27 N High St

Winchester, IL 62694

$64,900A-

2 bd · 1.0 ba · 1,152 sqft · Built 1965 · SingleFamily · Pending · 72 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $993/mo
• Mortgage (P&I): −$340
• Tax + insurance: −$85
• HOA: −$0
• Vac / Maint / Mgmt: −$209
• Net cashflow: $359/mo
• Annual: $4,308/yr
• Cap rate: 12.93%
• Cash-on-cash: 23.70%
• DSCR: 2.05
• 1% rule: 1.53%
• Cash to close: $18,172

Investor read

• This is a 2-bed/1.0-bath single-family listed at $65k.
• At list price, monthly cash flow is $359 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($993 rent vs $65k).
• It's been on market 72 days — a 6% lower offer ($61k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $61k (6.0% below list) — sets the bar for market timing.
• In year one you build about $2k of equity ($449 loan paydown + $2k appreciation (3.1% local appreciation)).
• Location reads 68/100 on livability (#474 in IL) — a middle-class / working-renter tenant base. Strengths: crime A+, cost of living A+, housing A+; Watch: schools D+, amenities F, commute F.
• Winchester CUSD 1 (rural): math 26% / reading 29% proficiency, ranked #281 of 620 in IL (top 45%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Market conditions: 8 active listings in the ZIP.
• Scott County population projected at -27% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 3 sale attempts since 6y 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 $42k; list at $65k implies a 55% gain — meaningful room to come down on a strong offer.
• At projected returns (3.1% appreciation + 3.0% rent growth), your $18k cash investment doubles in ~3 years — after that, you're playing with house money.

Questions for listing agent

• It's been on market 72 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
• Built in 1965 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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 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?
• 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.
• 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.
• 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.