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💰 This Week's Steals: Double-Digit Yields & Massive Discounts

Oct 14, 2025
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This week’s opportunities include a 127-year-old two-flat with 66 days on market creating negotiation leverage.

Plus a massive 64% discount on a vintage brick building that listed at $1.75M in 2022.

Also a turnkey two-flat with upgraded HVAC delivering 13-15% gross yields.

And a conforming duplex with rock-bottom taxes at just $135/sqft priced 40% below assessment.

Free readers get the Victorian house hack breakdown.

Paid subscribers get all 4 foreclosure deals.

Passive Cash-Flowing Properties

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Distressed Deals of The Week

🏚️ Victorian House Hack

$359,900 ask on 1898 two-flat 4 bed/3 bath + finished basement & attic + 66 days on market = negotiation opportunity.

🔥 64% Discount Rehab

$624,900 ask on 7-bed brick two-flat Was $1.75M in 2022 + rooftop deck with pergola + exposed brick = experienced rehabbers only.

⚡ Turnkey Cash Flow

$284,900 ask on upgraded two-flat Separate HVAC + walk-out basement + 13-15% gross yield = immediate rental income.

💰 Low-Tax Value Play

$325,000 ask on conforming two-flat $6.2K annual taxes + 2,400 sqft + $135/sqft = strong cash-on-cash returns.


1165 S Humphrey Ave, Oak Park, IL 60304

$359,900 | 4 beds | Multi-family | ~2,400 sqft (est.)

🏚️ Bank-owned foreclosure in desirable Oak Park.

Classic 1898 two-unit building with 4+ bedrooms total and 3 full bathrooms.

Property needs TLC but has solid bones with covered front porch, private deck off kitchen, and vinyl siding exterior.

💡 Pro Tip:

  • Historic appreciation: Sold for $250K in 2002, now asking $359.9K

  • Oak Park rental market strong - previous rental listing at $1,600/month (2015)

  • 4,199 sqft lot provides decent outdoor space for Chicago suburbs

  • House hack opportunity: live in one unit, rent the other

💰 Financial Snapshot

  • Est. Market Value: No Zestimate available

  • Current Ask: $359,900

  • Last Sale: $250,000 (2002)

  • Layout: 4 bed/3 bath (2 units)

  • Building Size: Not disclosed (est. ~2,400 sqft based on typical 1898 construction)

  • Lot Size: 4,199 sqft

  • Year Built: 1898

  • Price per Sq Ft: Not calculable (sqft not disclosed)

  • Rent Zestimate: Not available

  • Previous Rental Rate: $1,600/month (2015 listing)

  • Gross Yield: Est. 10-12% if both units rent $1,600-2,000/month

  • Annual Taxes: $11,410

  • Tax Assessment: $349,990 (2023)

⚠️ Heads Up

  • Needs TLC throughout - condition not specified but implied

  • 127-year-old building - expect old systems/infrastructure

  • 66 days on market suggests pricing or condition concerns

  • No square footage disclosure is a red flag

  • High property taxes ($11.4K annually)

🏆 Best For:

  • House hackers wanting Oak Park lifestyle at discount

  • Buy-and-hold investors comfortable with older properties

  • Handy buyers who can DIY cosmetic updates

  • Investors seeking cash flow in strong suburban rental market

Why it works:

  • Prime Oak Park location with excellent schools and transit access.

  • Dual income potential or owner-occupy strategy.

  • At tax assessed value of $350K, asking price is essentially at assessment with room for negotiation after 66 days on market.

  • Finished basement and attic add valuable livable space beyond main floors.

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