$475,000

beds

baths

2042 N Winchester Avenue #2E

Chicago, Illinois 60614

Name: 2042 N Winchester Avenue #2E, Chicago, IL 60614
Price: 475000 USD
Availability: InStock

New / MLS #12758906 / Loft / Logan Square

Listing information updated 10/7/2026 at 1:03pm

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!

See it in person

Open House

11:00am - 1:00pm Saturday, October 10th, 2026 10/10/26

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11:00am - 1:00pm Sunday, October 11th, 2026 10/11/26

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Full Features

Exterior Type:

Brick

Basement:

None

Beds Above Grade:

Cooling System:

Central Air

Heating System:

Natural Gas, Forced Air

Appliances:

Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal

Main Level Primary Bedroom:

Pool:

Age:

Unknown

Roof Type:

Asphalt

Parking Type:

Assigned,Off Alley,Yes,Owned

Parking Spaces:

Room Count:

Water Front:

Square Feet:

N/A

Pet Information:

Cats OK, Dogs OK

Internal Features:

Vaulted Ceiling(s), Storage

External Features:

Patio/Porch

Room Information

Living Room:

13x11 - Main

Dining Room:

19x9 - Main

Kitchen:

13x10 - Main

Family Room:

N/A

Primary Bedroom:

19x13 - Second Level

2nd Bedroom:

10x09 - Main

3rd Bedroom:

N/A

4th Bedroom:

N/A

Laundry:

N/A Level

Taxes & Assessments

Tax Amount:

$6,440

Tax Year:

2025

Assessments:

$195 / month

Location

Zip Code:

60614

City:

Chicago

County:

Cook

Schools

School District(s):

299

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Exterior Type:

Brick

Basement:

None

Beds Above Grade:

Cooling System:

Central Air

Heating System:

Natural Gas, Forced Air

Appliances:

Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal

Main Level Primary Bedroom:

Pool:

Age:

Unknown

Roof Type:

Asphalt

Parking Type:

Assigned,Off Alley,Yes,Owned

Parking Spaces:

Room Count:

Water Front:

Square Feet:

N/A

Pet Information:

Cats OK, Dogs OK

Internal Features:

Vaulted Ceiling(s), Storage

External Features:

Patio/Porch

Living Room:

13x11 - Main

Dining Room:

19x9 - Main

Kitchen:

13x10 - Main

Family Room:

N/A

Primary Bedroom:

19x13 - Second Level

2nd Bedroom:

10x09 - Main

3rd Bedroom:

N/A

4th Bedroom:

N/A

Laundry:

N/A Level

Tax Amount:

$6,440

Tax Year:

2025

Assessments:

$195 / month

Zip Code:

60614

City:

Chicago

County:

Cook

School District(s):

299

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Listing Office: Redfin Corporation

Listing Office Phone: 312.836.4263

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 10/7/2026 at 1:03pm. 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. Some listings have been excluded from this website.

2042 N Winchester Avenue #2E

Chicago, Illinois 60614