7414 Chappel Ave
BACK ON THE MARKET THROUGH NO FAULT OF THE PROPERTY! PRIOR FHA APPRAISAL: $575,000-$25,000 ABOVE THE $550,000 ASKING PRICE, WITH NO APPRAISER-REQUIRED REPAIRS! The previous FHA buyer reached the week of closing but could not proceed due to an unexpected family medical emergency, completely unrelated to the property, inspection, or appraisal. Here's a second chance to purchase an exceptional South Shore brick 3-flat offering income from day one, potential built-in equity, and significant room to grow! This well-maintained building features THREE JUMBO approximately 1,700 SF apartments, each with 3 bedrooms and 2 full bathrooms-9 bedrooms and 6 baths total. Enjoy spacious living rooms, formal dining rooms, hardwood floors, generous bedrooms, and layouts rarely found at this price. Fully occupied by established, long-term residents with a consistent payment history; ALL TENANTS PAID OCTOBER 2026 RENT ON TIME! Scheduled income is $3,912/month or $46,944/year, and all three tenancies are month-to-month, providing future flexibility subject to applicable tenant rights and notice requirements. INVESTORS: THE RENTAL UPSIDE IS SUBSTANTIAL! A rental comparable analysis identified an approximately $2,037/month average for similar 3-bedroom apartments within one mile. If all three units eventually reached that benchmark, gross scheduled rent could total $6,111/month or $73,332/year-an increase of $2,199/month or $26,388/year (about 56%). Unit 2 currently rents for $1,287/month; a CHA increase to $2,000/month has been requested and is pending approval, potentially adding $713/month or $8,556/year if approved. OWNER-OCCUPANTS: HOUSE HACK! When legally available, occupy one spacious 3-bedroom/2-bath unit and collect rent from the other two to help offset ownership costs. Tenants pay their own gas, heat, and electricity; each apartment has separate forced-air heating and individual controls. The full basement offers tenant and landlord storage, natural-gas basement heat, and coin-laundry facilities as reported in the prior listing. Its size, ceiling height, layout, and access may present an opportunity to investigate additional living space, a garden unit, or ADU, subject to zoning, permits, City approval, and buyer due diligence. An OWNED DETACHED 3-CAR GARAGE adds value! The prior listing reported a newer tear-off main-building roof with transferable warranty and a 2020 tear-off garage roof; buyers should verify. LET'S TALK EQUITY: The previous $575,000 FHA appraisal is $25,000 above today's $550,000 asking price, offering potential immediate equity (not guaranteed). Comparable-market analysis also identified renovated multifamily properties with finished garden space selling in the $700,000+ range-suggesting a potential $150,000+ gross valuation spread versus asking through thoughtful improvements, rent growth, and maximizing existing space. Comparable properties differ and future value is not guaranteed. Located in established South Shore near the lakefront, beaches, schools, shopping, and neighborhood amenities. Whether you're an investor seeking a performing asset or an owner-occupant seeking rental assistance with your mortgage, don't miss this opportunity! NEW SHOWING DATES WILL BE ANNOUNCED as management coordinates with residents to welcome prospective buyers back into the property.
Listing Information
Facts & Features
Location
Community Information
Architecture
Features & Amenities
Property Features
Tax & Financial Information
Schools
Madison Elementary School
Bouchet Elementary Math & Science Academy
Art in Motion Charter School
Powell Elementary Paideia Community Academy
Excel Academy of South Shore
Parkside Elementary Community Academy
OKeeffe Elementary School
School of Leadership High School
School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.
Historical Data
Price History
| Date | Event | Price |
|---|---|---|
| 08/22/2026 | Listed for sale | $550,000 |
Listed by Michael Applegate · Straight-A Realty, LLC · 6302882446
Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Midwest Real Estate Data (MRED). All rights reserved.
Last Updated: October 29, 2026 at 2:53 PM | Source: Midwest Real Estate Data (MRED) | MLS#: 12740010

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