4339 W Monroe Street
Chicago, IL, 60624 $ 375,000
Bedrooms7 Baths5.0 Sq 3,174 Monthly Estimate*
$ 2,340
for $375,000 with 7 bedrooms and 5 full baths. This 3,174 square foot home was built in 1903.
Classic Chicago Greystone two-flat in fast-rising West Garfield Park with RT-4 zoning and potential ADU eligibility-an exceptional, high-upside opportunity delivered with full architectural plans, drawings, and permits. Major improvements are already complete, including a newer roof with an added protective layer, all-new plumbing (city-passed), and all-new electrical (awaiting final approval). Each oversized unit-4BR/2BA up and 3BR/2BA down-offers approximately 1,600 sq ft with soaring ceilings, brand-new hardwood floors, updated bathrooms, and washer/dryer hookups in every unit, including the basement. The walkout basement (~2,100 sq ft with 7.5-ft ceilings and a full bath) is primed to become either a duplex-down, a fully legal third unit under existing RT-4 zoning (no upzoning required), or a potential ADU conversion unit for an owner-occupant. ARV is estimated at $456,000 as a two-flat and $505,000 as a three-unit, with strong rental comps showing demand for ~$2,350/month for 4BR/2BA units and ~$1,892/month for 3BR/2BA units. The home requires only minimal finishing work-with kitchen cabinets for Unit 1, bathroom tile, and drywall materials included on-site to complete the remaining finishes-and also features a two-car garage, convenient access to I-290 and CTA, and proximity to the rapidly expanding United Center redevelopment. The seller, a professional remodeling contractor, is not distressed and is offering a $10,000 closing credit, making this a rare, near-turnkey Greystone with tremendous equity and income potential for both investors and house hackers.
See more
FeaturesGeneralSewer Public Sewer
Heating Natural Gas Forced Air
Possession Closing Immediate
Zoning MULTI
Garage Spaces 2
Architectural Style Greystone
Construction Materials Brick Stone
Year Built 1903
Township West Chicago
Tax Year 2023
Ownership Fee Simple
County Cook
New Construction N
Property Type Residential Income Two to Four Units
Contingency Attorney/Inspection
Total Rooms 15
Status Contingent
Directions From I-290 (Eisenhower) exit Pulaski Rd go north to Monroe St then turn west and continue to 4339 W Monroe St (between Kildare Ave and Kostner Ave).
City Chicago
High School District 299
MLS Area CHI - West Garfield Park
Tax Annual Amount 2117
Standard Status Active Under Contract
Middle/Junior School District 299
Elementary School District 299
See more
InteriorBasement Unfinished Full Walk-Out Access
Total Bedrooms 7
Total Baths 5
Bedrooms Possible 7
Full Baths Building 5
Half Baths Building 0
Total Number of Units 2
See more
ExteriorParking Features Garage Door Opener Yes Garage Owned Detached Garage
Water Source Lake Michigan Public
Total Parking 2
Lot Dimensions 25 x 139
Waterfront Y/N N
See more
* Excluded FeaturesList ByStraight-A Realty, LlcBroker
m.applegate@straightarealty.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $2,340
- Monthly Property Taxes
- $176
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbyMulti-family listings in Chicago, IL
Average List Price $617,695
Percent of Sale Price 65%
About Chicago, IL 2,755,380 Population
-4% Since 2002
$ 53,088 Median Income
36.07 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
566059 Elementary School
566846 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/30/2025 | $375,000 | | Listed Price |