View All Kenwood Chicago IL Homes with Large Yard Listings

4 Beds ⋅ 2 Baths ⋅ 12675404 MLS ⋅ PRICE CHANGE Status

For the first time in 47 years, a rare value-add opportunity in the heart of the historic Kenwood Mansion District. This 4-bedroom, 1.1-bath townhome offers a functional three-level layout, including a partially finished basement, a private fenced yard, and access to a shared private community park-providing exceptional outdoor space in the city. Solid brick and concrete construction provides a strong foundation for renovation, with potential for owner-occupants looking to build equity. All four bedrooms are conveniently located on one level, however, some owners have reimagined the space and combined two bedrooms to make a large primary suite. Ideally located near Kenwood Community Park, Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this is a unique opportunity to renovate and create a home of your own in one of the Chicago's most sought-after neighborhoods.

4753 S Woodlawn Avenue, Chicago

$1,367,500

4 Beds ⋅ 4 Baths ⋅ 12617167 MLS ⋅ CLOSED Status

Experience a truly rare and unique blend of traditional charm plus modernized conveniences in one of Chicago's most intellectually vibrant and architecturally distinguished neighborhoods. This 19th century Queen Anne Victorian represents an exceptional combination of depth, history, and warmth coupled with extensive updates that will allow you to immediately move in and live comfortably in the space. Set on parts of three oversized city lots totaling 108' x 150', this property provides a quiet sanctuary in the midst of urban sophistication unlike any other property or neighborhood in the city. The property provides multiple areas of outdoor living space with a large multi level bluestone and brick paver patio with; built in brick walls that double as seating ledges, an outdoor kitchen with a built in gas Weber Grill, mature trees, professional landscaping, an extensive nine-zoned sprinkler system that covers the entire property, its huge side yard and multiple vegetable gardening beds which you can enjoy with the frequent bird, and bunny visitors to the property. This 1885 home was painstakingly restored (completed in August 2016) with an all-encompassing professional renovation (copies of specs available for serious buyers) that included all new electrical, plumbing, HVAC (dual zoned), improved insulation, and wired high speed Cat 6 internet capability throughout the home. The extensive renovations retained the appeal and the spaciousness of Kenwood mansions of yesteryear, while at the same time improving the home to accommodate a contemporary and modern sensibility. The home boasts three floors of finished living space in addition to a full unfinished basement that can be used for virtually limitless storage or can be finished for additional living space. The formal living room anchors the home with a stunning tiered crystal chandelier, custom sconces, and a sun-drenched original stained-glass transom window. One set of pocket doors separates the formal living and dining areas from a chef's kitchen, while another original set of pocket doors leads into a side family room that can be used as a study or reading/sitting room. This light-filled property boasts multiple bay and oriel window bays, window seats, and remote controlled custom blinds on the first floor. The upper floors feature window treatments that allow top down operation, which offers all of the benefits of bathing your rooms and yourself in sunlight while also maintaining privacy as desired. The kitchen and bathrooms were professionally and thoughtfully designed. The chef's kitchen features a 48 inch Wolf gas dual oven and range with included grill and griddle/Plancha cooking surface plus a custom commercial grade vent hood, a pot-filler, two large sinks, and a dual temperature zone SubZero wine/beverage fridge. The kitchen also features high end fixtures, including custom Crystal cabinets with leathered granite outer countertops and White Princess Quartzite on the large, custom island. The home boasts four bedrooms including two primary suites, each with an en suite bathroom and large walk in closets. The larger en suite bathroom includes an Oceania air jetted tub, as well as a separate shower with a stone floor. The third bedroom is also oversized and features a working fireplace and bay window. Situated near the border of South Kenwood and Hyde Park, this property is a short 12 minute drive to downtown Chicago, seven minute walk to the Metra, two blocks to Whole Foods and express to downtown CTA bus service, a ten minute walk to the lake front, across the street from the Solon Beman designed Blackstone Library, just over a mile to the center of the University of Chicago campus, and a short walking distance from restaurants, cafes, bookstores, parks, tennis courts, and local shopping. Truly everything you could desire in your urban retreat. Contact us today to schedule a private showing. ***Broker owned property, and broker's primary residence. ***

4916 S Blackstone Avenue, Chicago

$232,000

2 Beds ⋅ 1 Baths ⋅ 12540292 MLS ⋅ CLOSED Status

Spacious and sun-filled top-floor 2-bedroom, 1-bath condo located in the historic Kenwood neighborhood. This charming home features beautiful hardwood floors throughout, generously sized rooms, and classic vintage character. Enjoy a large rear patio and enclosed yard, perfect for entertaining or relaxing outdoors. Ideally situated near the University of Chicago, public transportation, Promontory Point, the Museum of Science and Industry, and a variety of neighborhood dining options. Pet-friendly building.

5008 S Dorchester Avenue Unit #3, Chicago

$987,500

5 Beds ⋅ 5 Baths ⋅ 12453495 MLS ⋅ CLOSED Status

Spacious is the word that comes to mind as you view this solid brick residence in the well sought after Hyde park area. This property has a connection to the 44th president Barack Obama as the family grew up with them & shared a backyard. The 2 1/2 garage was leased to the secret service detail assigned to protect the Obama's. The former garage, now two story coach house, was rehabbed to suit their needs and can be used as separate dwelling with its own HVAC, bath & kitchen or perhaps rented out for income or simply used as a guest house. As you enter into the residence you will notice the 10 ft beamed ceilings, dark woodwork, stained glass and hardwood floors throughout. This property features two fireplaces, two jacuzzi tubs, two stairways and a 2nd floor rear balcony. The 1st floor features a huge kitchen/dining room combo, pocket doors, kitchen nook, bathroom, & spare room. Front of basement is finished and boast a family room, game room, two bedrooms etc. Rear has mechanicals with newer furnace & hot water heaters, laundry room and walkout to yard. Second floor has master bedroom & 3 additional bedrooms. Third floor has 1 bedroom & two rooms that share a large hall closet. Did I mention the shed and long driveway? Showings for qualified buyers will be by appointment only. Come & see this Jewel and make it your own or invest and resale at a profit. "AS IS"

1036 E Hyde Park Boulevard, Chicago

$1,600,000

5 Beds ⋅ 5 Baths ⋅ 12421410 MLS ⋅ CLOSED Status

Custom renovation in Historic Kenwood! Sophisticated single-family home offers a perfect blend of mid-century charm and modern living. Large garden is a lovely oasis which includes a private pergola and formal dining area. Dine al fresco with family and friends using the large outdoor cooking area and expansive front yard. The home was completely reconstructed to the studs by the owner. The home features an open floor plan with intimate spaces filled with natural light and pre wired for entertainment through the house. Upon entering, you are welcomed by an elevated family room with a room-sized skylight, complemented by custom shelving and built-ins for both comfort and organization. This room boast floor-to-ceiling windows, creating a bright and airy atmosphere. The sunken living room features a vaulted ceiling, dual skylight, and modern double crystal chandeliers with pairing wall sconces. The dining room is adorned with a crystal chandelier and double archway doors. The room includes a built in custom wet bar and comfortably seats 12-14. Enjoy after-dinner wine or tea on the private enclosed patio. The sophisticated kitchen is a chef's dream, equipped with double ovens, microwave drawer, ample cabinetry, and a custom-designed built in armoire housing a Subzero refrigerator and pantry space. An oversized porcelain island and Wolf appliances complete this stunning culinary space, making it perfect for entertaining and cooking. On the second level, four of the five bedrooms are spacious and filled with natural light, with three featuring elegantly designed attached bathrooms. Custom closets are thoughtfully configured for optimal space usage. The primary bedroom is a standout, boasting a luxurious walk-in shower for two, a separate modern Victoria & Albert tub, a generous custom walk-in closet, and a private toilet room. The lower level offers 10-foot ceilings and contemporary spaces designed for relaxation and fun, including a game room, gym, guest bedroom, half bath, and a laundry room. Two attached heated garages provide convenient access from a gated, private entryway and heated driveway. A custom outdoor porch to patio perfect for outdoor cookouts, garden parties, and relaxation. Boasting white hydrangeas and other blooming flowers and trees all spring and summer long. Additional features include remotely operated skylights and custom door coverings, heated floors throughout, and numerous built-in custom closets for ample storage. This exquisite home seamlessly combines luxury and functionality, making it a must-see for discerning buyers.

1150 E 49Th Street, Chicago

$2,085,000

5 Beds ⋅ 4 Baths ⋅ 12415335 MLS ⋅ CLOSED Status

Luxury Living in the Kenwood Historic District - Award-Winning Design, Massive Yard! Nestled in the heart of the prestigious Kenwood Historic District, this luxurious residence is a true architectural gem, boasting a massive, beautifully landscaped yard that spans nearly half the length of a football field. Designed by award-winning architect, Anthony Akindele in 1999, this home blends timeless elegance with modern comfort, highlighted by a striking turret staircase, soaring ceilings, and walls of windows that bathe the interiors in natural light. Step inside to a formal foyer adorned with custom stonework that sets the tone for the craftsmanship throughout. The main level features an expansive living room with a wall of windows and a cozy double-sided fireplace that opens to the formal dining room-perfect for entertaining guests, holiday dinners, and family gatherings. A stylish powder room adds convenience, while the gourmet kitchen is a chef's dream with top-tier appliances, granite countertops, abundant cabinetry, double ovens, a cooktop with a vented hood, and an oversized refrigerator. The kitchen's serene view of the backyard makes it a tranquil space to cook, gather, and unwind. Ascend the gracefully curved turret staircase to the second floor, where you'll find three spacious bedrooms, two full bathrooms, and a utility room. The highlight of this level is the sprawling primary suite, featuring custom closets and a spa-like bathroom complete with granite floors and walls, a dual-sink vanity, an walk-in shower with body sprays, and an oversized luxurious elevated whirlpool tub-your personal sanctuary. The grand lower level offers high ceilings and a large family room with a fireplace and wet bar, two additional bedrooms, a full bathroom, and an impressive laundry room with tons of storage space. Whether you're hosting game nights or housing extended guests, there's room for everyone. The lower level does have an exterior door. But the crown jewel is the yard-truly breathtaking. From the elevated deck to the custom stone patio and the expansive grassy field lined with privacy trees, lush plants, and vibrant flowers, this outdoor oasis is ideal for everything from backyard parties to family sports tournaments. It's rare to find this kind of outdoor space in such a coveted urban setting. Additional features include a 3-car garage and a prime location within walking distance of Hyde Park's shops and restaurants, the lakefront, and the University of Chicago. Meticulously maintained and in pristine condition, this home is a one-of-a-kind masterpiece in one of Chicago's most storied neighborhoods. Welcome home!

925 E 49Th Street, Chicago

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 12321987 MLS ⋅ CLOSED Status

Nestled in the heart of the sought-after Kenwood Historic District on a tree-lined street, this beautifully renovated rowhouse blends timeless charm with modern comfort. Perfectly positioned across from the neighborhood's large scenic park, the gracious home is bathed in natural light and offers picturesque views year-round. Step inside to the flowing floor plan where the vestibule opens to a formal living room with gleaming hardwood floors, classic wainscoting, and a cozy fireplace. A handsome staircase provides a graceful separation between the living area and the spacious dining room adjacent to the chef's kitchen - complete with a wall of windows overlooking the lush backyard. The outdoor space is ideal for entertaining or relaxing, with an oversized deck and elegantly landscaped yard featuring a flagstone patio, perfect for play or gatherings. Upstairs, the second floor hosts a luxurious primary suite with a spa bath and walk-in closet, along with two additional bedrooms and a stylishly renovated bathroom. The top floor offers incredible flexibility, featuring a bright, open space with a panoramic view. There is a ton of natural light and the space is ideal as a fourth bedroom, family room or guest suite, with a full bath and a charming loft space for an office or creative nook. The walk-out basement has been upgraded with new drainage, houses the laundry area, and offers abundant storage with potential for future finishing to add even more living space. Additional features include zoned air conditioning, newer windows throughout, and classic details preserved with care. A rare opportunity to own a piece of history, updated for modern living, within walking distance to amenities and schools and is located in one of the city's most beloved neighborhoods - welcome home!

1329 E 50Th Street, Chicago

$400,000

4 Beds ⋅ 3 Baths ⋅ 12403863 MLS ⋅ CLOSED Status

Historic Kenwood neighborhood! Live among the notable and iconic homes in South Chicago. Just 3 blocks to Metra Train, walk to Lake Michigan and the walking trails, and close to Lake Shore Drive. Fabulous Opportunity to own this 4 Bedroom (all on 2nd floor), 2.1 Bath, large end unit. "True" townhome with ownership to the building and the land! The property includes over 2,550 SF with 1,725 SF above ground and a partially finished basement of 863 SF. Well-built structure with brick and concrete construction. Solid concrete divides each floor. The townhomes are in the neighborhood of notable historic homes valued over $2 million. It is located just 1 block from the Mohammed's Ali's home/museum and walking distance to the future Barack Obama's Presidential Library, Jackson Park and the University of Chicago campus. With some sweat equity, there is HUGE POTENTIAL and incredible upside on this amazing 4 Bedroom home. It includes a huge private, completely fenced-in yard. New fencing is in the plans by the HOA. Low HOA Assessment is only $600 per year. Owner is responsible for maintaining the entire structure and yard. ** New Furnace, A/C, and Hot Water Heater 2022. Home needs work and is being sold "AS IS". Structure is solid. Access to home is by appt only.

4741 S Woodlawn Avenue, Chicago

$1,495,000

8 Beds ⋅ 5 Baths ⋅ 12128447 MLS ⋅ CLOSED Status

Welcome to historic Kenwood, where yesterday's grandeur meets today's elegance. Nestled on a scenic double lot, this grand three-story home formerly known as The Duchisois Residence and designed by F.R. Schock is located in the South Kenwood Historical District. This stunning 8-bedroom, 5-bathroom home exudes vintage charm with its original oakwood floors, trim, solid core doors, and three original fireplaces. Offering nearly 6500 sq ft of luxurious living space, it features recessed lighting throughout, updated electric and plumbing, a new roof installed in 2014, a newly installed boiler, and separate central air systems. The grand foyer entry with parlor showcases gorgeous stained glass. The formal living and dining spaces and main level family room provide ample space for entertaining. The master bedroom suite includes a spa bath, while spacious bedrooms on the 2nd and 3rd floors offer comfort and style, including a large cedar closet. The modern gourmet kitchen boasts built-in custom appliances, and updated baths enhance the home's appeal. The lower recreational space has a wet bar and a second functional kitchen adding versatility. Outside, a huge detached 2-car garage with a 1000 sq ft coach house on top complements the incredible gated yard featuring a luxurious patio and mature landscaping. Walking distance to Lake Michigan, shopping, and museums. Easy to show with occupancy upon closing. This is a rare opportunity to own a piece of Kenwood history.

4800 S Kenwood Avenue, Chicago

$775,000

6 Beds ⋅ 5 Baths ⋅ 12048392 MLS ⋅ CLOSED Status

An incredible opportunity to invest in the potential of an historic home the Kenwood neighborhood. House requires work - but is gracious, spacious and is priced to move. At the time this home was constructed there were only four houses on the 4800 block of Greenwood Avenue; Kenwood was then a bucolic suburban retreat. The catalysts fostering the growth of the neighborhood (the founding of the University of Chicago and the 1893 World's Columbian Exposition) were years away. For a century and a half this home has stood proudly as the world evolved around it - a new century dawned (twice) and houses by architectural innovators including Frank Lloyd Wright and Burnham & Root rose nearby. A resurgence occurred as the community was landmarked, and a neighbor elected president. And through it all 4849 endured. The ambience of those earlier years remains: a handsome staircase, leaded windows, high ceilings, warming fireplaces and a verdant yard. This welcoming, spacious home offers a layout that can be reconceived for the 21st century, including space for a large kitchen and family room. With six bedrooms, four full and one-half baths, enclosed porches and lovely formal rooms on the main level, this house provides ample space indoors, and out. Hyde Park and Kenwood are vibrant communities - enhanced by the University of Chicago, adjacent to the city's magnificent lakefront and located a mere ten-minute drive from the Loop. This is an amazing opportunity to write the next chapter of this home's enduring legacy. Property is sold AS-IS.

4849 S Greenwood Avenue, Chicago

$600,000

4 Beds ⋅ 3 Baths ⋅ 11869182 MLS ⋅ CLOSED Status

Enchanting, sun-filled single family home built by David Swan in the early 1990s with 4 bedrooms including a large primary suite, 3 full baths, updated kitchen, fabulous living room with fireplace, family room, two decks, yard and attached garage. Hardwood floors on all three floors. The house is made even more lovely with light entering from the east, south, west and north. The Ancona School, a top-ranked Montessori-based school serving children in pre-K through 8th grade, sits across the street. Very close to the lakefront and bike path, express transportation to/from the Loop (both CTA and Metra) and Museum Campus, and within easy walking/biking distance to the UChicago campus and Hyde Park's restaurants and shops. Easy access to DuSable Lake Shore Dr, I-90/94 and I-55. Relish living in one of the City's prettiest and most walkable neighborhoods. Love where you live!

4755 S Dorchester Avenue, Chicago

Start Your Search

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.

Kenwood, Chicago IL · Curated MLS Search

Homes with Large Yard in Kenwood, Chicago IL

An editorially curated view of every active homes with large yard listing in Kenwood, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Kenwood, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Kenwood, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local Kenwood, Chicago IL expertise

Data Brief

Full Kenwood, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Kenwood, Chicago IL Listings

Every active property

← Back to Kenwood, Chicago IL Homes for Sale