2042 N Winchester Avenue # 2E Chicago, IL $ 475,000
2042 N Winchester Avenue # 2E
$ 475,000
Recently Listed
Open House 10/10 11am - 1pm
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2042 N Winchester Avenue # 2E

Chicago, IL, 60614
$ 475,000
Bedrooms2 Baths2.0

Monthly Estimate*

$ 3,281

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Condo for sale in Chicago, IL

for $475,000 with 2 bedrooms and 2 full baths.

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!

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Open House

10/10/2026 11:00 AM - 1:00 PM
10/11/2026 11:00 AM - 1:00 PM
2042 N Winchester Avenue # 2E Chicago, IL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Condo Active

Price

$ 475,000

Bedrooms

2

Full Bath

2

Property Type

Condo

Taxes

$ 6,440

Style

Condo,Condo-Duplex,Condo-Loft

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12758906

Features
General
Living Area 0
Sewer Public Sewer
Heating Natural Gas Forced Air
Cooling Central Air
Possession Closing
Roof Asphalt
Appliances Range Microwave Dishwasher Refrigerator Washer Dryer Disposal
HOA Fee 195
Association Fee Includes Water Insurance Exterior Maintenance Scavenger Snow Removal
Construction Materials Brick
Pets Allowed Cats OK Dogs OK
Township West Chicago
Unit Number 2E
Tax Year 2025
Ownership Condo
Assoc Fee Paid Per Monthly
County Cook
New Construction N
Property Type Residential Attached Single
Subdivision Name Bucktown
Total Rooms 5
Full Baths 2
Status New
Directions Armitage east or west to Winchester north to property
City Chicago
High School District 299
MLS Area CHI - Logan Square
Tax Annual Amount 6440.55
Virtual Tour https://my.matterport.com/show/?m=iinhcXrPjSU&brand=0
Standard Status Active
Middle/Junior School District 299
Elementary School District 299
Sub Type Condo Condo-Duplex Condo-Loft
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Interior
Interior Amenities Vaulted Ceiling(s) Storage
Basement None
Flooring Hardwood
Total Stories 3
Half Baths 0
Laundry Features In Unit In Bathroom
Total Bedrooms 2
Room Type No additional rooms
Total Baths 2
Bedrooms Possible 2
Total Number of Units 5
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Exterior
Parking Features Assigned Off Alley Yes Owned
Water Source Lake Michigan
Total Parking 1
Lot Dimensions COMMON
Waterfront Y/N N
Other Equipment CO Detectors Ceiling Fan(s)
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* Excluded Features
List By
Redfin Corporation

Broker

daniel.close@redfin.com

Email

Affordability Calculator

$3,817
Per Month
86%
14%
0%
Monthly Principal & Interest
$3,281
Monthly Property Taxes
$537
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
566059 Elementary School
566846 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
10/7/2026$475,000 Listed Price

Map


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2042 N Winchester Avenue # 2E, Chicago, IL, 60614 is a Condo for sale at $475,000. 2042 N Winchester Avenue # 2E has 2 bedrooms and 2.0 baths. The property's zip code is 60614 which is in Chicago, IL