$475,000

2042 N Winchester Avenue 2E, Chicago, IL 60614

2 beds |
2 baths

Condominium
Built in ——
—— sqft lot
—— car garage
$——/sqft
Listed ——

Property Description

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!

Listing Status:: Active
Data Last Updated:: October 9, 2026 at 6:18PM
Listing Office:: Redfin Corporation : 224-430-2643
Listing Agent:: Daniel Close : 224-430-2643
MLS ID:: 12758906

General: Vaulted Ceiling(s)Storage
Rooms: No additional rooms
Appliances: RangeMicrowaveDishwasherRefrigeratorWasherDryerDisposal
Dining: Combined w/ LivRm
Laundry: In UnitIn Bathroom
Basement: None
Flooring: Hardwood
A/C: Central Air
Heating: Natural GasForced Air
Disability Feature: None

Parking: AssignedOff AlleyYesOwnedParking spaces: 1

Roofing: Asphalt
Windows: Skylight(s)Double Pane Windows

HOA Amenities: WaterInsuranceExterior MaintenanceScavengerSnow Removal195.0Monthly
Originating MLS: mred
School District: 299
County: Cook

Zoning: 14312130461005

Water: Lake Michigan
Sewer: Public Sewer

Source: mred
Ownership: Condo

This listing courtesy of Daniel Close , Redfin Corporation

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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