View All Hyde Park Chicago IL Greystone Homes Listings

4 Beds ⋅ 4 Baths ⋅ 12755067 MLS ⋅ ACTIVE Status

Welcome to this stately Greystone row house in Chicago's architecturally rich and historic Hyde Park-Kenwood District. Offering an impressive 3,378 sq/ft across three stories, this timeless 4 bed, 3.1 bath residence presents a rare opportunity for inspired design or adaptive reuse. Many original architectural details remain including coffered ceilings, custom windows and millwork and original hardwood flooring, all reflecting the home's classic craftmanship. A full basement provides excellent potential for additional finished living space. Ideally located within walking distance to shopping and restaurants, parks, Kenwood Academy, the Metra, the University of Chicago and the lakefront, this property combines historic charm with everyday convenience. Formerly operated as an early learning center, the building is equipped with commercial grade fire protection, opening the door to alternative uses such as a day care, group home, or sober living house (buyer to verify permitted uses). A truly unique offering in one of Chicago's most distinguished neighborhoods. This property may be eligible for up to $25,000 in forgivable down payment assistance. Please check under the additional info tab for details on Wintrust's current DPA program specific to Cook County.

5114 S Dorchester Avenue, Chicago

$1,595,000

5 Beds ⋅ 5 Baths ⋅ 12714609 MLS ⋅ PENDING Status

Beautifully updated Hyde Park Greystone ideally located just steps from the University of Chicago Laboratory Schools and the University of Chicago campus. Offering over 4,500 square feet of thoughtfully designed living space, this exceptional single-family home features 5 bedrooms plus an office, 4.5 bathrooms, and an abundance of flexible living areas. Major updates include a newer roof and mechanical systems, including the air conditioning compressor and air handler, boiler, and hot water tank. The main level showcases timeless architectural details, beginning with a welcoming sitting room featuring inviting bay windows and a wall of built-in bookshelves. The elegant living room centers around a wood-burning fireplace with its stunning original mantel and flows seamlessly into a separate formal dining room through beautiful glass-paneled doors. The updated eat-in kitchen overlooks the expansive patio, backyard, and outdoor entertaining area. Upstairs features a spacious primary bedroom with an updated en-suite bath. Two additional large and one smaller bedroom and a full hall bath along with generous hallway closets complete this level. The versatile third floor provides exceptional flexibility with a large bedroom featuring bay windows, a full bath, walk-in closet, and a private office. This space functions equally well as a luxurious primary suite, guest suite, family room, or private retreat. The finished lower level adds even more living space with a large family room, full bath, laundry area, abundant storage, and a flexible room ideal as a sixth bedroom, second office, exercise room, or playroom. A covered exterior walkway accessible from the lower level provides convenient outdoor access and secure storage for bicycles, gardening equipment, outdoor furniture, and more. Combining classic Hyde Park architecture with extensive updates, generous living spaces, and an unbeatable location, this is a rare opportunity to own a move-in-ready historic home in one of Chicago's most sought-after neighborhoods.

5801 S Blackstone Avenue, Chicago

$315,000

3 Beds ⋅ 2 Baths ⋅ 12591217 MLS ⋅ CLOSED Status

Perfect Hyde Park location! In this beautiful Greystone building across from Bixler Park find this spacious, bright 3 bedroom, 2 bath condo with separate living and dining room, large eat-in kitchen (this was formerly a 4 bedroom unit) and a cute little balcony. Spacious rooms throughout, primary bathroom is updated and features a large walk-in bathtub. Well managed association, basement storage and free laundry room. Unit is in need of some TLC and work. Welcome!

5701 S Kenwood Avenue Unit #2, 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

$935,000

4 Beds ⋅ 4 Baths ⋅ 12505143 MLS ⋅ CLOSED Status

Breathtaking Greystone Row House PERFECTLY situated across the street from Nichols Park and super easy walk to shops, restaurants, Univ of Chi, transport, etc. Expect all the charm and character of a 1909 classic with all the updates and upgrades that honor the home and make for great living. Be TOTALLY surprised with the great light, high ceilings throughout and thoughtful + flex spaces. Main floor has double living room with wood burning fireplace, combo dining and oversized kitchen with loads of prep and serve space +stunning views in every direction, and a jewel of a powder room. Walk out to new deck, fenced in spacious and lush back yard. Upstairs find three bedrooms with ensuite baths, primary with an original fireplace and loads of light and more great views. Bright lower level is another great surprise with extra-large bedroom, family room, work room, laundry room, bath and loads of storage. Most work including tear off roof/HVAC/tuckpointing/kitchen and baths done in 2019, whole house refresh + new lower level floors, back deck, fenced yard in time for your visit! This is one happy house! Enjoy!

5408 S Kimbark Avenue, Chicago

$500,000

4 Beds ⋅ 2 Baths ⋅ 12466703 MLS ⋅ CLOSED Status

Historic Greystone just steps from the University of Chicago! This beautifully updated and spacious 4-bedroom, 2-bath condominium seamlessly blends vintage charm with modern comfort. Perfectly positioned just steps from the University of Chicago and The Laboratory Schools, this residence occupies the entire third floor of a classic greystone. Inside, abundant natural light fills every room, highlighting original hardwood floors, gleaming period woodwork, and a stylish fireplace surrounded by built in bookshelves. The enlarged kitchen and tastefully renovated bathrooms provide contemporary convenience, while the home's freshly painted interiors preserve its timeless elegance. Enjoy tree-top views, outdoor living on the large private deck overlooking a landscaped yard, plus a skylit entry, a full size washer/dryer in the basement, generous basement storage, and a lush communal yard and garden. This self-managed, well-maintained building boasts a strong, stable association and sits within one of Chicago's most historic and picturesque neighborhoods - the perfect combination of space, charm, and unbeatable location. Welcome home!

5741 S Kenwood Avenue Unit #3, Chicago

$650,000

4 Beds ⋅ 2 Baths ⋅ 12303717 MLS ⋅ CLOSED Status

5429 Drexel is a handsome, Victorian 4 bedroom, 2 bath SFH located the heart of Hyde Park. It is a classic Chicago Greystone with beautiful original architectural features including oak trim, pocket doors, built-ins, and excellent plaster moldings throughout. The spacious primary bedroom has west facing bay windows, a comfortable seating area and one of two decorative fireplaces. The sunny roof deck (20'x20') above the 2-car garage is private and quiet. The large walk-out basement has the potential to be incorporated into the home or developed into a separate living space with its own front entrance. Great location, a short walk to The University of Chicago and the U of C hospital complex, just steps from Bessie Coleman Park and close to all the amenities that Hyde Park has to offer. Being sold "As Is".

5429 S Drexel Avenue, Chicago

$699,000

4 Beds ⋅ 2 Baths ⋅ 12346829 MLS ⋅ CLOSED Status

Hyde Park 4Bedroom SFH with yard and two car garage parking! Located on a lovely tree lined street, the beautiful greystone residence was built in the Neoclassical design and has many original architectural features alongside updated neutral finishes creating a unique, warm and inviting interior. The living, family and dining room are bright spaces- all with hardwood flooring and 10 foot ceilings. In the dining room, the focal points are the beautifully tiled decorative fireplace and coffered ceiling. The space can easily accommodates a table of 12. Kitchen, mud room plus a half bath complete the floor plan on the main level. Kitchen has custom cabinetry with soft close drawers, all stainless steel appliances, butcher block counter tops and a pot filler plus sufficient space for a sitting area for meals or work. Along the side of the kitchen: a convenient and generous mud room- making arrivals and departures easy and effortless. All of the bedrooms are located on the second floor. The primary faces East and has a lovely bay area. The open concept partially finished basement is spacious with a separate laundry room. Outdoor spaces include a custom deck off the kitchen-with retractable flooring to assist with the delivery of items into the basement, two car garage, yard with areas for plants and a side yard. Recent updates and upgrades to note: freshly painted throughout, tankless water heater, whole house Aquasana water filtration system, R30 insulation in the 2nd floor and a new garage roof. Excellent location within easy walking distance of the University of Chicago and its Hospitals, green spaces, shopping District on 53rd street and 55th. A true Hyde Park gem!

5316 S Drexel Avenue, Chicago

$875,000

4 Beds ⋅ 4 Baths ⋅ 12213766 MLS ⋅ CLOSED Status

Beautifully restored oversized greystone with a two-story addition just steps to Bessie Coleman Park and the best of Hyde Park. This exquisitely renovated Greystone, nestled on a peaceful tree-lined street located in the heart of the University of Chicago with all the modern finishes you desire: open concept kitchen, recessed LED lights, up-lighting, hardwood floors throughout, steel balusters, window sills, and casing and pendant lighting. This stunning residence boasts four bedrooms, 3.1 bathrooms, and a multipurpose room blending historic charm with modern luxury. The first floor opens up to a large living, dining room, and parlor with an open kitchen featuring white shaker cabinets with pantry cabinet and glass backsplash; stainless steel appliances: range, microwave, chef's hood, and french door refrigerator; and large island for four. The second floor features four generous bedrooms, including the large master suite, which is a private retreat with dual closets and a primary en-suite. The fully finished lower level offers a full bathroom, laundry, storage, and a versatile recreation room, perfect for entertaining guests. Step out your back door to a rear deck with a pergola, backyard, and two-car garage with storage. Don't miss the opportunity to experience a historic facade and features with contemporary layout and design.

5344 S Drexel Avenue, Chicago

$1,225,000

5 Beds ⋅ 4 Baths ⋅ 12043767 MLS ⋅ CLOSED Status

This distinguished Greystone row house, in a prime campus location, spans approximately 3,000 square feet with five bedrooms and four full bathrooms. Built in the late nineteenth century and updated for modern living, this beautiful home retains many wonderful period elements such as the original inlaid floors, 10' cove ceilings and pocket doors. The main floor features a welcoming living room with bay window, decorative tile-surround fireplace and built-in shutters and bookshelves. It leads to a separate dining room that can be closed off with pocket doors and French doors, which, in turn, adjoins a large eat-in kitchen with a huge picture window that overlooks the leafy backyard. From the kitchen, there is access to an elevated deck for outdoor seating/dining and stairs to the backyard. A full bathroom and coat closet complete the space on this floor. As one ascends the stairs to the upper floor, a large skylight casts light on the upstairs hallway that leads to three sizeable bedrooms and two bathrooms. The primary bedroom, which was relocated from the front of the house to the back for greater privacy, was extensively remodeled to maximize views of the mature trees in the backyard and enhanced as an en suite with a walk-in closet, walk-in shower, dual vanities and radiant floors. The lower level features a family room that is equipped with HDMI cable, projector, retractable screen and built-in speakers for movie nights; two bedrooms; laundry and a work room. With a separate entrance leading to the street and egress at the back, this space can function as guest or extended family quarters. The house has triple zone heating and newer compressors (July 2023) for dual zone SpacePak air conditioning. There are two parking spaces behind the house, where a garage could be built. The location is one block from Lab School and around the corner from the eateries and book store on 57th St. Ray school district. See floor plans under "Additional Information".

5714 S Kimbark Avenue, Chicago

$1,700,000

6 Beds ⋅ 5 Baths ⋅ 11920145 MLS ⋅ CLOSED Status

How does it sound to basically roll out of bed to go to work or school? Amazing opportunity to live in the best location in Hyde Park! This bright and sunny classic greystone house dating back to the Columbian Exposition, and reportedly built by the chief electrician at the fair, is steps from UChicago and the Laboratory Schools with a generous yard and three-car garage. Lovely double-parlor living room with fireplace leading to a gracious dining room. Kitchen has an eat in space with a large picture window overlooking the backyard. This leads to a large solarium adding family room space to the first floor. The second floor has four comfortable bedrooms and two full baths, as well as a smaller room that could be used as an office space or additional storage. The third floor has two more bedrooms and another full bath. The basement has laundry room, playroom/family room, workroom and a half bath. This home awaits your updates and improvements. And it has a 3-car garage!

5747 S Kimbark Avenue, Chicago

$625,000

4 Beds ⋅ 3 Baths ⋅ 11855116 MLS ⋅ CLOSED Status

Step into the heart of Hyde Park and discover the essence of modern comfort and timeless sophistication in this meticulously renovated greystone condo. Boasting a generous 2400 sqft, this residence is designed to embrace your lifestyle with 4 spacious bedrooms and 2.5 baths, offering an abundance of space for family and guests. Indulge your culinary passions in the gourmet kitchen, a haven of culinary excellence equipped with premium stainless steel appliances, including a Viking oven-a chef's dream. Beyond functionality, the kitchen seamlessly blends with the living space, making entertaining a delight. Immerse yourself in the welcoming atmosphere created by the interplay of beautiful hardwood floors and soaring ceilings that channel natural light through expansive windows. The primary bedroom is a haven of tranquility, featuring a generous walk-in closet and an opulent en-suite bathroom boasting a jetted tub and a separate shower. Safety and convenience are paramount, and this residence delivers on both fronts. A garage ensures your vehicle is secure, while the fenced-in front and back yards provide privacy and outdoor space. The elegant bay window at the front adds a touch of classic charm to the facade. Recent updates elevate this residence to the pinnacle of modern living. The entire interior has been refreshed with Benjamin Moore paints, and the living room's wood floor has been expertly refinished. LED Ambient Lighting, vanity lights, and decorative lights have been thoughtfully installed throughout, all with dimmable features. Functional beauty continues in the kitchen with new task lighting under the 42" cabinets. Modern appliances, including a dishwasher, have been seamlessly integrated, and new carpets grace three of the bedrooms. Comfort meets technology with new ceiling fans featuring built-in LED lights and remote controls in all bedrooms. The bathrooms are equipped with fans featuring convenient timers. The appeal extends beyond the unit, with newer amenities such as a washer/dryer combo, disposal, and refrigerator. The building's roof, less than a year old, offers peace of mind. Location is key, and this residence places you just steps away from UChicago campus, North Dorm, and an array of conveniences. A Starbucks on the corner, walking distance to Chicago Lab, a private school K-12, and inclusion in the Ray School District make this an enviable address. Elevate your lifestyle and embrace the allure of Hyde Park living. Your new home awaits!

5482 S Woodlawn Avenue Unit #2, Chicago

$1,600,000

11806992 MLS ⋅ CLOSED Status

RARE OPPORTUNITY TO ACQUIRE 5132-5136 S BLACKSTONE AVE., A 12 UNIT APARTMENT BUILDING IN THE HYDE PARK NEIGHBORHOOD OF CHICAGO. THE PROPERTY IS ON A HUGE 72 X 151 LOT AND IS ZONED RM5. ORIGINALLY DESIGNED BY THE WORLD-FAMOUS ARCHITECT AND ARTISAN, EDGAR MILLER, THE PROPERTY CONSISTS OF TWO ATTRACTIVE GREYSTONE BUILDINGS SEPARATED BY A COURTYARD IN THE REAR. THE 5136 BUILDING, ORIGINALLY A 15 ROOM SINGLE FAMILY RESIDENCE, NOW HAS 5 UNITS. THE 5132 BUILDING, ORIGINALLY A VERY LARGE 3 FLAT, NOW HAS 7 UNITS. THE TOTAL UNIT MIX CONSISTS OF ONE 3 BEDROOM 3 BATH UNIT, ONE 2 BDROOM 1 BATH UNIT, NINE 1 BEDROOM ONE BATH UNITS, AND ONE VERY LARGE LOFT STUDIO. THERE IS ALSO A 2 CAR GARAGE AND A PARKING PAD FOR 2 ADDITIONAL CARS. THE BUILDING HAS HAD A CONSISTENTLY HIGH OCCUPANCY AND THE APARTMENTS ARE EASY TO RENT. WHILE A FEW OF THE UNITS HAVE BEEN RENOVATED, AND THERE IS A NEWER BOILER AND NEW HOT WATER HEATER, THE BUIDINGS COULD STILL USE FURTHER IMPROVEMENTS AND IS BEING SOLD "AS IS."

5136 S Blackstone Avenue, Chicago

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Hyde Park, Chicago IL · Curated MLS Search

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