Chi - Kenwood Homes for Sale

Welcome to Chi-Kenwood, a vibrant neighborhood located in the heart of Chicago, Illinois. Situated in Cook County, this area offers a unique blend of history, culture, and modern amenities that make it an ideal place to call home.

One of the highlights of Chi-Kenwood is its diverse range of homes for sale. Whether you're a first-time buyer or looking to upgrade, you'll find a variety of options to suit your needs. From charming townhouses to spacious single-family homes, there's something for everyone in this neighborhood. The real estate market in Chi-Kenwood is thriving, with properties that offer both character and value.

Beyond the homes themselves, Chi-Kenwood boasts a vibrant community with plenty to offer. Residents can enjoy easy access to a range of amenities, including parks, restaurants, and shopping centers. The area is also known for its excellent schools, making it an attractive choice for families.

In terms of location, Chi-Kenwood offers the best of both worlds. It's nestled in a peaceful residential area, yet it's just a short drive away from the bustling downtown Chicago. This means you can enjoy the tranquility of suburban living while still being close to all the excitement that the city has to offer.

If you're considering a move to Chi-Kenwood, now is the perfect time to explore the available homes for sale. With its rich history, convenient location, and strong sense of community, this neighborhood has something for everyone. Don't miss out on the opportunity to make Chi-Kenwood your new home.

Newest Chi - Kenwood Homes for Sale

$2,175,000

8 Beds ⋅ 5 Baths ⋅ 12752094 MLS ⋅ NEW Status

Situated on one of the most desirable blocks in the heart of the Kenwood Historic District, this remarkable residence is distinguished by its striking crow-stepped gable and extraordinary architectural detail. Built in 1896, at the height of Chicago's fascination with revival architecture, the home was designed by noted architect William Otis, a graduate of Paris's prestigious Ecole des Beaux-Arts. His design captures the elegance and craftsmanship of 17th-century Dutch architecture, adding to the neighborhood's character. Exceptionally preserved, the house offers a rare combination of architectural authenticity, gracious scale, and thoughtful modern updates. Beyond its richly detailed brick facade, the interior unfolds with abundant natural light and an extraordinary collection of original craftsmanship, including finely carved woodwork, art glass, and decorative tile. Expansive formal living and dining rooms provide an elegant setting for entertaining, while the warm, inviting kitchen flows naturally into a sun-filled family room and out to a spacious deck - creating an effortless connection between formal and everyday living. With eight bedrooms, multiple fireplaces, and a dramatic third-floor family room featuring soaring 15-foot ceilings, the home offers remarkable scale and versatility. Every floor reveals another layer of the house's architectural character and thoughtful design. The beautifully landscaped, tree-lined lot is further enhanced by a charming coach house with a two-bedroom apartment, offering exceptional flexibility for guests, extended family, a private office, or supplemental income. Timeless in character and sophisticated in its proportions, this extraordinary residence represents a rare opportunity to become the steward of one of Kenwood's treasured pieces of architectural heritage-a home where history, craftsmanship, and modern living come together with grace.

4923 S Greenwood Avenue, Chicago

$1,775,000

6 Beds ⋅ 5 Baths ⋅ 12753755 MLS ⋅ NEW Status

4801 S Kimbark Avenue, Chicago

$450,000

4 Beds ⋅ 3 Baths ⋅ 12743931 MLS ⋅ ACTIVE Status

Historic Kenwood. Live in the entire space or subsidize your income with the separate ADU compliant garden unit. If you are looking to add your finishing touches and walk in with instant equity, this home could be for you. This home combines the beauty of Historic Chicago, including built-in bookshelves, hardwood floors, original millwork, and more; thoughtful updates with an extremely spacious layout and creative room for your own special touches. Inside, you'll find tall ceilings, new flooring, and an open flow between the living and dining areas. The kitchen includes stainless steel appliances, granite countertops, and plenty of cabinet storage. There are four bedrooms upstairs with a full bathroom and a powder room. There is room to add a second full bath to create a stunning primary oasis. Downstairs, there is a separate unfinished basement with two points of entry, perfect for additional living space, Airbnb/short-term rentals, or related living. Located on a quiet, tree-lined street, the property is close to parks, schools, public transit, and local shops and restaurants.

928 E 46Th Street, Chicago

$674,500

3 Beds ⋅ 4 Baths ⋅ 12721995 MLS ⋅ ACTIVE Status

Come home to this charming, Kenwood Greystone located on quiet, historic block. Featuring 4 bedrooms, 3 1/2 baths, gorgeous, dark stained, hardwood flooring on main level, premium, wood laminate flooring upstairs, modern kitchen and full, finished, lower level. Chef inspired kitchen with 42" custom cabinets, SS appliances and granite countertops. Primary bedroom with ample closets, en-suite bath that features dual vanities, jacuzzi tub, and separate, oversized shower. Dual zone HVAC system, contemporary feature wall with a built-in electric heater and decorative flame effect in living room, finished basement has custom, epoxy flooring and wet bar area complete with custom cabinetry and beverage refrigerator in the family room for entertaining family and friends. Near parks, the lakefront, bike trails, Lake Shore Drive and minutes from Hyde Park and Downtown. Pack your bags and move right in! Pre-qualified buyers only.

4420 S Berkeley Avenue, Chicago

$1,695,000

6 Beds ⋅ 6 Baths ⋅ 12705893 MLS ⋅ ACTIVE Status

An extraordinary Kenwood greystone where historic craftsmanship takes center stage. Designed by celebrated Chicago builder Horatio Wilson, this remarkable 7-bedroom, 6-bath residence showcases more than 5,000 square feet of gracious living space, blending the grandeur of Chicago's architectural past with the comforts of modern living. Rich hardwood floors, extraordinary original millwork, handcrafted built-in cabinetry, decorative columns, pocket doors, and intricate wood detailing reflect a level of craftsmanship rarely found today. Formal living and dining rooms provide elegant spaces for entertaining and everyday living. Just beyond the dining room, a cozy lounge invites morning coffee or evening cocktails, while the adjoining butler's pantry offers a timeless transition into the kitchen. Tucked discreetly behind the kitchen, the original servant's staircase provides a charming connection between the home's first and second floors. Throughout the residence, seven fireplaces further celebrate its architectural heritage. The spacious primary suite serves as a private retreat with abundant closet space and a spa-inspired ensuite featuring a steam shower, soaking tub, dual vanities, and a walk-in closet. A finished lower level lives like a residence of its own with a second full kitchen, dining area, expansive family room, additional bedroom, and full bath-ideal for extended family, guests, or flexible living. Outside, a lush private garden offers a peaceful escape with mature landscaping and seasonal blooms. Ideally situated on a picturesque, tree-lined block in Kenwood near Hyde Park and the University of Chicago, this exceptional residence places you among one of Chicago's most architecturally significant neighborhoods, surrounded by historic homes, cultural institutions, acclaimed dining, and everyday conveniences. Homes of this caliber rarely become available, offering the opportunity to own not simply a remarkable residence, but an enduring chapter in Chicago's architectural story.

4942 S Ellis Avenue, Chicago

$865,000

4 Beds ⋅ 4 Baths ⋅ 12713781 MLS ⋅ ACTIVE Status

Rarely available and newly renovated single family home in the desirable Cornell Square Community in Hyde Park/Kenwood. The home overlooks a tree-lined private park/courtyard and offers 3 levels of spacious living areas with 3 bedrooms, 4 bathrooms, and a den/office. This stunning home is light and bright with a wall of windows overlooking the private park. 4 new spa-style bathrooms feature gorgeous finishes with floating vanities, quartz tops, and Kohler fixtures. The whole house is freshly painted in neutral tones with new carpeting in bedrooms. This home has been thoughtfully updated and meticulously maintained, featuring: new stainless steel kitchen appliances with granite countertops and eat-in kitchen, newly stained hardwood floors, and a cozy wood burning fireplace. Enjoy an outdoor balcony for grilling and outdoor patio for dining with lush landscaping. The ground level has a room with a private half bath, perfect for a guest room, in-law suite, office or den. The top floor features a primary suite with two large closets with custom organizers, an en-suite bath with double sink vanity and a separate shower and soaking tub, as well as two additional large bedrooms and a full bath. A real plus is the attached 2-car garage. Never scrape snow off your car again! The many improvements of this modern home include a new a new furnace in 2024, new A/C in 2023, and exterior wood recently painted. Walk one block to Lake Michigan bike path and beach. Walk to the 51st St. Metra stop and be downtown in 15 minutes. Easy access to Lake Shore Drive and ideal location for University of Chicago, the Laboratory Schools, and UC Medical Center. Walk to restaurants and retail shops on 53rd Street. Steps from Whole Foods and Trader Joe's. This is a warm and inviting single family home in a wonderful community with access to the best that Hyde Park and Chicago have to offer.

4922 S Cornell Avenue, Chicago

$2,371,500

5 Beds ⋅ 6 Baths ⋅ 12711888 MLS ⋅ ACTIVE Status

An exceptional expression of architectural elegance and refined living, this distinguished 6-bedoom, 5.5-bath Kenwood residence offers the rare combination of grandeur, scale, and gracious comfort. Set on one of the neighborhood's most beautiful, tree-lined streets, this magnificent early 20th-century home is distinguished by its handsome brick facade, generous proportions and timeless craftsmanship, along with many significant modern upgrades. Spanning approximately 6,700 square feet, the residence unfolds across an impressive and thoughtfully designed floor plan, with soaring ceilings, exquisite hardwood floors, elegant millwork, and a wealth of original architectural character. The gracious entry leads to beautifully proportioned formal rooms, including an expansive living room anchored by a fireplace and an elegant dining room designed for memorable entertaining. The sophisticated yet inviting kitchen features top-quality stainless-steel appliances, a substantial center island, farmhouse sink, and abundant cabinetry, creating a refined setting for both intimate meals and large-scale gatherings. A private den offers an ideal retreat for work or relaxation. The sumptuous primary suite is a true sanctuary, featuring generous proportions, two large walk-in closets, and a luxurious marble bath with dual vanities, a deep soaking tub, and separate shower. Additional bedrooms are also generously sized and complemented by beautifully appointed baths, offering exceptional comfort and privacy. The lower level further enhances the home's remarkable livability, with an expansive finished recreation room featuring built-in shelving, and recessed lighting -- an ideal setting for casual entertaining, recreation. A separate guest room with private full bath completes this level. Outside, meticulously landscaped grounds create a private and serene urban oasis, complemented by a spacious backyard and a concrete drive from the street leading to a detached two-car garage. Perfectly positioned near the lakefront, parks, premier schools, downtown transportation, and the cultural and academic institutions of the greater Hyde Park community, 4900 S. Kimbark Avenue represents a rare opportunity to experience the grandeur of a classic Chicago residence with the comfort and sophistication of modern living. The home is truly in move-in condition, having undergone extensive mechanical & structural renovations from sub-foundation to roof, including multi-zone radiant heat and air conditioning, continuous hot water, 400 AMP electrical service, and replaced water, gas and sewer lines.

4900 S Kimbark Avenue, Chicago

$999,000

3 Beds ⋅ 4 Baths ⋅ 12706221 MLS ⋅ ACTIVE Status

Move-in ready new construction at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences nestled on a quiet, tree-lined cul-de-sac in historic Kenwood. Thoughtfully designed as a full masonry build, each three-level residence delivers the scale and privacy of a single-family home with the ease of modern new construction, offering expansive living spaces, refined designer finishes, private outdoor living, and a 2-car garage. Sun-filled interiors are complemented by clean architectural lines and timeless finishes throughout. The beautifully appointed kitchen is designed for both everyday living and effortless entertaining, featuring custom dark wood Studio 41 cabinetry, an oversized quartz island, and a spacious pantry offering exceptional storage. Limited opportunity remains for buyer customization and select finish selections. The open-concept main living spaces flow seamlessly into a rare private outdoor retreat, ideal for entertaining, relaxing, and indoor-outdoor living rarely found in the neighborhood. With no monthly HOA assessment, The Kenwood Reserve delivers a rare combination of privacy, autonomy, and boutique luxury living. The lower level offers a warm and versatile secondary living space perfect for a media room, lounge, playroom, or fitness area, alongside a private fourth bedroom ideal for guests or a home office. A unique additional 230 SF unfinished space presents endless possibilities for customization, including a wine cellar, creative studio, wellness room, or additional storage. Dual HVAC systems with two furnaces and two central air-conditioning units for efficient, zoned comfort throughout.Located moments from Hyde Park, the University of Chicago, lakefront parks, dining, and cultural institutions, The Kenwood Reserve offers a rare opportunity to own full masonry new construction with private outdoor space, garage parking, and boutique luxury living in one of Chicago's most historic neighborhoods.

4721 S Ingleside Avenue, Chicago

$1,485,000

4 Beds ⋅ 5 Baths ⋅ 12614239 MLS ⋅ ACTIVE Status

4558 S Ellis Avenue, Chicago

$569,900

3 Beds ⋅ 4 Baths ⋅ 12510798 MLS ⋅ ACTIVE Status

Welcome home to this fully updated 2-story Greystone sitting right in the historic North Kenwood neighborhood. With 4 bedrooms, 3 full baths, 1 half bath and a spacious master suite, this home is designed for both comfort and style. You'll love the open flow with vinyl flooring throughout, central air, and a finished basement for extra space. The kitchen is the heart of the home-brand-new black stainless-steel stove, fridge, dishwasher, and microwave are all included. Every detail was done with care, blending that timeless Greystone charm with modern updates.

4343 S Ellis 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.