5337 Waterbury Ct #2505

Crestwood, IL 60418

$157,900D

2 bd · 1.0 ba · 1,000 sqft · Built 1976 · Condo · Active · 17 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,844/mo
• Mortgage (P&I): −$828
• Tax + insurance: −$274
• HOA: −$364
• Vac / Maint / Mgmt: −$387
• Net cashflow: $-10/mo
• Annual: $-115/yr
• Cap rate: 6.22%
• Cash-on-cash: -0.26%
• DSCR: 0.99
• 1% rule: 1.17%
• Cash to close: $44,212

Investor read

• This is a 2-bed/1.0-bath condo listed at $158k.
• At list price, monthly cash flow is $-10 ($-115/yr) — negative.
• To cash-flow at today's rent, offer at most $156k (1.1% below list).
• Meets the 1% rule at list price ($2k rent vs $158k).
• It's been on market 17 days — a 2% lower offer ($156k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $156k (1.5% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $1k of loan paydown is wiped out by about $5k of value loss. Plan a longer hold.
• Location reads 82/100 on livability (#75 in IL, #1,220 nationally) — a professional / high-income tenant draw. Strengths: commute A+, cost of living A+, housing A+.
• Bremen Chsd 228 (suburban): math 15% / reading 17% proficiency, ranked #468 of 620 in IL (top 76%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Zoned schools: Lee R Foster Elem School (math 27% / reading 27%, grade F, #749 of 2,056 statewide, top 40%, 395 students, 0% FRL); Jack Hille Middle School (math 20% / reading 28%, grade F, #364 of 665 statewide, top 56%, 528 students, 0% FRL); Oak Forest High School (math 26% / reading 26%, grade F, #244 of 693 statewide, top 35%, 1,370 students, 0% FRL).
• Market conditions: 30 active listings in the ZIP; 6 comparable units currently listed for rent nearby; rentals leasing fast (median 10d on market — plan ~1-2 weeks tenant-placement turnaround); 6,272 units permitted in Cook County in 2024 (4,658 in 5+ unit buildings).
• 2 sale attempts since 19y 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 $117k; 35% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• Cap rate 6.2% vs local median 4.9% in Crestwood — meaningfully above typical; check what's discounted (condition, days-on-market, listing class) to confirm the premium yield is real.

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?
• Built in 1976 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• 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?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• Schools are D-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?
• 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.