999 Enbrook Loop · Winding Cypress, FL 34114

$415,000

2 bd · 2.0 ba · 1,496 sqft · SingleFamily public records · 142 Days on market

Built 2023 3,484 sqft lot $198/mo HOA · 6% of rent ↓ 59% since listing

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Why this score? — see what drove the D- 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 +8.5/30.0
• ARV discount +7.5/15.0
• Schools +5.0/10.0
• Appreciation +4.3/10.0
• Rent growth +3.3/5.0
• 1% rule +3.0/10.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +2.3/10.0

Listing remarks

This price reduction reflects how this home is an exceptional opportunity for buyers looking for space, comfort and value! Let’s make a deal. Welcome to this beautifully updated 2-bedroom plus den home, perfectly situated in one of Naples' newest communities. Freshly painted with new carpet in bedrooms, and featuring a new Samsung wash and dryer, this residence is truly move-in ready. The open floorplan showcases a gourmet kitchen with a dining bar that flows seamlessly into the living area, creating an inviting space for entertaining. Enjoy added privacy and relaxation in the screened-in patio. This modern yet comfortable home is equipped with Smart Home features including ADT Secur

Key facts

• Low hoa fees
• Gourmet kitchen
• Screened in patio

Tags

• GOURMET KITCHEN
• SCREENED IN PATIO
• SMART HOME FEATURES
• ROOM DARKENING SHADES
• ATTACHED TWO CAR GARAGE
• LOW HOA FEES

Property features AI

Finance

• HOA & community: Mandatory HOA; Quarterly HOA fee (reported $594); Professional management; HOA covers irrigation water, lawn/land maintenance, recreation facilities, street lights, street maintenance; Community amenities include clubhouse, community pool, exercise room, billiards, bocce court, tennis court, pickleball, sidewalks, streetlights, internet access, community room, underground utilities; Gated community; Total annual recurring fees reported $2,376; total one-time fees reported $150

Exterior

• Parking: Attached 2-car garage
• Security: Monitored alarm; Entry keypad; Gated community; Security system
• Utilities: Central water; Central sewer; Cable available
• Home design: Attached villa (duplex); 1 story / ranch; Rear exposure faces north; Residential property in ENBROOK community
• Construction: Built in 2023; Concrete block construction; Stucco exterior; Tile roof; Impact resistant windows and doors
• Exterior features: Patio; Screened lanai/porch; Automatic sprinkler system; Landscaped area view; Regular lot

Interior

• Kitchen: Pantry; Dishwasher; Range; Microwave; Self-cleaning oven; Refrigerator/Freezer; Refrigerator/Icemaker
• Bedrooms: 2 bedrooms plus a den; Split bedroom layout
• Flooring: Laminate flooring
• Bathrooms: 2 full bathrooms; Primary bath with dual sinks and shower (no tub)
• Heating & cooling: Central electric heat; Central electric cooling; Ceiling fans
• Interior features: Cable prewire; French doors; Smoke detectors; Walk-in closet; Window coverings; Great room floor plan; 2 ceiling fans; Unfurnished
• Laundry & utility: Washer and dryer in residence; Laundry in residence; Auto garage door

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath single-family listed at $415k.

Deal economics

• At list price, monthly cash flow is $-788 ($-9k/yr) — negative.
• To cash-flow at today's rent, offer at most $276k (33.5% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $332k (20.0% below list).
• Recommended offer: $276k (33.5% below list) — sets the bar for cash-flow.

Location & tenants

• Location reads: area grade D — 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); Manatee Middle School (math 61% / reading 43%, grade C+, #217 of 571 statewide, top 40%, 749 students, 64% 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); 904 active listings in the ZIP; 34 comparable units currently listed for rent nearby; rentals at typical pace (median 26d 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).
• This rent runs 45% of the median local income ($89k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

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.

Negotiation context

• It's been on market 142 days — a 12% lower offer ($365k) 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 6→24/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $275,842 (33.5% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 142 days. Have you received any prior offers? Is the seller open to a 34% concession, seller financing, or rate buy-down credit?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
4. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
8. 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.
9. 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.
10. 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: 0.80% ✗
• Cap rate: 5.25%
• Cash-on-cash: -3.73%
• DSCR: 0.83
• GRM: 10.4

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: -18.9%
• Equity multiple: 0.23×
• Total profit: $-89,256
• Equity at exit: $90,683

10-year hold

• IRR: -11.9%
• Equity multiple: 0.03×
• Total profit: $-113,065
• Equity at exit: $87,353

Cash invested: $116,200 (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: 904
• Price-to-rent: 10.4×

Monthly cashflow live

• Estimated rent: $3,320 high
• Mortgage (P&I): −$2,176
• Tax from tax record: −$437 /mo · $5,245/yr
• Insurance: −$173
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$198
• Vacancy / Maint / Mgmt: −$697
• Net cashflow: $-788

Break-even live

Break-even rent $4,318

Max offer price $275,842

Occupancy floor —

Sensitivity live

Price	-10% $-553	-5% $-670	+0% $-788	+5% $-905	+10% $-1,023
Rent	-10% $-1,050	-5% $-919	+0% $-788	+5% $-657	+10% $-525
Rate	-1.0pp $-579	-0.5pp $-682	base $-788	+0.5pp $-895	+1.0pp $-1,005

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: $103,750
• Closing costs: $12,450
• Reserves months: —
• Total cash needed: —

Rent comps 34 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
847 Enbrook Loop Naples, FL	2.0	2.0	1503	$2,950	$1.96	25d	1	0.10mi
842 Enbrook Loop Naples, FL	2.0	2.0	1503	$2,800	$1.86	25d	1	0.12mi
1078 Rolling Brook Ln Naples, FL	2.0	2.0	1503	$2,750	$1.83	23d	1	0.14mi
2000 Rookery Bay Dr Naples, FL	1.0–3.0	1.0–2.0	929	$1,772	$1.91	25d	9	0.15mi
1157 Enbrook Loop Naples, FL	2.0	2.0	1503	$3,000	$2.00	25d	1	0.16mi
1014 Manatee Rd Unit F307 Naples, FL	2.0	2.0	900	$1,800	$2.00	25d	1	0.21mi
1212 Enbrook Loop Naples, FL	2.0	2.0	1496	$2,850	$1.91	25d	1	0.24mi
1022 Manatee Rd Unit D107 Naples, FL	2.0	2.0	1000	$2,000	$2.00	25d	1	0.27mi
1000 Manatee Rd Unit A201 Naples, FL	2.0	2.0	1000	$1,695	$1.70	25d	1	0.31mi
1171 Tranquil Brook Dr Naples, FL	2.0	2.0	1503	$4,500	$2.99	15d	1	0.32mi
1010 Manatee Rd Unit B304 Naples, FL	2.0	2.0	1000	$1,800	$1.80	25d	1	0.32mi
1276 Enbrook Loop Naples, FL	2.0	2.0	1503	$5,000	$3.33	25d	1	0.33mi
158 Rookery Rd Naples, FL	3.0	2.0	1456	$2,450	$1.68	25d	1	0.43mi
1747 Beverly Dr Naples, FL	2.0	2.0	1080	$2,300	$2.13	25d	1	0.46mi
274 Riverwood Rd Unit 1546056P Naples, FL	2.0	2.0	1496	$4,451	$2.98	15d	1	0.50mi
4685 Hawks Nest Way #103 Naples, FL	2.0	2.0	1440	$6,500	$4.51	15d	1	0.77mi
4680 Hawks Nest Way Unit D-103 Naples, FL	2.0	2.0	1414	$3,000	$2.12	15d	1	0.81mi
4529 Cardinal Cove Ln #7 Naples, FL	2.0	2.0	1539	$6,500	$4.22	25d	1	0.82mi
4650 Hawks Nest Way Unit M202 Naples, FL	3.0	2.0	1840	$9,600	$5.22	15d	1	0.89mi
3955 Deer Crossing Ct #103 Naples, FL	3.0	2.0	1812	$7,500	$4.14	25d	1	0.91mi
2235 Yellowfin Cir Naples, FL	2.0	2.0	1500	$2,795	$1.86	25d	1	1.07mi
2244 Yellowfin Cir Naples, FL	3.0	2.0	1655	$3,300	$1.99	15d	1	1.11mi
6750 Beach Resort Dr #7 Naples, FL	2.0	2.0	1351	$3,900	$2.89	25d	1	1.24mi
6750 Beach Resort Dr Naples, FL	2.0	2.0	1351	$3,200	$2.37	15d	2	1.24mi
6680 Beach Resort Dr Unit 1214 Naples, FL	2.0	2.0	1351	$4,500	$3.33	15d	1	1.27mi
22 Cypress View Dr Unit B22 Naples, FL	2.0	2.0	1534	$7,000	$4.56	25d	1	1.30mi
1414 Oceania Dr S Naples, FL	3.0	2.0	1572	$5,000	$3.18	25d	1	1.30mi
6650 Beach Resort Dr Unit 908 Naples, FL	2.0	2.0	1351	$4,600	$3.40	15d	1	1.35mi
163 Indies Dr E #203 Naples, FL	2.0	2.0	1448	$7,200	$4.97	25d	1	1.39mi
163 Indies Dr E #206 Naples, FL	3.0	2.0	1698	$6,000	$3.53	25d	1	1.39mi
163 Indies Dr E #106 Naples, FL	3.0	2.0	1698	$7,500	$4.42	25d	1	1.39mi
1367 Artesia Dr E #302 Naples, FL	2.0	2.5	1583	$2,800	$1.77	25d	1	1.40mi
6590 Beach Resort Dr Unit 305 Naples, FL	2.0	2.0	1351	$4,500	$3.33	15d	1	1.48mi
268 Indies Dr E #102 Naples, FL	2.0	2.0	1537	$7,500	$4.88	25d	1	1.50mi

HOA detail

• Monthly dues: $198 · $2,376/yr

Listing history 5 events

1. 2026-05-30
   days on market $415,000 Active 142 DOM
2. 2026-04-27
   price $415,000
3. 2026-01-08
   listed $434,000 Active
4. 2023-11-02
   soldstatus $445,540
5. 2023-02-03
   soldstatus $1,018,349

ⓘ 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: $5,245 · $437/mo
• Projected year-2 tax: $5,245 · $437/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 9/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 10/10 Extreme 6 d/yr ≥108°F today · 24 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: $39,845
• − Mortgage interest: −$23,246
• − Property taxes: −$5,245
• − Insurance: −$7,194
• − Repairs & maintenance: −$3,188
• − Management: −$3,188
• − HOA: −$2,376
• − Depreciation: −$12,073
• Taxable loss: −$16,664
• Est. tax savings @ 24.0%: +$3,999
• After-tax cash flow: $-5,454/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

-59.2% since first listed

4 events — show timeline

• 2026-04-27 Price Changed $415,000 NAPLESMLS
• 2026-01-08 Listed $434,000 NAPLESMLS
• 2023-11-02 Sold (Public Records) $445,540 Public Records
• 2023-02-03 Sold (Public Records) $1,018,349 Public Records

Property tax history

+32.4%/yr

Latest (2025): $5,245 · +1.6% YoY. Source: county tax records.