585 14th St N · Naples, FL 34102

$649,000

3 bd · 2.0 ba · 981 sqft · SingleFamily public records · 165 Days on market

Built 1968 6,098 sqft lot

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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 +24.1/30.0
• DSCR +7.8/10.0
• ARV discount +7.5/15.0
• Appreciation +7.0/10.0
• 1% rule +5.3/10.0
• Schools +5.0/10.0
• Rent growth +4.7/5.0
• Livability +4.0/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Location, Location, Location, rarely available waterfront property in downtown Naples. Three bedrooms 2 bath single family home situated at the end of the street on a pie shaped completely fenced lot, offering wide water views. Home has newer roof, and windows and its ready to move in or take advantage of the vacation short term rental. Walk to everything Downtown Naples has to offer and whats more to come to come to this area.

Key facts

• Seawall to fill-in
• Quiet cul-de-sac
• Build boat dock

Tags

• WATERFRONT LOCATION
• GULF ACCESS
• SCREENED IN LANAI
• BUILD BOAT DOCK
• SEAWALL TO FILL-IN
• QUIET CUL-DE-SAC

Property features AI

Finance

• Other: Property is in the River Park development; Lot is approximately 0.14 acres; Canal width approximately 31–80 feet
• Financial info: No additional financial details provided
• HOA & community: No HOA maintenance; Community park; Non-gated community

Exterior

• Parking: No parking information provided
• Security: Impact resistant windows and sliding glass; Impact resistant doors
• Utilities: Central water; Central sewer; Cable available
• Home design: Residential single-family home; 1 story (ranch); Rear exposure faces north; Located on a cul-de-sac
• Construction: Concrete block construction; Stucco exterior; Shingle roof; Built in 1968
• Exterior features: Patio; Canal view; Gulf access via bridges

Interior

• Kitchen: Electric cooktop; Range; Microwave; Refrigerator
• Bedrooms: 3 bedrooms
• Flooring: Tile
• Bathrooms: 2 full bathrooms; Master bath with shower only
• Heating & cooling: Central electric heat; Central electric cooling; Ceiling fans
• Interior features: High speed internet available; Smoke detectors; Walk-in closet; Window coverings; Eat-in kitchen; Screened lanai/porch; Great room floor plan
• Laundry & utility: Washer; Dryer

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $649k.

Deal economics

• At list price, monthly cash flow is $854 ($10k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($7k rent vs $649k).
• Recommended offer: $571k (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 80/100 on livability (#126 in FL, #1,903 nationally) — a professional / high-income tenant draw. Strengths: crime A+, amenities A+, employment A+; Watch: commute D+, cost of living F.
• Market conditions: Rents rising fast (+8.8%/yr); 614 active listings in the ZIP; 28 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 3,520 units permitted in Collier County in 2024 (959 in 5+ unit buildings).
• At $6,658/mo this rent would consume 61% of the median local household income ($131k/yr) (locally 333% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $31k of equity ($4k loan paydown + $27k appreciation (4.1% local appreciation)).
• Collier County population projected at +30% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• At projected returns (4.1% appreciation + 8.0% rent growth), your $182k cash investment doubles in ~4 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$50k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 165 days — a 12% lower offer ($571k) is reasonable based on typical stale-listing flexibility.
• 6 sale attempts since 15y 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 $500k; 30% above their basis — modest negotiation headroom, anchor on the comps not their cost.

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→27/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $571,120 (12.0% below list)

Questions for the listing agent

1. It's been on market 165 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1968 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
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. Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
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 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: 1.03% ✓
• Cap rate: 8.66%
• Cash-on-cash: 8.46%
• DSCR: 1.38
• GRM: 8.1

CMA / ARV

No comps found within radius.

Projected returns pro-forma

4.08% appreciation · 8.0% rent growth · sell at horizon

5-year hold

• IRR: 18.2%
• Equity multiple: 2.13×
• Total profit: $205,792
• Equity at exit: $332,225

10-year hold

• IRR: 21.2%
• Equity multiple: 4.73×
• Total profit: $677,297
• Equity at exit: $545,926

Cash invested: $181,720 (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 34102

• Home prices YoY: 1.3%
• Rents YoY: 8.8%
• Active inventory: 614
• Price-to-rent: 8.1×

Monthly cashflow live

• Estimated rent: $6,658 medium
• Mortgage (P&I): −$3,403
• Tax from tax record: −$306 /mo · $3,670/yr
• Insurance: −$270
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,398
• Net cashflow: $854

Break-even live

Break-even rent $5,578

Max offer price $649,000

Occupancy floor 82%

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: $162,250
• Closing costs: $19,470
• Reserves months: —
• Total cash needed: —

Rent comps 28 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
766 Central Ave Naples, FL	2.0–3.0	2.0	943	$6,500	$6.89	14d	4	0.82mi
766 Central Ave Naples, FL	2.0–3.0	2.0	855	$6,500	$7.60	21d	3	0.82mi
410 Bayfront Pl Naples, FL	1.0–3.0	1.0–2.0	1242	$9,750	$7.85	23d	6	0.83mi
450 Bayfront Pl Naples, FL	1.0–3.0	1.0–2.5	1324	$12,000	$9.06	23d	6	0.86mi
1334 Crayton Rd #1 Naples, FL	2.0	2.0	1100	$6,800	$6.18	23d	1	1.15mi
1100 8th Ave S Naples, FL	2.0	2.0	1218	$9,000	$7.39	14d	5	1.17mi
290 4th St S #202 Naples, FL	2.0	2.0	1058	$10,000	$9.45	23d	1	1.19mi
284 4th St S #103 Naples, FL	2.0	2.0	979	$9,000	$9.19	23d	1	1.19mi
286 4th St S #203 Naples, FL	2.0	2.0	1058	$10,000	$9.45	23d	1	1.19mi
282 4th St S Naples, FL	2.0	2.0	1058	$11,000	$10.40	23d	1	1.19mi
1100 Gulf Shore Blvd N Naples, FL	2.0	2.0	945	$6,000	$6.35	23d	2	1.22mi
1395 Curlew Ave Unit 4-3 Naples, FL	2.0	2.0	975	$7,000	$7.18	23d	1	1.25mi
1435 Curlew Ave #1 Naples, FL	2.0	2.0	975	$2,850	$2.92	21d	1	1.26mi
1435 Curlew Ave #1 Naples, FL	2.0	2.0	975	$2,850	$2.92	23d	1	1.26mi
388 4th Ave S #388 Naples, FL	2.0	2.0	965	$13,000	$13.47	23d	1	1.26mi
1300 Gulf Shore Blvd N #205 Naples, FL	2.0	2.0	850	$5,900	$6.94	23d	1	1.27mi
1300 Gulf Shore Blvd N #406 Naples, FL	2.0	2.0	850	$6,500	$7.65	23d	1	1.27mi
1300 Gulf Shore Blvd N #700 Naples, FL	2.0	2.0	850	$6,250	$7.35	23d	1	1.27mi
1300 Gulf Shore Blvd N #304 Naples, FL	2.0	2.0	850	$5,500	$6.47	23d	1	1.27mi
365 5th Ave S #303 Naples, FL	2.0	2.0	1090	$13,000	$11.93	23d	1	1.31mi
230 3rd Ave S #4 Naples, FL	2.0	2.5	978	$12,000	$12.27	23d	1	1.32mi
296 4th Ave S #296 Naples, FL	2.0	2.5	1120	$2,950	$2.63	21d	1	1.33mi
1950 Mayfair St Naples, FL	3.0	1.0–3.5	1514	$11,999	$7.92	14d	109	1.37mi
1950 Mayfair ST Unit 901 Naples, FL	2.0	2.0	1025	$4,560	$4.45	14d	1	1.39mi
175 5th Ave S Naples, FL	2.0	2.0	732	$14,000	$19.13	23d	2	1.42mi
351 8th Ave S #351 Naples, FL	2.0	2.0	930	$4,000	$4.30	23d	1	1.46mi
666 3rd St S Naples, FL	1.0–2.0	1.0–2.0	932	$8,000	$8.58	14d	2	1.47mi
250 7th Ave S #301 Naples, FL	2.0	2.0	1000	$10,000	$10.00	23d	1	1.49mi

Listing history 27 events

1. 2026-06-18
   days on market $649,000 Active 165 DOM
2. 2026-06-17
   days on market $649,000 Active 164 DOM
3. 2026-06-16
   days on market $649,000 Active 163 DOM
4. 2026-06-15
   days on market $649,000 Active 162 DOM
5. 2026-06-10
   days on market $649,000 Active 157 DOM
6. 2026-06-09
   days on market $649,000 Active 156 DOM
7. 2026-06-08
   days on market $649,000 Active 155 DOM
8. 2026-06-07
   days on market $649,000 Active 154 DOM
9. 2026-06-03
   days on market $649,000 Active 150 DOM
10. 2026-06-02
    days on market $649,000 Active 149 DOM
11. 2026-06-01
    days on market $649,000 Active 148 DOM
12. 2026-05-31
    days on market $649,000 Active 147 DOM
13. 2026-05-30
    days on market $649,000 Active 146 DOM
14. 2026-01-04
    listed $649,000 Active
15. 2022-04-14
    soldstatus $500,000 Sold 431-char remark

    Show marketing remark (431 chars)

    Location, Location, Location, rarely available waterfront property in downtown Naples. Three bedrooms 2 bath single family home situated at the end of the street on a pie shaped completely fenced lot, offering wide water views. Home has newer roof, and windows and its ready to move in or take advantage of the vacation short term rental. Walk to everything Downtown Naples has to offer and whats more to come to come to this area.

16. 2022-01-25
    status Pending 431-char remark

    Show marketing remark (431 chars)

    Location, Location, Location, rarely available waterfront property in downtown Naples. Three bedrooms 2 bath single family home situated at the end of the street on a pie shaped completely fenced lot, offering wide water views. Home has newer roof, and windows and its ready to move in or take advantage of the vacation short term rental. Walk to everything Downtown Naples has to offer and whats more to come to come to this area.

17. 2022-01-20
    listed $699,000 Active 431-char remark

    Show marketing remark (431 chars)

    Location, Location, Location, rarely available waterfront property in downtown Naples. Three bedrooms 2 bath single family home situated at the end of the street on a pie shaped completely fenced lot, offering wide water views. Home has newer roof, and windows and its ready to move in or take advantage of the vacation short term rental. Walk to everything Downtown Naples has to offer and whats more to come to come to this area.

18. 2021-04-13
    historical
19. 2021-04-06
    status Pending With Contingencies
20. 2021-03-31
    status Active
21. 2021-01-19
    historical
22. 2020-11-18
    listed $369,000 Active
23. 2018-07-20
    soldstatus $240,000
24. 2014-04-30
    price $87,900
25. 2014-04-25
    soldstatus $102,000
26. 2014-04-07
    listed $102,000
27. 2011-08-29
    listed $74,900

ⓘ 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: $3,670 · $306/mo
• Projected year-2 tax: $5,387 · $449/mo
• Expected delta: +$1,717/yr (+$143/mo · 46.8%)

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

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 10/10 Extreme 7 d/yr ≥107°F today · 27 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: $79,901
• − Mortgage interest: −$36,354
• − Property taxes: −$3,670
• − Insurance: −$8,364
• − Repairs & maintenance: −$6,392
• − Management: −$6,392
• − Depreciation: −$18,880
• Taxable loss: −$151
• Est. tax savings @ 24.0%: +$36
• After-tax cash flow: $10,284/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)

No district data.

Livability — Naples

• Score: 80/100
• State rank: #126
• US rank: #1903

Category grades

Amenities A+ Commute D+ Cost of living F Crime A+ Employment A+ Housing C+ Health & safety A+ User ratings C+

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Naples, FL
• County: Collier County · 396,295 people
• City population: 344,941
• Metro: Naples-Marco Island, FL
• Population (ZIP): 11,179
• Household income: $130,929
• Rent vs Own: 24.1% rent · 75.9% own
• Severe rent burden: 333.0

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 (79%)
• Race & ethnicity: White 79% Hispanic / Latino 9% Two or more races 8% Black 8% Asian 1%
• Hispanic origin (detail): Cuban 6%
• Common ancestry: Hispanic 4% Lithuanian 4% Romanian 4%
• Foreign-born: 17% · Canada, China
• Languages at home: 87% English-only · Spanish 7% French/Haitian/Cajun 4% German/W. Germanic 1%

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: ▲ 4.08%
• Current HPI: 328.2755
• Rent YoY: ▲ 8.75%
• 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

+766.5% since first listed

14 events — show timeline

• 2026-01-04 Listed $649,000 NAPLESMLS
• 2022-04-14 Sold (MLS) $500,000 NAPLESMLS
• 2022-01-25 Pending — NAPLESMLS
• 2022-01-20 Listed $699,000 NAPLESMLS
• 2021-04-13 Listing Removed — NAPLESMLS
• 2021-04-06 Pending — NAPLESMLS
• 2021-03-31 Relisted — NAPLESMLS
• 2021-01-19 Listing Removed — NAPLESMLS
• 2020-11-18 Listed $369,000 NAPLESMLS
• 2018-07-20 Sold (Public Records) $240,000 Public Records
• 2014-04-30 Price Changed $87,900 NAPLESMLS
• 2014-04-25 Sold (MLS) $102,000 NAPLESMLS
• 2014-04-07 Listed $102,000 NAPLESMLS
• 2011-08-29 Listed $74,900 NAPLESMLS

Property tax history

+16.3%/yr

Latest (2025): $3,670 · +20.9% YoY. Source: county tax records.