3429 N Oakley Avenue

Chicago IL, 60618



6 Beds

3 Baths


Built in 1890

Courtesy of Coldwell Banker Realty

You have 3 amazing opportunities with this unbelievably located Roscoe Village home. Ready?? To live in.. or invest in? Or both?? Those are the questions. BOTH you say?? YES! HOUSEHACKING at its finest. Buy this property, live in one unit and use the rental income from both of the other two units to cover your mortgage.. LIVE FOR FREE!! This opportunity doesn't come around very often.. and, it is also the ideal path for young real estate investors. This strategy could help you jump start your way into potential financial freedom, and lead you to building a portfolio of investment properties and long term generational wealth. Onto the other option - TO LIVE IN.. Convert this home into another one of the many beautifully designed single family rebuilt homes in Roscoe Village and watch the value increase to 1.9M-2.2M, and enjoy your own space in this great neighborhood. Equipped with solid bones, a newer garage, tall ceilings in the basement, a nice sized yard and a layout that can easily be converted.. this is a fantastic option for someone who loves the neighborhood and wants to live in a 5000+sqft home. With plenty of parks, great schools, friendly neighbors and a plethora of restaurants and entertainment.. you'd love to call this "home". - TO INVEST IN.. Roscoe Village is known for its great location and livability, but its rental market.. and its ability to bring in professional grade tenants who are willing to pay at or above market rents is also a huge plus for investors. This home currently brings in $6075/month - almost $73,000/year in gross rent and there are still opportunities for value-add in this building. The first floor unit is duplexed down into the basement making it a 2-story unit, but the basement is currently unfinished. Finish the basement and add at least another $13,000/year to the gross rent. Cosmetically update the 2nd and 3rd floors and add another $15,000/year to the gross rent. With updated 2nd and 3rd floor units and a finished basement, this 3 flat can bring in $100,000/year in gross rent.. AWESEOME!! Or... convert this three unit property into two, 2-story townhomes. The first floor unit is already duplexed down making it a 2-story townhouse.. combine the 2nd and 3rd floors to make two beautiful 2-story townhouses, split the pin, create an association and sell each townhouse separately... Mind blowing creativity right there! *****NOTABLES***** This is a legal 3 flat building that has 3 nicely updated 2 Bedroom 1 Bath 1100 sqft units, currently fully rented, each with all their own utilities, including in-unit washer/dryer, furnace/central AC, dishwashers and private decks with storage.***** The building itself has been well maintained inside and out, and the first floor unit is fully updated. Each unit also has hardwood floors throughout, and the fact that each unit has their own separate utilities will make it a breeze for the savvy investor. Each unit also has their own furnace/Central AC, Washer/dryer, dishwasher and private balconies. There is also a 2.5 car garage that was built in 2016.



October 17, 2022


December 9, 2023



3429 N Oakley Avenue
Chicago IL, 60618

Interior Features


6 Beds


3 Baths







Heating Description

Natural Gas

Exterior/Building Features

Exterior Features

Balcony, Deck, Patio

Architectual Style



Public Sewer

School Information

School District


High School

Lake View High School

Elementary School

Audubon Elementary School

Other Property Details

Area Name

CHI - North Center



Tax Frequency


Days on Market


Association Amenities

Park, Curbs, Sidewalks, Street Lights, Street Paved



Garage Spaces








Water Source

Lake Michigan





Buyer Agency Compensation

2.5% MINUS $475

Courtesy of Coldwell Banker Realty, Blaine Kosek,
Listing Contact:  

The data relating to real estate for sale on this website comes in part from the Broker ReciprocitySM Program of Midwest Real Estate Data. Real estate listings held by brokerage firms other than PCR Group are marked with the Broker ReciprocitySM logo or the Broker ReciprocitySM thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers.

Based on information submitted to the  MLS GRID for MRED 12/9/2023. All data is obtained from various sources and has not been, and will not be, verified by broker, MRED or MLS GRID. MLS Grid and MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is 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. Data is deemed reliable but is not guaranteed by MTP or MRED. The use of the MRED Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.

©2023 Listings Courtesy of MRED as distributed by MLS GRID. All rights reserved.

Data last updated 7:14 PM UTC, 12/9/2023



Powered byLuxury Presence