5742 N 99th St #5744 · Milwaukee, WI 53225

$219,500

6 bd · 2.0 ba · 2,024 sqft · MultiFamily · 20 Days on market

Built 1964 Fair condition 5,662 sqft lot Est $206k · 6% over

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Why this score? — see what drove the C 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 +26.0/30.0
• DSCR +8.7/10.0
• 1% rule +6.9/10.0
• ARV discount +4.7/15.0
• Rent growth +4.3/5.0
• Livability +4.0/5.0
• Condition / age +2.2/5.0
• Schools +1.2/10.0
• Appreciation +0.0/10.0

Multi-family units

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

Listing remarks MLS

This 2 story duplex is perfect if you are looking for an investment property. Both units feature 3 bedrooms and one bath. Property features a detached garage. This duplex is fully rented at a total of $1,850/month with month to month leases. Property is being sold in AS IS Condition.

Key facts

• 3 bedroom layouts
• 3 car garage
• 5,662 sq ft lot

Tags

• INCOME PRODUCING DUPLEX
• 3 BEDROOM LAYOUTS
• 3 CAR GARAGE

Property features AI

Finance

• Other: Two separate residential units

Exterior

• Parking: Detached 3-car garage
• Utilities: Municipal water; Municipal sewer; 2 electric meters; 2 gas meters
• Home design: 2-story duplex; Multi-family property
• Construction: Less than 1/2 acre lot (approximately 0.13 acre); Zoned RT2
• Exterior features: Brick, stone and vinyl exterior

Interior

• Kitchen: Unit 2 kitchen located on upper level
• Bedrooms: Unit 1: 3 bedrooms; Unit 2: 3 bedrooms (master and other bedrooms on upper level)
• Bathrooms: Unit 1: 1 full bathroom; Unit 2: 1 full bathroom
• Interior features: Full basement with block construction

What this means for you Summary

Snapshot

• This is a 2 × 3-bed/1.0-bath units multifamily listed at $220k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $544 ($7k/yr) — positive. Per door: $272/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $220k).
• Recommended offer: $216k (1.5% below list) — sets the bar for market timing.
• Cap rate 9.3% vs local median 5.1% in Milwaukee — 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 81/100 on livability (#55 in WI, #1,534 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, cost of living A+; Watch: employment D+, schools F, crime F.
• Milwaukee School District (urban): math 10% / reading 18% proficiency, ranked #337 of 342 in WI (top 98%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 77% free/reduced lunch — lower-income household profile, screen leases tightly.
• Market conditions: Rents rising fast (+7.1%/yr); 45 active listings in the ZIP; 1,017 units permitted in Milwaukee County in 2024 (803 in 5+ unit buildings).
• At $2,609/mo this rent would consume 55% of the median local household income ($57k/yr) (locally 1391% 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 $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Milwaukee County population projected at +4% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• At projected returns (-3.0% appreciation + 7.1% rent growth), your $61k cash investment doubles in ~8 years — after that, you're playing with house money.

Negotiation context

• It's been on market 20 days — a 2% lower offer ($216k) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 5y 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 $138k; list at $220k implies a 60% gain — meaningful room to come down on a strong offer.

Recommended offer $216,207 (1.5% below list)

Questions for the listing agent

1. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
2. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
3. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
4. Built in 1964 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. Schools are F-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
7. Crime grade is F 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?
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 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: 1.19% ✓
• Cap rate: 9.27%
• Cash-on-cash: 10.63%
• DSCR: 1.47
• GRM: 7.0

CMA / ARV

• ARV (on-the-fly): $206,448
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
5728 N 98th St #5730	0.06mi	5/2.0 (-1)	2,021 (-0%)	14mo	$207,000	$102	81
5671 N 98th St #5673	0.09mi	5/2.0 (-1)	2,041 (+1%)	13mo	$245,000	$120	79
5723 N 97th St #5725	0.09mi	5/2.0 (-1)	2,077 (+3%)	10mo	$205,150	$99	78
5812 N 94th St #5814	0.33mi	6/2.0	1,983 (-2%)	12mo	$230,000	$116	71
5368 N 103rd St #5370	0.56mi	6/2.0	2,056 (+2%)	4mo	$245,000	$119	68
5666 N 97th St #5668	0.15mi	5/2.0 (-1)	1,799 (-11%)	3mo	$194,900	$108	67
5822 N 92nd St	0.45mi	5/2.5 (-1)	2,168 (+7%)	4mo	$158,000	$73	57
5743 N 91st St #5745	0.46mi	6/2.0	2,144 (+6%)	20mo	$199,900	$93	52
5816 N 94th St #5818	0.33mi	5/2.0 (-1)	1,856 (-8%)	17mo	$167,100	$90	52
5806 N 92nd St Unit 5806A	0.44mi	5/2.5 (-1)	2,276 (+12%)	17mo	$195,000	$86	37
10741 W Wren Ave #10743	0.61mi	6/3.0	2,242 (+11%)	19mo	$264,500	$118	33
6294 N Denmark St #6296	0.70mi	6/3.0	2,324 (+15%)	22mo	$195,000	$84	21

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 · 7.14% rent growth · sell at horizon

5-year hold

• IRR: 4.2%
• Equity multiple: 1.17×
• Total profit: $10,451
• Equity at exit: $32,728

10-year hold

• IRR: 17.3%
• Equity multiple: 2.70×
• Total profit: $104,489
• Equity at exit: $18,978

Cash invested: $61,460 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 73 Landlord-Friendly
• State Wisconsin: 73 Landlord-Friendly · R+2
• County: — inherits STATE
• City: — inherits STATE

5-day notice; preempted; Madison / Milwaukee have some local enforcement.

Methodology + full state rankings →

ZIP-level market 53225

• Home prices YoY: -21.1%
• Rents YoY: 7.1%
• Active inventory: 45
• Price-to-rent: 14.0×

Monthly cashflow live

• Estimated rent: $2,609 high
• Mortgage (P&I): −$1,151
• Tax est. 1.5%: −$274 /mo · $3,292/yr
• Insurance: −$91
• HOA: −$0
• Vacancy / Maint / Mgmt: −$548
• Net cashflow: $544

Break-even live

Break-even rent $1,920

Max offer price $219,500

Occupancy floor 74%

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

Units	Beds	Baths	Est. rent
▸ 2× units	3	1	$2,608
Total (2 units)			$2,609

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: $54,875
• Closing costs: $6,585
• Reserves months: —
• Total cash needed: —

Listing history 14 events

1. 2026-06-18
   days on market $219,500 Active 20 DOM
2. 2026-06-17
   days on market $219,500 Active 19 DOM
3. 2026-06-16
   statusdays on market $219,500 Active 18 DOM
4. 2026-06-15
   days on market $219,500 Contingent 17 DOM
5. 2026-06-13
   days on market $219,500 Contingent 15 DOM
6. 2026-06-13
   days on market $219,500 Contingent 14 DOM
7. 2026-06-09
   days on market $219,500 Contingent 11 DOM
8. 2026-06-08
   days on market $219,500 Contingent 10 DOM
9. 2026-06-07
   days on market $219,500 Contingent 9 DOM
10. 2026-06-05
    days on market $219,500 Contingent 6 DOM
11. 2026-06-03
    statusdays on market $219,500 Contingent 5 DOM
12. 2026-06-02
    days on market $219,500 Active 4 DOM
13. 2026-06-01
    days on market $219,500 Active 3 DOM
14. 2026-05-31
    days on market $219,500 Active 2 DOM

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 2/10 Low 7 d/yr ≥101°F today · 13 d/yr by 30 yrs out
• 💨 Wind 2/10 Low
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $31,308
• − Mortgage interest: −$12,295
• − Property taxes: −$3,292
• − Insurance: −$1,098
• − Repairs & maintenance: −$2,505
• − Management: −$2,505
• − Depreciation: −$6,385
• Taxable income: $3,228
• Est. tax owed @ 24.0%: −$775
• After-tax cash flow: $5,756/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.

Condition & rehab AI · 12 photos

Fair 45/100 Moderate rehab

This multi-family property requires moderate renovations to update the kitchen and bathrooms, which will significantly increase its resale and rental value.

Repairs flagged

• Major kitchen cabinets — severely dated and worn
• Major kitchen countertops — severely worn and outdated
• Major bathroom fixtures — dated and cluttered
• Major flooring — worn linoleum

Value-add opportunities

• Both update kitchen cabinets and countertops — modernizing the kitchen will appeal to both buyers and renters
• Both update bathroom fixtures and organization — modernizing the bathroom will appeal to both buyers and renters
• Both replace worn flooring — new flooring will improve the overall appearance and functionality of the home

Renovation cost estimate screening

Repair item	Severity	Est. cost
kitchen cabinets · severely dated and worn	Major	$15,000–50,000
kitchen countertops · severely worn and outdated	Major	$15,000–50,000
bathroom fixtures · dated and cluttered	Major	$15,000–50,000
flooring · worn linoleum	Major	$15,000–50,000
Total estimated repair cost · 4 items		$60,000–200,000

Value-add ROI direction

• Both update kitchen cabinets and countertops — modernizing the kitchen will appeal to both buyers and renters ↑
• Both update bathroom fixtures and organization — modernizing the bathroom will appeal to both buyers and renters ↑
• Both replace worn flooring — new flooring will improve the overall appearance and functionality of the home ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Milwaukee School District
• NCES district ID: 5509600
• Math proficiency: 10% ▼ -5.00%
• Reading proficiency: 18% ▬ 0.00%
• Median HH income: $36,339
• Composite: 11.61/100
• National rank: #9696
• State rank: #337 of 342 in WI

Livability — Milwaukee

• Score: 81/100
• State rank: #55
• US rank: #1534

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Milwaukee, WI
• County: Milwaukee County · 926,379 people
• City population: 573,768
• Metro: Milwaukee-Waukesha, WI
• Population (ZIP): 25,187
• Household income: $56,545
• Rent vs Own: 60.1% rent · 39.9% own
• Severe rent burden: 1391.0

Population outlook (Milwaukee County) Hauer SSP2

• Today (2025): 995,758 people
• By 2030: 1,009,124 · +1.3%
• By 2040: 1,028,128 · +3.3%
• By 2050: 1,040,066 · +4.4%
• By 2075: 1,057,849 · +6.2%
• By 2100: 1,039,774 · +4.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.59)
• Race & ethnicity: Black 58% White 26% Two or more races 7% Asian 6% Hispanic / Latino 5%
• Hispanic origin (detail): Mexican 2% Puerto Rican 3%
• Common ancestry: Romanian 2% Lithuanian 2% Iranian 1%
• Foreign-born: 8% · Canada, Vietnam
• Languages at home: 89% English-only · Other Asian/Pacific 4% Spanish 3% Other Indo-European 1%

Political lean MEDSL · Milwaukee

• 2024 margin: Solid D (+38.5) · D 68.3% · R 29.8% · Other 1.8%
• 2008→2024 swing: +2.7pp toward D · 2008: 35.9pp · 2024: 38.5pp
• All cycles: 2024: D+38.5 2020: D+39.9 2016: D+37.5 2012: D+34.6 2008: D+35.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -70.59%
• Current HPI: 264.1941
• Rent YoY: ▲ 7.14%
• Metro: Milwaukee-Waukesha, WI
• State GDP YoY: ▲ 2.10%
• F500 in state: 20

Industry mix (Fortune 500 HQ in WI)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$23B
▸Industrial Technology	2	$36B
▸Insurance	1	$36B
▸Professional Services	1	$19B
▸Utilities	1	$9B
▸Consumer Goods	1	$3B

Price history

+15.6% since first listed

26 events — show timeline

• 2026-05-29 Listed $219,500 METROMLS
• 2024-10-24 Rental Removed $845 APPFOLIO
• 2024-10-09 Listed for Rent $845 APPFOLIO
• 2022-07-01 Listing Removed — METROMLS
• 2022-06-08 Sold (MLS) $137,500 METROMLS
• 2022-06-01 Relisted — METROMLS
• 2022-06-01 Listing Removed — METROMLS
• 2022-04-22 Contingent — METROMLS
• 2022-04-21 Price Changed $149,900 METROMLS
• 2022-04-17 Price Changed $154,900 METROMLS
• 2022-04-04 Price Changed $159,900 METROMLS
• 2022-03-21 Relisted — METROMLS
• 2022-02-04 Contingent — METROMLS
• 2022-01-01 Listing Removed — METROMLS
• 2022-01-01 Listed $164,900 METROMLS
• 2021-12-08 Price Changed $164,900 METROMLS
• 2021-11-20 Relisted — METROMLS
• 2021-11-15 Contingent — METROMLS
• 2021-10-23 Price Changed $171,900 METROMLS
• 2021-10-16 Price Changed $172,900 METROMLS
• 2021-09-15 Price Changed $173,900 METROMLS
• 2021-08-28 Price Changed $174,900 METROMLS
• 2021-08-05 Price Changed $179,900 METROMLS
• 2021-07-27 Price Changed $184,900 METROMLS
• 2021-07-11 Price Changed $188,900 METROMLS
• 2021-06-19 Listed $189,900 METROMLS