252 Chasteen Dr · Middlesborough, KY 40965

$99,999

3 bd · 2.0 ba · 1,296 sqft · SingleFamily public records · 263 Days on market

Built 1948 7,840 sqft lot $77/sqft · 33% below area Est $148k · 33% under

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Why this score? — see what drove the B 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 +26.7/30.0
• ARV discount +15.0/15.0
• DSCR +9.2/10.0
• Appreciation +6.8/10.0
• 1% rule +6.6/10.0
• 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

Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

Key facts

• Multiple kitchens
• Laundry areas
• Fenced backyard

Tags

• NEW ROOF
• FENCED BACKYARD
• MULTIPLE KITCHENS
• LAUNDRY AREAS
• OFF-STREET PARKING
• SEASONAL MOUNTAIN VIEWS

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $100k.

Deal economics

• At list price, monthly cash flow is $271 ($3k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($1k rent vs $100k).
• Recommended offer: $88k (12.0% below list) — sets the bar for market timing.
• Cap rate 9.5% vs local median 3.2% 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: 71 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 $4k of equity ($691 loan paydown + $4k 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 $28k cash investment doubles in ~4 years — after that, you're playing with house money.
• By year 8, paydown + projected appreciation supports a ~$32k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 263 days — a 12% lower offer ($88k) is reasonable based on typical stale-listing flexibility.
• 9 sale attempts since 9y ago; this cycle's ask has dropped $19k (16%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $33k; list at $100k implies a 203% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1948 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: extreme-heat days projected 8→22/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $87,999 (12.0% below list)

Questions for the listing agent

1. It's been on market 263 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 1948 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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.
7. 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.
8. 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: 1.16% ✓
• Cap rate: 9.54%
• Cash-on-cash: 11.59%
• DSCR: 1.52
• GRM: 7.2

CMA / ARV

• ARV (median comp): $148,263
• List price: $99,999
• Delta: -32.55%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
106 S 38th St	0.32mi	3/2.0	1,408 (+9%)	8mo	$180,000	$128	64
409 Meadow Ln	0.22mi	4/1.5 (+1)	1,120 (-14%)	2mo	$168,000	$150	58
1720 Exeter Ave	0.23mi	2/1.0 (-1)	1,456 (+12%)	2mo	$84,000	$58	58
1408 Exeter Ave	0.47mi	3/2.0	1,404 (+8%)	20mo	$159,000	$113	47
3806 W Cumberland Ave	0.44mi	3/1.0	1,120 (-14%)	18mo	$139,999	$125	38

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: 19.7%
• Equity multiple: 2.16×
• Total profit: $32,483
• Equity at exit: $48,386

10-year hold

• IRR: 20.5%
• Equity multiple: 4.13×
• Total profit: $87,609
• Equity at exit: $77,347

Cash invested: $28,000 (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: 71
• Price-to-rent: 7.2×

Monthly cashflow live

• Estimated rent: $1,161 medium
• Mortgage (P&I): −$524
• Tax from tax record: −$81 /mo · $970/yr
• Insurance: −$42
• HOA: −$0
• Vacancy / Maint / Mgmt: −$244
• Net cashflow: $271

Break-even live

Break-even rent $819

Max offer price $99,999

Occupancy floor 72%

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: $25,000
• Closing costs: $3,000
• Reserves months: —
• Total cash needed: —

Listing history 40 events

1. 2026-06-18
   days on market $99,999 Active 263 DOM
2. 2026-06-17
   days on market $99,999 Active 262 DOM
3. 2026-06-16
   days on market $99,999 Active 261 DOM
4. 2026-06-15
   days on market $99,999 Active 260 DOM
5. 2026-06-13
   days on market $99,999 Active 258 DOM
6. 2026-06-12
   days on market $99,999 Active 257 DOM
7. 2026-06-09
   days on market $99,999 Active 254 DOM
8. 2026-06-08
   days on market $99,999 Active 253 DOM
9. 2026-06-07
   days on market $99,999 Active 252 DOM
10. 2026-06-07
    days on market $99,999 Active 251 DOM
11. 2026-06-04
    days on market $99,999 Active 248 DOM
12. 2026-06-02
    days on market $99,999 Active 247 DOM
13. 2026-06-01
    days on market $99,999 Active 246 DOM
14. 2026-05-31
    days on market $99,999 Active 245 DOM
15. 2026-05-31
    days on market $99,999 Active 244 DOM
16. 2026-05-14
    price $99,999 974-char remark

    Show marketing remark (974 chars)

    Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

17. 2025-12-10
    price $109,000 974-char remark

    Show marketing remark (974 chars)

    Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

18. 2025-10-22
    price $115,000 974-char remark

    Show marketing remark (974 chars)

    Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

19. 2025-09-27
    listed $119,000 Active 974-char remark

    Show marketing remark (974 chars)

    Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential. Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience. The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout. Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!

20. 2025-05-18
    price $119,000
21. 2025-03-18
    status Active
22. 2025-03-13
    status Pending
23. 2025-03-13
    historical
24. 2025-01-13
    price $105,000
25. 2024-09-26
    status Active
26. 2024-08-30
    historical Pending - Continue to Show - Financing
27. 2024-06-04
    status Active
28. 2024-05-16
    historical Pending - Continue to Show - Inspection
29. 2024-01-31
    price $109,000
30. 2023-09-28
    listed $115,000 Active
31. 2023-09-24
    historical
32. 2023-09-23
    historical
33. 2023-04-22
    status Active
34. 2023-04-19
    historical Pending - Continue to Show
35. 2023-04-16
    listed $119,000 Active
36. 2023-03-23
    listed $119,000 Active
37. 2018-04-13
    soldstatus $33,000
38. 2018-04-13
    soldstatus $33,000
39. 2017-10-17
    listed $44,900
40. 2006-09-01
    soldstatus $30,000

ⓘ 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: $970 · $81/mo
• Projected year-2 tax: $970 · $81/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 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 5/10 Major 8 d/yr ≥100°F today · 22 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: $13,936
• − Mortgage interest: −$5,601
• − Property taxes: −$970
• − Insurance: −$500
• − Repairs & maintenance: −$1,115
• − Management: −$1,115
• − Depreciation: −$2,909
• Taxable income: $1,725
• Est. tax owed @ 24.0%: −$414
• After-tax cash flow: $2,832/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

+233.3% since first listed

25 events — show timeline

• 2026-05-14 Price Changed $99,999 Knoxville MLS
• 2025-12-10 Price Changed $109,000 Knoxville MLS
• 2025-10-22 Price Changed $115,000 Knoxville MLS
• 2025-09-27 Listed $119,000 Knoxville MLS
• 2025-05-18 Price Changed $119,000 Knoxville MLS
• 2025-03-18 Relisted — Knoxville MLS
• 2025-03-13 Pending — Knoxville MLS
• 2025-03-13 Listing Removed — Knoxville MLS
• 2025-01-13 Price Changed $105,000 Knoxville MLS
• 2024-09-26 Relisted — Knoxville MLS
• 2024-08-30 Contingent — Knoxville MLS
• 2024-06-04 Relisted — Knoxville MLS
• 2024-05-16 Contingent — Knoxville MLS
• 2024-01-31 Price Changed $109,000 Knoxville MLS
• 2023-09-28 Listed $115,000 Knoxville MLS
• 2023-09-24 Listing Removed — Knoxville MLS
• 2023-09-23 Listing Removed — ImagineMLS
• 2023-04-22 Relisted — Knoxville MLS
• 2023-04-19 Contingent — Knoxville MLS
• 2023-04-16 Listed $119,000 ImagineMLS
• 2023-03-23 Listed $119,000 Knoxville MLS
• 2018-04-13 Sold (Public Records) $33,000 Public Records
• 2018-04-13 Sold (MLS) $33,000 Knoxville MLS
• 2017-10-17 Listed $44,900 Knoxville MLS
• 2006-09-01 Sold (Public Records) $30,000 Public Records

Property tax history

+12.1%/yr

Latest (2025): $970 · +3.0% YoY. Source: county tax records.