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5 Beds ⋅ 3 Baths ⋅ 12527685 MLS ⋅ CLOSED Status

An exceptional opportunity to own a beautifully renovated brick 2-flat in the highly sought-after Hyde Park neighborhood - just steps from the University of Chicago, shopping and dining, and area scenic parklands. This turnkey property features two spacious residences, including a bright 3-bedroom unit and a well-appointed 2-bedroom unit, along with a fully finished basement offering valuable additional space. Each unit has been thoughtfully updated with modern finishes, showcasing renovated kitchens with quartz countertops, stainless steel appliances, and contemporary cabinetry, as well as fully updated bathrooms. Recent improvements include newer windows, individual forced-air heating and central air conditioning systems for each unit, ensuring year-round comfort and efficiency. The finished basement offers flexible additional living space ideal for a recreation room, home office, or extended living arrangement. Outdoor amenities include rear porches, a private yard perfect for summer enjoyment, and a 2-car garage for added convenience. Ideal for both owner-occupants and investors, this property offers strong rental potential in one of Chicago's most desirable neighborhoods, just moments from the University of Chicago campus.

5337 S Maryland Avenue, Chicago

$405,000

9 Beds ⋅ 3 Baths ⋅ 12549706 MLS ⋅ CLOSED Status

Exceptional investment opportunity in a prime Hyde Park location. Solid all-brick 2-unit building with a potential bonus garden apartment presents the perfect opportunity for investors or owner-occupants looking to build sweat equity. The main floor features a spacious 3-bedroom, 1-bath unit, while the upper level offers a generous 4-bedroom, 1-bath layout. The finished walk-out basement was configured as a 2-bedroom, 1-bath unit with laundry hookups-ideal for added rental income. Situated on an extra-deep, fully fenced lot with a 2-car garage, this property is just blocks from the University of Chicago campus and the future Chicago Medicine cancer center, ensuring a steady stream of student and professional tenants. A rare chance to own a historic Hyde Park gem in an unbeatable location.

5239 S Ingleside Avenue, Chicago

$975,000

12 Beds ⋅ 7 Baths ⋅ 12544884 MLS ⋅ CLOSED Status

MULTIPLE OFFERS RECEIVED. HIGHEST AND BEST/ OFFER DEADLINE 1/19/2026 AT 12:00 pm. 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!

5319 S Maryland Avenue, Chicago

$1,175,000

15 Beds ⋅ 10 Baths ⋅ 12385728 MLS ⋅ CLOSED Status

BIG PRICE REDUCTION!!! ATTENTION REHABBERS AND REMODELERS! TREMENDOUS VALUE ADD PLAY! PRIME HYDE PARK LOCATION, CLOSE TO THEUNIVERSITY OF CHICAGO. THREE (3) MASSIVE APARTMENTS - 9 ROOM, 5 BEDROOM, 3 BATHROOM-2800 SQ FT EACH, PLUS A PARTIALLY FINISHED BASEMENT WITH8.5 CEILINGS, LARGE WINDOWS, AND A FULL BATHROOM. 11,250 TOTAL BUILDING SQ.FT. BUILDING IS VACANT AND NEEDS COSMETIC REHAB. PRICE REDUCED TO$1,175,000! DON'T MISS OUT ON THIS RARE GEM! CONTACT US FOR A PRIVATE TOUR.

1347 E Hyde Park Boulevard, Chicago

$500,000

5 Beds ⋅ 2 Baths ⋅ 12284808 MLS ⋅ CLOSED Status

Zoned as 2-Family. This Hyde Park home offers a rare opportunity to own a historic gem in a prime location. This versatile layout provides separate living spaces, offering multifamily use or rental income. Lower unit level has a family room, dining area, kitchen, 2 bedrooms, and 1 full bath while the Upper unit has its own living room, dining area, 3 bedrooms, a bonus room, and 1 full bath. Laundry area in the unfinished basement. Situated on a deep fenced 25x162 lot and currently designed for multifamily living, it provides versatile options for living or rental income. Just two blocks away from the prestigious University of Chicago Campus. Estate sale, sold as is.

5476 S Woodlawn Avenue, Chicago

$870,888

7 Beds ⋅ 5 Baths ⋅ 12054666 MLS ⋅ CLOSED Status

$50K price reduction from $945K to $895K! Completely renovated LEGAL 3 flat 1 block from U of C campus and 2 blocks from the future $815 million University of Chicago Medicine cancer center in Hyde Park. All units have been remodeled which include 3bd/2bath top floor, 2bd/2bath middle floor, and 2Bd/1bath garden unit. $85K of rental income in-place ($7108/mo); with parking (vacant) would be ~$89K. So nearly 10x GRM deal in attractive Hyde Park! Renovations include copper and pvc plumbing, electric (new 200 amp electric service to building), kitchens, bathrooms, and appliances. All NEW pvc sewer line under the building, drain tile system throughout garden, water heaters (3), boilers (2nd and 1st floor), HVAC (garden), side secure metal gate, and rear balcony steel stairs. Garden unit (nearly finished and expected to be done in next couple weeks) has been completely remodeled to the studs with full plans and permits. Seller to close out all paperwork on permits prior to closing. Amazing opportunity for live in owner or investor with strong current rents and long term appreciation in this location. The University of Chicago ranked #12 Nationally in the United States last year and is home to roughly 18,500 students (undergrad and graduate).

5428 S Drexel Avenue, Chicago

$360,000

5 Beds ⋅ 2 Baths ⋅ 11950267 MLS ⋅ CLOSED Status

ATTENTION DEVELOPERS & BUILDERS!! RT-4 Legal 2 flat with 3 units perfect for deconversion to SFH or Duplex-up 2nd unit and convert to 3 or 4 bed. Was orignally a 3 story SFH, converted to 3 units. Owner began rehab - new electrical and plumbing 2011. Needs experienced developer/builder to rehab. No garage, unfinished basement. "As-is" Cash only. Seller requires 3-5 week post-closing possession

5455 S Kenwood Avenue, Chicago

$770,139

6 Beds ⋅ 5 Baths ⋅ 11971486 MLS ⋅ CLOSED Status

Rarely available HUGE three (3) unit building with two (2) car garage in sought after HYDE PARK location. This hidden gem has two massive 2,200 SF three (3) bedroom, two (2) bath apartments and one 1,000 SF loft garden apartment. All apartments have been meticulously renovated with newer kitchens and baths and have fantastic layouts with large room sizes and large eat-in kitchens. The three(3) bedroom units have huge dining rooms with coved ceilings and butler's pantries, and abundant closets including a cedar closet. The building has also been upgraded with new 400-amp electric service and new wiring, new copper plumbing and in unit sleeve air conditioning. Tremendous opportunity for someone looking for a great place to live with additional income.

822 E 52Nd Street, Chicago

$592,500

8 Beds ⋅ 5 Baths ⋅ 11821387 MLS ⋅ CLOSED Status

Attention investors and house hackers!!! Welcome to 5319 S. Ellis Ave., a remarkable multi-family building in the heart of Hyde Park. This elegant brick walk- up exudes timeless charm, showcasing classic historic Chicago architecture while boasting excellent income. The property has two spacious 3-bedroom | 2-bathroom units and a bonus non-conforming garden unit with 2 bedrooms and 1 bathroom. Meticulously cared for, this building has undergone regular maintenance and updates since its 2009 renovation. Each apartment offers an irresistible blend of desirable features, including open floor plans, generous square footage, ample bedroom space, and abundant natural light. The units have been thoughtfully enhanced with updated kitchens and the convenience of in-unit laundry. Owner expenses are minimized through individual and separate utilities. 5319 S. Ellis Avenue presents a remarkable investment opportunity for those seeking to acquire a property in the highly sought-after Hyde Park neighborhood, one of Chicago's most dynamic and rapidly developing areas. With this investment, a new owner can capitalize on the potential to add value without incurring the substantial costs associated with a full-scale construction renovation. By adjusting rental rates to match those already achieved within the building, the incoming owner can further enhance its income potential. Live in one unit and let the rest of the building pay your mortgage or add to your portfolio for a long term hold. This unique offering allows for the acquisition of a stable investment with upside in an excellent location, ensuring a solid cash-on- cash return for years to come.

5319 S Ellis Avenue, Chicago

$888,888

7 Beds ⋅ 4 Baths ⋅ 11625689 MLS ⋅ CLOSED Status

A truly unique opportunity! Steps from both the best of Hyde Park as well as the University of Chicago Campus and Hospital, this residential property offers 5,456 square feet of opportunity rarely available. Since its purchase in 1956, a nearly 2,700 sq. ft. family home occupied the top two floors of this brick 3-flat while also offering a large 1st-floor rental to extended family and friends. Effectively, a 4,100 sq. ft. above-grade private home in a highly-coveted area of Hyde Park. That was the building's most recent past. Today ... its abundance of livable space, prime location, and large yard and multi-car garage will provide the new owner with a blank canvas. You're invited to view the property and determine for yourself its future. Property sold As-Is. Viewings by appointment only. Lot: 4,966 sq. ft. (28' 4 1/2" x 175') PIN: 20114200190000. LEGAL DESCRIPTION: The North 28 feet 4 1/2 inches of Lot 12 in the Block 29 in Kimbark's Addition to Hyde Park in Section 11, Township 38 North, Range 14, East of the Third Principal Meridian, commonly known as 5431 South Woodlawn Avenue

5431 S Woodlawn Avenue, Chicago

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