27 N High St · Winchester, IL 62694

$64,900

2 bd · 1.0 ba · 1,152 sqft · SingleFamily public records · 72 Days on market

Built 1965 3,450 sqft lot $56/sqft · 18% below area Est $79k · 18% under

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Why this score? — see what drove the A- 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
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Appreciation +6.5/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Schools +2.4/10.0

Listing remarks MLS

Perfect for the first time homeowner or someone wanting to downsize, this 2 bedroom home has an updated bath, large laundry room, large living room, easy to take care of small lot. You will love the screened porch off the back to drink your morning coffee or evening glass of wine. Storage bld. for the mower and extra storage. Selling As Is.

Key facts

• Updated bath
• Large living room
• Large laundry room

Tags

• UPDATED BATH
• LARGE LAUNDRY ROOM
• LARGE LIVING ROOM
• SCREENED PORCH
• STORAGE BLD

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $65k.

Deal economics

• At list price, monthly cash flow is $359 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($993 rent vs $65k).
• Recommended offer: $61k (6.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 68/100 on livability (#474 in IL) — a middle-class / working-renter tenant base. Strengths: crime A+, cost of living A+, housing A+; Watch: schools D+, amenities F, commute F.
• Winchester CUSD 1 (rural): math 26% / reading 29% proficiency, ranked #281 of 620 in IL (top 45%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Market conditions: 8 active listings in the ZIP.

Forward outlook

• In year one you build about $2k of equity ($449 loan paydown + $2k appreciation (3.1% local appreciation)).
• Scott County population projected at -27% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (3.1% appreciation + 3.0% rent growth), your $18k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• It's been on market 72 days — a 6% lower offer ($61k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 6y 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 $42k; list at $65k implies a 55% gain — meaningful room to come down on a strong offer.

Recommended offer $61,006 (6.0% below list)

Questions for the listing agent

1. It's been on market 72 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 1965 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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.
7. 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.
8. 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: 1.53% ✓
• Cap rate: 12.93%
• Cash-on-cash: 23.70%
• DSCR: 2.05
• GRM: 5.4

CMA / ARV

• ARV (median comp): $79,391
• List price: $64,900
• Delta: -18.25%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
163 S Mechanic St	0.49mi	2/1.0	1,128 (-2%)	8mo	$75,000	$66	67
131 Railroad St	0.43mi	3/2.0 (+1)	1,074 (-7%)	21mo	$139,900	$130	42

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

3.07% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 30.0%
• Equity multiple: 2.70×
• Total profit: $30,912
• Equity at exit: $29,427

10-year hold

• IRR: 30.3%
• Equity multiple: 5.28×
• Total profit: $77,730
• Equity at exit: $45,543

Cash invested: $18,172 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 43 Moderately Tenant-Leaning
• State Illinois: 43 Moderately Tenant-Leaning · D+7
• County: — inherits STATE
• City: — inherits STATE

Chicago RTLO is among the strongest tenant ordinances in the Midwest; downstate is more landlord-friendly.

Methodology + full state rankings →

ZIP-level market 62694

• Home prices YoY: 4.5%
• Active inventory: 8
• Price-to-rent: 5.4×

Monthly cashflow live

• Estimated rent: $993 medium
• Mortgage (P&I): −$340
• Tax from tax record: −$58 /mo · $699/yr
• Insurance: −$27
• HOA: −$0
• Vacancy / Maint / Mgmt: −$209
• Net cashflow: $359

Break-even live

Break-even rent $539

Max offer price $64,900

Occupancy floor 59%

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: $16,225
• Closing costs: $1,947
• Reserves months: —
• Total cash needed: —

Listing history 14 events

1. 2026-06-07
   statusdays on market $64,900 Pending 72 DOM
2. 2026-06-04
   days on market $64,900 Active 71 DOM
3. 2026-06-02
   days on market $64,900 Active 70 DOM
4. 2026-06-01
   days on market $64,900 Active 69 DOM
5. 2026-05-31
   days on market $64,900 Active 68 DOM
6. 2026-05-31
   days on market $64,900 Active 67 DOM
7. 2026-03-24
   listed $64,900 Active 343-char remark

   Show marketing remark (343 chars)

   Perfect for the first time homeowner or someone wanting to downsize, this 2 bedroom home has an updated bath, large laundry room, large living room, easy to take care of small lot. You will love the screened porch off the back to drink your morning coffee or evening glass of wine. Storage bld. for the mower and extra storage. Selling As Is.

8. 2020-10-20
   soldstatus $42,000 113-char remark

   Show marketing remark (113 chars)

   This is a partial mobile home with an addition built on and it has a 8 x 12 screened porch and sm. stg. building.

9. 2020-10-20
   soldstatus $42,000 113-char remark

   Show marketing remark (113 chars)

   This is a partial mobile home with an addition built on and it has a 8 x 12 screened porch and sm. stg. building.

10. 2020-10-20
    soldstatus $42,000

    Show marketing remark (113 chars)

    This is a partial mobile home with an addition built on and it has a 8 x 12 screened porch and sm. stg. building.

11. 2020-06-02
    listed $44,900 113-char remark

    Show marketing remark (113 chars)

    This is a partial mobile home with an addition built on and it has a 8 x 12 screened porch and sm. stg. building.

12. 2020-06-02
    listed $44,900 113-char remark

    Show marketing remark (113 chars)

    This is a partial mobile home with an addition built on and it has a 8 x 12 screened porch and sm. stg. building.

13. 2019-05-31
    soldstatus $40,000
14. 1992-03-13
    soldstatus $18,500

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

Tax reassessment forecast IL · Partial reset (capped growth)

• Current annual tax: $699 · $58/mo
• Projected year-2 tax: $1,086 · $91/mo
• Expected delta: +$387/yr (+$32/mo · 55.4%)

ⓘ 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 1/10 Low
• 🌡 Heat 4/10 Moderate 7 d/yr ≥106°F today · 19 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 2% chance of damaging wind over 30 yrs
• 🫁 Air quality 1/10 Low 0 unhealthy d/yr today · 0 by 30 yrs out

Taxation est. · year 1

• Rental income: $11,918
• − Mortgage interest: −$3,635
• − Property taxes: −$699
• − Insurance: −$324
• − Repairs & maintenance: −$953
• − Management: −$953
• − Depreciation: −$1,888
• Taxable income: $3,464
• Est. tax owed @ 24.0%: −$831
• After-tax cash flow: $3,476/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: Winchester CUSD 1
• NCES district ID: 1742660
• Math proficiency: 26% ▼ -3.00%
• Reading proficiency: 29% ▼ -5.00%
• Median HH income: $47,710
• Composite: 23.9/100
• National rank: #7792
• State rank: #281 of 620 in IL

Livability — Winchester

• Score: 68/100
• State rank: #474
• US rank: #9790

Category grades

Amenities F Commute F Cost of living A+ Crime A+ Employment C Housing A+ Health & safety F User ratings B+

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Winchester, IL
• Population (ZIP): 2,944

Population outlook (Scott County) Hauer SSP2

• Today (2025): 4,701 people
• By 2030: 4,451 · -5.3%
• By 2040: 3,970 · -15.5%
• By 2050: 3,445 · -26.7%
• By 2075: 2,371 · -49.6%
• By 2100: 1,506 · -68.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (97%)
• Race & ethnicity: White 97% Two or more races 2%
• Common ancestry: Italian 4% Romanian 2% Portuguese 1%
• Foreign-born: 1%
• Languages at home: 99% English-only · Other Indo-European 1% Spanish 1%

Political lean MEDSL · Scott

• 2024 margin: Solid R (+61.2) · D 18.9% · R 80.0% · Other 1.1%
• 2008→2024 swing: -47.1pp toward R · 2008: -14.0pp · 2024: -61.2pp
• All cycles: 2024: R+61.2 2020: R+56.3 2016: R+55.6 2012: R+26.5 2008: R+14.0

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 3.07%
• Current HPI: 71.3116
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 1.59%
• F500 in state: 60

Industry mix (Fortune 500 HQ in IL)

Industry	F500 HQs	Revenue
▸Insurance	4	$201B
▸Consumer Goods	4	$87B
▸Industrial Machinery	3	$64B
▸Healthcare	2	$55B
▸Retail / Pharmacy	1	$148B
▸Agriculture / Food	1	$86B

Price history

+250.8% since first listed

8 events — show timeline

• 2026-03-24 Listed $64,900 RMLSA as Distributed by MLS Grid
• 2020-10-20 Sold (Public Records) $42,000 Public Records
• 2020-10-20 Sold (MLS) $42,000 MRED as Distributed by MLS Grid
• 2020-10-20 Sold (MLS) $42,000 RMLSA as Distributed by MLS Grid
• 2020-06-02 Listed $44,900 MRED as Distributed by MLS Grid
• 2020-06-02 Listed $44,900 RMLSA as Distributed by MLS Grid
• 2019-05-31 Sold (Public Records) $40,000 Public Records
• 1992-03-13 Sold (Public Records) $18,500 Public Records

Property tax history

+5.7%/yr

Latest (2024): $699 · +29.0% YoY. Source: county tax records.