Busy Developer Adds Three More Three-Flats On South Maryland Avenue In Woodlawn

South Maryland Avenue three-flats permitted6549-6553 South Maryland Avenue, via Google Street View

A local developer that’s been busy on the South Side added three more permits to their Woodlawn collection of three-flat builds last week. Using the entity of Maryland Flats LLC, Kasper Development LLC scored permission for three-unit residences at 6549, 6551. and 6553 South Maryland Avenue on June 25, each including reported costs or $450,000. All show application start dates of May 4, spending 52 days apiece in the data portal.

South Maryland Avenue three-flats permitted

Site context of 6549-6553 South Maryland Avenue, via Google Maps

Peter Sterniuk is named as the architect of record, with Kasper handing general contracting duties. The three-story structures will not include basement levels, and there will be no garages. Instead, three surface parking spaces will be added at the rear of each lot, accessed from the alley connecting East 65th Street and Marquette Road. Each building will have rear three-story stairways with landing decks.

Across the street, Kasper Development got three permits in June and July of last summer to build another trio of three-flats, which Google Street View shows under construction back in October of last year. They are now listed for rent.  And on the east side of the same block, they got permission for two three-flats at 6543 and 6547 South Maryland two months ago. A third building, at 641 South Maryland, was permitted to a different owner back in December, with Kasper serving as the general contractor. But in January of this year, a revision was issued naming them as the new property owner. That means nine buildings and 27 dwelling units filling in several vacant parcels.

Listing photo of 6550 South Maryland Avenue rental, via redfin

Listing photo of 6550 South Maryland Avenue rental, via redfin

6541 South Maryland Avenue three-flat permitted

6548-6552 South Maryland under construction, via Google Street View

South Maryland Avenue three-flats permitted

Local transit options, via Google Maps

Residents of 6549 South Maryland et al will live within one block’s walk of CTA service via the Route 4 bus at South Cottage Grove Avenue. Less than two blocks south are stops for Routes 4, X4, 67, 95, and N5 buses at Cottage Grove and East 67th Street. The Cottage Grove Green Line elevated platform is about three blocks to the north.

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7 Comments on "Busy Developer Adds Three More Three-Flats On South Maryland Avenue In Woodlawn"

  1. Le Courvoisier | July 7, 2026 at 9:13 am | Reply

    A side gallery is not something you see every day.

    • Former Housing Architect | July 7, 2026 at 12:46 pm | Reply

      Came here to say that, very curious as to how the interior units are laid out, as it seems to be a mid building entry to the units.

  2. “Residents will have access to an abandoned e-bike sprawled on the sidewalk near a fire plug, just steps from the Divvy station at 67th Street and Cottage Grove.” 🙂

  3. This is my Grammer school and playground my memories , hate to see it all gone except from the boarded up convent. Please
    let’s have some diversity, imagination! no more of the same o same o that is being built especially in Woodlawn!

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