14095 Winchester Ct #603 · Winding Cypress, FL 34114

$375,000

3 bd · 2.5 ba · 1,507 sqft · Townhouse public records · 26 Days on market

Built 2005 $701/mo HOA · 14% 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 +25.2/30.0
• 1% rule +8.3/10.0
• DSCR +8.3/10.0
• 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

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to luxury living in this beautifully updated two-story townhome condo, perfectly situated in the sought-after gated community of Reflection Lakes at Naples. Thoughtfully designed for comfort and style, this home offers impeccable upgrades and breathtaking views. Step outside to the show-stopping, extended screened lanai with a coveted Southwestern exposure. Sip your favorite drink as you take in scenic lake views and experience stunning sunsets that paint the sky in vibrant hues — your private outdoor sanctuary awaits! Inside, soaring vaulted ceilings and a spacious living area create an airy, inviting a

Key facts

• Scenic lake views
• Long driveway
• $701 HOA

Tags

• EXTENDED SCREENED LANAI
• SCENIC LAKE VIEWS
• LUXURIOUSLY UPDATED KITCHEN
• UPDATED ENSUITE BATHROOM
• ATTACHED ONE-CAR GARAGE
• LONG DRIVEWAY

Property features AI

Finance

• Other: Property is one unit per floor within a complex of 76 units and a building of 4 units; Possession at closing; Restrictions include architectural approvals, deeded restrictions, no commercial use, and no RVs
• Financial info: Total annual recurring fees listed; Total one-time fees listed
• HOA & community: Mandatory HOA; Master HOA fee collected monthly; Condo fee collected monthly; Professional management; Master association fee included in some services; HOA maintenance covers cable, insurance, internet/WiFi access, irrigation water, lawn/land maintenance, legal/accounting, manager, exterior pest control, recreation facilities, and reserves; Community amenities include clubhouse, community pool, exercise room, library, hobby room, billiards, bocce court, BBQ/picnic area, sidewalks, and streetlights; Gated community

Exterior

• Parking: Paved driveway; Attached garage with 1 garage space
• Security: Gated community; Manual storm shutters
• Utilities: Central water; Central sewer; Cable available
• Home design: Residential townhouse; 2-story; Rear exposure faces southwest; Lot unit 603
• Construction: Built in 2005; Concrete block construction; Stucco exterior; Tile roof; Single-hung windows; Foundation information not provided
• Exterior features: Pond on the property; Cul-de-sac location; Landscaped views; Lake view; Paved road access; Irrigation with reclaimed water (assessment paid)

Interior

• Kitchen: Pantry; Dishwasher; Disposal; Microwave; Range; Refrigerator/freezer; Self-cleaning oven
• Bedrooms: 3 bedrooms; First-floor bedroom; Master bedroom on ground level; Split bedroom arrangement
• Flooring: Carpet; Tile; Vinyl
• Bathrooms: 2 full bathrooms; 1 half bathroom; Master bath with dual sinks and a shower
• Heating & cooling: Central electric heat; Heat pump; Central electric cooling; Ceiling fans
• Interior features: Cable prewire; Fire sprinkler system; High-speed internet available; Laundry tub; Pantry; Smoke detectors; Vaulted ceiling; Window coverings; Screened lanai/porch; Dining area in living room; Eat-in kitchen; Great room floor plan; Split bedroom layout; Two-story plan; Four ceiling fans; Eight total rooms
• Laundry & utility: Washer and dryer included; Laundry in residence

What this means for you Summary

Snapshot

• This is a 3-bed/2.5-bath townhouse listed at $375k.

Deal economics

• At list price, monthly cash flow is $838 ($10k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $375k).
• Recommended offer: $369k (1.5% 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; 40 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 $4,991/mo this rent would consume 67% 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 $105k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 26 days — a 2% lower offer ($369k) is reasonable based on typical stale-listing flexibility.
• 6 sale attempts since 21y 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 $293k; 28% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Climate carrying-cost: major flood risk; severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 7→29/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $369,375 (1.5% below list)

Questions for the listing agent

1. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. 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.
4. 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.
5. 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: 1.33% ✓
• Cap rate: 8.97%
• Cash-on-cash: 9.57%
• DSCR: 1.43
• GRM: 6.3

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: 4.1%
• Equity multiple: 1.18×
• Total profit: $18,499
• Equity at exit: $81,942

10-year hold

• IRR: 11.5%
• Equity multiple: 2.08×
• Total profit: $113,163
• Equity at exit: $78,933

Cash invested: $105,000 (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: 6.3×

Monthly cashflow live

• Estimated rent: $4,991 high
• Mortgage (P&I): −$1,967
• Tax from tax record: −$281 /mo · $3,373/yr
• Insurance: −$156
• HOA: −$701
• Vacancy / Maint / Mgmt: −$1,048
• Net cashflow: $838

Break-even live

Break-even rent $3,930

Max offer price $375,000

Occupancy floor 78%

Sensitivity live

Price	-10% $1,050	-5% $944	+0% $838	+5% $732	+10% $625
Rent	-10% $443	-5% $641	+0% $838	+5% $1,035	+10% $1,232
Rate	-1.0pp $1,027	-0.5pp $933	base $838	+0.5pp $740	+1.0pp $642

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: $93,750
• Closing costs: $11,250
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,800	$1.79	24d	1	0.21mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,700	$1.73	22d	1	0.21mi
14678 Fern Lake Ct Unit 1049694P Naples, FL	3.0	2.0	2142	$6,065	$2.83	14d	1	0.31mi
14796 Canton Ct Naples, FL	3.0	2.0	1677	$7,000	$4.17	24d	1	0.41mi
14837 Windward Ln Naples, FL	4.0	2.0	2046	$4,995	$2.44	24d	1	0.41mi
9267 Museo Cir Unit 204 Naples, FL	3.0	3.5	2100	$5,200	$2.48	24d	1	0.45mi
9259 Museo Cir #102 Naples, FL	3.0	3.0	2100	$4,150	$1.98	24d	1	0.51mi
9255 Museo #103 Naples, FL	3.0	3.0	2100	$9,000	$4.29	24d	1	0.55mi
14103 Nautica Ct Naples, FL	3.0	2.5	1850	$3,650	$1.97	24d	1	0.55mi
14162 Nautica Ct Naples, FL	3.0	2.0	1684	$3,800	$2.26	24d	1	0.57mi
2244 Yellowfin Cir Naples, FL	3.0	2.0	1655	$3,300	$1.99	14d	1	0.60mi
1937 Yellowfin Cir Naples, FL	3.0	2.0	2214	$3,830	$1.73	22d	1	0.63mi
2235 Yellowfin Cir Naples, FL	2.0	2.0	1500	$2,795	$1.86	24d	1	0.63mi
9243 Tesoro Ln Unit 2 Naples, FL	3.0	3.0	2100	$6,500	$3.10	14d	1	0.66mi
130 Grassy Key Ln #37 Naples, FL	3.0	2.0	1248	$1,795	$1.44	14d	1	0.68mi
130 Grassy Key Ln Naples, FL	3.0	2.0	1248	$1,850	$1.48	14d	1	0.68mi
9242 Tesoro Ln Unit 1-102 Naples, FL	3.0	3.0	2237	$3,000	$1.34	24d	1	0.71mi
14670 Catamaran Pl Naples, FL	3.0	2.0	1816	$7,000	$3.85	24d	1	0.72mi
14662 Catamaran Pl Naples, FL	3.0	2.0	2034	$7,000	$3.44	24d	1	0.74mi
2057 Yellowfin Cir Naples, FL	3.0	3.0	2080	$7,800	$3.75	24d	1	0.81mi
7674 Jacaranda Ln Naples, FL	2.0	2.0	1554	$3,800	$2.45	24d	1	0.82mi
2122 Yellowfin Cir Naples, FL	4.0	3.0	2200	$3,200	$1.45	14d	1	0.82mi
7662 Jacaranda Ln Naples, FL	2.0	2.0	1555	$3,500	$2.25	14d	1	0.84mi
14546 Tropical Dr Naples, FL	4.0	2.0	2046	$5,500	$2.69	24d	1	0.90mi
7631 Jacaranda Ln Naples, FL	2.0	2.0	1542	$7,000	$4.54	24d	1	0.90mi
14827 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	24d	1	0.91mi
7567 Winding Cypress Dr Naples, FL	3.0	2.0	1805	$11,500	$6.37	24d	1	0.94mi
14606 Tropical Dr Naples, FL	3.0	2.0	2046	$9,500	$4.64	24d	1	0.94mi
14888 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,200	$4.09	24d	1	0.95mi
14715 Kelson Cir Naples, FL	3.0	3.5	2225	$12,000	$5.39	24d	1	0.97mi
14940 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,200	$4.74	24d	1	1.00mi
14551 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,000	$3.96	24d	1	1.04mi
14558 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	24d	1	1.06mi
14567 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	24d	1	1.07mi
14680 Edgewater Cir Naples, FL	2.0	2.0	1515	$3,195	$2.11	24d	1	1.07mi
14582 Edgewater Cir Naples, FL	2.0	2.0	1515	$7,500	$4.95	24d	1	1.07mi
2850 Aviamar Cir Naples, FL	3.0	2.0	2246	$12,000	$5.34	24d	1	1.08mi
14672 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	24d	1	1.08mi
3031 Marengo Ct Unit 203 Naples, FL	3.0	3.0	2200	$3,500	$1.59	14d	1	1.09mi
14610 Edgewater Cir Naples, FL	2.0	2.0	1894	$7,500	$3.96	24d	1	1.10mi

HOA detail

• Monthly dues: $701 · $8,412/yr
• Likely covers: cablesecurity

Listing history 26 events

1. 2026-06-18
   days on market $375,000 Active 26 DOM
2. 2026-06-17
   days on market $375,000 Active 25 DOM
3. 2026-06-16
   days on market $375,000 Active 24 DOM
4. 2026-06-15
   days on market $375,000 Active 23 DOM
5. 2026-06-14
   days on market $375,000 Active 21 DOM
6. 2026-06-10
   days on market $375,000 Active 18 DOM
7. 2026-06-09
   days on market $375,000 Active 17 DOM
8. 2026-06-08
   days on market $375,000 Active 16 DOM
9. 2026-06-07
   days on market $375,000 Active 15 DOM
10. 2026-06-03
    days on market $375,000 Active 11 DOM
11. 2026-06-02
    days on market $375,000 Active 10 DOM
12. 2026-06-01
    days on market $375,000 Active 9 DOM
13. 2026-05-31
    days on market $375,000 Active 8 DOM
14. 2026-05-30
    days on market $375,000 Active 7 DOM
15. 2026-05-23
    listed $375,000 Active
16. 2026-05-19
    listed $2,395
17. 2025-04-09
    historical
18. 2025-03-30
    historical $2,495
19. 2025-03-14
    listed $2,495
20. 2025-03-09
    price $395,000
21. 2025-01-30
    listed $410,000 Active
22. 2020-12-08
    historical
23. 2020-12-04
    listed $228,000 Active
24. 2005-11-18
    soldstatus $292,900
25. 2005-10-17
    soldstatus $194,205
26. 2005-05-24
    listed $299,900

ⓘ 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: $3,373 · $281/mo
• Projected year-2 tax: $3,373 · $281/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 6/10 Major FEMA zone X (shaded) · 67% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 10/10 Extreme 7 d/yr ≥108°F today · 29 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $59,886
• − Mortgage interest: −$21,006
• − Property taxes: −$3,373
• − Insurance: −$1,875
• − Repairs & maintenance: −$4,791
• − Management: −$4,791
• − HOA: −$8,412
• − Depreciation: −$10,909
• Taxable income: $4,730
• Est. tax owed @ 24.0%: −$1,135
• After-tax cash flow: $8,917/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

+25.0% since first listed

12 events — show timeline

• 2026-05-23 Listed $375,000 NAPLESMLS
• 2026-05-19 Listed for Rent $2,395 Avail
• 2025-04-09 Listing Removed — NAPLESMLS
• 2025-03-30 Rental Removed $2,495 Avail
• 2025-03-14 Listed for Rent $2,495 Avail
• 2025-03-09 Price Changed $395,000 NAPLESMLS
• 2025-01-30 Listed $410,000 NAPLESMLS
• 2020-12-08 Listing Removed — NAPLESMLS
• 2020-12-04 Listed $228,000 NAPLESMLS
• 2005-11-18 Sold (Public Records) $292,900 Public Records
• 2005-10-17 Sold (Public Records) $194,205 Public Records
• 2005-05-24 Listed $299,900 MIML

Property tax history

+7.6%/yr

Latest (2025): $3,373 · +5.4% YoY. Source: county tax records.