322 N Milwaukee Ave

Wheeling, IL 60090

$539,000F

4 bd · 3.5 ba · 3,125 sqft · Built 1926 · Condo · Active · 73 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,768/mo
• Mortgage (P&I): −$2,827
• Tax + insurance: −$1,030
• HOA: −$0
• Vac / Maint / Mgmt: −$581
• Net cashflow: $-1,670/mo
• Annual: $-20,040/yr
• Cap rate: 2.57%
• Cash-on-cash: -13.28%
• DSCR: 0.41
• 1% rule: 0.51%
• Cash to close: $150,920

Investor read

• This is a 4-bed/3.5-bath condo listed at $539k.
• At list price, monthly cash flow is $-2k ($-20k/yr) — negative.
• To cash-flow at today's rent, offer at most $244k (54.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $277k (48.6% below list).
• It's been on market 73 days — a 6% lower offer ($507k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $244k (54.7% below list) — sets the bar for cash-flow.
• Local home prices are declining (-3.0%/yr); year-one equity from $4k of loan paydown is wiped out by about $16k of value loss. Plan a longer hold.
• Location reads 71/100 on livability (#335 in IL) — a middle-class / working-renter tenant base. Strengths: crime A+, commute A+, employment A+; Watch: amenities F, health & safety F.
• Township Hsd 214 (suburban): math 42% / reading 45% proficiency, ranked #103 of 620 in IL (top 17%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Eugene Field Elem School (math 12% / reading 12%, grade F, #1,403 of 2,056 statewide, top 71%, 577 students, 0% FRL); Jack London Middle School (math 21% / reading 25%, grade F, #377 of 665 statewide, top 58%, 596 students, 0% FRL); Wheeling High School (math 25% / reading 30%, grade F, #215 of 693 statewide, top 31%, 1,760 students, 0% FRL).
• Zoned-school proficiency averages 21% at this address vs 44% district-wide (-23 pts) — the specific schools serving this property underperform the Township Hsd 214 average; the district grade overstates school quality for this exact location.
• Watch-outs: built in 1926 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: Rents rising (+1.8%/yr); 62 active listings in the ZIP; solid renter incomes; 6,272 units permitted in Cook County in 2024 (4,658 in 5+ unit buildings).
• Current owner paid $450k; 20% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• Cap rate 2.6% vs local median 3.8% in Wheeling — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.
• This rent runs 39% of the median local income ($85k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Questions for listing agent

• 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?
• It's been on market 73 days. Have you received any prior offers? Is the seller open to a 55% concession, seller financing, or rate buy-down credit?
• Built in 1926 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
• Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• 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?
• 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?