221 Grassy Key Ln · Winding Cypress, FL 34114

$138,500

2 bd · 1.0 ba · 734 sqft · SingleFamily · 5 Days on market

Built 1989 3,049 sqft lot $125/mo HOA · 5% 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

Adorable home in the fun-festive community of West Wind Estates. This 2 bedroom home has been beautifully updated. Lighting, flooring, cabinets, quartz counters - everything is new. The home features a washer/dryer indoors, an oversized storage room or workshop, and a lovely screen room to enjoy your morning coffee or evening cocktail. West Wind Estates is a fun, pet friendly 55+ neighborhood with so many activities to keep you busy including pickleball, shuffleboard, corn hole, game nights, monthly brunches, and too many celebrations to mention. You own the land and the community fees are a very low $125/mth. No lot rent!!! Home is located just 12 miles from either downtown Naples or Marco

Key facts

• Washer dryer indoors
• 3,049 sq ft lot
• Garage

Tags

• OVERSIZED STORAGE ROOM
• WASHER DRYER INDOORS
• PET FRIENDLY NEIGHBORHOOD

Property features AI

Finance

• Financial info: Pets allowed (size limit; more than 20 lbs allowed)
• HOA & community: Monthly association fee of $125; Senior community; Community clubhouse, fitness center, game room, park, pickleball, shuffleboard, tennis courts, pool

Exterior

• Parking: Attached covered carport (1 covered space); Driveway; Golf cart garage
• Utilities: Public water; Public sewer; Cable available
• Home design: Manufactured home; One story; Faces west; Updated/remodeled
• Construction: Metal roof; Manufactured construction
• Exterior features: Enclosed porch; Screened porch; Patio; Fruit trees; Community pool

Interior

• Kitchen: Electric range; Refrigerator
• Bedrooms: Bedroom on main level
• Flooring: Tile; Vinyl
• Bathrooms: 1 full bathroom
• Heating & cooling: Central heating (electric); Central air conditioning; Ceiling fan(s)
• Interior features: Impact glass windows; First-floor entry; Bedroom on main level; Workshop
• Laundry & utility: Washer and dryer; Laundry located in garage; Electric water heater

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $138k.

Deal economics

• At list price, monthly cash flow is $320 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $138k).

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.
• 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 $958 of loan paydown is wiped out by about $2k 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 $39k cash investment doubles in ~8 years — after that, you're playing with house money.

Negotiation context

• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• 4 sale attempts since 18y 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 $40k; list at $138k implies a 246% 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 $138,500

Questions for the listing agent

1. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
2. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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.
5. 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.
6. 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: 1.67% ✓
• Cap rate: 12.76%
• Cash-on-cash: 23.10%
• DSCR: 2.03
• GRM: 5.0

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: 4.7%
• Equity multiple: 1.20×
• Total profit: $7,840
• Equity at exit: $30,264

10-year hold

• IRR: 12.2%
• Equity multiple: 2.16×
• Total profit: $44,890
• Equity at exit: $29,153

Cash invested: $38,780 (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: 5.0×

Monthly cashflow live

• Estimated rent: $2,315 medium
• Mortgage (P&I): −$726
• Tax est. 1.5%: −$173 /mo · $2,078/yr
• Insurance: −$58
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$125
• Vacancy / Maint / Mgmt: −$486
• Net cashflow: $320

Break-even live

Break-even rent $1,910

Max offer price $138,500

Occupancy floor 81%

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: $34,625
• Closing costs: $4,155
• Reserves months: —
• Total cash needed: —

HOA detail

• Monthly dues: $125 · $1,500/yr

Listing history 16 events

1. 2026-06-18
   days on market $138,500 Active 5 DOM
2. 2026-06-17
   days on market $138,500 Active 4 DOM
3. 2026-06-16
   days on market $138,500 Active 3 DOM
4. 2026-06-15
   days on market $138,500 Active 2 DOM
5. 2026-06-14
   statusdays on marketlisting id $138,500 Active 1 DOM
6. 2026-06-02
   days on market $138,500 Active Under Contract 56 DOM
7. 2026-06-01
   days on market $138,500 Active Under Contract 55 DOM
8. 2026-05-31
   days on market $138,500 Active Under Contract 54 DOM
9. 2026-05-30
   days on market $138,500 Active Under Contract 53 DOM
10. 2026-03-27
    historical
11. 2026-03-26
    listed $138,500 Active
12. 2026-03-26
    listed $138,500 Active
13. 2026-02-27
    historical
14. 2025-12-03
    listed $145,000 Active
15. 2009-04-01
    soldstatus $40,000
16. 2008-07-19
    listed $45,000

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

Climate risk First Street

• 🌊 Flood 8/10 Severe FEMA zone AE · 97% chance over 30 yrs
• 🔥 Wildfire 4/10 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: $27,778
• − Mortgage interest: −$7,758
• − Property taxes: −$2,078
• − Insurance: −$5,811
• − Repairs & maintenance: −$2,222
• − Management: −$2,222
• − HOA: −$1,500
• − Depreciation: −$4,029
• Taxable income: $2,158
• Est. tax owed @ 24.0%: −$518
• After-tax cash flow: $3,322/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

+207.8% since first listed

7 events — show timeline

• 2026-03-27 Listing Removed — MARMLS
• 2026-03-26 Listed $138,500 MARMLS
• 2026-03-26 Listed $138,500 MARMLS
• 2026-02-27 Listing Removed — MARMLS
• 2025-12-03 Listed $145,000 MARMLS
• 2009-04-01 Sold (MLS) $40,000 MIML
• 2008-07-19 Listed $45,000 MIML