2016 Roosevelt Dr · Key West, FL 33040

$1,300,000

7 bd · 5.0 ba · 2,957 sqft · MultiFamily public records · 120 Days on market

Built 1950 7,000 sqft lot Est $1437k · 10% under

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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
• ARV discount +11.8/15.0
• DSCR +10.0/10.0
• 1% rule +7.7/10.0
• Schools +4.6/10.0
• Livability +4.1/5.0
• Rent growth +3.6/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 4 units. confirmed

Listing remarks

Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.

Key facts

• 7000 square ft lot
• Midtown key west
• 7,000 sq ft lot

Tags

• 7000 SQUARE FT LOT
• MIDTOWN KEY WEST

Property features AI

Finance

• Financial info: Multi-unit property with 4 total units
• HOA & community: No association fees; No HOA first right of refusal; No fee-included services

Exterior

• Utilities: Public sewer hookup available (buyer to verify other utilities)
• Home design: 2-story building; Built in 1950; Above flood elevation: No
• Construction: CBS and stucco construction; Other construction details listed
• Exterior features: No waterfront or dockage; Pets allowed; Rentals permitted; Property in FEMA Flood Zone AE; Zoned CL (Limited Commercial); Approximately 0.16 acres (less than 1/4 acre); Subdivision: Sunshine Sub Plat 3 (Sunshine Sub Plat 3)

Interior

• Bathrooms: 5 full bathrooms
• Interior features: No appliances included

What this means for you Summary

Snapshot

• This is a 4 × 7-bed/5.0-bath units multifamily listed at $1.30M.

Deal economics

• At list price, monthly cash flow is $4k ($53k/yr) — positive. Per door: $1k/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($16k rent vs $1.30M).
• Recommended offer: $1.18M (9.0% below list) — sets the bar for market timing.
• Cap rate 10.8% vs local median 0.8% in Key West — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 82/100 on livability (#65 in FL, #1,123 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, employment A+; Watch: crime D+, cost of living F.
• Monroe (town): math 50% / reading 55% proficiency, ranked #23 of 73 in FL (top 32%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents rising fast (+4.5%/yr); 496 active listings in the ZIP; solid renter incomes; 332 units permitted in Monroe County in 2024 (42 in 5+ unit buildings).
• At $16,491/mo this rent would consume 229% of the median local household income ($87k/yr) (locally 2502% 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 (-3.0%/yr); year-one equity from $9k of loan paydown is wiped out by about $39k of value loss. Plan a longer hold.
• Monroe County population projected at +28% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• At projected returns (-3.0% appreciation + 4.5% rent growth), your $364k cash investment doubles in ~8 years — after that, you're playing with house money.

Negotiation context

• It's been on market 120 days — a 9% lower offer ($1.18M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 2y 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 $800k; list at $1.30M implies a 62% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $427/mo; built in 1950 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: in FEMA flood zone AE (mandatory federal flood insurance); severe wind risk, 99% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,183,000 (9.0% below list)

Questions for the listing agent

1. It's been on market 120 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1950 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
6. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
7. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
8. 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?
9. Crime grade is D in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
10. 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.
11. 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.
12. 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: 1.27% ✓
• Cap rate: 10.76%
• Cash-on-cash: 15.95%
• DSCR: 1.71
• GRM: 6.6

CMA / ARV

• ARV (on-the-fly): $1,437,102
• Comps found: 1

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
2616 Patterson Ave	0.51mi	8/4.0 (+1)	2,880 (-3%)	9mo	$1,400,000	$486	56

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 4.52% rent growth · sell at horizon

5-year hold

• IRR: 6.6%
• Equity multiple: 1.26×
• Total profit: $95,926
• Equity at exit: $193,834

10-year hold

• IRR: 17.3%
• Equity multiple: 2.52×
• Total profit: $553,770
• Equity at exit: $112,400

Cash invested: $364,000 (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 33040

• Rents YoY: 4.5%
• Active inventory: 496
• Price-to-rent: 26.3×

Monthly cashflow live

• Estimated rent: $16,491 medium
• Mortgage (P&I): −$6,817
• Tax from tax record: −$831 /mo · $9,973/yr
• Insurance: −$542
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,463
• Net cashflow: $4,411

Break-even live

Break-even rent $10,907

Max offer price $1,300,000

Occupancy floor 68%

4-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 4× units	7	5	$16,492
Total (4 units)			$16,491

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: $325,000
• Closing costs: $39,000
• Reserves months: —
• Total cash needed: —

Listing history 30 events

1. 2026-06-19
   days on market $1,300,000 Active 120 DOM
2. 2026-06-18
   days on market $1,300,000 Active 119 DOM
3. 2026-06-17
   days on market $1,300,000 Active 118 DOM
4. 2026-06-16
   days on market $1,300,000 Active 117 DOM
5. 2026-06-15
   days on market $1,300,000 Active 116 DOM
6. 2026-06-14
   days on market $1,300,000 Active 114 DOM
7. 2026-06-13
   days on market $1,300,000 Active 113 DOM
8. 2026-06-10
   days on market $1,300,000 Active 111 DOM
9. 2026-06-09
   days on market $1,300,000 Active 110 DOM
10. 2026-06-08
    days on market $1,300,000 Active 109 DOM
11. 2026-06-07
    days on market $1,300,000 Active 108 DOM
12. 2026-06-05
    days on market $1,300,000 Active 105 DOM
13. 2026-06-03
    days on market $1,300,000 Active 104 DOM
14. 2026-06-02
    days on market $1,300,000 Active 103 DOM
15. 2026-06-01
    days on market $1,300,000 Active 102 DOM
16. 2026-05-31
    days on market $1,300,000 Active 101 DOM
17. 2026-05-30
    days on market $1,300,000 Active 100 DOM
18. 2026-02-19
    listed $1,300,000 Active
19. 2025-01-18
    historical
20. 2024-05-07
    price $1,395,000
21. 2024-04-24
    price $1,495,000
22. 2024-03-28
    price $1,695,000
23. 2024-01-30
    price $1,895,000
24. 2024-01-18
    listed $2,049,000 Active
25. 2006-09-11
    soldstatus $800,000
26. 2003-07-25
    soldstatus $585,000
27. 2002-07-12
    soldstatus $529,000
28. 1996-12-03
    soldstatus $335,000
29. 1989-09-14
    soldstatus $265,000
30. 1985-11-01
    soldstatus $180,000

ⓘ 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: $9,973 · $831/mo
• Projected year-2 tax: $10,790 · $899/mo
• Expected delta: +$817/yr (+$68/mo · 8.2%)

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

Climate risk First Street

• 🌊 Flood 10/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 1/10 Low 0 unhealthy d/yr today · 0 by 30 yrs out

Taxation est. · year 1

• Rental income: $197,892
• − Mortgage interest: −$72,820
• − Property taxes: −$9,973
• − Insurance: −$11,618
• − Repairs & maintenance: −$15,831
• − Management: −$15,831
• − Depreciation: −$37,818
• Taxable income: $34,000
• Est. tax owed @ 24.0%: −$8,160
• After-tax cash flow: $44,776/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: Monroe
• NCES district ID: 1201320
• Math proficiency: 50% ▼ -14.00%
• Reading proficiency: 55% ▼ -6.00%
• Median HH income: $56,955
• Composite: 45.51/100
• National rank: #2608
• State rank: #23 of 73 in FL

Livability — Key West

• Score: 82/100
• State rank: #65
• US rank: #1123

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Key West, FL
• County: Monroe County · 66,185 people
• City population: 35,429
• Metro: Key West, FL
• Population (ZIP): 35,429
• Household income: $86,586
• Rent vs Own: 49.8% rent · 50.2% own
• Severe rent burden: 2502.0

Population outlook (Monroe County) Hauer SSP2

• Today (2025): 90,706 people
• By 2030: 96,308 · +6.2%
• By 2040: 106,565 · +17.5%
• By 2050: 116,500 · +28.4%
• By 2075: 141,423 · +55.9%
• By 2100: 151,947 · +67.5%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.61)
• Race & ethnicity: White 56% Hispanic / Latino 26% Two or more races 16% Black 12% Asian 2%
• Hispanic origin (detail): Mexican 2% Puerto Rican 2% Cuban 14%
• Common ancestry: Hispanic 6% Romanian 2% Scotch-Irish 2%
• Foreign-born: 22% · Canada, Dominican Republic
• Languages at home: 76% English-only · Spanish 17% French/Haitian/Cajun 2% Russian/Polish/Slavic 2%

Political lean MEDSL · Monroe

• 2024 margin: R (+18.3) · D 40.5% · R 58.8%
• 2008→2024 swing: -23.2pp toward R · 2008: 4.9pp · 2024: -18.3pp
• All cycles: 2024: R+18.3 2020: R+7.9 2016: R+6.9 2012: D+0.4 2008: D+4.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -814.48%
• Current HPI: 168.5706
• Rent YoY: ▲ 4.52%
• Metro: Key West, 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

+622.2% since first listed

13 events — show timeline

• 2026-02-19 Listed $1,300,000 FLKMLS
• 2025-01-18 Listing Removed — FLKMLS
• 2024-05-07 Price Changed $1,395,000 FLKMLS
• 2024-04-24 Price Changed $1,495,000 FLKMLS
• 2024-03-28 Price Changed $1,695,000 FLKMLS
• 2024-01-30 Price Changed $1,895,000 FLKMLS
• 2024-01-18 Listed $2,049,000 FLKMLS
• 2006-09-11 Sold (Public Records) $800,000 Public Records
• 2003-07-25 Sold (Public Records) $585,000 Public Records
• 2002-07-12 Sold (Public Records) $529,000 Public Records
• 1996-12-03 Sold (Public Records) $335,000 Public Records
• 1989-09-14 Sold (Public Records) $265,000 Public Records
• 1985-11-01 Sold (Public Records) $180,000 Public Records

Property tax history

+3.4%/yr

Latest (2025): $9,973 · +7.4% YoY. Source: county tax records.