923 Winchester Ave

Middlesborough, KY 40965

$79,000A-

1 bd · 1.0 ba · 1,344 sqft · Built 1940 · SingleFamily · Pending · 160 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,079/mo
• Mortgage (P&I): −$414
• Tax + insurance: −$157
• HOA: −$0
• Vac / Maint / Mgmt: −$227
• Net cashflow: $280/mo
• Annual: $3,365/yr
• Cap rate: 11.56%
• Cash-on-cash: 18.82%
• DSCR: 1.84
• 1% rule: 1.37%
• Cash to close: $22,120

Investor read

• This is a 1-bed/1.0-bath single-family listed at $79k.
• At list price, monthly cash flow is $280 ($3k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($1k rent vs $79k).
• It's been on market 160 days — a 12% lower offer ($70k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $70k (12.0% below list) — sets the bar for market timing.
• In year one you build about $3k of equity ($546 loan paydown + $3k appreciation (3.6% local appreciation)).
• Location reads 56/100 on livability (#456 in KY) — a working-class tenant base; expect higher turnover. Strengths: cost of living A+, housing A-; Watch: amenities F, commute F, employment F.
• Middlesboro Independent (town): math 14% / reading 34% proficiency, ranked #153 of 165 in KY (top 93%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 63% free/reduced lunch — lower-income household profile, screen leases tightly.
• Zoned schools: Middlesboro Elementary School (math 12% / reading 27%, grade F, #572 of 676 statewide, top 88%, 453 students, 83% FRL); Middlesboro Middle School (math 17% / reading 41%, grade F, #156 of 217 statewide, top 74%, 281 students, 82% FRL); Middlesboro High School (math 12% / reading 22%, grade F, #222 of 254 statewide, top 89%, 352 students, 73% FRL) — zoned schools average 79% FRL vs 63% district-wide (17 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Watch-outs: flood insurance adds $66/mo; built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 72 active listings in the ZIP; 44 units permitted in Bell County in 2024 (0 in 5+ unit buildings).
• Bell County population projected at -30% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (3.6% appreciation + 3.0% rent growth), your $22k cash investment doubles in ~4 years — after that, you're playing with house money.
• By year 10, paydown + projected appreciation supports a ~$33k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: severe flood risk; extreme-heat days projected 8→21/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
• Cap rate 11.6% vs local median 3.3% in Middlesborough — 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

• It's been on market 160 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
• 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.