About This Home

This 2-bedroom, 2-bathroom condo at 2042 N Winchester Avenue #2E in Chicago, IL is listed for $475,000. on a N/A lot.

Key Features

  • 3 stories
  • 1 parking spaces

Property Details

3 stories
2 full
1 space
#2E

Amenities

HardwoodA/C
Listing Description

SHORT TERM RENTAL FRIENDLY HOA WITH NO RENTAL CAP OR MINIMUM LEASE REQUIREMENTS - 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, flexible investment opportunity, as this HOA allows short term rentals. Ask for details and schedule your showing today!

Monthly Cost Estimate

$2,735/mo

20% down · 6.5% · 30 years

Principal$344
Interest$2,058
Insurance$139
HOA$195

Estimates only. Actual payments may vary.

Location

2042 N Winchester Avenue #2E

Chicago, IL 60614

Bucktown

Features & Amenities

Interior Features

Vaulted Ceiling(s)Storage

Property Details

Flooring

Hardwood

Construction

Brick

Outdoor Features

Patio

Parking

AssignedOwnedOff Alley

Heating

Natural GasForced Air

Cooling

Central Air

Appliances

RangeMicrowaveDishwasherRefrigeratorWasherDryerDisposal

Questions & Answers

This 2-bedroom, 2-bathroom condo at 2042 N Winchester Avenue is listed at $475,000. The estimated monthly payment is $2,736 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance, HOA fees.

HOA fees are $195/month.

Key features include: 3 stories, 1 parking spaces. Interior Features: Vaulted Ceiling(s), Storage.

This property is listed by Daniel Close.

DC

Daniel Close

Agent at Redfin Corporation

Listed by Redfin Corporation · Broker phone: (773) 308-4896 · View on Broker Site · Broker website

MLS# 12787211· Source: Midwest Real Estate Data, LLC· 15 days on PropertySimple

Copyright © 2026 Midwest Real Estate Data, LLC. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

2042 N Winchester Avenue #2E, Chicago, IL 60614

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