433 Cheetah Dr #433 · Winding Cypress, FL 34114

$108,000

1 bd · 2.0 ba · 396 sqft · Condo public records · 321 Days on market

Built 1987 $299/mo HOA · 16% 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 MLS

Thank you for viewing 433 Cheetah Drive in Imperial Wilderness, a fun and active 55+ community! This cozy home has a cheerful vibe and makes living in Naples, FL an affordable dream come true! It boasts a large kitchen, 2 full bathrooms, a laundry/office/storage area, and is being sold fully furnished. The floor plan features a comfortable flow, and tile floors encompass the kitchen, hallway, one bathroom, and the bedroom. The rear of the home offers a private view while the front provides a spacious driveway area. Some of the updates include the following features: drywall, water tank (2014) washer/dryer (2014), and the roof (2016). On top of all of this, YOU OWN THE LAND, and the reasonable HOA ($750.50 per quarter) covers so much: water, lawn care, basic cable, community amenities, and trash/recycling. Community amenities include the following: 2 pools with spas, bocce, pickleball, tennis, shuffleboard, billiards, a library, clubhouse, dog parks, and more!

Key facts

• Gated community
• Large kitchen
• Tile flooring

Tags

• GATED COMMUNITY
• YOU OWN THE LAND
• TILE FLOORING
• LARGE KITCHEN
• CLAMSHELL STORM SHADES
• GREAT STORAGE SPACE

Property features AI

Finance

• Other: Complex has 546 units; 1 unit in building; 1 unit per floor; 1 floor
• HOA & community: Quarterly condo fee ($898); Professional management; Community amenities: clubhouse, community pool, exercise room, library, billiards, bocce court, pickleball, tennis court, shuffleboard, sidewalks, streetlights, fishing pier, dog park, common laundry, internet access; Maintenance covered: cable, irrigation water, sewer, street lights, street maintenance, trash removal, water; Community type: Gated; Total annual recurring fees: $3,592; Total one-time fees: $150

Exterior

• Parking: Paved parking
• Security: Gated community
• Utilities: Central water; Central sewer; Cable available
• Home design: Manufactured residential home; Single-story; Built in 1987; Located in the Imperial Wilderness community
• Construction: Manufactured construction; Roof over
• Exterior features: Patio; Vinyl siding; Single-hung windows; Shutters (manual); Rear exposure faces south; Paved road access; Regular lot; limited number of vehicles allowed

Interior

• Kitchen: Range; Microwave; Refrigerator/Freezer; Eat-in kitchen
• Bedrooms: 1 bedroom
• Flooring: Carpet; Tile
• Bathrooms: 2 full bathrooms; Master bath: None
• Heating & cooling: Central electric heat; Central electric cooling
• Interior features: Window coverings; Eat-in kitchen; Laundry in residence; Furnished
• Laundry & utility: Washer; Dryer; Common laundry (community amenity)

What this means for you Summary

Snapshot

• This is a 1-bed/2.0-bath condo listed at $108k.

Deal economics

• At list price, monthly cash flow is $42 ($507/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $108k).
• Recommended offer: $95k (12.0% 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; solid renter incomes; 3,520 units permitted in Collier County in 2024 (959 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-1.5%/yr); year-one equity from $747 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.

Negotiation context

• It's been on market 321 days — a 12% lower offer ($95k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 3y ago; this cycle's ask has dropped $17k (14%) from the opening price — seller is motivated, your offer sets the floor, not the list.

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 $95,040 (12.0% below list)

Questions for the listing agent

1. It's been on market 321 days. Have you received any prior offers? Is the seller open to a 12% 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: 1.71% ✓
• Cap rate: 11.50%
• Cash-on-cash: 18.60%
• DSCR: 1.83
• GRM: 4.9

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: -5.4%
• Equity multiple: 0.77×
• Total profit: $-6,933
• Equity at exit: $23,599

10-year hold

• IRR: 2.6%
• Equity multiple: 1.24×
• Total profit: $7,284
• Equity at exit: $22,733

Cash invested: $30,240 (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: 4.9×

Monthly cashflow live

• Estimated rent: $1,849 medium
• Mortgage (P&I): −$566
• Tax from tax record: −$82 /mo · $979/yr
• Insurance: −$45
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$299
• Vacancy / Maint / Mgmt: −$388
• Net cashflow: $42

Break-even live

Break-even rent $1,796

Max offer price $108,000

Occupancy floor 93%

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: $27,000
• Closing costs: $3,240
• Reserves months: —
• Total cash needed: —

HOA detail condo

• Monthly dues: $299 · $3,588/yr
• Likely covers: watertrashcablelandscapingpool
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 23 events

1. 2026-06-18
   days on market $108,000 Active 321 DOM
2. 2026-06-17
   days on market $108,000 Active 320 DOM
3. 2026-06-16
   days on market $108,000 Active 319 DOM
4. 2026-06-15
   days on market $108,000 Active 318 DOM
5. 2026-06-10
   days on market $108,000 Active 313 DOM
6. 2026-06-09
   days on market $108,000 Active 312 DOM
7. 2026-06-08
   days on market $108,000 Active 311 DOM
8. 2026-06-07
   days on market $108,000 Active 310 DOM
9. 2026-06-02
   days on market $108,000 Active 305 DOM
10. 2026-06-01
    days on market $108,000 Active 304 DOM
11. 2026-05-31
    days on market $108,000 Active 303 DOM
12. 2026-05-30
    days on market $108,000 Active 302 DOM
13. 2026-02-24
    price $108,000
14. 2025-12-30
    price $118,000
15. 2025-08-01
    listed $125,000 Active
16. 2025-04-18
    historical
17. 2024-10-21
    listed $130,000 Active
18. 2023-05-18
    soldstatus $123,500
19. 2023-05-16
    soldstatus $123,500 Sold 974-char remark

    Show marketing remark (974 chars)

    Thank you for viewing 433 Cheetah Drive in Imperial Wilderness, a fun and active 55+ community! This cozy home has a cheerful vibe and makes living in Naples, FL an affordable dream come true! It boasts a large kitchen, 2 full bathrooms, a laundry/office/storage area, and is being sold fully furnished. The floor plan features a comfortable flow, and tile floors encompass the kitchen, hallway, one bathroom, and the bedroom. The rear of the home offers a private view while the front provides a spacious driveway area. Some of the updates include the following features: drywall, water tank (2014) washer/dryer (2014), and the roof (2016). On top of all of this, YOU OWN THE LAND, and the reasonable HOA ($750.50 per quarter) covers so much: water, lawn care, basic cable, community amenities, and trash/recycling. Community amenities include the following: 2 pools with spas, bocce, pickleball, tennis, shuffleboard, billiards, a library, clubhouse, dog parks, and more!

20. 2023-04-18
    status Pending 974-char remark

    Show marketing remark (974 chars)

    Thank you for viewing 433 Cheetah Drive in Imperial Wilderness, a fun and active 55+ community! This cozy home has a cheerful vibe and makes living in Naples, FL an affordable dream come true! It boasts a large kitchen, 2 full bathrooms, a laundry/office/storage area, and is being sold fully furnished. The floor plan features a comfortable flow, and tile floors encompass the kitchen, hallway, one bathroom, and the bedroom. The rear of the home offers a private view while the front provides a spacious driveway area. Some of the updates include the following features: drywall, water tank (2014) washer/dryer (2014), and the roof (2016). On top of all of this, YOU OWN THE LAND, and the reasonable HOA ($750.50 per quarter) covers so much: water, lawn care, basic cable, community amenities, and trash/recycling. Community amenities include the following: 2 pools with spas, bocce, pickleball, tennis, shuffleboard, billiards, a library, clubhouse, dog parks, and more!

21. 2023-04-13
    listed $132,000 Active 974-char remark

    Show marketing remark (974 chars)

    Thank you for viewing 433 Cheetah Drive in Imperial Wilderness, a fun and active 55+ community! This cozy home has a cheerful vibe and makes living in Naples, FL an affordable dream come true! It boasts a large kitchen, 2 full bathrooms, a laundry/office/storage area, and is being sold fully furnished. The floor plan features a comfortable flow, and tile floors encompass the kitchen, hallway, one bathroom, and the bedroom. The rear of the home offers a private view while the front provides a spacious driveway area. Some of the updates include the following features: drywall, water tank (2014) washer/dryer (2014), and the roof (2016). On top of all of this, YOU OWN THE LAND, and the reasonable HOA ($750.50 per quarter) covers so much: water, lawn care, basic cable, community amenities, and trash/recycling. Community amenities include the following: 2 pools with spas, bocce, pickleball, tennis, shuffleboard, billiards, a library, clubhouse, dog parks, and more!

22. 2011-04-13
    soldstatus $55,000
23. 1998-04-09
    soldstatus $22,000

ⓘ 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: $979 · $82/mo
• Projected year-2 tax: $979 · $82/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 8/10 Severe FEMA zone AE · 98% 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: $22,187
• − Mortgage interest: −$6,050
• − Property taxes: −$979
• − Insurance: −$5,658
• − Repairs & maintenance: −$1,775
• − Management: −$1,775
• − HOA: −$3,588
• − Depreciation: −$3,142
• Taxable loss: −$779
• Est. tax savings @ 24.0%: +$187
• After-tax cash flow: $694/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

+390.9% since first listed

11 events — show timeline

• 2026-02-24 Price Changed $108,000 NAPLESMLS
• 2025-12-30 Price Changed $118,000 NAPLESMLS
• 2025-08-01 Listed $125,000 NAPLESMLS
• 2025-04-18 Listing Removed — NAPLESMLS
• 2024-10-21 Listed $130,000 NAPLESMLS
• 2023-05-18 Sold (Public Records) $123,500 Public Records
• 2023-05-16 Sold (MLS) $123,500 NAPLESMLS
• 2023-04-18 Pending — NAPLESMLS
• 2023-04-13 Listed $132,000 NAPLESMLS
• 2011-04-13 Sold (Public Records) $55,000 Public Records
• 1998-04-09 Sold (Public Records) $22,000 Public Records

Property tax history

+7.0%/yr

Latest (2025): $979 · -4.4% YoY. Source: county tax records.