3248 Oakley Avenue, North Center, Chicago, Illinois 60618


$1,275,000

For Sale
Status: Contingent
Sqft: 0
Cost/Sqft:
Beds: 8
Baths: 0
Year Built: 1916
Property Taxes: $14,666
Days On Market: 12
Lot Size: 0,00
Map
Street View

Description

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.

Property Specifics

Multi-unit
1916
No
Cook
— / —
12737803
14193240370000

Nearby Schools

NAME: DISTRICT: DISTANCE:
Grade School
Audubon Elementary School
299
Middle School
Audubon Elementary School
299 Not in DB
High School
Lake View High School
299 Not in DB

Property History

DATE: EVENT: PRICE: SOURCE:
24 Aug, 2026 Under contract $1,275,000 MRED MLS
19 Aug, 2026 Listed for sale $1,275,000 MRED MLS

Room Specifics

All Bedroom Info:
Total Bedrooms: 8
Bedrooms Above Ground: 8
Bedrooms Below Ground: 0
Second Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Third Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Fourth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Fifth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Sixth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Seventh Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Eighth Bedroom Info:
Dimensions: —
Location: —
Floor Type: —
Bathroom Info:
Full Bathrooms: 3
Partial Bathrooms: —
Bathroom Amenities: Soaking Tub
Bathroom in Basement: —
Additional Rooms Info:
Rooms: —
Basement: —
Basement Description: —

Other Specifics

2
30x120
Not in DB

Tax History

Year Property Taxes
2026 $14,666

Nearby Similar Homes

3008 Clybourn Avenue, Chicago, Illinois 60618
For Sale
$635,000
6 beds / 0.0 baths / 0 ft2
Multi-unit / Built: 1890
10

2959 Elston Avenue, Chicago, Illinois 60618
For Sale
$650,000
4 beds / 0.0 baths / 0 ft2
Multi-unit / Built: 1902
12

Nearby Sold Comparables

2315 School Street, Chicago, Illinois 60618
Sold
$749,000
5 beds / 0.0 baths / 0 ft2
Multi-unit / Built: —
3819

2319 School Street, Chicago, Illinois 60618
Sold
$749,900
6 beds / 0.0 baths / 0 ft2
Multi-unit / Built: —
1965

2316 Melrose, Chicago, Illinois 60618
Sold
$589,000
6 beds / 5.0 baths / 0 ft2
Multi-unit / Built: 1891
7247

2316 Melrose Street, Chicago, Illinois 60618
Sold
$699,000
6 beds / 0.0 baths / 0 ft2
Multi-unit / Built: 1891
1973

2316 Melrose Street, Chicago, Illinois 60618
Sold
$799,000
6 beds / 0.0 baths / 0 ft2
Multi-unit / Built: 1891
1039

3241 Oakley Avenue, Chicago, Illinois 60618
Sold
$649,900
6 beds / 2.0 baths / 0 ft2
Multi-unit / Built: 1908
6963


Contact Agent

Listing Provided By

Mark Allen Realty ERA Powered