$475,000
Chicago, IL 60614
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!
Estimated monthly cost for this home
$3,470/mo
Estimate only, not a quote or offer of credit. Rate starts from today's market rate (7.28%, 2026-10-01). Taxes from the listing's MRED record. Talk to a lender for real numbers; a Subdiview agent can introduce you to a good one.
| 2025 property taxes | $6,441/yr |
From the listing's MRED record. MRED does not publish per-change dates through IDX, so price changes are shown without one rather than guessed.
MRED Broker ReciprocityThis listing is part of the MRED data exchange program provided courtesy of Redfin Corporation, listed by Daniel Close.
Information last updated Oct 7, 2026, 5:40 PM.
2042 Winchester Avenue
Chicago, IL 60614

Talk to a Subdiview agent.
Local. They live in the area and know what’s behind these floor plans, not someone who paid for a lead.
Get the full disclosure packet, recent comps, and a private showing within 24 hours.
Call 224-385-8779Sourced from the MRED MLS feed. Last updated when the listing was modified.