229 S Highland St

Winchester, KY 40391

$180,000C-

4 bd · 3.0 ba · 3,462 sqft · Built 1930 · Other · Active · 60 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,869/mo
• Mortgage (P&I): −$944
• Tax + insurance: −$240
• HOA: −$0
• Vac / Maint / Mgmt: −$392
• Net cashflow: $292/mo
• Annual: $3,508/yr
• Cap rate: 8.24%
• Cash-on-cash: 6.96%
• DSCR: 1.31
• 1% rule: 1.04%
• Cash to close: $50,400

Investor read

• This is a 4-bed/3.0-bath other listed at $180k.
• At list price, monthly cash flow is $292 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $180k).
• It's been on market 60 days — a 3% lower offer ($175k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $175k (3.0% 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 60/100 on livability (#393 in KY) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+; Watch: amenities F, commute F, employment 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.
• Zoned schools: Shearer Elementary School (math 27% / reading 37%, grade F, #348 of 676 statewide, top 55%, 392 students, 68% FRL); Robert D. Campbell Jr. High (math 28% / reading 47%, grade F, #73 of 217 statewide, top 36%, 820 students, 57% FRL); George Rogers Clark High School (math 28% / reading 34%, grade F, #118 of 254 statewide, top 47%, 1,645 students, 53% FRL).
• Watch-outs: built in 1930 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 291 active listings in the ZIP; 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.
• Current owner paid $120k; list at $180k implies a 50% gain — meaningful room to come down on a strong offer.
• Cap rate 8.2% 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.
• This rent runs 35% of the median local income ($64k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Questions for listing agent

• It's been on market 60 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
• Built in 1930 — 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.