181 Pine Key Ln #29 · Winding Cypress, FL 34114

$177,000

3 bd · 3.0 ba · 1,512 sqft · Condo public records · 89 Days on market

Built 1982 $125/mo HOA · 2% 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 +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

INCREDIBLE VALUE PER SQUARE FOOT on this spacious home located in the welcoming 55+ community of West Wind Estates! Best of all, the land is owned—no land lease! This well-maintained home features brand-new vinyl flooring throughout most of the house, fresh interior paint, and elegant touches like wide baseboards and crown molding. Major updates provide peace of mind, including a newer A/C unit (2020), water heater (2021), and roof (2018). Offering 3 bedrooms and 3 bathrooms, this home provides generous living space with a well-sized kitchen featuring ample cabinetry and beautiful granite countertops. The interior laundry room adds convenience, while the layout includes two master

Key facts

• Vinyl flooring
• Newer a/c unit
• Interior paint

Tags

• OWNED LAND
• VINYL FLOORING
• INTERIOR PAINT
• WIDE BASEBOARDS
• CROWN MOLDING
• NEWER A/C UNIT

Property features AI

Finance

• Other: Homestead tax status
• HOA & community: Mandatory HOA; Monthly fee of $125; Annual recurring fees approximately $1,500; one-time fees approximately $150; Professional management; Maintenance covers insurance, lawn/land maintenance, legal/accounting, manager, recreation facilities; Community amenities include community pool, community room, exercise room, library, tennis, pickleball, shuffleboard, BBQ/picnic area, boat storage, common laundry

Exterior

• Parking: Driveway (paved) with 2+ parking spaces; Attached 1-car garage
• Utilities: Central water; Central sewer; Cable available; Electric service (central)
• Home design: Manufactured residential home; 1 story / ranch; Rear exposure faces north; Located in West Wind Estates (mobile/manufactured community)
• Construction: Manufactured construction; 1982 year built; Vinyl siding exterior; Shingle roof; Single hung windows; Regular lot
• Exterior features: Fenced yard; Paved public road access; Landscaped area view; Central irrigation

Interior

• Kitchen: Pantry; Microwave; Range; Refrigerator/Freezer; Reverse osmosis
• Bedrooms: 3 bedrooms (including two master suites)
• Flooring: Tile; Vinyl
• Bathrooms: 3 full bathrooms; Master baths feature dual sinks and shower-only configuration
• Heating & cooling: Central electric heat; Central electric cooling
• Interior features: Built-in cabinets; Cable prewire / cable available; Fireplace; Foyer; High-speed internet available; Laundry tub; Multi phone lines; Pantry; Window coverings; Split bedroom floor plan; Two master suites
• Laundry & utility: Washer and Dryer included; Laundry in residence; Auto garage door

What this means for you Summary

Snapshot

• This is a 3-bed/3.0-bath condo listed at $177k.

Deal economics

• At list price, monthly cash flow is $3k ($39k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $177k).
• Recommended offer: $166k (6.0% 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.
• Market conditions: Rents rising (+3.2%/yr); 900 active listings in the ZIP; 40 comparable units currently listed for rent nearby; rentals at typical pace (median 23d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 3,520 units permitted in Collier County in 2024 (959 in 5+ unit buildings).
• At $6,114/mo this rent would consume 82% of the median local household income ($89k/yr) (locally 550% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-1.5%/yr); year-one equity from $1k of loan paydown is wiped out by about $3k 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 $50k cash investment doubles in ~2 years — after that, you're playing with house money.

Negotiation context

• It's been on market 89 days — a 6% lower offer ($166k) is reasonable based on typical stale-listing flexibility.
• 11 sale attempts since 8y 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 $60k; list at $177k implies a 195% 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 $166,380 (6.0% below list)

Questions for the listing agent

1. It's been on market 89 days. Have you received any prior offers? Is the seller open to a 6% 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. 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?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
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: 3.45% ✓
• Cap rate: 31.19%
• Cash-on-cash: 88.92%
• DSCR: 4.96
• GRM: 2.4

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: 80.1%
• Equity multiple: 4.86×
• Total profit: $191,198
• Equity at exit: $38,677

10-year hold

• IRR: 82.6%
• Equity multiple: 10.08×
• Total profit: $449,871
• Equity at exit: $37,257

Cash invested: $49,560 (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: 2.4×

Monthly cashflow live

• Estimated rent: $6,114 high
• Mortgage (P&I): −$928
• Tax from tax record: −$31 /mo · $373/yr
• Insurance: −$74
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$125
• Vacancy / Maint / Mgmt: −$1,284
• Net cashflow: $3,246

Break-even live

Break-even rent $2,006

Max offer price $177,000

Occupancy floor 42%

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: $44,250
• Closing costs: $5,310
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
130 Grassy Key Ln #37 Naples, FL	3.0	2.0	1248	$1,795	$1.44	13d	1	0.05mi
130 Grassy Key Ln Naples, FL	3.0	2.0	1248	$1,850	$1.48	13d	1	0.05mi
14796 Canton Ct Naples, FL	3.0	2.0	1677	$7,000	$4.17	23d	1	0.35mi
14678 Fern Lake Ct Unit 1049694P Naples, FL	3.0	2.0	2142	$6,065	$2.83	13d	1	0.37mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,800	$1.79	23d	1	0.59mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,700	$1.73	21d	1	0.59mi
2850 Aviamar Cir Naples, FL	3.0	2.0	2246	$12,000	$5.34	23d	1	0.61mi
14670 Catamaran Pl Naples, FL	3.0	2.0	1816	$7,000	$3.85	23d	1	0.62mi
14837 Windward Ln Naples, FL	4.0	2.0	2046	$4,995	$2.44	23d	1	0.62mi
14662 Catamaran Pl Naples, FL	3.0	2.0	2034	$7,000	$3.44	23d	1	0.62mi
14546 Tropical Dr Naples, FL	4.0	2.0	2046	$5,500	$2.69	23d	1	0.63mi
9259 Museo Cir #102 Naples, FL	3.0	3.0	2100	$4,150	$1.98	23d	1	0.76mi
14606 Tropical Dr Naples, FL	3.0	2.0	2046	$9,500	$4.64	23d	1	0.76mi
9267 Museo Cir Unit 204 Naples, FL	3.0	3.5	2100	$5,200	$2.48	23d	1	0.78mi
2713 Callista Ct #103 Naples, FL	3.0	3.0	2237	$6,999	$3.13	23d	1	0.83mi
9255 Museo #103 Naples, FL	3.0	3.0	2100	$9,000	$4.29	23d	1	0.86mi
14827 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	23d	1	0.86mi
3031 Marengo Ct Unit 203 Naples, FL	3.0	3.0	2200	$3,500	$1.59	13d	1	0.91mi
9243 Tesoro Ln Unit 2 Naples, FL	3.0	3.0	2100	$6,500	$3.10	13d	1	0.93mi
9242 Tesoro Ln Unit 1-102 Naples, FL	3.0	3.0	2237	$3,000	$1.34	23d	1	0.94mi
14888 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,200	$4.09	23d	1	0.95mi
14162 Nautica Ct Naples, FL	3.0	2.0	1684	$3,800	$2.26	23d	1	0.98mi
3149 Aviamar Cir #101 Naples, FL	3.0	2.0	1890	$7,500	$3.97	13d	1	1.01mi
14940 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,200	$4.74	23d	1	1.02mi
14103 Nautica Ct Naples, FL	3.0	2.5	1850	$3,650	$1.97	23d	1	1.03mi
14680 Edgewater Cir Naples, FL	2.0	2.0	1515	$3,195	$2.11	23d	1	1.04mi
14672 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	23d	1	1.06mi
14663 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,000	$4.61	23d	1	1.08mi
14558 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	23d	1	1.09mi
14644 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,000	$4.61	23d	1	1.09mi
15137 Sacile St Naples, FL	3.0	2.0	1905	$3,750	$1.97	23d	1	1.09mi
14551 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,000	$3.96	23d	1	1.10mi
14632 Edgewater Cir Unit 1049696P Naples, FL	2.0	2.0	1506	$6,237	$4.14	13d	1	1.10mi
14582 Edgewater Cir Naples, FL	2.0	2.0	1515	$7,500	$4.95	23d	1	1.10mi
14610 Edgewater Cir Naples, FL	2.0	2.0	1894	$7,500	$3.96	23d	1	1.10mi
15155 Tolmino St Naples, FL	3.0	2.0	1930	$9,000	$4.66	23d	1	1.11mi
14639 Edgewater Cir Naples, FL	2.0	2.0	1557	$6,000	$3.85	23d	1	1.12mi
14567 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	23d	1	1.12mi
15158 Tolmino St Naples, FL	2.0	2.0	1676	$3,000	$1.79	13d	1	1.12mi
14715 Kelson Cir Naples, FL	3.0	3.5	2225	$12,000	$5.39	23d	1	1.12mi

HOA detail condo

• Monthly dues: $125 · $1,500/yr
• Likely covers: water
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 45 events

1. 2026-06-18
   days on market $177,000 Active 89 DOM
2. 2026-06-17
   days on market $177,000 Active 88 DOM
3. 2026-06-16
   days on market $177,000 Active 87 DOM
4. 2026-06-15
   days on market $177,000 Active 86 DOM
5. 2026-06-14
   days on market $177,000 Active 84 DOM
6. 2026-06-10
   days on market $177,000 Active 81 DOM
7. 2026-06-09
   days on market $177,000 Active 80 DOM
8. 2026-06-08
   days on market $177,000 Active 79 DOM
9. 2026-06-07
   days on market $177,000 Active 78 DOM
10. 2026-06-03
    days on market $177,000 Active 74 DOM
11. 2026-06-02
    days on market $177,000 Active 73 DOM
12. 2026-06-01
    days on market $177,000 Active 72 DOM
13. 2026-05-31
    days on market $177,000 Active 71 DOM
14. 2026-05-30
    days on market $177,000 Active 70 DOM
15. 2026-03-21
    listed $177,000 Active
16. 2025-10-01
    historical
17. 2025-07-16
    price $203,000
18. 2025-06-03
    status Active
19. 2025-05-31
    status Pending With Contingencies
20. 2025-05-23
    listed $210,000 Active
21. 2024-12-03
    historical
22. 2024-12-03
    status Active
23. 2024-11-19
    status Pending With Contingencies
24. 2024-10-05
    price $220,000
25. 2024-07-24
    status Active
26. 2024-07-11
    status Pending With Contingencies
27. 2024-04-13
    price $233,500
28. 2024-03-30
    listed $244,500 Active
29. 2022-10-27
    historical
30. 2022-08-22
    status Active
31. 2022-08-20
    historical
32. 2022-08-19
    price $240,000
33. 2022-08-18
    listed $225,000 Active
34. 2021-02-28
    historical
35. 2020-08-07
    listed $179,000 Active
36. 2019-09-30
    historical
37. 2019-07-19
    listed $170,000 Active
38. 2018-12-28
    historical
39. 2018-11-01
    price $190,000
40. 2018-10-23
    price $200,000
41. 2018-10-09
    price $197,000
42. 2018-10-01
    listed $200,000 Active
43. 2018-01-26
    soldstatus $60,000
44. 2016-09-26
    soldstatus $37,000
45. 1982-08-01
    soldstatus $9,500

ⓘ 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: $373 · $31/mo
• Projected year-2 tax: $1,469 · $122/mo
• Expected delta: +$1,097/yr (+$91/mo · 294.3%)

ⓘ 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: $73,371
• − Mortgage interest: −$9,915
• − Property taxes: −$373
• − Insurance: −$6,004
• − Repairs & maintenance: −$5,870
• − Management: −$5,870
• − HOA: −$1,500
• − Depreciation: −$5,149
• Taxable income: $38,692
• Est. tax owed @ 24.0%: −$9,286
• After-tax cash flow: $29,663/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

+1763.2% since first listed

31 events — show timeline

• 2026-03-21 Listed $177,000 NAPLESMLS
• 2025-10-01 Listing Removed — NAPLESMLS
• 2025-07-16 Price Changed $203,000 NAPLESMLS
• 2025-06-03 Relisted — NAPLESMLS
• 2025-05-31 Pending — NAPLESMLS
• 2025-05-23 Listed $210,000 NAPLESMLS
• 2024-12-03 Listing Removed — NAPLESMLS
• 2024-12-03 Relisted — NAPLESMLS
• 2024-11-19 Pending — NAPLESMLS
• 2024-10-05 Price Changed $220,000 NAPLESMLS
• 2024-07-24 Relisted — NAPLESMLS
• 2024-07-11 Pending — NAPLESMLS
• 2024-04-13 Price Changed $233,500 NAPLESMLS
• 2024-03-30 Listed $244,500 NAPLESMLS
• 2022-10-27 Listing Removed — NAPLESMLS
• 2022-08-22 Relisted — NAPLESMLS
• 2022-08-20 Listing Removed — NAPLESMLS
• 2022-08-19 Price Changed $240,000 NAPLESMLS
• 2022-08-18 Listed $225,000 NAPLESMLS
• 2021-02-28 Listing Removed — NAPLESMLS
• 2020-08-07 Listed $179,000 NAPLESMLS
• 2019-09-30 Listing Removed — NAPLESMLS
• 2019-07-19 Listed $170,000 NAPLESMLS
• 2018-12-28 Listing Removed — NAPLESMLS
• 2018-11-01 Price Changed $190,000 NAPLESMLS
• 2018-10-23 Price Changed $200,000 NAPLESMLS
• 2018-10-09 Price Changed $197,000 NAPLESMLS
• 2018-10-01 Listed $200,000 NAPLESMLS
• 2018-01-26 Sold (Public Records) $60,000 Public Records
• 2016-09-26 Sold (Public Records) $37,000 Public Records
• 1982-08-01 Sold (Public Records) $9,500 Public Records

Property tax history

-4.2%/yr

Latest (2025): $373 · +6.0% YoY. Source: county tax records.