923 Winchester Ave · Middlesborough, KY 40965

$79,000

1 bd · 1.0 ba · 1,344 sqft · SingleFamily public records · 160 Days on market

Built 1940 8,276 sqft lot $59/sqft · 58% below area Est $112k · 29% under ↓ 1% since listing

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Why this score? — see what drove the A- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +30.0/30.0
• ARV discount +15.0/15.0
• DSCR +10.0/10.0
• 1% rule +8.7/10.0
• Appreciation +6.8/10.0
• Livability +2.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Schools +1.9/10.0

Listing remarks MLS

This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

Key facts

• Storage room
• Office attached
• Paved driveway

Tags

• OFFICE ATTACHED
• STORAGE ROOM
• PAVED DRIVEWAY
• CORNER LEVEL LOT
• NATURAL GAS AVAILABLE
• HIGH SPEED INTERNET AVAILABLE

What this means for you Summary

Snapshot

• This is a 1-bed/1.0-bath single-family listed at $79k.

Deal economics

• 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).
• Recommended offer: $70k (12.0% below list) — sets the bar for market timing.
• Cap rate 11.6% vs local median 3.4% 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.

Location & tenants

• 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: schools D-, amenities F, commute 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.
• Market conditions: 72 active listings in the ZIP; 44 units permitted in Bell County in 2024 (0 in 5+ unit buildings).

Forward outlook

• In year one you build about $3k of equity ($546 loan paydown + $3k appreciation (3.6% local appreciation)).
• 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.

Negotiation context

• It's been on market 160 days — a 12% lower offer ($70k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: flood insurance adds $66/mo; built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• 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.

Recommended offer $69,520 (12.0% below list)

Questions for the listing agent

1. 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?
2. Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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.
8. 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.
9. 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.

Investment metrics

• 1% rule: 1.37% ✓
• Cap rate: 11.56%
• Cash-on-cash: 18.82%
• DSCR: 1.84
• GRM: 6.1

CMA / ARV

• ARV (median comp): $111,873
• List price: $79,000
• Delta: -29.38%
• Verdict: UNDERPRICED
• Comps: 11 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1720 Exeter Ave	0.67mi	2/1.0 (+1)	1,456 (+8%)	2mo	$84,000	$58	48
808 Manchester Ave	0.57mi	2/2.0 (+1)	1,237 (-8%)	21mo	$139,000	$112	33

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

3.6% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 23.1%
• Equity multiple: 2.35×
• Total profit: $29,949
• Equity at exit: $38,226

10-year hold

• IRR: 23.5%
• Equity multiple: 4.55×
• Total profit: $78,576
• Equity at exit: $61,105

Cash invested: $22,120 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 83 Strongly Landlord-Friendly
• State Kentucky: 83 Strongly Landlord-Friendly · R+16
• County: — inherits STATE
• City: — inherits STATE

7-day pay-or-quit (URLTA cities); generally landlord-friendly.

Methodology + full state rankings →

ZIP-level market 40965

• Home prices YoY: 2.7%
• Active inventory: 72
• Price-to-rent: 6.1×

Monthly cashflow live

• Estimated rent: $1,079 medium
• Mortgage (P&I): −$414
• Tax from tax record: −$58 /mo · $697/yr
• Insurance: −$33
• Flood insurance flood zone: −$66 /mo · $798/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$227
• Net cashflow: $280

Break-even live

Break-even rent $724

Max offer price $79,000

Occupancy floor 69%

Sensitivity live

Price	-10% $325	-5% $303	+0% $280	+5% $258	+10% $236
Rent	-10% $195	-5% $238	+0% $280	+5% $323	+10% $366
Rate	-1.0pp $320	-0.5pp $300	base $280	+0.5pp $260	+1.0pp $239

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $19,750
• Closing costs: $2,370
• Reserves months: —
• Total cash needed: —

Listing history 4 events

1. 2026-05-20
   price $79,000 243-char remark

   Show marketing remark (243 chars)

   This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

2. 2026-04-20
   price $85,000 243-char remark

   Show marketing remark (243 chars)

   This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

3. 2025-12-19
   listed $99,000 Active 243-char remark

   Show marketing remark (243 chars)

   This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

4. 2001-08-01
   soldstatus $80,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast KY · Resets to sale price

• Current annual tax: $697 · $58/mo
• Projected year-2 tax: $697 · $58/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone X (shaded) · 99% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 5/10 Major 8 d/yr ≥100°F today · 21 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 5% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $12,944
• − Mortgage interest: −$4,425
• − Property taxes: −$697
• − Insurance: −$1,192
• − Repairs & maintenance: −$1,035
• − Management: −$1,035
• − Depreciation: −$2,298
• Taxable income: $2,260
• Est. tax owed @ 24.0%: −$542
• After-tax cash flow: $2,822/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Middlesboro Independent
• NCES district ID: 2104170
• Math proficiency: 14% ▼ -20.00%
• Reading proficiency: 34% ▼ -17.00%
• Median HH income: $23,442
• Composite: 18.61/100
• National rank: #8900
• State rank: #153 of 165 in KY

Livability — Middlesborough

• Score: 56/100
• State rank: #456
• US rank: #22662

Category grades

Amenities F Commute F Cost of living A+ Crime C+ Employment F Housing A- Health & safety F User ratings F

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Middlesborough, KY
• City population: 11,698
• Population (ZIP): 11,698

Population outlook (Bell County) Hauer SSP2

• Today (2025): 24,501 people
• By 2030: 22,923 · -6.4%
• By 2040: 19,860 · -18.9%
• By 2050: 17,161 · -30.0%
• By 2075: 12,070 · -50.7%
• By 2100: 8,525 · -65.2%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (91%)
• Race & ethnicity: White 91% Two or more races 5% Black 3% Hispanic / Latino 1%
• Common ancestry: Serbian 2% Slovak 2% Romanian 1%
• Foreign-born: 0%

Political lean MEDSL · Bell

• 2024 margin: Solid R (+68.7) · D 15.2% · R 83.9%
• 2008→2024 swing: -28.1pp toward R · 2008: -40.6pp · 2024: -68.7pp
• All cycles: 2024: R+68.7 2020: R+63.2 2016: R+62.2 2012: R+51.7 2008: R+40.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 3.60%
• Current HPI: 134.9069
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 1.81%
• F500 in state: 4

Industry mix (Fortune 500 HQ in KY)

Industry	F500 HQs	Revenue
▸Healthcare	1	$118B
▸Food / Beverage	1	$7B

Price history

-1.2% since first listed

4 events — show timeline

• 2026-05-20 Price Changed $79,000 Knoxville MLS
• 2026-04-20 Price Changed $85,000 Knoxville MLS
• 2025-12-19 Listed $99,000 Knoxville MLS
• 2001-08-01 Sold (Public Records) $80,000 Public Records

Property tax history

+1.4%/yr

Latest (2025): $697 · +3.0% YoY. Source: county tax records.