148 W Lexington Ave · Winchester, KY 40391

$199,900

5 bd · 2.0 ba · 2,444 sqft · Other · 58 Days on market

Built 1940 392 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 +21.0/30.0
• ARV discount +7.5/15.0
• DSCR +6.7/10.0
• 1% rule +4.4/10.0
• 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

Located in the heart of Winchester, this spacious and versatile two-story home offers incredible potential for both homeowners and savvy investors alike. With a total of 5 BR- this property provides ample space to accommodate a variety of living arrangements, from a large single-family home to a high -demand rental opportunity. The home features a welcoming covered front porch, perfect for relaxing, along with classic architectural charm that's ready to be enhanced with your personal touch. Inside the generous layout allows for flexible use of space, whether you're looking to create comfortable shared living areas or maximize rental income potential. This home is minutes from downtown shopp

Key facts

• Covered front porch
• Community pool
• Built 1940

Tags

• COVERED FRONT PORCH
• FLEXIBLE USE OF SPACE
• HIGHLY DESIRABLE LOCATION

Property features AI

Finance

• Other: Building total area approximately 2,444; Lot recorded in public records

Exterior

• Utilities: Public sewer; Cable available; Electricity available; Natural gas available; Sewer available; Water available
• Home design: Two levels
• Construction: Stone foundation; Aluminum and vinyl siding; Composition roof; Built with established construction materials
• Exterior features: Stone foundation; Composition roof; Aluminum siding; Vinyl siding; Public water; Not on waterfront; No significant view

Interior

• Kitchen: Refrigerator; Range
• Flooring: Hardwood
• Bathrooms: 2 full bathrooms
• Heating & cooling: Forced air heating; Gas cooling
• Interior features: Entrance foyer; Ceiling fan(s); Insulated windows
• Laundry & utility: Washer hookup; Electric dryer hookup

What this means for you Summary

Snapshot

• This is a 5-bed/2.0-bath other listed at $200k.

Deal economics

• At list price, monthly cash flow is $282 ($3k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $188k (6.1% below list).
• Recommended offer: $188k (6.1% below list) — sets the bar for 1% rule.
• Cap rate 8.0% 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).
• 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 $6k 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 58 days — a 3% lower offer ($194k) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 26y ago; this cycle's ask has dropped $40k (17%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $38k; list at $200k implies a 433% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $187,672 (6.1% below list)

Questions for the listing agent

1. It's been on market 58 days. Have you received any prior offers? Is the seller open to a 6% 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. 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: 0.94% ✗
• Cap rate: 7.99%
• Cash-on-cash: 6.05%
• DSCR: 1.27
• GRM: 8.9

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: -7.0%
• Equity multiple: 0.74×
• Total profit: $-14,505
• Equity at exit: $29,806

10-year hold

• IRR: 2.5%
• Equity multiple: 1.18×
• Total profit: $10,172
• Equity at exit: $17,284

Cash invested: $55,972 (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: 8.9×

Monthly cashflow live

• Estimated rent: $1,877 medium
• Mortgage (P&I): −$1,048
• Tax from tax record: −$69 /mo · $826/yr
• Insurance: −$83
• HOA: −$0
• Vacancy / Maint / Mgmt: −$394
• Net cashflow: $282

Break-even live

Break-even rent $1,520

Max offer price $199,900

Occupancy floor 80%

Sensitivity live

Price	-10% $395	-5% $339	+0% $282	+5% $226	+10% $169
Rent	-10% $134	-5% $208	+0% $282	+5% $356	+10% $430
Rate	-1.0pp $383	-0.5pp $333	base $282	+0.5pp $230	+1.0pp $178

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: $49,975
• Closing costs: $5,997
• Reserves months: —
• Total cash needed: —

Listing history 34 events

1. 2026-06-21
   days on market $199,900 Active 58 DOM
2. 2026-06-18
   days on market $199,900 Active 55 DOM
3. 2026-06-17
   days on market $199,900 Active 54 DOM
4. 2026-06-16
   days on market $199,900 Active 53 DOM
5. 2026-06-15
   days on market $199,900 Active 52 DOM
6. 2026-06-14
   days on market $199,900 Active 50 DOM
7. 2026-06-13
   days on market $199,900 Active 49 DOM
8. 2026-06-10
   days on market $199,900 Active 47 DOM
9. 2026-06-09
   days on market $199,900 Active 46 DOM
10. 2026-06-08
    days on market $199,900 Active 45 DOM
11. 2026-06-07
    days on market $199,900 Active 44 DOM
12. 2026-06-05
    days on market $199,900 Active 41 DOM
13. 2026-06-03
    days on market $199,900 Active 40 DOM
14. 2026-06-02
    days on market $199,900 Active 39 DOM
15. 2026-06-01
    days on market $199,900 Active 38 DOM
16. 2026-05-31
    days on market $199,900 Active 37 DOM
17. 2026-05-31
    days on market $199,900 Active 36 DOM
18. 2026-05-14
    price $199,900
19. 2026-05-06
    price $219,900
20. 2026-05-01
    price $229,900
21. 2026-04-24
    listed $239,900 Active
22. 2020-07-17
    historical
23. 2020-04-23
    listed $350,000 Active
24. 2014-11-14
    historical
25. 2013-11-14
    listed $69,900
26. 2009-08-22
    historical
27. 2009-02-24
    listed $59,000
28. 2007-12-31
    historical
29. 2006-10-24
    historical
30. 2006-09-01
    listed $59,900
31. 2006-09-01
    listed $59,900
32. 2002-12-31
    historical
33. 2000-03-22
    listed $63,900
34. 1995-01-01
    soldstatus $37,500

ⓘ 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: $826 · $69/mo
• Projected year-2 tax: $1,719 · $143/mo
• Expected delta: +$893/yr (+$74/mo · 108.0%)

ⓘ 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: $22,521
• − Mortgage interest: −$11,198
• − Property taxes: −$826
• − Insurance: −$1,000
• − Repairs & maintenance: −$1,802
• − Management: −$1,802
• − Depreciation: −$5,815
• Taxable income: $79
• Est. tax owed @ 24.0%: −$19
• After-tax cash flow: $3,367/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

+433.1% since first listed

17 events — show timeline

• 2026-05-14 Price Changed $199,900 ImagineMLS
• 2026-05-06 Price Changed $219,900 ImagineMLS
• 2026-05-01 Price Changed $229,900 ImagineMLS
• 2026-04-24 Listed $239,900 ImagineMLS
• 2020-07-17 Listing Removed — ImagineMLS
• 2020-04-23 Listed $350,000 ImagineMLS
• 2014-11-14 Listing Removed — ImagineMLS
• 2013-11-14 Listed $69,900 ImagineMLS
• 2009-08-22 Listing Removed — ImagineMLS
• 2009-02-24 Listed $59,000 ImagineMLS
• 2007-12-31 Listing Removed — ImagineMLS
• 2006-10-24 Listing Removed — ImagineMLS
• 2006-09-01 Listed $59,900 ImagineMLS
• 2006-09-01 Listed $59,900 ImagineMLS
• 2002-12-31 Listing Removed — ImagineMLS
• 2000-03-22 Listed $63,900 ImagineMLS
• 1995-01-01 Sold (Public Records) $37,500 Public Records

Property tax history

+3.6%/yr

Latest (2025): $826 · +29.8% YoY. Source: county tax records.