O'Neil Property Group

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$1,275,000
55 Days On Site

3248 N Oakley Avenue
Chicago, IL 60618

For Sale|Multi Family|Active Under Contract
8
Beds
3
Total Baths
1916
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Mark Allen Realty ERA Powered
3248 N Oakley Avenue3248 N Oakley Avenue3248 N Oakley Avenue3248 N Oakley Avenue
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Set on one of Roscoe Village's beautiful tree-lined streets, this extraordinary and rarely available greystone is anything but typical. With a distinctive layout, oversized lot, detached greystone garage, finished studio space, and an abundance of original architectural character, this property offers a level of flexibility that is incredibly hard to find. Located in the highly sought-after Audubon School District, it is an exceptional opportunity for a single family home, owner-occupant investor, or multi-generational household. Owned and lovingly maintained by the same owner for more than 20 years, the main residence encompasses the first and second floors. Each floor features 3 bedrooms, 1 bathroom, a formal living room, formal dining room, and a beautiful custom wood-burning fireplace. Original details throughout the home include rich oak millwork, hardwood flooring, stained-glass accents, oversized windows, and spacious rooms that showcase the scale and craftsmanship of a bygone era. The kitchen was thoughtfully renovated in 2016 and features custom cabinetry, stone countertops, stainless steel appliances, and a large center island that creates an inviting gathering space. The bathroom was updated in 2021, providing a fresh complement to the home's classic architectural details. The garden apartment adds another layer of flexibility and potential. Currently configured as a 2-bedroom, 1-bath residence, it includes a full kitchen, comfortable living space, and excellent storage. The apartment was previously used as a 3-bedroom layout, offering additional possibilities for future use. One of the property's most unusual features is the detached greystone garage. Above the garage, a finished loft currently serves as a fitness studio and is already plumbed for a bathroom. Whether envisioned as a private office, art or creative studio, gym, workshop, guest space, or future finished living area, this bonus space provides tremendous potential. The property also includes a separate carport and an oversized yard with plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying the space. The home's substantial construction is further highlighted by approximately 12-inch-thick limestone walls, reflecting the quality, permanence, and craftsmanship characteristic of Chicago's historic architecture. And the location is hard to beat! Just two blocks south of the popular Roscoe Street corridor, you'll be close to neighborhood restaurants, cafes, parks, boutique shopping, and everyday conveniences, while still enjoying the peaceful residential atmosphere of this sought-after pocket of Roscoe Village. Properties with this combination of architectural character, scale, outdoor space, additional living space, and flexibility rarely come to market. A truly special opportunity to own a distinctive piece of Roscoe Village with the potential to adapt to a variety of lifestyles and investment strategies.

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Listing Snapshot
Price 
$1,275,000
Days On Site 
55 Days
Bedrooms 
8
Inside Area (SqFt) 
N/A
Total Baths 
3
Full Baths 
N/A
Partial Baths 
N/A
Lot Size 
N/A
Year Built 
1916
MLS® Number 
12737803
Status 
Active Under Contract
Property Tax 
$14,666.27
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 months agoListing updated with changes from the MLS®
2 months agoStatus changed to Active Under Contract
2 months agoListing first seen on site
General Features
Garage 
Yes
Garage Spaces 
2
Parking 
Garage Door OpenerDetachedGarage
Parking Spaces 
5
Property Sub Type 
Multi Family
Sewer 
Public Sewer
Style 
Greystone
Interior Features
Basement 
FinishedFullWalk-Out Access
Cooling 
Ceiling Fan(s)
Heating 
Natural GasForced Air
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Community Features
MLS Area 
CHI - North Center
School District 
Lake View High School
Township 
Lake View
Schools
School District
Lake View High School
Elementary School
Audubon Elementary School
Middle School
Audubon Elementary School
High School
Lake View High School
Listing Courtesy of MRED as distributed by MLS Grid of Mark Allen Realty ERA Powered



Based on information submitted to the MLS GRID as of 2026-10-14 03:54 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. 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.
Last checked: 2026-10-14 03:54 AM UTC
MRED DMCA Copyright Information Copyright © 2026 Midwest Real Estate Data LLC. All rights reserved.

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