Refine Search
Sort by
$975,000
3 Beds 4 Baths 12697117 MLS ACTIVE Status
Price improvement! A rare opportunity to own a quintessential vintage rowhome in the heart of historic Hyde Park-where timeless architecture and thoughtful modern updates come together to create an exceptional place to call home. Offering 3 bedrooms plus a bonus room, 3.5 bathrooms, a fully finished walk-out basement, private outdoor space, 2nd floor laundry, central AC, and heat (dual zoned) and a garage, this spacious residence delivers the character of a classic Chicago home with the comfort and functionality of today's lifestyle. From the moment you arrive, you'll be captivated by the home's striking historic facade, intricate architectural details, and inviting front porch. Step through the private vestibule into a gracious foyer that opens to an expansive main level filled with warmth and natural light. Oversized west-facing windows illuminate the home from front to back, while original-inspired moldings, soaring ceilings, and rich architectural details showcase the craftsmanship that makes Hyde Park's historic homes so beloved. Designed for both elegant entertaining and everyday living, the open floor plan offers generous spaces for formal living and dining rooms, a comfortable family room, and a spectacular chef's kitchen that serves as the heart of the home. Beautifully blending classic style with contemporary design, the kitchen features custom cabinetry, an oversized quartz island, double ovens, designer lighting, abundant storage, and premium finishes that make every gathering effortless. A convenient powder room completes the main level. The home's beautiful staircase serves as a stunning architectural centerpiece, leading to the second floor where you'll find three spacious bedrooms, two full bathrooms, and a versatile bonus room-ideal as a home office, nursery, reading room, or dressing area. The serene primary suite offers oversized windows that flood the room with natural light, along with a spacious en-suite bathroom designed for comfort and privacy. A full-size laundry room on the second floor adds everyday convenience. The fully finished walk-out basement expands the home's incredible living space with a large recreation room, flexible bonus area perfect for a home gym, media room, or guest suite, a full bathroom, another laundry room, and an exterior exit for added convenience and versatility. Outside, enjoy your own private retreat featuring a spacious deck, generous backyard, and garage parking-an uncommon combination in one of Chicago's most sought-after historic neighborhoods. Perfectly situated just moments from the University of Chicago, neighborhood parks, acclaimed restaurants, charming cafes, shopping, and the lakefront, this exceptional home offers the best of Hyde Park living while preserving the timeless character that makes the neighborhood one of Chicago's architectural treasures. Welcome home.

5403 S Greenwood Avenue, Chicago

$875,000
4 Beds 3 Baths 12559482 MLS CLOSED Status
DRAMATIC PRICE REDUCTION TO $925,000. A time-sensitive seller relocation creates an incredible opportunity for one savvy buyer. The sellers are serious, and this home is now priced for an immediate sale. Bring your offers; this will not last. Vintage charm and modern versatility in this lovingly maintained 1892 worker cottage in Hyde Park, owned by the same family for 40 years. Enter through a welcoming foyer on the lower level, featuring a flexible bedroom/office, open-concept laundry area with kitchenette, mechanical room, a newly remodeled full bath with walk-in shower and heated floors, and a second bedroom with backyard access. Upstairs, the first level offers a spacious kitchen with an extended breakfast area under an oversized skylight and a patio door leading to a large wood deck and mature garden. A full bath with soaking tub, bright living room highlighted by a gorgeous fireplace-once wood-burning, now electric, with its original mantel and firebox preserved for historic charm, and a spacious dining room with built-ins complete this floor. The second level includes a vaulted-ceiling primary suite with skylights, walk-in closet, and tandem room with built-ins, plus a second bedroom and updated full bath with walk-in shower. The third (attic) level features an open loft/library with built-in bookcases and soaring ceilings. No basement-every square foot is a functional living space. Upgrades include split air-conditioning, updated mechanicals, fresh paint, and new carpet. Enjoy this unique and landmark status home which reflects design of early Hyde Park homes built around the Columbian Exposition. Schedule a private tour today!

5428 S Blackstone Avenue, Chicago

$560,000
3 Beds 2 Baths 12196742 MLS CLOSED Status
This "original" on Professors' Row in Hyde Park is located on the most beautiful one-way block of Greenwood. These distinctive brick and stone homes were developed in 1903 by Samuel E. Gross, and the architect was J.C. Brompton. This gem of a location is stolen out of storybooks. Surrounded by a cascade of trees, you feel like you're in the country, not the city. It's an extraordinary place that grabs hold of you; many live their entire lives here. Rarely do these treasures become available. Stepping into the foyer, you're immediately drawn into the living and formal dining rooms with 10 ft ceilings, an original wood-burning fireplace, and an adjacent rounded parlor room bathed in natural light from three windows. The open, spacious kitchen offers a separate eat-in area. A full bathroom on the main floor makes this an ideal layout. The grand staircase is flooded with natural light from the skylight, leading to three spacious bedrooms + an office, and another full bath. Many original details throughout include wood trim, doors, and hardware. All can be revealed and restored to the original. Closet space is plentiful in each room. Outside, you step onto your private deck off the kitchen overlooking your deep backyard and separate 2-car garage. Easy access in and out of the garage as it opens onto Berkley Street. The full height, unfinished basement features side-by-side laundry. This stunning vintage home is one of only 20 in Hyde Park and has been owned by the same family for 60+ years. This is an 'As-Is' Estate Sale. I don't have guaranteed information, but to the best recollection, most windows were replaced in the early 2000s, the furnace in 2006, the water heater and electricity were updated in 2015, and appliances were replaced in 2017-2023. This is a fantastic opportunity to revive a unique piece of history. The location can't be beat and is within walking distance of the University of Chicago, Hyde Park shopping center, restaurants, parks, beaches, and public transportation.

5226 S Greenwood Avenue, Chicago

$1,275,000
4 Beds 3 Baths 12064083 MLS CLOSED Status
This charming home was a part of Hyde Park's first planned community, built way back in the 1880s and then known as Rosalie Villas. To this day, Harper Avenue remains one of Hyde Park's most special and coveted locations. When the current owners purchased 5724, the house has been in the hands of the same family for the forty-two years. They then undertook a thoughtful renovation, preserving the character of 19th century details while upgrading the house for modern living. With new electrical, zoned air conditioning, new hot water heater, water filtration system, new bathroom, new flooring and lighting, and a completion of the entire third level (formerly an unfinished attic) - the house has been beautifully updated. The large front porch opens into the foyer, where one is immediately impressed with spaciousness. This is a warm and welcoming house, with an open floor plan that defies its age. Light fills the living and family rooms; a lovely separate dining room, large kitchen with pantry, breakfast room and powder room complete this level. The breakfast room opens to a deck that overlooks the lush back yard. Moving up the beautifully detailed staircase, there are four bedrooms that can be used in a variety of ways, and two full baths. From there one sees a remarkable transformation - the entire third level has been renovated into handsomely finished flexible space. The open area is accented by two smaller rooms and under the eaves is a charming space to relax. Heading downstairs, the lower level is a work in progress but offers all new windows, storage, a laundry room with new washer/dryer and full size freezer, and the space is plumbed for a full bath. The owners are offering a home warranty plan for all appliances. And the property offers a rarity on the block, a large two-car garage. Located a short walk from the University of Chicago, the Laboratory Schools and all Hyde Park has to offer. And now just a bit of background history. Remarkably, nearly all of the Queen Anne and shingle-style homes on Harper are still standing nearly a century and a half later. Years before the founding of the University of Chicago, the development was established by Rosalie Buckingham, a wealthy heiress whose name Chicagoans will likely recognize from Buckingham Fountain in Grant Park, named for Rosalie's cousin. As she neared the age of twenty-five, Rosalie decided to become a property developer in the rapidly expanding Hyde Park Township, which was then still a separate suburb. In 1883, she acquired two city blocks from 57th Street to 59th Street near the Illinois Central tracks and hired Solon S. Beman, who had just designed Chicago's most famous planned community Pullman, to oversee a plan for her land. Beman provided the overall vision and there were rules that homeowners and other architects had to follow for each of the 42 houses. This led to the continuity of size and style of homes visible and appreciated to this day. We do not know the architect of 5724 Rosalie Court, but early records list attorney Addison Beardsley as the resident. All of this is to say .... 5724 Harper is one very special place.

5724 S Harper Avenue, Chicago

$170,000
1 Beds 1 Baths 12070748 MLS CLOSED Status
Beautiful, top floor corner unit with unobstructed north, east and south exposure! Vintage charm abounds. Large south-facing living room has custom, built-in wooden bookcase that matches the natural woodwork throughout the condo. Separate dining area with beautiful view of the homes on Kenwood. Quaint kitchen with light granite counters, white cabinets and great storage. Private deck off the kitchen. Tons of storage thoughout the unit, deep closets in the bedrooms and hallway. Great floorplan! Newer roller shades throughout the unit. The unit has a separate, large storage closet in the basement. Coin laundry and bike rack in basement. Small work out room on the Kimbark side of the building. Janitor on site. Boilers recently replaced! Well maintained building with little turnover! Quick walk to UofC and downtown Hyde Park.

1314 E 56Th Street Unit #3, Chicago

$903,952
3 Beds 3 Baths 12027296 MLS CLOSED Status
Introducing 5114 Kenwood - a collection of new construction luxury condominium residences coming soon to Hyde Park. Tucked along a quiet, tree-lined, one-way street, 5114 Kenwood is set to deliver the product missing in the neighborhood: single-level contemporary living and light-filled duplex residences - boasting incredible private outdoor living spaces - in an elevator-accessible building with secure parking. Acclaimed developer ZSD, having achieved success with mid-rise developments in West Loop, Lincoln Park, and Noble Square, brings their skillful experience and thoughtful design to Hyde Park. Residence 3A is the best-priced single level condo in the building and stretches the length of the 3rd level, with south, west, and east exposures. The elevator delivers residents and guests to a posh foyer and sleek entry. A clean, contemporary aesthetic is carried throughout the home beginning with a massive 19-ft kitchen with flat front cabinetry, large island, pantry closet, and integrated appliances: Bosch dishwasher, Fisher & Paykel refrigerator/freezer, Kitchen-Aid induction range, and externally-vented exhaust hood. The 22-ft wide living room and dining spaces open to a 200 SF east-facing walkout balcony with gas, water, and electric hookups included. Wide-plank wood flooring runs throughout the home. The secluded Primary Suite features a 15-ft wide bedroom, massive dressing room, and contemporary bathroom with floating double vanity, European glass shower, and private water closet. Two secondary bedrooms are designed to easily accommodate a queen bed with nightstands and share an ensuite bathroom featuring porcelain tile, bathtub, wall-hung vanity, and quartz countertop. A powder room is located off the main hallway for non-overnight guests. The private office with natural south light creates a desirable workspace, play area, or game room. Take the elevator to the rooftop to enjoy a private 386 SF rooftop deck with composite decking - entirely private for this residence. One secure parking space included in purchase price. This is the first opportunity for new construction condominium residences in prime Hyde Park in decades -- and is expected to sell out before construction completes. Three homes were already sold before public launch. From 799K to 1.1M. Delivering Summer 2025. Don't miss your chance to call 5114 Kenwood your next home.

5114 S Kenwood Avenue Unit #3A, Chicago

$949,641
3 Beds 3 Baths 12027316 MLS CLOSED Status
Introducing 5114 Kenwood - a collection of new construction luxury condominium residences coming soon to Hyde Park. Tucked along a quiet, tree-lined, one-way street, 5114 Kenwood is set to deliver the product missing in the neighborhood: single-level contemporary living and light-filled duplex residences - boasting incredible private outdoor living spaces - in an elevator-accessible building with secure parking. Acclaimed developer ZSD, having achieved success with mid-rise developments in West Loop, Lincoln Park, and Noble Square, brings their skillful experience and thoughtful design to Hyde Park. Residence 4A stretches the length of the 4th level, with south, west, and east exposures. The elevator delivers residents and guests to a posh foyer and sleek entry. A clean, contemporary aesthetic is carried throughout the home beginning with a massive 19-ft kitchen with flat front cabinetry, large island, pantry closet, and integrated appliances: Bosch dishwasher, Fisher & Paykel refrigerator/freezer, Kitchen-Aid induction range, and externally-vented exhaust hood. The 22-ft wide living room and dining spaces open to a 200 SF east-facing walkout balcony with gas, water, and electric hookups included. Wide-plank wood flooring runs throughout the home. The secluded Primary Suite features a 15-ft wide bedroom, massive dressing room, and contemporary bathroom with floating double vanity, European glass shower, and private water closet. Two secondary bedrooms are designed to easily accommodate a queen bed with nightstands and share an ensuite bathroom featuring porcelain tile, bathtub, wall-hung vanity, and quartz countertop. A powder room is located off the main hallway for non-overnight guests. The private office with natural north light creates a desirable workspace, play area, or game room. Take the elevator to the rooftop to enjoy a private 386 SF rooftop deck with composite decking - entirely private for this residence. One EV-prepped secure parking space included in purchase price. This is the first opportunity for new construction condominium residences in prime Hyde Park in decades -- and is expected to sell out before construction completes. Three homes were already sold before public launch. From 799K to 1.1M. Delivering Summer 2025. Don't miss your chance to call 5114 Kenwood your next home.

5114 S Kenwood Avenue Unit #4A, Chicago

$435,000
5 Beds 3 Baths 11898345 MLS CLOSED Status
This is the opportunity of the year to purchase a mid-century IM Pei E1 row house in close to original condition aggressively priced to reflect a new owner doing substantial work to bring it to 2024 finish. On the University of Chicago campus, it is a terrific location across from the lovely Nichols Park with playgrounds, tennis courts, dog friendly areas and just a lovely place to hang out in all sorts of weather. There is a dedicated parking spot out back, although there is often street parking right out front. A protected bike lane on 55th will get you to the lakefront in minutes if you like to pedal. Trader Joes and Walgreens are down the street and you are surrounded by restaurants at every turn. The house itself is a classic E1 with hardwood floors on the main and third level and hardwood stairs edged by the vertical wood balustrades on the main floor and iron balustrades above. The sunny kitchen has original wood cabinets, the original harvest gold double oven which is currently inoperable, as are the dishwasher, cooktop and vent fan above it. The refrigerator works. The hot water heater and A/C are working well and the roof has had no leaks. Several of the ceilings have been redone. The primary bedroom with ensuite bath extends the entire width of the house with room for the king size bed as well as two closets. The other two bedrooms are flooded with south sunshine all day long. Below them, the dining room and kitchen share the sliding glass doors to the south facing balcony. There was carpeting covering the entire main level for many years which was recently removed to reveal hardwood floors in very good shape. Having all the floors and stairs refinished would bring them back to like-new condition. On the lower level, the owners historically worked from home years before it became the rage in 2020. They worked in their respective offices, so they built a corridor to the back door and enclosed what customarily would be the open family room in the back. One could keep them as separate closed rooms or open the rear one up to its original configuration. In the last many years, the owner was confined to this floor. Luckily the back room is filled with light overlooking the backyard which has a gazebo deck. The washer and dryer were moved out of the utility room into the closet of the front bedroom. The HVAC and hot water heater were enclosed by glass sliding doors and a large roll-in tiled shower was installed. There are no steps into the house from the parking in the back, so the lower level is wheelchair accessible. After rehab, the house will have great value because these are homes that people love to settle into and rarely leave. The perfect location with the Ray School, the Murray School, the Lab School and St. Thomas schools all close by as well as the Hyde Park Neighborhood Center right across the street. And of course, in this most walkable of neighborhoods, all of buildings of the University are just a short walk or roll away. This is, emphatically, an AS-IS sale. Assume that you will have to do everything and then be surprised when you don't.

1315 E 55Th Street, Chicago

$575,000
4 Beds 4 Baths 11916032 MLS CLOSED Status
A wonderful opportunity to own a contemporary free standing single family home with attached garage in Hyde Park!! The property was designed by Y.C. Wong & Associates. Y.C. Wong received his Bachelor of Science in Architecture from the National Central University of Nanjing, China and later studied under Mies van der Rohe at ITT. Built in 1995, 5742 South Dorchester Avenue is one of the newer single free standing homes on Dorchester. The interior has a mid-century modern design featuring 4 bedrooms and 3.5 baths. The main level has a spacious living room with large windows, kitchen and dining room plus a half bath. Both the kitchen and dining room have a beautiful view of the backyard via glass slider doors. The second floor has three bedrooms and two baths. The large primary bedroom is appointed with an ensuite bath. The finished basement features a large bedroom and a full bath plus access to the garage and exterior, separate entrances. The deck, lower-level patio plus a back yard contribute to outdoor living areas. Both the roof and furnace are newer. Home is appointed with central air and a spacious attached garage which easily accommodates one automobile with room to spare. This is the first time the property has been on the market and could benefit from a refresh. Excellent Location within walking distance to the University of Chicago, Lab School, Hyde Park shopping, parks, beaches and public transportation.

5472 S Dorchester Avenue, Chicago



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.