Date
Details
Price
Change
Source
1/15/2026
Listed
$1,000,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/28
$1,000,000 Just Listed
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/28
Property Description
Tucked along a quiet, tree-lined street in the heart of Jefferson Park, this light-filled home offers a thoughtful layout designed for everyday family living. Hardwood floors and 9-foot ceilings create an open, airy feel throughout, anchored by a well-designed kitchen with custom cabinetry, new appliances, and an oversized quartz island that naturally brings everyone together. The family room opens directly to the backyard, making it easy to move between indoor and outdoor play, gatherings, and daily routines. Upstairs, the primary suite provides a comfortable retreat with a walk-in closet and en-suite bath, while three additional bedrooms, a full bath, and convenient second-floor laundry make day-to-day living efficient and practical. The finished lower level adds valuable flexibility with a generous rec room, fifth bedroom, full bath, office or flex space, rough-in plumbing for a wet bar, and a customized storage room-ideal for homework zones, guests, or hobbies. Outside, enjoy a fully fenced yard with patio and a two-car detached garage, all set within an established neighborhood close to parks, schools, Starbucks, and the local spots Jefferson Park families enjoy.
Full Property Details
Full Property Details for 5744 W Ainslie St
General
- Price: $1,000,000
- Taxes: $16,200 (2024)
- Status: Active
- Type: Single Family
- Source: MRED
- MLS ID: 12537616
- Updated: 1/15/2026
- Added to Site: 2 day(s) ago
Rental Information
- Complex Features: Curbs, Sidewalks, Street Lights
Interior
- Basement: Finished, R
- Interior Features: Vaulted Ceiling(s), In-Law Floorplan, Built-in Features, Walk-In Closet(s), High Ceilings, Open Floorplan, Separate Dining Room
- Appliances: Range, Microwave, Dishwasher, High-End Refrigerator, Washer, Dryer, Stainless Steel Appliance(s)
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Basement Baths: Yes
- Bathroom Features: Double Sink, Full Body Spray Shower, Soaking Tub
Bedrooms
- Total Bedrooms: 5
- Bedrooms(Blw Grade): 1
Additional Information
- Other Features: Commuter Bus, Commuter Train, Interstate Access
Exterior
- Exterior Features: Roof Deck
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Garage
Location
- Area: CHI - Jefferson Park
- County: Cook
- Township: Jefferson
- Driving Directions: Central Ave north of Lawrence Ave to Ainsile St west.
School Information
- School District: 299
- Elem School District: 299
- Midd School District: 299
- High School District: 299
- Elementary School: Prussing Elementary School
- Middle School: Prussing Elementary School
- High School: Taft High School
- Private School: Taft High School
Community
- Assoc. Fees Include: None
Heating & Cooling
- Cooling Type: Central Air Conditioning, Zoned
- Heating Type: Natural Gas, Forced Air
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Construction: Stone, Other
- Exterior Const.: Stone, Other
- Basement: Yes
- Basement Desc.: Finished, Rec/Family Area, Full
- Foundation: Concrete Perimeter
- Roof: Asphalt
- Sub-Flooring: Hardwood
- Square Feet: 2,730
- Sq. Ft. Source: Estimated
- Year Built: 2016
Lot Features
- Lot Size (Acres): 0.163
- Lot Size Range: Oversized Chicago Lot
- Lot Dimensions: 25 x 145 x 27 x 154
- Fence: Yes
- Fencing (Description): Fenced
Financial Considerations
- Parking Included: Yes
- Assessment Year: 2016
- Tax Amount: $16,200
- Tax Year: 2024
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 13084251690000
Listed by @properties Christie�s International Real Estate
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 5744 W Ainslie St —
@properties Christie�s International Real Estate
@properties Christie�s International Real Estate
NMLS#: 1598647
Get Pre-Approved Today
Get a Great Insurance Rate
Schools
Schools serving 5744 W Ainslie St
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Prussing Elementary School 4650 North Menard Avenue, Chicago, IL 60630 | PK-8 | 0.3 mi |
Taft High School 6530 West Bryn Mawr Avenue, Chicago, IL 60631 | 9-12 | 1.4 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5744 W Ainslie St
Tax History
Tax History for 5744 W Ainslie St
Year
Property Taxes
Change
Tax Assessment
Change
2023
$13,233
3%
$66,000
—
2022
$12,879
2%
$66,000
—
2021
$12,610
12%
$66,000
23%
2020
$11,245
—
$53,550
-10%
2019
$11,272
2%
$59,500
—
2018
$11,081
21%
$59,500
30%
2017
$9,133
-11%
$45,778
-11%
2016
$10,307
1065%
$51,431
965%
2015
$885
—
$4,828
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5744 W Ainslie St
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 2 days ago
- 5Beds
- 4Total Baths
- 3,558Sq. Ft.
- Single Family
- Active
- Updated 2 hours ago
- 5Beds
- 4Total Baths
- 3,000Sq. Ft.
- Single Family
- Active
- Updated 23 hours ago
- 5Beds
- 4Total Baths
- 3,300Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 2 hours ago
- 3Beds
- 2Total Baths
- 2,187Sq. Ft.
- Condo / Townhouse
- Active
- Updated 3 days ago
- 2Beds
- 1Total Bath
- 1,100Sq. Ft.
- Single Family
- Active
- Updated 8 hours ago
- 5Beds
- 3Total Baths
- 1,738Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 2Total Baths
- 1,700Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Closed
- Updated 4 days ago
- 5Beds
- 4Total Baths
- 3,558Sq. Ft.
5744 W Ainslie Street, Chicago, IL 60630 (MLS# 12537616) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 5744 W Ainslie Street is currently listed for $1,000,000 and was received on January 15, 2026. Want to learn more about 5744 W Ainslie Street? Do you have questions about finding other Single Family real estate for sale in Jefferson Park? You can browse all Jefferson Park real estate or contact a Coldwell Banker agent to request more information.