Rarely available top-floor loft offering approximately 1,850 square feet in an intimate 6-unit boutique building on a picturesque tree-lined street in the heart of Bucktown! Just one flight of stairs to the unit with no neighbors above or below. This beautifully updated 3-bedroom, 2-bath residence combines authentic loft character with modern finishes, featuring exposed brick, soaring ceilings, skylights, and hardwood floors throughout. The expansive open-concept living and dining area is ideal for everyday living and entertaining, flowing seamlessly into a sleek contemporary kitchen appointed with quartz countertops, abundant cabinetry, a generous pantry, and premium Viking and Bosch stainless steel appliances. The spacious primary suite features custom Preston luxury closets and a beautifully renovated bath with an oversized glass shower and dual vanity, while two additional fully enclosed bedrooms each offer windows for abundant natural light. Enjoy exceptional outdoor living on the private rooftop deck with views of The 606 and The Robey, complete with a propane grill, oversized cedar planters, and water and electrical hookups. Additional features include in-unit laundry and large private storage room in lower level of building. Perfectly situated just steps from The 606 Trail, Churchill Park, the Blue Line, Wicker Park, Six Corners, Olivia's Market, Mindy's Bakery, Le Bouchon, Club Lucky, Goddess and the Grocer, La Colombe, Big Star, and countless neighborhood restaurants, cafes, and boutiques. Located within the Burr Elementary School attendance boundary. An exceptional opportunity to lease a truly one-of-a-kind Bucktown loft. 1 garage parking space included in rental price of $6000/mo. 2 attached garage spaces available for +$250/mo each. $1500 non-refundable move in fee to landlord. No security deposit. Tenant responsible for all move in/out fees and/or deposits charged by association. Pets ok but must be approved by landlord. $50/mo additional pet rent per pet if approved. Available Sept 1. Agent owned, but not affiliated with listing brokerage.
1742 N Winchester Ave
Chicago, IL 60622
Apartment building
2-3 beds
Available units
This building may have units for rent or for sale. Select a unit to contact.
What's special
Top-floor loftExposed brickModern finishesSoaring ceilingsCustom preston luxury closetsSleek contemporary kitchenPrivate rooftop deck
Neighborhood: Bucktown
Areas of interest
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Travel times
Walk, Transit & Bike Scores
Walk Score®
/ 100
Walker's ParadiseTransit Score®
/ 100
Excellent TransitBike Score®
/ 100
Biker's ParadiseNearby schools in Chicago
GreatSchools rating
- 8/10Burr Elementary SchoolGrades: K-8Distance: 0.5 mi
- 1/10Wells Community Academy High SchoolGrades: 9-12Distance: 1.1 mi
Nearby apartments for rent
Listing order may reflect relevance, quality, and paid promotion.
Frequently asked questions
Based on the latest Zillow data, the average rent across all unit types in Chicago is currently $2,795 per month. Prices vary by neighborhood, floor plan, and building amenities.
Rent in Chicago has increased by $100 month-over-month, according to the latest Zillow rental data.
The schools assigned to 1742 N Winchester Ave include Burr Elementary School and Wells Community Academy High School.








