14165 Winchester Ct #204 · Winding Cypress, FL 34114

$370,000

3 bd · 2.0 ba · 1,368 sqft · Condo public records · 9 Days on market

Built 2006 $701/mo HOA · 13% 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
• DSCR +10.0/10.0
• 1% rule +9.8/10.0
• 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

Beautifully updated 3-bedroom, 2-bath condo with a one-car garage, ideally situated at the end of a quiet street offering added privacy and serene views. This move-in-ready home features new tile flooring throughout the main living areas and new wood flooring in all bedrooms. The updated kitchen showcases granite countertops and stainless steel appliances, offering both style and functionality. The guest bathroom has been tastefully refreshed with a newer vanity and light fixture. Fresh interior paint and elegant crown molding throughout create a bright, modern feel. A rare highlight is the extra-long driveway with parking for up to six vehicles, perfect for guests or multi-car households. Enjoy peaceful views of lush green space from this desirable end-location property. Combining comfort, style, and convenience. Reflection Lakes is gated and offers a beautiful pool, clubhouse with community room, billiards, exercise room, library and card room. Location is great close to Naples and Marco Island!

Key facts

• Gated community
• Extra-long driveway
• Updated kitchen

Tags

• UPDATED KITCHEN
• GRANITE COUNTERTOPS
• STAINLESS STEEL APPLIANCES
• EXTRA-LONG DRIVEWAY
• GATED COMMUNITY
• BEAUTIFUL POOL

Property features AI

Finance

• Other: Unit is one of 76 in the complex and one of 4 in the building; Single-floor unit
• Financial info: Special assessment collected monthly
• HOA & community: Mandatory HOA; Master association fee billed monthly; Condo fee billed monthly; Maintenance covers cable, insurance, lawn/land maintenance, manager, recreation facilities, security, sewer, trash removal and water; Amenities include clubhouse, community pool, exercise room, library, billiards, bocce court, BBQ/picnic area and bike storage; Gated community; On-site management; Total annual recurring HOA/association fees provided

Exterior

• Parking: Attached garage with 1 garage space; Paved driveway
• Security: Unmonitored alarm; Entry keypad; Gated community; On-site management; Community security included in maintenance
• Utilities: Central water; Central sewer; Cable available; Electric service (central)
• Home design: Residential property in a low-rise (1–3) building; Carriage/coach style unit; Rear exposure to the east; Located in the Reflection Lakes of Naples community
• Construction: Built in 2006; Concrete block construction; Stucco exterior finish; Tile roof; Casement and sliding windows; Manual storm shutters
• Exterior features: Patio; Lake and landscaped area views; Cul-de-sac lot; Paved road access; Central irrigation

Interior

• Kitchen: Electric cooktop; Disposal; Microwave; Refrigerator; Freezer; Refrigerator with icemaker; Pantry
• Bedrooms: 3 bedrooms; Primary on the first floor
• Flooring: Tile flooring; Wood flooring
• Bathrooms: 2 full bathrooms; Primary bathroom with shower (no tub)
• Heating & cooling: Central electric heat; Central electric air conditioning; Ceiling fans
• Interior features: Fire sprinkler system; High-speed internet available; Laundry tub; Pantry; Smoke detectors; Window coverings; Formal dining area; Split bedroom floor plan; Screened lanai/porch; Laundry in residence; Six ceiling fans; Unfurnished
• Laundry & utility: Washer; Dryer; Laundry tub

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath condo listed at $370k.

Deal economics

• At list price, monthly cash flow is $1k ($17k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $370k).

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; 38 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 $5,463/mo this rent would consume 73% 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 $5k 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 $104k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• Only 9 days on market — expect competitive offers; lowballing is unlikely to land.
• 5 sale attempts since 14y 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 $135k; list at $370k implies a 174% gain — meaningful room to come down on a strong offer.

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 $370,000

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. 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?
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 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: 1.48% ✓
• Cap rate: 10.84%
• Cash-on-cash: 16.24%
• DSCR: 1.72
• GRM: 5.6

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: 12.1%
• Equity multiple: 1.53×
• Total profit: $54,942
• Equity at exit: $80,850

10-year hold

• IRR: 19.0%
• Equity multiple: 2.84×
• Total profit: $190,936
• Equity at exit: $77,881

Cash invested: $103,600 (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: 5.6×

Monthly cashflow live

• Estimated rent: $5,463 high
• Mortgage (P&I): −$1,940
• Tax from tax record: −$118 /mo · $1,415/yr
• Insurance: −$154
• HOA: −$701
• Vacancy / Maint / Mgmt: −$1,147
• Net cashflow: $1,402

Break-even live

Break-even rent $3,688

Max offer price $370,000

Occupancy floor 69%

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: $92,500
• Closing costs: $11,100
• Reserves months: —
• Total cash needed: —

Rent comps 38 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,700	$1.73	21d	1	0.21mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,800	$1.79	23d	1	0.21mi
14796 Canton Ct Naples, FL	3.0	2.0	1677	$7,000	$4.17	23d	1	0.45mi
2244 Yellowfin Cir Naples, FL	3.0	2.0	1655	$3,300	$1.99	13d	1	0.54mi
14103 Nautica Ct Naples, FL	3.0	2.5	1850	$3,650	$1.97	23d	1	0.56mi
2235 Yellowfin Cir Naples, FL	2.0	2.0	1500	$2,795	$1.86	23d	1	0.57mi
14162 Nautica Ct Naples, FL	3.0	2.0	1684	$3,800	$2.26	23d	1	0.60mi
130 Grassy Key Ln #37 Naples, FL	3.0	2.0	1248	$1,795	$1.44	13d	1	0.74mi
130 Grassy Key Ln Naples, FL	3.0	2.0	1248	$1,850	$1.48	13d	1	0.74mi
14670 Catamaran Pl Naples, FL	3.0	2.0	1816	$7,000	$3.85	23d	1	0.78mi
7674 Jacaranda Ln Naples, FL	2.0	2.0	1554	$3,800	$2.45	23d	1	0.81mi
7662 Jacaranda Ln Naples, FL	2.0	2.0	1555	$3,500	$2.25	13d	1	0.83mi
7631 Jacaranda Ln Naples, FL	2.0	2.0	1542	$7,000	$4.54	23d	1	0.89mi
7567 Winding Cypress Dr Naples, FL	3.0	2.0	1805	$11,500	$6.37	23d	1	0.93mi
14827 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	23d	1	0.96mi
14888 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,200	$4.09	23d	1	1.00mi
14940 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,200	$4.74	23d	1	1.04mi
14551 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,000	$3.96	23d	1	1.08mi
14558 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	23d	1	1.10mi
14567 Edgewater Cir Naples, FL	2.0	2.0	1515	$6,500	$4.29	23d	1	1.11mi
14582 Edgewater Cir Naples, FL	2.0	2.0	1515	$7,500	$4.95	23d	1	1.12mi
14680 Edgewater Cir Naples, FL	2.0	2.0	1515	$3,195	$2.11	23d	1	1.12mi
14672 Edgewater Cir Naples, FL	2.0	2.0	1519	$6,500	$4.28	23d	1	1.13mi
14644 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,000	$4.61	23d	1	1.15mi
14632 Edgewater Cir Unit 1049696P Naples, FL	2.0	2.0	1506	$6,237	$4.14	13d	1	1.15mi
14663 Edgewater Cir Naples, FL	2.0	2.0	1519	$7,000	$4.61	23d	1	1.16mi
14639 Edgewater Cir Naples, FL	2.0	2.0	1557	$6,000	$3.85	23d	1	1.18mi
14631 Edgewater Cir Naples, FL	2.0	2.0	1515	$2,795	$1.84	13d	1	1.18mi
14471 Stillwater Way Naples, FL	3.0	2.0	1816	$8,500	$4.68	23d	1	1.22mi
14541 Stern Way Naples, FL	2.0	2.0	1819	$8,000	$4.40	23d	1	1.24mi
14488 Stillwater Way Naples, FL	3.0	2.0	1830	$8,500	$4.64	23d	1	1.28mi
1276 Enbrook Loop Naples, FL	2.0	2.0	1503	$5,000	$3.33	23d	1	1.38mi
1212 Enbrook Loop Naples, FL	2.0	2.0	1496	$2,850	$1.91	23d	1	1.40mi
274 Riverwood Rd Unit 1546056P Naples, FL	2.0	2.0	1496	$4,451	$2.98	13d	1	1.40mi
1171 Tranquil Brook Dr Naples, FL	2.0	2.0	1503	$4,500	$2.99	13d	1	1.44mi
1157 Enbrook Loop Naples, FL	2.0	2.0	1503	$3,000	$2.00	23d	1	1.45mi
842 Enbrook Loop Naples, FL	2.0	2.0	1503	$2,800	$1.86	23d	1	1.49mi
6680 Beach Resort Dr Unit 1214 Naples, FL	2.0	2.0	1351	$4,500	$3.33	13d	1	1.49mi

HOA detail condo

• Monthly dues: $701 · $8,412/yr
• Likely covers: poolsecurity
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 7 events

1. 2026-06-18
   days on market $370,000 Active 9 DOM
2. 2026-06-17
   days on market $370,000 Active 8 DOM
3. 2026-06-16
   days on market $370,000 Active 7 DOM
4. 2026-06-15
   days on market $370,000 Active 6 DOM
5. 2026-06-14
   days on market $370,000 Active 4 DOM
6. 2026-06-09
   remarks 699-char remark

   Show marketing remark (1012 chars)

   Beautifully updated 3-bedroom, 2-bath condo with a one-car garage, ideally situated at the end of a quiet street offering added privacy and serene views. This move-in-ready home features new tile flooring throughout the main living areas and new wood flooring in all bedrooms. The updated kitchen showcases granite countertops and stainless steel appliances, offering both style and functionality. The guest bathroom has been tastefully refreshed with a newer vanity and light fixture. Fresh interior paint and elegant crown molding throughout create a bright, modern feel. A rare highlight is the extra-long driveway with parking for up to six vehicles, perfect for guests or multi-car households. Enjoy peaceful views of lush green space from this desirable end-location property. Combining comfort, style, and convenience. Reflection Lakes is gated and offers a beautiful pool, clubhouse with community room, billiards, exercise room, library and card room. Location is great close to Naples and Marco Island!

7. 2026-06-09
   listed $370,000 Active 1 DOM

   Show marketing remark (1012 chars)

   Beautifully updated 3-bedroom, 2-bath condo with a one-car garage, ideally situated at the end of a quiet street offering added privacy and serene views. This move-in-ready home features new tile flooring throughout the main living areas and new wood flooring in all bedrooms. The updated kitchen showcases granite countertops and stainless steel appliances, offering both style and functionality. The guest bathroom has been tastefully refreshed with a newer vanity and light fixture. Fresh interior paint and elegant crown molding throughout create a bright, modern feel. A rare highlight is the extra-long driveway with parking for up to six vehicles, perfect for guests or multi-car households. Enjoy peaceful views of lush green space from this desirable end-location property. Combining comfort, style, and convenience. Reflection Lakes is gated and offers a beautiful pool, clubhouse with community room, billiards, exercise room, library and card room. Location is great close to Naples and Marco Island!

ⓘ 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: $1,415 · $118/mo
• Projected year-2 tax: $3,071 · $256/mo
• Expected delta: +$1,656/yr (+$138/mo · 117.0%)

ⓘ 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: $65,552
• − Mortgage interest: −$20,726
• − Property taxes: −$1,415
• − Insurance: −$1,850
• − Repairs & maintenance: −$5,244
• − Management: −$5,244
• − HOA: −$8,412
• − Depreciation: −$10,764
• Taxable income: $11,897
• Est. tax owed @ 24.0%: −$2,855
• After-tax cash flow: $13,970/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

+55.3% since first listed

10 events — show timeline

• 2026-06-09 Listed $370,000 MIML
• 2026-06-09 Listed $370,000 NAPLESMLS
• 2013-10-04 Sold (Public Records) $135,000 Public Records
• 2013-10-01 Sold (MLS) $135,000 NAPLESMLS
• 2013-08-29 Listed $149,875 NAPLESMLS
• 2013-08-27 Listing Removed — NAPLESMLS
• 2012-12-06 Listed $149,875 NAPLESMLS
• 2012-12-01 Listed $149,875 MIML
• 2006-08-01 Sold (Public Records) $265,000 Public Records
• 2006-05-10 Sold (Public Records) $238,300 Public Records

Property tax history

+3.6%/yr

Latest (2025): $1,415 · +6.5% YoY. Source: county tax records.