2 N Main St · Winchester, KY 40391

$1,575,000

36 bd · 19.2 ba · 26,124 sqft · MultiFamily · 269 Days on market

9,583 sqft lot ↓ 1% since listing

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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 +27.4/30.0
• DSCR +9.6/10.0
• 1% rule +7.5/10.0
• ARV discount +7.5/15.0
• 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

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 12 units. confirmed

5+ unit building — per-unit beds/baths from public records are typically unavailable; the breakdown below (if shown) is an estimate from the listing text.

Listing remarks

Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated. Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC apartments and 2 renovated ground-floor offices totaling 20 income-producing units. Additional space at 4-10 Main Street offers a blank canvas for tenant improvements and added cash flow. Downtown Winchester is thriving — turn-key, stabilized, and priced to sell. Seize this opportu

Key facts

• Central hvac
• Fully restored
• New roofing

Tags

• FULLY RESTORED
• STRUCTURAL REPAIRS
• NEW ROOFING
• BRICK TUCK-POINTING
• SECURE KEY-FOB ENTRANCES
• CENTRAL HVAC

Property features AI

Finance

• Financial info: 20 total units

Exterior

• Home design: 4-story building; Total building area approximately 26,124
• Construction: Parcel number 054-3209-018-020
• Exterior features: Lot in a business zoning area; Located in the Downtown subdivision; Property is near downtown Main and Broadway

Interior

• Bathrooms: 19 full bathrooms; 1 half bathroom
• Interior features: Located downtown

What this means for you Summary

Snapshot

• This is a 12 × 3-bed/1.6-bath units multifamily listed at $1.57M.

Deal economics

• At list price, monthly cash flow is $5k ($55k/yr) — positive. Per door: $385/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $1.57M).
• Recommended offer: $1.39M (12.0% below list) — sets the bar for market timing.
• Cap rate 9.8% 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: Willis H. Justice Elementary School (math 27% / reading 27%, grade F, #434 of 676 statewide, top 69%, 427 students, 66% 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).
• At $19,629/mo this rent would consume 367% of the median local household income ($64k/yr) (locally 854% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $11k of loan paydown is wiped out by about $47k 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.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $441k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 269 days — a 12% lower offer ($1.39M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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.

Recommended offer $1,386,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 269 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
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 apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 1.25% ✓
• Cap rate: 9.81%
• Cash-on-cash: 12.58%
• DSCR: 1.56
• GRM: 6.7

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: 2.3%
• Equity multiple: 1.09×
• Total profit: $39,484
• Equity at exit: $234,838

10-year hold

• IRR: 11.9%
• Equity multiple: 1.94×
• Total profit: $414,680
• Equity at exit: $136,177

Cash invested: $441,000 (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 40391

• Home prices YoY: -17.0%
• Active inventory: 291
• Price-to-rent: 80.2×

Monthly cashflow live

• Estimated rent: $19,629 high
• Mortgage (P&I): −$8,259
• Tax est. 1.5%: −$1,969 /mo · $23,625/yr
• Insurance: −$656
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,122
• Net cashflow: $4,622

Break-even live

Break-even rent $13,778

Max offer price $1,575,000

Occupancy floor 71%

12-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 12× units	3	1.6	$19,632
Total (12 units)			$19,629

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: $393,750
• Closing costs: $47,250
• Reserves months: —
• Total cash needed: —

Listing history 20 events

1. 2026-06-18
   days on market $1,575,000 Active 269 DOM
2. 2026-06-17
   days on market $1,575,000 Active 268 DOM
3. 2026-06-16
   days on market $1,575,000 Active 267 DOM
4. 2026-06-15
   days on market $1,575,000 Active 266 DOM
5. 2026-06-14
   days on market $1,575,000 Active 264 DOM
6. 2026-06-13
   days on market $1,575,000 Active 263 DOM
7. 2026-06-10
   days on market $1,575,000 Active 261 DOM
8. 2026-06-09
   days on market $1,575,000 Active 260 DOM
9. 2026-06-08
   days on market $1,575,000 Active 259 DOM
10. 2026-06-07
    days on market $1,575,000 Active 258 DOM
11. 2026-06-05
    days on market $1,575,000 Active 255 DOM
12. 2026-06-03
    days on market $1,575,000 Active 254 DOM
13. 2026-06-02
    days on market $1,575,000 Active 253 DOM
14. 2026-06-01
    days on market $1,575,000 Active 252 DOM
15. 2026-05-31
    days on market $1,575,000 Active 251 DOM
16. 2026-05-31
    days on market $1,575,000 Active 250 DOM
17. 2026-04-07
    price $1,575,000
18. 2026-02-13
    status Active
19. 2025-12-31
    historical
20. 2025-08-09
    listed $1,595,000 Active

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

Taxation est. · year 1

• Rental income: $235,548
• − Mortgage interest: −$88,224
• − Property taxes: −$23,625
• − Insurance: −$7,875
• − Repairs & maintenance: −$18,844
• − Management: −$18,844
• − Depreciation: −$45,818
• Taxable income: $32,318
• Est. tax owed @ 24.0%: −$7,756
• After-tax cash flow: $47,713/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

-1.3% since first listed

4 events — show timeline

• 2026-04-07 Price Changed $1,575,000 ImagineMLS
• 2026-02-13 Relisted — ImagineMLS
• 2025-12-31 Listing Removed — ImagineMLS
• 2025-08-09 Listed $1,595,000 ImagineMLS

Property tax history

+2.8%/yr

Latest (2016): $2,461 · +2.5% YoY. Source: county tax records.