14536 Grapevine Dr · Winding Cypress, FL 34114

$385,000

3 bd · 2.0 ba · 1,445 sqft · SingleFamily public records · 79 Days on market

Built 2014 4,791 sqft lot $335/mo HOA · 6% of rent ↓ 5% since listing

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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

Welcome to your slice of paradise in the highly sought-after gated community of Reflection of Naples. This beautifully maintained attached villa offers serene lake views and a layout designed for comfort and relaxation. Featuring 3 spacious bedrooms, 2 full bathrooms, and a 2-car garage, this home is perfect for full-time living or a seasonal retreat. Enjoy a lifestyle of ease and leisure with resort-style amenities, including two sparkling pools, a kids’ splash pad, a full fitness center, community room, billiards, and a quiet library—all just steps from your door. Ideally located, the home provides easy access to Naples roads and Marco Island, making it simple to enjoy world-c

Key facts

• Gated community
• Full fitness center
• Two sparkling pools

Tags

• GATED COMMUNITY
• LAKE VIEWS
• RESORT STYLE AMENITIES
• TWO SPARKLING POOLS
• FULL FITNESS CENTER
• COMMUNITY ROOM

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $385k.

Deal economics

• At list price, monthly cash flow is $2k ($19k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $385k).
• Recommended offer: $362k (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; 32 comparable units currently listed for rent nearby; rentals at typical pace (median 24d 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 $5,988/mo this rent would consume 80% 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 $3k of loan paydown is wiped out by about $6k 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 $108k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 79 days — a 6% lower offer ($362k) is reasonable based on typical stale-listing flexibility.

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; moderate wildfire risk; extreme-heat days projected 7→31/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $361,900 (6.0% below list)

Questions for the listing agent

1. It's been on market 79 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. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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.
7. 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.
8. 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: 1.56% ✓
• Cap rate: 12.64%
• Cash-on-cash: 22.67%
• DSCR: 2.01
• GRM: 5.4

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: 14.1%
• Equity multiple: 1.62×
• Total profit: $66,897
• Equity at exit: $84,128

10-year hold

• IRR: 20.8%
• Equity multiple: 3.04×
• Total profit: $220,019
• Equity at exit: $81,038

Cash invested: $107,800 (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: 5.4×

Monthly cashflow live

• Estimated rent: $5,988 high
• Mortgage (P&I): −$2,019
• Tax from tax record: −$180 /mo · $2,154/yr
• Insurance: −$160
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$335
• Vacancy / Maint / Mgmt: −$1,257
• Net cashflow: $1,610

Break-even live

Break-even rent $3,950

Max offer price $385,000

Occupancy floor 68%

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: $96,250
• Closing costs: $11,550
• Reserves months: —
• Total cash needed: —

Rent comps 32 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
14796 Canton Ct Naples, FL	3.0	2.0	1677	$7,000	$4.17	23d	1	0.24mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,700	$1.73	21d	1	0.33mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,800	$1.79	23d	1	0.33mi
130 Grassy Key Ln #37 Naples, FL	3.0	2.0	1248	$1,795	$1.44	13d	1	0.34mi
130 Grassy Key Ln Naples, FL	3.0	2.0	1248	$1,850	$1.48	13d	1	0.34mi
14670 Catamaran Pl Naples, FL	3.0	2.0	1816	$7,000	$3.85	23d	1	0.54mi
14162 Nautica Ct Naples, FL	3.0	2.0	1684	$3,800	$2.26	23d	1	0.71mi
14103 Nautica Ct Naples, FL	3.0	2.5	1850	$3,650	$1.97	23d	1	0.74mi
14827 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	23d	1	0.78mi
14888 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,200	$4.09	23d	1	0.84mi
14940 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,200	$4.74	23d	1	0.91mi
2244 Yellowfin Cir Naples, FL	3.0	2.0	1655	$3,300	$1.99	13d	1	0.93mi
2235 Yellowfin Cir Naples, FL	2.0	2.0	1500	$2,795	$1.86	23d	1	0.95mi
14680 Edgewater Cir Naples, FL	2.0	2.0	1515	$3,195	$2.11	23d	1	0.96mi
14672 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	23d	1	0.97mi
14551 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,000	$3.96	23d	1	0.97mi
14558 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	23d	1	0.98mi
14582 Edgewater Cir Naples, FL	2.0	2.0	1515	$7,500	$4.95	23d	1	0.99mi
14567 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	23d	1	1.00mi
14663 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,000	$4.61	23d	1	1.00mi
14644 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,000	$4.61	23d	1	1.00mi
14632 Edgewater Cir Unit 1049696P Naples, FL	2.0	2.0	1506	$6,237	$4.14	13d	1	1.00mi
14639 Edgewater Cir Naples, FL	2.0	2.0	1557	$6,000	$3.85	23d	1	1.03mi
14631 Edgewater Cir Naples, FL	2.0	2.0	1515	$2,795	$1.84	13d	1	1.04mi
7674 Jacaranda Ln Naples, FL	2.0	2.0	1554	$3,800	$2.45	23d	1	1.04mi
7662 Jacaranda Ln Naples, FL	2.0	2.0	1555	$3,500	$2.25	13d	1	1.06mi
7631 Jacaranda Ln Naples, FL	2.0	2.0	1542	$7,000	$4.54	23d	1	1.13mi
14541 Stern Way Naples, FL	2.0	2.0	1819	$8,000	$4.40	23d	1	1.15mi
7567 Winding Cypress Dr Naples, FL	3.0	2.0	1805	$11,500	$6.37	23d	1	1.19mi
14471 Stillwater Way Naples, FL	3.0	2.0	1816	$8,500	$4.68	23d	1	1.19mi
14488 Stillwater Way Naples, FL	3.0	2.0	1830	$8,500	$4.64	23d	1	1.24mi
15158 Tolmino St Naples, FL	2.0	2.0	1676	$3,000	$1.79	13d	1	1.42mi

HOA detail

• Monthly dues: $335 · $4,020/yr
• Likely covers: poolgymsecurity

Listing history 4 events

1. 2026-05-13
   status Pending
2. 2026-04-27
   status Pending With Contingencies
3. 2026-04-16
   price $385,000
4. 2026-02-07
   listed $405,000 Active

ⓘ 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: $2,154 · $180/mo
• Projected year-2 tax: $3,196 · $266/mo
• Expected delta: +$1,041/yr (+$87/mo · 48.3%)

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

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone AE · 71% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 10/10 Extreme 7 d/yr ≥108°F today · 31 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: $71,851
• − Mortgage interest: −$21,566
• − Property taxes: −$2,154
• − Insurance: −$7,044
• − Repairs & maintenance: −$5,748
• − Management: −$5,748
• − HOA: −$4,020
• − Depreciation: −$11,200
• Taxable income: $14,371
• Est. tax owed @ 24.0%: −$3,449
• After-tax cash flow: $15,868/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

-4.9% since first listed

4 events — show timeline

• 2026-05-13 Pending — NAPLESMLS
• 2026-04-27 Pending — NAPLESMLS
• 2026-04-16 Price Changed $385,000 NAPLESMLS
• 2026-02-07 Listed $405,000 NAPLESMLS

Property tax history

+20.5%/yr

Latest (2025): $2,154 · +6.8% YoY. Source: county tax records.