5319 S Maryland Avenue Meticulously maintained 3-unit solid Greystone on an oversized 50' x 120' lot with a 4 car detached garage and recently refurbished rear decks. This property combines classic architecture with modern upgrades and strong investment potential. Each unit gets truly amazing light through oversized windows and 4 direction exposures. Steps to CTA Express bus downtown, DuSable Lake Shore Drive, Kenwood High School, Lab Schools, Whole Foods, Starbucks, 'Downtown Hyde Park' shopping/ dining, and University of Chicago Medical complex. This absolutely massive 3-unit property features: 12 total Bedrooms. 7 total baths. Huge rear decks. 4- car detached brick garage. Lush perennial side and rear gardens. Original hardwood floors. Units 2 and 3 feature 4- bedrooms, 2- baths, and double parlors. Unit 1 (owners unit) features 3- bedrooms, 2- baths and connects with a separate studio garden unit via a private interior stair. All units have formal dining rooms Additional features: Original millwork. Pocket doors. Working transoms. Major upgrades include: Three furnaces (oldest 2021, serviced annually). Two of the three water heaters replaced in 2022-2023. Parapet walls refurbished (2022 & 2024). Roof resurfaced & silver-coated (2024). Sewer lines cleaned & epoxy-coated (50-year transferable warranty, 2021). 17 of the double-pane windows replaced (2024). Owner's Unit: New washer/dryer, newer stove & refrigerator (2023). Garden Unit: Private side entrance via new, secure storm door, Full bath with deep soaker spa tub, offering excellent in- law arrangement or short-term rental potential (Airbnb-ready). Tenant Amenities: New coin-operated laundry in basement. Each unit pays its own utilities. Located in the sought-after Kenwood/Hyde Park- steps from the University of Chicago, lakefront trails, parks, dining, and cultural landmarks. Perfect for owner-occupant or investor seeking turnkey income and long-term durability. Please check out the 3 virtual tours!