290 S Main St · Winchester, KY 40391

$179,900

6 bd · 2.0 ba · 3,008 sqft · Other · 40 Days on market

Built 1917

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Why this score? — see what drove the C 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 +24.9/30.0
• DSCR +8.1/10.0
• ARV discount +7.5/15.0
• 1% rule +5.6/10.0
• Schools +3.0/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Duplex 3/2 & Atilde; & mdash; 2.

Key facts

• Built 1917
• Listed 39 days

What this means for you Summary

Snapshot

• This is a 6-bed/2.0-bath other listed at $180k.

Deal economics

• At list price, monthly cash flow is $388 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $180k).
• Recommended offer: $175k (3.0% below list) — sets the bar for market timing.
• Cap rate 8.9% 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.

Location & tenants

• 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: George Rogers Clark High School (math 28% / reading 34%, grade F, #118 of 254 statewide, top 47%, 1,645 students, 53% FRL) — zoned schools at 53% FRL track the district average.
• Market conditions: 291 active listings in the ZIP; 160 units permitted in Clark County in 2024 (61 in 5+ unit buildings).
• This rent runs 36% of the median local income ($64k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• 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.
• Clark County population projected to shrink 7% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.

Negotiation context

• It's been on market 40 days — a 3% lower offer ($175k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 8y 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 $21k; list at $180k implies a 757% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1917 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $174,503 (3.0% below list)

Questions for the listing agent

1. It's been on market 40 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1917 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
5. 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.
6. 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.
7. 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: 1.06% ✓
• Cap rate: 8.88%
• Cash-on-cash: 9.24%
• DSCR: 1.41
• GRM: 7.9

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: -2.4%
• Equity multiple: 0.91×
• Total profit: $-4,498
• Equity at exit: $26,824

10-year hold

• IRR: 7.3%
• Equity multiple: 1.55×
• Total profit: $27,688
• Equity at exit: $15,554

Cash invested: $50,372 (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 40391

• Home prices YoY: -17.0%
• Active inventory: 291
• Price-to-rent: 7.9×

Monthly cashflow live

• Estimated rent: $1,901 medium
• Mortgage (P&I): −$943
• Tax from tax record: −$95 /mo · $1,142/yr
• Insurance: −$75
• HOA: −$0
• Vacancy / Maint / Mgmt: −$399
• Net cashflow: $388

Break-even live

Break-even rent $1,410

Max offer price $179,900

Occupancy floor 75%

Sensitivity live

Price	-10% $490	-5% $439	+0% $388	+5% $337	+10% $286
Rent	-10% $238	-5% $313	+0% $388	+5% $463	+10% $538
Rate	-1.0pp $478	-0.5pp $434	base $388	+0.5pp $341	+1.0pp $294

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: $44,975
• Closing costs: $5,397
• Reserves months: —
• Total cash needed: —

Listing history 27 events

1. 2026-06-21
   days on market $179,900 Active 40 DOM
2. 2026-06-18
   days on market $179,900 Active 37 DOM
3. 2026-06-17
   days on market $179,900 Active 36 DOM
4. 2026-06-16
   days on market $179,900 Active 35 DOM
5. 2026-06-15
   days on market $179,900 Active 34 DOM
6. 2026-06-14
   days on market $179,900 Active 32 DOM
7. 2026-06-13
   days on market $179,900 Active 31 DOM
8. 2026-06-10
   days on market $179,900 Active 29 DOM
9. 2026-06-09
   days on market $179,900 Active 28 DOM
10. 2026-06-08
    days on market $179,900 Active 27 DOM
11. 2026-06-07
    days on market $179,900 Active 26 DOM
12. 2026-06-05
    days on market $179,900 Active 23 DOM
13. 2026-06-03
    days on market $179,900 Active 22 DOM
14. 2026-06-02
    days on market $179,900 Active 21 DOM
15. 2026-06-01
    days on market $179,900 Active 20 DOM
16. 2026-05-31
    days on market $179,900 Active 19 DOM
17. 2026-05-31
    days on market $179,900 Active 18 DOM
18. 2026-05-12
    listed $179,900 Active
19. 2022-07-24
    price $750
20. 2019-04-29
    historical
21. 2019-02-13
    status Active
22. 2019-02-01
    status Pending
23. 2019-01-23
    listed $85,000 Active
24. 2018-08-12
    historical
25. 2018-05-31
    price $111,500
26. 2018-02-12
    listed $115,500 Active
27. 1975-11-01
    soldstatus $21,000

ⓘ 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: $1,142 · $95/mo
• Projected year-2 tax: $1,547 · $129/mo
• Expected delta: +$405/yr (+$34/mo · 35.5%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥101°F today · 19 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 3% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $22,806
• − Mortgage interest: −$10,077
• − Property taxes: −$1,142
• − Insurance: −$900
• − Repairs & maintenance: −$1,824
• − Management: −$1,824
• − Depreciation: −$5,233
• Taxable income: $1,805
• Est. tax owed @ 24.0%: −$433
• After-tax cash flow: $4,221/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: Clark County
• NCES district ID: 2101200
• Math proficiency: 28% ▼ -25.00%
• Reading proficiency: 41% ▼ -18.00%
• Median HH income: $47,282
• Composite: 29.63/100
• National rank: #6469
• State rank: #64 of 165 in KY

Livability — Winchester

• Score: 60/100
• State rank: #393
• US rank: #18931

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: Winchester, KY
• County: Clark County · 36,796 people
• City population: 36,796
• Metro: Lexington-Fayette, KY
• Population (ZIP): 36,796
• Household income: $64,144
• Rent vs Own: 29.4% rent · 70.6% own
• Severe rent burden: 854.0

Population outlook (Clark County) Hauer SSP2

• Today (2025): 35,849 people
• By 2030: 35,616 · -0.6%
• By 2040: 34,727 · -3.1%
• By 2050: 33,195 · -7.4%
• By 2075: 29,439 · -17.9%
• By 2100: 24,744 · -31.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (88%)
• Race & ethnicity: White 88% Black 4% Hispanic / Latino 4% Two or more races 3%
• Common ancestry: Slovak 3% Italian 2% Serbian 2%
• Foreign-born: 2% · Canada
• Languages at home: 97% English-only · Spanish 2%

Political lean MEDSL · Clark

• 2024 margin: Solid R (+35.3) · D 31.6% · R 66.9% · Other 1.6%
• 2008→2024 swing: -10.3pp toward R · 2008: -25.1pp · 2024: -35.3pp
• All cycles: 2024: R+35.3 2020: R+32.0 2016: R+37.1 2012: R+30.5 2008: R+25.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -58.24%
• Current HPI: 283.7839
• Rent YoY: —
• Metro: Lexington-Fayette, KY
• 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

+756.7% since first listed

10 events — show timeline

• 2026-05-12 Listed $179,900 FSBO.com
• 2022-07-24 Price Changed $750 RENT.
• 2019-04-29 Listing Removed — ImagineMLS
• 2019-02-13 Relisted — ImagineMLS
• 2019-02-01 Pending — ImagineMLS
• 2019-01-23 Listed $85,000 ImagineMLS
• 2018-08-12 Listing Removed — ImagineMLS
• 2018-05-31 Price Changed $111,500 ImagineMLS
• 2018-02-12 Listed $115,500 ImagineMLS
• 1975-11-01 Sold (Public Records) $21,000 Public Records

Property tax history

+3.8%/yr

Latest (2025): $1,142 · +45.0% YoY. Source: county tax records.