SHORT TERM RENTAL AND AIRBNB FRIENDLY – RARE OPPORTUNITY! Sun-filled and full of character, this 2-bedroom, 2-bathroom duplex-up blends vintage Chicago charm with modern loft-style living in the heart of Bucktown. Soaring ceilings, exposed brick and beautiful hardwood floors create a warm, airy backdrop, while oversized windows and skylights fill the home with natural light. The updated kitchen features crisp white cabinetry, granite countertops, stainless steel appliances and a breakfast island that flows seamlessly into the living and dining space. A dramatic spiral staircase leads to the spacious lofted primary suite with vaulted ceilings and skylights. The second bedroom offers wonderful flexibility for guests or a home office, while two full baths and in-unit laundry add everyday convenience. Outside, a large private deck creates your own urban retreat. Central air, additional storage and deeded exterior parking complete this distinctive home in a prime Bucktown location steps from local retail shopping, restaurants, and the 606 trail. This fantastic home is perfect not only for owner-occupants but also presents an incredible investment opportunity, as this HOA allows short term and nightly vacation rentals. Ask for details and schedule your showing today!
Property Details
Price:
$475,000
MLS #:
MRD12758906
Status:
Active Under Contract
Beds:
2
Baths:
2
Type:
Condo
Subdivision:
Bucktown
Neighborhood:
chilogansquare
Listed Date:
Oct 7, 2026
See this Listing
Schools
School District:
299
Interior
Appliances
Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Hardwood
Heating
Natural Gas, Forced Air
Interior Features
Vaulted Ceiling(s), Storage
Laundry Features
In Unit, In Bathroom
Exterior
Construction Materials
Brick
Parking Features
Assigned, Off Alley, Yes, Owned
Parking Spots
1
Parking Total
1
Patio And Porch Features
Patio
Roof
Asphalt
Window Features
Skylight(s), Double Pane Windows
Financial
HOA Fee
$195
HOA Fee Frequency
Monthly
HOA Includes
Water, Insurance, Exterior Maintenance, Scavenger, Snow Removal
Tax Year
2025
Taxes
$6,441
Map
Community
- Address2042 N Winchester Avenue #2E Chicago IL
- SubdivisionBucktown
- CityChicago
- CountyCook
- Zip Code60614
Market Summary
Property Summary
- Located in the Bucktown subdivision, 2042 N Winchester Avenue #2E Chicago IL is a Condo for sale in Chicago, IL, 60614. It is listed for $475,000 and features 2 beds, 2 baths, and has approximately 0 square feet of living space.The average price per square foot for Condo listings in Chicago is $376. The average listing price for Condo in Chicago is $639,785.
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2042 N Winchester Avenue #2E
Chicago, IL


