109 Jackson St

Winchester, KY 40391

$90,000B-

2 bd · 1.0 ba · 1,218 sqft · Built 1940 · Other · Active · 20 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,234/mo
• Mortgage (P&I): −$472
• Tax + insurance: −$70
• HOA: −$0
• Vac / Maint / Mgmt: −$259
• Net cashflow: $432/mo
• Annual: $5,187/yr
• Cap rate: 12.06%
• Cash-on-cash: 20.58%
• DSCR: 1.92
• 1% rule: 1.37%
• Cash to close: $25,200

Investor read

• This is a 2-bed/1.0-bath other listed at $90k.
• At list price, monthly cash flow is $432 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($1k rent vs $90k).
• It's been on market 20 days — a 2% lower offer ($89k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $89k (1.5% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $622 of loan paydown is wiped out by about $3k of value loss. Plan a longer hold.
• Location reads 60/100 on livability (#393 in KY) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+; Watch: schools D+, amenities F, commute F.
• Clark County (town): math 28% / reading 41% proficiency, ranked #64 of 165 in KY (top 39%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 291 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 160 units permitted in Clark County in 2024 (61 in 5+ unit buildings).
• Clark County population projected to shrink 7% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• 2 sale attempts since 13y 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 $14k; list at $90k implies a 567% gain — meaningful room to come down on a strong offer.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $25k cash investment doubles in ~6 years — after that, you're playing with house money.
• Cap rate 12.1% vs local median 4.0% in Winchester — 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.

Questions for listing agent

• Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.