310 W Hickman St · Winchester, KY 40391

$109,900

4 bd · 2.5 ba · 1,391 sqft · Other · 18 Days on market

Built 1940 4,356 sqft lot

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• 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

Listing remarks

Opportunity knocks for the buyer with vision! This spacious 4-bedroom, 2.5-bath home is mid renovation and is well on its way to becoming something truly special. With a first-floor primary suite, walk-in closets, partial basement with sump pump already installed, many major systems already in place, and a storage shed in the backyard, many of the big-ticket features are done for you. The home is currently unfinished, with flooring, wall finishes, the kitchen, and the bathrooms still needing completion, gives you the rare chance to customize the final touches to your own style and preferences. The heavy lifting has already begun - now it's your opportunity to bring the project across the fi

Key facts

• Partial basement
• Walk-in closets
• Storage shed

Tags

• FIRST-FLOOR PRIMARY SUITE
• WALK-IN CLOSETS
• PARTIAL BASEMENT
• STORAGE SHED

Property features AI

Exterior

• Parking: Off-street parking
• Utilities: Public sewer; Public water
• Home design: House; Two levels
• Construction: Vinyl siding; Metal roof; Concrete perimeter foundation; Built area approximately 1,391 total
• Exterior features: Partial fencing; Shed(s) on the property; Public water

Interior

• Kitchen: No appliances listed
• Bedrooms: Primary bedroom on the first floor
• Bathrooms: 2 full bathrooms; 1 half bathroom
• Heating & cooling: Heat pump; Central air; Multi-unit cooling
• Interior features: Primary bedroom on the first floor; Walk-in closet(s); 9 total rooms; Unfinished basement with interior entry and sump pump; No fireplace
• Laundry & utility: Washer/dryer not specified

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath other listed at $110k.

Deal economics

• At list price, monthly cash flow is $572 ($7k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $110k).
• Recommended offer: $108k (1.5% below list) — sets the bar for market timing.
• Cap rate 12.5% 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); George Rogers Clark High School (math 28% / reading 34%, grade F, #118 of 254 statewide, top 47%, 1,645 students, 53% FRL).
• Market conditions: 291 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals at typical pace (median 16d on market — plan ~3-4 weeks tenant-placement turnaround); 160 units permitted in Clark County in 2024 (61 in 5+ unit buildings).
• This rent runs 32% 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 $760 of loan paydown is wiped out by about $3k 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 $31k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 18 days — a 2% lower offer ($108k) is reasonable based on typical stale-listing flexibility.
• 6 sale attempts since 20y 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.

Risks & watch-outs

• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate flood risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $108,251 (1.5% below list)

Questions for the listing agent

1. Built in 1940 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. 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?
4. 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.
5. 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.
6. 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: 1.54% ✓
• Cap rate: 12.53%
• Cash-on-cash: 22.29%
• DSCR: 1.99
• GRM: 5.4

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: 15.1%
• Equity multiple: 1.61×
• Total profit: $18,623
• Equity at exit: $16,386

10-year hold

• IRR: 23.8%
• Equity multiple: 3.05×
• Total profit: $63,207
• Equity at exit: $9,502

Cash invested: $30,772 (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: 5.4×

Monthly cashflow live

• Estimated rent: $1,691 high
• Mortgage (P&I): −$576
• Tax from tax record: −$142 /mo · $1,703/yr
• Insurance: −$46
• HOA: −$0
• Vacancy / Maint / Mgmt: −$355
• Net cashflow: $572

Break-even live

Break-even rent $967

Max offer price $109,900

Occupancy floor 61%

Sensitivity live

Price	-10% $634	-5% $603	+0% $572	+5% $540	+10% $509
Rent	-10% $438	-5% $505	+0% $572	+5% $638	+10% $705
Rate	-1.0pp $627	-0.5pp $600	base $572	+0.5pp $543	+1.0pp $514

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: $27,475
• Closing costs: $3,297
• Reserves months: —
• Total cash needed: —

Rent comps 5 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
161 Milwood Dr Unit Na Winchester, KY	3.0	2.0	1750	$1,650	$0.94	15d	1	0.26mi
308 Graves St Winchester, KY	3.0	1.5	1670	$1,549	$0.93	25d	1	0.36mi
502 Evans St Unit 3 Winchester, KY	3.0	1.0	1200	$1,400	$1.17	25d	1	0.58mi
135 Winn Ave Unit A Winchester, KY	3.0	2.0	1600	$1,800	$1.12	15d	1	0.89mi
1419 Westwood Dr Winchester, KY	3.0	2.5	1255	$1,450	$1.16	15d	1	1.43mi

Listing history 13 events

1. 2026-06-21
   days on market $109,900 Active 18 DOM
2. 2026-06-18
   days on market $109,900 Active 15 DOM
3. 2026-06-17
   days on market $109,900 Active 14 DOM
4. 2026-06-16
   days on market $109,900 Active 13 DOM
5. 2026-06-15
   days on market $109,900 Active 12 DOM
6. 2026-06-14
   days on market $109,900 Active 10 DOM
7. 2026-06-13
   days on market $109,900 Active 9 DOM
8. 2026-06-10
   days on market $109,900 Active 7 DOM
9. 2026-06-09
   days on market $109,900 Active 6 DOM
10. 2026-06-08
    days on market $109,900 Active 5 DOM
11. 2026-06-07
    days on market $109,900 Active 4 DOM
12. 2026-06-05
    remarks 699-char remark
13. 2026-06-05
    listed $109,900 Active 1 DOM

ⓘ 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: $1,703 · $142/mo
• Projected year-2 tax: $1,703 · $142/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 5/10 Major FEMA zone X (unshaded) · 67% 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: $20,288
• − Mortgage interest: −$6,156
• − Property taxes: −$1,703
• − Insurance: −$550
• − Repairs & maintenance: −$1,623
• − Management: −$1,623
• − Depreciation: −$3,197
• Taxable income: $5,436
• Est. tax owed @ 24.0%: −$1,305
• After-tax cash flow: $5,554/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

+70.5% since first listed

20 events — show timeline

• 2026-06-03 Listed $109,900 ImagineMLS
• 2024-05-31 Listing Removed — ImagineMLS
• 2023-11-24 Listed $200,000 ImagineMLS
• 2023-03-01 Listing Removed — ImagineMLS
• 2022-12-12 Price Changed $209,000 ImagineMLS
• 2022-09-29 Listed $225,000 ImagineMLS
• 2020-03-02 Sold (MLS) $176,000 ImagineMLS
• 2020-01-27 Pending — ImagineMLS
• 2020-01-14 Price Changed $169,900 ImagineMLS
• 2019-11-19 Price Changed $174,900 ImagineMLS
• 2019-10-19 Price Changed $179,900 ImagineMLS
• 2019-09-25 Listed $189,900 ImagineMLS
• 2019-05-24 Sold (Public Records) $35,000 Public Records
• 2019-05-24 Sold (MLS) $35,000 ImagineMLS
• 2019-05-06 Pending — ImagineMLS
• 2019-04-28 Listed $38,900 ImagineMLS
• 2006-04-13 Sold (Public Records) $56,000 Public Records
• 2006-04-13 Sold (MLS) $56,000 ImagineMLS
• 2006-03-13 Listing Removed — ImagineMLS
• 2006-01-02 Listed $64,450 ImagineMLS

Property tax history

+9.7%/yr

Latest (2025): $1,703 · +33.5% YoY. Source: county tax records.