239 Sheridan Ave · Highwood, IL 60040

$350,000

3 bd · 1.0 ba · 1,450 sqft · SingleFamily public records · 233 Days on market

Built 1923 6,600 sqft lot Est $392k · 11% under ↓ 7% 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 +14.6/30.0
• ARV discount +12.3/15.0
• Schools +5.9/10.0
• DSCR +4.5/10.0
• Livability +4.2/5.0
• 1% rule +3.7/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Charming Home Steps from Downtown Highwood! Welcome to this inviting 3-bedroom, 1-bath home located just steps from vibrant downtown Highwood. Featuring a large kitchen with an attached dining room, this home offers the perfect blend of comfort and convenience. The partially finished basement provides additional living space or room to grow, while the 2-car garage adds valuable storage and parking. Enjoy everything Highwood has to offer-restaurants, bars, festivals, and community events-all just a short walk away. With close proximity to Lake Michigan, parks, and transportation, this is an ideal location for those who want it all. Don't miss your chance to own a piece of Highwood living!

Key facts

• 6,600 sq ft lot
• 2 garage spots
• Built 1923

Property features AI

Finance

• Other: Not currently leased; Possession at closing
• HOA & community: No master association fee required

Exterior

• Parking: Detached owned garage (2 garage spaces, 2 total parking spaces)
• Utilities: Water from Lake Michigan; Public sewer
• Home design: Detached single-family home; One-story layout; Fee simple ownership; Property over 100 years old; Built before 1978
• Construction: Block and stone construction
• Exterior features: Lot dimensions approximately 50 x 132; Lot less than 0.25 acre

Interior

• Kitchen: Range; Dishwasher; Refrigerator; Kitchen on main level (16 x 16) with wood laminate flooring
• Bedrooms: Master bedroom on main level (14 x 16) with carpet; Bedroom on main level (10 x 13) with carpet; Bedroom on main level (11 x 14) with carpet
• Flooring: Carpet in living areas and bedrooms; Wood laminate in kitchen and dining room; Other flooring in finished basement family room
• Bathrooms: One full bathroom
• Heating & cooling: Natural gas heating with forced air; Central air conditioning
• Interior features: Seven total rooms; Partially finished full basement; Separate dining room
• Laundry & utility: Laundry room

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $350k.

Deal economics

• At list price, monthly cash flow is $83 ($995/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 $304k (13.1% below list).
• Recommended offer: $304k (13.1% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 83/100 on livability (#59 in IL, #1,042 nationally) — a professional / high-income tenant draw. Strengths: crime A+, commute A+, employment A+; Watch: cost of living F.
• Twp Hsd 113 (suburban): math 60% / reading 63% proficiency, ranked #19 of 620 in IL (top 3%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Oak Terrace Elem School (math 32% / reading 40%, grade F, #503 of 2,056 statewide, top 25%, 373 students, 0% FRL); Northwood Middle School (math 31% / reading 37%, grade F, #209 of 665 statewide, top 32%, 478 students, 0% FRL); Highland Park High School (math 53% / reading 57%, grade C, #27 of 693 statewide, top 4%, 1,739 students, 0% FRL).
• Zoned-school proficiency averages 42% at this address vs 62% district-wide (-20 pts) — the specific schools serving this property underperform the Twp Hsd 113 average; the district grade overstates school quality for this exact location.
• Market conditions: 10 active listings in the ZIP; 12 comparable units currently listed for rent nearby; rentals at typical pace (median 17d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 948 units permitted in Lake County in 2024 (424 in 5+ unit buildings).
• This rent runs 34% of the median local income ($108k/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 $2k of loan paydown is wiped out by about $10k of value loss. Plan a longer hold.
• Lake County population projected to shrink 8% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.

Negotiation context

• It's been on market 233 days — a 12% lower offer ($308k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1923 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $304,046 (13.1% below list)

Questions for the listing agent

1. It's been on market 233 days. Have you received any prior offers? Is the seller open to a 13% concession, seller financing, or rate buy-down credit?
2. Built in 1923 — 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: 0.87% ✗
• Cap rate: 6.58%
• Cash-on-cash: 1.02%
• DSCR: 1.05
• GRM: 9.6

CMA / ARV

• ARV (on-the-fly): $391,500
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
228 Llewellyn Ave	0.10mi	3/2.5	1,480 (+2%)	6mo	$375,000	$253	81
540 Green Bay Rd	0.09mi	3/1.5	1,350 (-7%)	10mo	$287,500	$213	74
328 Oak Terrace Ave	0.20mi	2/2.0 (-1)	1,397 (-4%)	12mo	$355,000	$254	65
2954 Greenwood Ave	0.31mi	4/2.0 (+1)	1,550 (+7%)	9mo	$419,000	$270	57
218 Llewellyn Ave	0.11mi	4/1.0 (+1)	1,297 (-11%)	18mo	$200,000	$154	57
2904 Summit Ave	0.54mi	3/2.0	1,496 (+3%)	13mo	$550,000	$368	55
732 Hill St	0.58mi	3/2.0	1,519 (+5%)	8mo	$405,000	$267	54
1029 Half Day Rd	0.59mi	3/2.0	1,400 (-3%)	18mo	$420,000	$300	48
3399 Krenn Ave	0.70mi	3/2.0	1,334 (-8%)	4mo	$742,000	$556	47
2903 Summit Ave	0.51mi	3/2.5	1,539 (+6%)	18mo	$480,000	$312	45
238 Jeffreys Pl	0.35mi	4/3.0 (+1)	1,638 (+13%)	12mo	$350,000	$214	39
3319 Western Ave	0.51mi	3/2.0	1,650 (+14%)	17mo	$499,900	$303	35

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

Projected returns pro-forma

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

5-year hold

• IRR: -14.7%
• Equity multiple: 0.47×
• Total profit: $-51,450
• Equity at exit: $52,186

10-year hold

• IRR: -6.0%
• Equity multiple: 0.61×
• Total profit: $-38,066
• Equity at exit: $30,262

Cash invested: $98,000 (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 60040

• Home prices YoY: -12.3%
• Active inventory: 10
• Price-to-rent: 9.6×

Monthly cashflow live

• Estimated rent: $3,040 high
• Mortgage (P&I): −$1,835
• Tax from tax record: −$338 /mo · $4,054/yr
• Insurance: −$146
• HOA: −$0
• Vacancy / Maint / Mgmt: −$638
• Net cashflow: $83

Break-even live

Break-even rent $2,936

Max offer price $350,000

Occupancy floor 92%

Sensitivity live

Price	-10% $281	-5% $182	+0% $83	+5% $-16	+10% $-115
Rent	-10% $-157	-5% $-37	+0% $83	+5% $203	+10% $323
Rate	-1.0pp $259	-0.5pp $172	base $83	+0.5pp $-8	+1.0pp $-100

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: $87,500
• Closing costs: $10,500
• Reserves months: —
• Total cash needed: —

Rent comps 12 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
546 Green Bay Rd Highwood, IL	1.0–2.0	1.0–2.0	965	$3,399	$3.52	0d	7	0.08mi
440 Green Bay Rd Highwood, IL	1.0–2.0	1.0–2.0	907	$3,361	$3.70	0d	9	0.16mi
624 Sheridan Rd Highwood, IL	1.0–3.0	1.0–2.0	871	$2,879	$3.30	0d	21	0.17mi
624 Sheridan Rd Evanston, IL	3.0	2.0	1172	$2,879	$2.46	5d	1	0.21mi
20 Webster Ave Unit C Highwood, IL	3.0	2.5	1791	$4,249	$2.37	17d	1	0.30mi
350 Prairie Ave Unit B Highwood, IL	3.0	1.0	1200	$2,100	$1.75	23d	1	0.44mi
318 Walker Ave Unit 10 Highland Park, IL	2.0	1.0	1308	$2,400	$1.83	9d	1	0.50mi
560 Vine Ave #203 Highland Park, IL	2.0	2.0	950	$2,500	$2.63	20d	1	1.11mi
1250 Park Ave W Unit 421 Highland Park, IL	2.0	2.0	1027	$2,300	$2.24	26d	1	1.27mi
2066 Saint Johns Ave #303 Highland Park, IL	2.0	2.0	1532	$2,300	$1.50	14d	1	1.33mi
1978 Green Bay Rd Highland Park, IL	2.0	1.5	1200	$2,300	$1.92	26d	1	1.34mi
434 Elm Pl Unit 1 Highland Park, IL	3.0	2.5	1600	$3,400	$2.12	26d	1	1.49mi

Listing history 17 events

1. 2026-06-21
   days on market $350,000 Active 233 DOM
2. 2026-06-18
   days on market $350,000 Active 230 DOM
3. 2026-06-17
   days on market $350,000 Active 229 DOM
4. 2026-06-16
   days on market $350,000 Active 228 DOM
5. 2026-06-15
   days on market $350,000 Active 227 DOM
6. 2026-06-13
   days on market $350,000 Active 225 DOM
7. 2026-06-13
   days on market $350,000 Active 224 DOM
8. 2026-06-09
   days on market $350,000 Active 221 DOM
9. 2026-06-08
   days on market $350,000 Active 220 DOM
10. 2026-06-07
    days on market $350,000 Active 219 DOM
11. 2026-06-04
    days on market $350,000 Active 216 DOM
12. 2026-06-03
    days on market $350,000 Active 215 DOM
13. 2026-06-02
    days on market $350,000 Active 214 DOM
14. 2026-06-01
    days on market $350,000 Active 213 DOM
15. 2026-05-31
    days on market $350,000 Active 212 DOM
16. 2026-05-24
    price $350,000
17. 2025-10-31
    listed $375,000 Active

ⓘ 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: $4,054 · $338/mo
• Projected year-2 tax: $5,999 · $500/mo
• Expected delta: +$1,946/yr (+$162/mo · 48.0%)

ⓘ 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 1/10 Low
• 🌡 Heat 2/10 Low 7 d/yr ≥98°F today · 14 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 0% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 4 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $36,486
• − Mortgage interest: −$19,605
• − Property taxes: −$4,054
• − Insurance: −$1,750
• − Repairs & maintenance: −$2,919
• − Management: −$2,919
• − Depreciation: −$10,182
• Taxable loss: −$4,943
• Est. tax savings @ 24.0%: +$1,186
• After-tax cash flow: $2,181/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: Twp Hsd 113
• NCES district ID: 1719080
• Math proficiency: 60% ▼ -6.00%
• Reading proficiency: 63% ▼ -5.00%
• Median HH income: $122,404
• Composite: 59.23/100
• National rank: #937
• State rank: #19 of 620 in IL

Livability — Highwood

• Score: 83/100
• State rank: #59
• US rank: #1042

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Highwood, IL
• County: Lake County · 591,991 people
• City population: 5,301
• Metro: Chicago-Naperville-Elgin, IL-IN-WI
• Population (ZIP): 5,301
• Household income: $107,875
• Rent vs Own: 44.0% rent · 56.0% own
• Severe rent burden: 254.0

Population outlook (Lake County) Hauer SSP2

• Today (2025): 700,217 people
• By 2030: 693,290 · -1.0%
• By 2040: 673,588 · -3.8%
• By 2050: 643,556 · -8.1%
• By 2075: 562,792 · -19.6%
• By 2100: 457,715 · -34.6%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.55)
• Race & ethnicity: White 53% Hispanic / Latino 41% Two or more races 8% Black 3% Asian 2%
• Hispanic origin (detail): Mexican 39%
• Common ancestry: Romanian 8% Scotch-Irish 3% Scandinavian 2%
• Foreign-born: 23% · Canada, China, South Korea
• Languages at home: 53% English-only · Spanish 39% Russian/Polish/Slavic 3% Other Indo-European 3%

Political lean MEDSL · Lake

• 2024 margin: Strong D (+20.8) · D 59.7% · R 38.9% · Other 1.4%
• 2008→2024 swing: +1.1pp toward D · 2008: 19.6pp · 2024: 20.8pp
• All cycles: 2024: D+20.8 2020: D+24.1 2016: D+20.3 2012: D+8.1 2008: D+19.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -28.02%
• Current HPI: 198.968
• Rent YoY: —
• Metro: Chicago-Naperville-Elgin, IL-IN-WI
• 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

-6.7% since first listed

2 events — show timeline

• 2026-05-24 Price Changed $350,000 MRED as Distributed by MLS Grid
• 2025-10-31 Listed $375,000 MRED as Distributed by MLS Grid

Property tax history

-1.5%/yr

Latest (2024): $4,054 · -4.0% YoY. Source: county tax records.