229 S Highland St · Winchester, KY 40391

$180,000

4 bd · 3.0 ba · 3,462 sqft · Other · 60 Days on market

Built 1930 4,791 sqft lot

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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 +22.2/30.0
• ARV discount +7.5/15.0
• DSCR +7.1/10.0
• 1% rule +5.4/10.0
• 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

Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to

Key facts

• Detailed woodwork
• Striking staircase
• Corner lot

Tags

• CORNER LOT
• ORIGINAL HARDWOOD FLOORS
• DETAILED WOODWORK
• WELCOMING FRONT PORCH
• STRIKING STAIRCASE
• STAINED GLASS ACCENTS

Property features AI

Exterior

• Parking: Basement parking; Garage that faces the side; Has garage
• Utilities: Public sewer; Electricity connected; Natural gas connected; Water connected
• Home design: House; Two levels
• Construction: HardiPlank and wood siding construction; Stone foundation; Metal roof
• Exterior features: Stone foundation; Metal roof; HardiPlank and wood siding; Public water; Not on waterfront

Interior

• Kitchen: Refrigerator
• Flooring: Hardwood
• Bathrooms: 3 full bathrooms
• Heating & cooling: Forced air heating (natural gas); Electric cooling
• Interior features: Refrigerator included; Hardwood floors; Fireplace; 13 total rooms; Basement with crawl space, interior entry, and walk-out access

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath other listed at $180k.

Deal economics

• 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).
• Recommended offer: $175k (3.0% below list) — sets the bar for market timing.
• 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.

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: 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).
• Market conditions: 291 active listings in the ZIP; 160 units permitted in Clark County in 2024 (61 in 5+ unit buildings).
• This rent runs 35% 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 60 days — a 3% lower offer ($175k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $120k; list at $180k implies a 50% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1930 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $174,600 (3.0% below list)

Questions for the listing agent

1. 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?
2. Built in 1930 — 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: 1.04% ✓
• Cap rate: 8.24%
• Cash-on-cash: 6.96%
• DSCR: 1.31
• GRM: 8.0

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: -5.6%
• Equity multiple: 0.79×
• Total profit: $-10,556
• Equity at exit: $26,839

10-year hold

• IRR: 4.0%
• Equity multiple: 1.29×
• Total profit: $14,749
• Equity at exit: $15,563

Cash invested: $50,400 (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: 8.0×

Monthly cashflow live

• Estimated rent: $1,869 medium
• Mortgage (P&I): −$944
• Tax from tax record: −$165 /mo · $1,979/yr
• Insurance: −$75
• HOA: −$0
• Vacancy / Maint / Mgmt: −$392
• Net cashflow: $292

Break-even live

Break-even rent $1,499

Max offer price $180,000

Occupancy floor 79%

Sensitivity live

Price	-10% $394	-5% $343	+0% $292	+5% $241	+10% $190
Rent	-10% $145	-5% $219	+0% $292	+5% $366	+10% $440
Rate	-1.0pp $383	-0.5pp $338	base $292	+0.5pp $246	+1.0pp $198

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: $45,000
• Closing costs: $5,400
• Reserves months: —
• Total cash needed: —

Listing history 20 events

1. 2026-06-21
   days on market $180,000 Active 60 DOM
2. 2026-06-18
   days on market $180,000 Active 57 DOM
3. 2026-06-17
   days on market $180,000 Active 56 DOM
4. 2026-06-16
   days on market $180,000 Active 55 DOM
5. 2026-06-15
   days on market $180,000 Active 54 DOM
6. 2026-06-14
   days on market $180,000 Active 52 DOM
7. 2026-06-13
   days on market $180,000 Active 51 DOM
8. 2026-06-10
   days on market $180,000 Active 49 DOM
9. 2026-06-09
   days on market $180,000 Active 48 DOM
10. 2026-06-08
    days on market $180,000 Active 47 DOM
11. 2026-06-07
    days on market $180,000 Active 46 DOM
12. 2026-06-05
    days on market $180,000 Active 43 DOM
13. 2026-06-03
    days on market $180,000 Active 42 DOM
14. 2026-06-02
    days on market $180,000 Active 41 DOM
15. 2026-06-01
    days on market $180,000 Active 40 DOM
16. 2026-05-31
    days on market $180,000 Active 39 DOM
17. 2026-05-31
    days on market $180,000 Active 38 DOM
18. 2026-04-22
    listed $180,000 Active
19. 2020-11-05
    soldstatus $120,000
20. 1996-02-01
    soldstatus $40,000

ⓘ 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: $1,979 · $165/mo
• Projected year-2 tax: $1,979 · $165/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 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥101°F today · 20 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: $22,423
• − Mortgage interest: −$10,083
• − Property taxes: −$1,979
• − Insurance: −$900
• − Repairs & maintenance: −$1,794
• − Management: −$1,794
• − Depreciation: −$5,236
• Taxable income: $638
• Est. tax owed @ 24.0%: −$153
• After-tax cash flow: $3,355/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

+350.0% since first listed

3 events — show timeline

• 2026-04-22 Listed $180,000 ImagineMLS
• 2020-11-05 Sold (Public Records) $120,000 Public Records
• 1996-02-01 Sold (Public Records) $40,000 Public Records

Property tax history

+9.4%/yr

Latest (2025): $1,979 · -2.3% YoY. Source: county tax records.