Records) $118,600 Public Records

Property tax history

-0.3%/yr

Latest (2025): $2,272 · -63.1% YoY. Source: county tax records.