7515-21 N. Winchester Ave. Chicago, IL 60626

Essex Realty Group, Inc. is pleased to present 7515-21 N. Winchester Ave., a twenty-seven unit courtyard apartment building located on a sunny block in the East Rogers Park neighborhood of Chicago. The property has been under the same ownership for nearly 20 years and has been meticulously maintained during its tenure.

The building’s unit mix consists of three (3) one-bedroom / one-bath gardens, twelve (12) spacious one-bedroom / one-bath layouts, six (6) large one-bedroom / one-bath apartments, and six (6) enormous two-bedroom / one-bath floorplans. All the apartments include oversized family rooms, high ceilings, ornate trim, tremendous closet space, and hardwood flooring throughout. Twelve of the layouts include large formal dining rooms. Additionally, over the years, most of the units received moderate updates.

Notable improvements to the building include separately metered electric with a 400 AMP service, a new tar roof layer and flashing in 2019, new wood porches, and mostly galvanized plumbing. Steam heat is provided to all the apartments via a Smith Cast Iron Boiler and domestic hot water is provided by an A.O Smith Hot Water Heater.

7515-21 N. Winchester Ave. is an extremely low-maintenance property with very manageable expenses. Based on comparable properties in the area, the subject’s rents are arguably 20% below the market. The property also offers a new owner multiple value-add opportunities. With the favorably sized units and an unprecedented demand for housing in this East Rogers Park location, a new owner can achieve tremendous future upside.


Known for its beaches, vintage apartments, cultural diversity, and Loyola University, Rogers Park is one of Chicago's most robust lakefront communities. Just ten miles North of Chicago's Central Business District, Rogers Park has convenient transportation to and from the city including four CTA "L" stops (Loyola, Morse, Jarvis, & Howard stops); one Metra Train stop at Lunt Avenue; five local bus lines; and the Howard Bus and "L" terminal which is the starting point for north suburban travel.

Rogers Park, boasting a population of just over 60,000 people, stretches along Lake Michigan between Devon and Howard and runs west to Ridge Avenue. The neighborhood is home to over 130 restaurants and just as many diverse retail offerings along its central corridors and quaint, tree-lined streets.

Also of great impact to the Rogers Park neighborhood is the explosive growth in enrollment at Loyola University. The University’s Lake Shore Campus is just steps away from the subject property and is home to over 16,000 students and 1,000 faculty members. Eighteen of Loyola University’s nineteen residence hall buildings are located in the Edgewater and Rogers Park neighborhoods, prompting established retailers and eateries to open convenient locations along the campus’ perimeter.

  • Prime Location in East Rogers Park
  • 27-Unit Courtyard Apartment Building
  • Family Owned for Nearly 20 Years and Extremely Well Maintained
  • Enormous One- & Two-Bedroom Layouts
  • Twelve Apartments Include Large Separate Dining Rooms
  • True Value-Add Opportunity with Ability to Increase Revenue by ~20%
  • First Time on the Market in Decades
Steven Livaditis
Jacob Goldstein