14503 Manchester Dr · Winding Cypress, FL 34114

$580,000

4 bd · 2.5 ba · 2,248 sqft · SingleFamily public records · 193 Days on market

Built 2016 6,969 sqft lot $367/mo HOA · 5% 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 +26.2/30.0
• DSCR +8.9/10.0
• ARV discount +7.5/15.0
• 1% rule +6.6/10.0
• 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

Reduced! Bring Offers!! Lowest Priced per square foot single family home currently on the market! Discover this Boutique Gated community where resort-style amenities meet everyday comfort. This beautifully maintained 2016 home is truly move-in ready, showcasing an open-concept design filled with Natural Light, Elegant Tray and Volume Ceilings, Diagonal Tile Flooring in the main living areas complemented by Luxury Vinyl Plank in the bedrooms. Offering 4 Bedrooms and 2.5 baths, the home provides generous space for family and guests, with two bedrooms currently serving as a game room and home office. The Gourmet Kitchen is a Chef’s Delight, featuring 42" shaker cabinetry, stainless

Key facts

• Heated lakeside pool
• Natural light
• Gourmet kitchen

Tags

• BOUTIQUE GATED COMMUNITY
• NATURAL LIGHT
• GOURMET KITCHEN
• WALK-IN PANTRY
• COVERED LANAI
• HEATED LAKESIDE POOL

Property features AI

Finance

• Other: Property zoned SFR; Regular lot with approximate total area 2,952 (measure source: Property Appraiser Office); Lot dimensions approx. 55' x 125'; Restrictions: Architectural and deeded
• HOA & community: Mandatory HOA; Monthly HOA fee (master): $367.63; Total annual recurring HOA fees: $4,416; One-time fees: $1,100; Professional management; HOA maintains cable/internet, irrigation, lawn/land, recreation facilities, street lights and maintenance; Community amenities include clubhouse, community pool, exercise room, library, billiards, bocce court, bike/jog paths, play area, BBQ/picnic area, community room, sidewalks, and underground utilities

Exterior

• Parking: Attached 2-car garage; Driveway parking for 2+ vehicles
• Security: Gated community; Owned private security system; Community gate access
• Utilities: Central water; Central sewer; Electric service (central)
• Home design: Single-family home; 1 story (Ranch) / Traditional; Rear exposure facing north; Residential property in Reflection Lakes of Naples
• Construction: Built in 2016; Concrete block construction; Stucco exterior; Tile roof; Single-hung windows; Manual storm shutters
• Exterior features: Automatic sprinkler system; Screened lanai/porch; Paved driveway; Private paved road access; Preserve and wooded area views; Lake/canal irrigation

Interior

• Kitchen: Island; Walk-in pantry; Range; Microwave; Dishwasher; Disposal; Refrigerator/Freezer
• Bedrooms: 4 bedrooms; First-floor bedroom; Master bedroom on ground level
• Flooring: Tile; Vinyl
• Bathrooms: 2 full bathrooms; 1 half bathroom; Master bath with dual sinks and shower (no tub)
• Heating & cooling: Central electric heat; Central electric air conditioning; Ceiling fans; Cable available
• Interior features: Bar; Cable prewire; Foyer; French doors; High-speed internet available; Laundry tub; Pantry; Smoke detectors; Tray ceiling; Volume ceiling; Walk-in closet; Window coverings; Great room floor plan; One ceiling fan
• Laundry & utility: Washer; Dryer; Laundry tub; Auto garage door

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $580k.

Deal economics

• At list price, monthly cash flow is $1k ($13k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($7k rent vs $580k).
• Recommended offer: $510k (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.
• 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 $6,752/mo this rent would consume 91% 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 $4k of loan paydown is wiped out by about $9k 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 $162k cash investment doubles in ~10 years — after that, you're playing with house money.

Negotiation context

• It's been on market 193 days — a 12% lower offer ($510k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 10y 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.

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 $510,400 (12.0% below list)

Questions for the listing agent

1. It's been on market 193 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. 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: 1.16% ✓
• Cap rate: 9.36%
• Cash-on-cash: 10.95%
• DSCR: 1.49
• GRM: 7.2

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: 1.8%
• Equity multiple: 1.08×
• Total profit: $12,780
• Equity at exit: $126,738

10-year hold

• IRR: 9.2%
• Equity multiple: 1.86×
• Total profit: $139,339
• Equity at exit: $122,084

Cash invested: $162,400 (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: 7.2×

Monthly cashflow live

• Estimated rent: $6,752 high
• Mortgage (P&I): −$3,042
• Tax from tax record: −$202 /mo · $2,419/yr
• Insurance: −$242
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$367
• Vacancy / Maint / Mgmt: −$1,418
• Net cashflow: $1,056

Break-even live

Break-even rent $5,416

Max offer price $580,000

Occupancy floor 79%

Sensitivity live

Price	-10% $1,384	-5% $1,220	+0% $1,056	+5% $891	+10% $727
Rent	-10% $522	-5% $789	+0% $1,056	+5% $1,322	+10% $1,589
Rate	-1.0pp $1,348	-0.5pp $1,203	base $1,056	+0.5pp $905	+1.0pp $752

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: $145,000
• Closing costs: $17,400
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
14837 Windward Ln Naples, FL	4.0	2.0	2046	$4,995	$2.44	24d	1	0.20mi
14849 Windward Ln Naples, FL	3.0	2.5	2344	$11,000	$4.69	24d	1	0.22mi
14670 Catamaran Pl Naples, FL	3.0	2.0	1816	$7,000	$3.85	24d	1	0.31mi
14662 Catamaran Pl Naples, FL	3.0	2.0	2034	$7,000	$3.44	24d	1	0.32mi
14678 Fern Lake Ct Unit 1049694P Naples, FL	3.0	2.0	2142	$6,065	$2.83	14d	1	0.38mi
14265 Manchester Dr Naples, FL	4.0	2.0	2362	$7,000	$2.96	24d	1	0.44mi
14653 Tropical Dr Naples, FL	3.0	2.5	2550	$7,500	$2.94	24d	1	0.45mi
14546 Tropical Dr Naples, FL	4.0	2.0	2046	$5,500	$2.69	24d	1	0.46mi
14796 Canton Ct Naples, FL	3.0	2.0	1677	$7,000	$4.17	24d	1	0.48mi
14586 Tropical Dr Naples, FL	4.0	3.5	2438	$9,500	$3.90	24d	1	0.50mi
14606 Tropical Dr Naples, FL	3.0	2.0	2046	$9,500	$4.64	24d	1	0.52mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,800	$1.79	24d	1	0.53mi
14214 Manchester Dr Naples, FL	3.0	2.0	1560	$2,700	$1.73	21d	1	0.53mi
14162 Nautica Ct Naples, FL	3.0	2.0	1684	$3,800	$2.26	24d	1	0.56mi
14103 Nautica Ct Naples, FL	3.0	2.5	1850	$3,650	$1.97	24d	1	0.62mi
14715 Kelson Cir Naples, FL	3.0	3.5	2225	$12,000	$5.39	24d	1	0.73mi
9267 Museo Cir Unit 204 Naples, FL	3.0	3.5	2100	$5,200	$2.48	24d	1	0.80mi
9259 Museo Cir #102 Naples, FL	3.0	3.0	2100	$4,150	$1.98	24d	1	0.83mi
9255 Museo #103 Naples, FL	3.0	3.0	2100	$9,000	$4.29	24d	1	0.90mi
14258 Galley Ct Naples, FL	3.0	3.0	2704	$5,850	$2.16	14d	1	0.91mi
14537 Stern Way Naples, FL	4.0	2.0	2034	$5,000	$2.46	24d	1	0.93mi
14471 Stillwater Way Naples, FL	3.0	2.0	1816	$8,500	$4.68	24d	1	0.96mi
9239 Tesoro Ln Unit 3-203 Naples, FL	3.0	3.0	2300	$8,000	$3.48	24d	1	0.97mi
9243 Tesoro Ln Unit 2 Naples, FL	3.0	3.0	2100	$6,500	$3.10	14d	1	1.00mi
14488 Stillwater Way Naples, FL	3.0	2.0	1830	$8,500	$4.64	24d	1	1.00mi
2850 Aviamar Cir Naples, FL	3.0	2.0	2246	$12,000	$5.34	24d	1	1.02mi
14265 Laguna Springs Ln Naples, FL	4.0	3.0	2467	$15,000	$6.08	24d	1	1.03mi
2244 Yellowfin Cir Naples, FL	3.0	2.0	1655	$3,300	$1.99	14d	1	1.04mi
9242 Tesoro Ln Unit 1-102 Naples, FL	3.0	3.0	2237	$3,000	$1.34	24d	1	1.04mi
14614 Stillwater Way Naples, FL	4.0	3.5	2431	$13,000	$5.35	24d	1	1.04mi
1937 Yellowfin Cir Naples, FL	3.0	2.0	2214	$3,830	$1.73	21d	1	1.06mi
7567 Winding Cypress Dr Naples, FL	3.0	2.0	1805	$11,500	$6.37	24d	1	1.08mi
1973 Yellowfin Cir Naples, FL	4.0	3.0	2894	$9,800	$3.39	24d	1	1.13mi
9209 Museo Cir Unit 102 Naples, FL	3.0	3.0	2502	$7,200	$2.88	14d	1	1.15mi
9224 Campanile Cir Unit 203 Naples, FL	3.0	3.0	2512	$6,495	$2.59	14d	1	1.17mi
9205 Museo Cir Unit 201 Naples, FL	4.0	3.0	3000	$10,000	$3.33	14d	1	1.19mi
2147 Yellowfin Cir Naples, FL	4.0	3.0	2615	$11,000	$4.21	24d	1	1.20mi
2710 Callista Ct #104 Naples, FL	3.0	3.0	2502	$9,000	$3.60	24d	1	1.20mi
3031 Marengo Ct Unit 203 Naples, FL	3.0	3.0	2200	$3,500	$1.59	14d	1	1.22mi
2713 Callista Ct #103 Naples, FL	3.0	3.0	2237	$6,999	$3.13	24d	1	1.24mi

HOA detail

• Monthly dues: $367 · $4,404/yr
• Likely covers: security

Listing history 26 events

1. 2026-06-18
   days on market $580,000 Active 193 DOM
2. 2026-06-17
   days on market $580,000 Active 192 DOM
3. 2026-06-16
   days on market $580,000 Active 191 DOM
4. 2026-06-15
   remarks 688-char remark
5. 2026-06-15
   days on market $580,000 Active 190 DOM
6. 2026-06-10
   days on market $580,000 Active 185 DOM
7. 2026-06-09
   days on market $580,000 Active 184 DOM
8. 2026-06-08
   days on market $580,000 Active 183 DOM
9. 2026-06-07
   days on market $580,000 Active 182 DOM
10. 2026-06-03
    days on market $580,000 Active 178 DOM
11. 2026-06-02
    days on market $580,000 Active 177 DOM
12. 2026-06-01
    days on market $580,000 Active 176 DOM
13. 2026-05-31
    days on market $580,000 Active 175 DOM
14. 2026-05-30
    days on market $580,000 Active 174 DOM
15. 2026-05-01
    price $580,000
16. 2026-03-27
    price $585,000
17. 2026-03-13
    price $595,000
18. 2026-03-06
    price $596,000
19. 2026-02-26
    price $597,000
20. 2026-02-18
    price $598,000
21. 2025-12-07
    listed $599,000 Active
22. 2017-04-23
    historical
23. 2016-07-22
    status Pending
24. 2016-07-01
    price $392,554
25. 2016-04-22
    listed $390,554 Active
26. 2013-12-18
    soldstatus $5,200,000

ⓘ 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: $2,419 · $202/mo
• Projected year-2 tax: $4,814 · $401/mo
• Expected delta: +$2,395/yr (+$200/mo · 99.0%)

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

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone AE · 69% 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: $81,021
• − Mortgage interest: −$32,489
• − Property taxes: −$2,419
• − Insurance: −$8,018
• − Repairs & maintenance: −$6,482
• − Management: −$6,482
• − HOA: −$4,404
• − Depreciation: −$16,873
• Taxable income: $3,854
• Est. tax owed @ 24.0%: −$925
• After-tax cash flow: $11,741/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

-88.8% since first listed

12 events — show timeline

• 2026-05-01 Price Changed $580,000 NAPLESMLS
• 2026-03-27 Price Changed $585,000 NAPLESMLS
• 2026-03-13 Price Changed $595,000 NAPLESMLS
• 2026-03-06 Price Changed $596,000 NAPLESMLS
• 2026-02-26 Price Changed $597,000 NAPLESMLS
• 2026-02-18 Price Changed $598,000 NAPLESMLS
• 2025-12-07 Listed $599,000 NAPLESMLS
• 2017-04-23 Listing Removed — NAPLESMLS
• 2016-07-22 Pending — NAPLESMLS
• 2016-07-01 Price Changed $392,554 NAPLESMLS
• 2016-04-22 Listed $390,554 NAPLESMLS
• 2013-12-18 Sold (Public Records) $5,200,000 Public Records

Property tax history

+31.4%/yr

Latest (2025): $2,419 · +6.9% YoY. Source: county tax records.