181 Grassy Key Ln #49 · Winding Cypress, FL 34114

$99,900

2 bd · 2.0 ba · 648 sqft · Condo public records · 35 Days on market

Built 1976 $250/mo HOA · 11% of rent

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Schools +5.0/10.0
• Appreciation +4.3/10.0
• Rent growth +3.3/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Opportunity awaits in West Wind Estates! Own your piece of Naples for under $100,000 in this quiet 55+ community conveniently located near Marco Island, downtown Naples, shopping, dining, local beaches, and public boat ramps with quick Gulf access. This property is ideal for investors, seasonal residents, or buyers willing to put some sweat equity into creating their own Florida retreat. The home needs TLC and is priced accordingly, offering a chance to renovate, update, or reimagine the space while enjoying all the benefits of the community and location. West Wind Estates features low fees and amenities including a clubhouse, community pool, shuffleboard, pickleball, billiards, fitness are

Key facts

• Clubhouse
• Billiards
• Community pool

Tags

• CLUBHOUSE
• COMMUNITY POOL
• SHUFFLEBOARD
• PICKLEBALL
• BILLIARDS
• FITNESS AREA

Property features AI

Finance

• Other: Property is in the WEST WIND ESTATES development; Directions: US 41 to West Wind Estates, turn right onto Grassy Key Lane
• HOA & community: Mandatory HOA; Annual HOA fee $1,500; Quarterly condo fee $375; Professional management; Community type: Mobile/Manufactured; Community amenities include: BBQ/picnic area, bike storage, billiards, bocce court, community pool, exercise room, pickleball, play area, shuffleboard, tennis court; Total annual recurring fees $3,000; Total one-time fees $195

Exterior

• Parking: Paved driveway; Attached carport with 1 carport space
• Utilities: Central water; Central sewer; Cable available
• Home design: Residential manufactured home; Manufactured building design; One story
• Construction: Manufactured construction; Built in 1976
• Exterior features: Decorative shutters; Metal roof; Windows — see remarks; Aluminum siding; Lot unit 49; Total area approximately 1502 (unit of measure as provided); Rear exposure facing south; No RV allowed

Interior

• Kitchen: Electric cooktop
• Bedrooms: 2 bedrooms (split bedroom floor plan)
• Flooring: Laminate flooring
• Bathrooms: 2 full bathrooms; Master bath with shower only
• Heating & cooling: Central electric heat; Central electric cooling; Ceiling fans for cooling
• Interior features: Window coverings; Eat-in kitchen; Family room; Screened lanai/porch; Partially furnished; 3 ceiling fans

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath condo listed at $100k.

Deal economics

• At list price, monthly cash flow is $524 ($6k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $100k).
• Recommended offer: $97k (3.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Collier (suburban): math 60% / reading 56% proficiency, ranked #16 of 73 in FL (top 22%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Manatee Elementary School (math 58% / reading 51%, grade C, #892 of 2,144 statewide, top 44%, 584 students, 73% FRL); Lely High School (math 40% / reading 39%, grade F, #304 of 667 statewide, top 47%, 1,504 students, 54% FRL).
• Market conditions: Rents rising (+3.2%/yr); 900 active listings in the ZIP; solid renter incomes; 3,520 units permitted in Collier County in 2024 (959 in 5+ unit buildings).
• This rent runs 31% of the median local income ($89k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-1.5%/yr); year-one equity from $691 of loan paydown is wiped out by about $1k of value loss. Plan a longer hold.
• Collier County population projected at +30% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• At projected returns (-1.5% appreciation + 3.2% rent growth), your $28k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• It's been on market 35 days — a 3% lower offer ($97k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $30k; list at $100k implies a 239% 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→30/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $96,903 (3.0% below list)

Questions for the listing agent

1. It's been on market 35 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1976 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
4. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
5. 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?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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 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: 2.29% ✓
• Cap rate: 17.72%
• Cash-on-cash: 40.79%
• DSCR: 2.82
• GRM: 3.6

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-1.48% appreciation · 3.21% rent growth · sell at horizon

5-year hold

• IRR: 19.7%
• Equity multiple: 1.88×
• Total profit: $24,607
• Equity at exit: $21,829

10-year hold

• IRR: 26.2%
• Equity multiple: 3.65×
• Total profit: $74,007
• Equity at exit: $21,028

Cash invested: $27,972 (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 34114

• Home prices YoY: -0.6%
• Rents YoY: 3.2%
• Active inventory: 900
• Price-to-rent: 3.6×

Monthly cashflow live

• Estimated rent: $2,284 medium
• Mortgage (P&I): −$524
• Tax from tax record: −$38 /mo · $452/yr
• Insurance: −$42
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$250
• Vacancy / Maint / Mgmt: −$480
• Net cashflow: $524

Break-even live

Break-even rent $1,620

Max offer price $99,900

Occupancy floor 72%

Sensitivity live

Price	-10% $581	-5% $553	+0% $524	+5% $496	+10% $468
Rent	-10% $344	-5% $434	+0% $524	+5% $615	+10% $705
Rate	-1.0pp $575	-0.5pp $550	base $524	+0.5pp $498	+1.0pp $472

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: $24,975
• Closing costs: $2,997
• Reserves months: —
• Total cash needed: —

HOA detail condo

• Monthly dues: $250 · $3,000/yr
• Likely covers: pool
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 19 events

1. 2026-06-18
   days on market $99,900 Active 35 DOM
2. 2026-06-17
   days on market $99,900 Active 34 DOM
3. 2026-06-16
   days on market $99,900 Active 33 DOM
4. 2026-06-15
   days on market $99,900 Active 32 DOM
5. 2026-06-14
   days on market $99,900 Active 30 DOM
6. 2026-06-10
   days on market $99,900 Active 27 DOM
7. 2026-06-09
   days on market $99,900 Active 26 DOM
8. 2026-06-08
   days on market $99,900 Active 25 DOM
9. 2026-06-07
   days on market $99,900 Active 24 DOM
10. 2026-06-03
    days on market $99,900 Active 20 DOM
11. 2026-06-02
    days on market $99,900 Active 19 DOM
12. 2026-06-01
    days on market $99,900 Active 18 DOM
13. 2026-05-31
    days on market $99,900 Active 17 DOM
14. 2026-05-30
    days on market $99,900 Active 16 DOM
15. 2026-05-14
    listed $99,900 Active
16. 2002-04-04
    soldstatus $29,500
17. 1999-10-20
    soldstatus $21,500
18. 1985-03-01
    soldstatus $12,000
19. 1985-03-01
    soldstatus $37,500

ⓘ 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: $452 · $38/mo
• Projected year-2 tax: $829 · $69/mo
• Expected delta: +$377/yr (+$31/mo · 83.5%)

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

Climate risk First Street

• 🌊 Flood 8/10 Severe FEMA zone AE · 97% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 10/10 Extreme 7 d/yr ≥108°F today · 30 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $27,404
• − Mortgage interest: −$5,596
• − Property taxes: −$452
• − Insurance: −$5,618
• − Repairs & maintenance: −$2,192
• − Management: −$2,192
• − HOA: −$3,000
• − Depreciation: −$2,906
• Taxable income: $5,447
• Est. tax owed @ 24.0%: −$1,307
• After-tax cash flow: $4,985/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: Collier
• NCES district ID: 1200330
• Math proficiency: 60% ▼ -4.00%
• Reading proficiency: 56% ▼ -2.00%
• Median HH income: $58,275
• Composite: 50.23/100
• National rank: #1892
• State rank: #16 of 73 in FL

Livability — Winding Cypress

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• County: Collier County · 396,295 people
• Metro: Naples-Marco Island, FL
• Population (ZIP): 23,559
• Household income: $89,334
• Rent vs Own: 15.3% rent · 84.7% own
• Severe rent burden: 550.0

Population outlook (Collier County) Hauer SSP2

• Today (2025): 420,858 people
• By 2030: 450,054 · +6.9%
• By 2040: 502,232 · +19.3%
• By 2050: 544,932 · +29.5%
• By 2075: 627,203 · +49.0%
• By 2100: 659,015 · +56.6%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (72%)
• Race & ethnicity: White 72% Hispanic / Latino 17% Two or more races 13% Black 7%
• Hispanic origin (detail): Mexican 7% Puerto Rican 1% Cuban 3%
• Common ancestry: Hispanic 5% Romanian 4% Lithuanian 1%
• Foreign-born: 21% · Canada, Jamaica
• Languages at home: 75% English-only · Spanish 15% French/Haitian/Cajun 5% Other Indo-European 4%

Political lean MEDSL · Collier

• 2024 margin: Solid R (+33.1) · D 33.1% · R 66.2%
• 2008→2024 swing: -10.6pp toward R · 2008: -22.5pp · 2024: -33.1pp
• All cycles: 2024: R+33.1 2020: R+24.7 2016: R+26.0 2012: R+30.1 2008: R+22.5

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -1.48%
• Current HPI: 266.5545
• Rent YoY: ▲ 3.21%
• Metro: Naples-Marco Island, 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

+732.5% since first listed

5 events — show timeline

• 2026-05-14 Listed $99,900 NAPLESMLS
• 2002-04-04 Sold (Public Records) $29,500 Public Records
• 1999-10-20 Sold (Public Records) $21,500 Public Records
• 1985-03-01 Sold (Public Records) $37,500 Public Records
• 1985-03-01 Sold (Public Records) $12,000 Public Records

Property tax history

+13.8%/yr

Latest (2025): $452 · +6.2% YoY. Source: county tax records.