Chi - Kenwood Real Estate

Located in the heart of Chicago, Illinois, the neighborhood of Kenwood offers residents a unique blend of history, culture, and community. Situated in Cook County, Kenwood is a vibrant and diverse neighborhood that has become a sought-after destination for both homebuyers and visitors alike.

One of the standout features of Kenwood is its rich architectural heritage. The neighborhood is renowned for its stunning historic homes, many of which were designed by renowned architects such as Frank Lloyd Wright and George Maher. These beautiful residences showcase a variety of architectural styles, including Victorian, Queen Anne, and Prairie School, adding to the charm and character of the area.

In addition to its architectural splendor, Kenwood is also home to several cultural landmarks. The neighborhood is known for its close proximity to the University of Chicago, where renowned scholars and intellectuals have made their mark. The DuSable Museum of African American History, located in Kenwood, is another notable attraction that celebrates the contributions of African Americans to the cultural fabric of the United States.

When it comes to amenities, Kenwood has plenty to offer. Residents can enjoy easy access to a range of dining options, boutique shops, and recreational facilities. The neighborhood is also well-connected to the rest of Chicago, with convenient public transportation options available.

With its rich history, diverse community, and convenient location, Kenwood is undoubtedly an attractive neighborhood for those seeking a unique and vibrant place to call home.

Newest Listings in Chi - Kenwood

$875,000

3 Beds ⋅ 4 Baths ⋅ 12713781 MLS ⋅ NEW 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

$129,900

1 Beds ⋅ 1 Baths ⋅ 12712232 MLS ⋅ NEW Status

Luxury living awaits at The Newport, one of Hyde Park's premier full-amenity buildings. This spacious 1-bedroom, 1-bathroom condo offers an incredible opportunity to add your personal touches while enjoying exceptional building amenities and an unbeatable location. Step inside to discover a bright, expansive living space featuring a dramatic wall of windows that fills the home with natural light. The generous open-concept layout offers flexible living and dining arrangements, while the kitchen provides abundant cabinet storage and plenty of potential for customization. Conveniently located just steps from the elevators, this unit makes everyday tasks, including bringing in groceries, effortless. Heated valet parking is included in the price, and the monthly assessment covers heat, water, cable TV, internet, parking, and a storage locker, offering outstanding value. The Newport is a full-service, professionally managed building featuring 24-hour door staff and security, on-site management and maintenance, beautifully maintained common areas, a complimentary shuttle service, laundry facilities, a bike room, and additional storage. For an additional fee residents can enjoy the indoor pool, jacuzzi, sauna, and fitness center. Ideally situated in the heart of Hyde Park, this home is just minutes from downtown Chicago and a short walk to the scenic lakefront, parks, museums, restaurants, cafes, shopping, public transportation, the University of Chicago, and the new Obama Presidential Center. Whether you're searching for a primary residence, a city retreat, or an investment opportunity, this condo offers outstanding value in one of Chicago's most sought-after neighborhoods.

4800 S Chicago Beach Drive Unit #1503S, Chicago

$2,440,000

5 Beds ⋅ 6 Baths ⋅ 12711888 MLS ⋅ NEW 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

$140,000

1 Beds ⋅ 1 Baths ⋅ 12711682 MLS ⋅ ACTIVE Status

Enjoy lakefront living in this beautifully updated one-bedroom condo at 4800 S. Chicago Beach Drive. Located in a full-service high-rise, this bright and spacious residence features a generous open layout, luxury vinyl flooring, newer kitchen cabinetry and countertops, and stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave. Large windows fill the unit with natural light and offer attractive neighborhood and lake views. The flexible living and dining area provides plenty of space for relaxing, entertaining, or working from home. Residents enjoy a wide range of building amenities, including 24-hour door staff, an indoor swimming pool, fitness center, onsite management, receiving room, laundry facilities, bike storage, and well-maintained common areas. Parking may also be available for rent. Ideally located near Chicago's lakefront, Jackson Park, the Lakefront Trail, beaches, the University of Chicago, the Museum of Science and Industry, public transportation, shopping, dining, and the Obama Presidential Center. This is an excellent opportunity for an owner-occupant or investor seeking comfort, convenience, and value in the Hyde Park-Kenwood area.

4800 S Chicago Beach Drive Unit #308S, Chicago

$304,900

2 Beds ⋅ 3 Baths ⋅ 12699716 MLS ⋅ ACTIVE Status

Welcome to this beautifully appointed 2-bedroom, 2.5-bath duplex that lives like a townhome, offering an exceptional combination of space, comfort, and modern convenience. Designed with both comfort and functionality in mind, this expansive home features hardwood flooring throughout the upper level, abundant natural light, and an open, inviting floor plan. The contemporary kitchen is appointed with granite countertops, rich cherry cabinetry, stainless steel appliances, and generous cabinet and prep space, making it ideal for everyday living and entertaining alike. The lower level has been enhanced with new flooring and new windows, adding both style and energy efficiency to the home's living space. The upper level offers two spacious bedroom suites, each with direct access to its own full bathroom. The primary suite features a private ensuite bath, while the second bedroom enjoys direct access to the hall bath, creating an ideal layout for guests, family, or a home office. A versatile loft-style flex space provides endless possibilities as a home office, reading nook, workout area, or creative space. Additional highlights include an in-unit washer and dryer, a convenient main-level powder room, a large private storage locker, an assigned parking space, and a private rear balcony-the perfect place to enjoy your morning coffee or unwind at the end of the day. Ideally situated on a quiet, tree-lined cul-de-sac, this home is just moments from neighborhood cafes, local dining, shopping, the lakefront, the University of Chicago, public transportation, Whole Foods, Trader Joe's, and the vibrant 53rd Street shopping corridor. With easy access to Lake Shore Drive, downtown Chicago is just minutes away. Whether you're looking for your first home, a place to entertain, or simply more room to live, this move-in-ready duplex offers the perfect blend of location, lifestyle, and value. Don't miss this exceptional opportunity!

4731 S Ingleside Avenue Unit #D1, Chicago

$935,000

5 Beds ⋅ 5 Baths ⋅ 12707060 MLS ⋅ ACTIVE Status

4553 S Ellis 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

$83,500

3 Beds ⋅ 2 Baths ⋅ 12705188 MLS ⋅ ACTIVE Status

THIS TASTEFULLY RENOVATED THREE BEDROOM UNIT FEATURES AN OPEN FLOOR PLAN WITH RIGID CORE FLOORING THROUGHOUT. THE FIRE PLACE IN THE LIVING ROOM IS FLANKED WITH SHELVING. THERE IS A DINING ROOM FOR MORE FORMAL ENTERTAINING. THE KITCHEN IS AMAZING! STAINLESS STEEL APPLIANCES, MARBLE COUNTER TOPS WITH BEVELED EDGES, ISLAND AND LOTS OF CABINETS AND STORAGE. THE SPACIOUS BEDROOMS OFFER LOTS OF CLOSETS AND LOVELY CITY VIEWS. RENTAL GARAGE PARKING FOR A SMALL FEE IS AVAILABLE. EXCELLENT DOOR AND MAINTENANCE STAFF. ONSITE MANAGEMENT. HOSPITALITY ROOM, EXERCISE ROOM, LAUNDRY ROOM, COMMISSARY ALL ENHANCE YOUR CAREFREE LIFESTYLE. THIS HYDE PARK KENWOOD LOCATION HAS IT ALL. EASY INTERSTATE ACCESS, GREAT SHOPPING, WALK TO LAKEFRONT AND SO MUCH MORE. CASH ONLY. BOARD APPROVAL - MUST BUY INTO SHARES. TAKE A LOOK. YOU WON'T BE DISAPPOINTED. PROOF OF FUNDS PRIOR TO SHOWINGS.

4850 S Lake Park Avenue Unit #1201, Chicago

$195,000

1 Beds ⋅ 1 Baths ⋅ 12703440 MLS ⋅ PRICE CHANGE Status

Investor Special!!! Turnkey income-producing opportunity in the highly sought-after historic Drexel Boulevard corridor. This spacious 1-bedroom, 1-bath condominium offers wood-finish flooring throughout, a cozy fireplace, a large bathroom with dual vanities, and an efficient layout that appeals to long-term tenants. The well-maintained building features secure fob entry, an assigned exterior parking space, and low HOA dues. The unit is currently leased to an excellent long-term tenant paying $1,750 per month through March 1, 2027, providing immediate, stable cash flow from day one with no vacancy concerns. Seller is also offering a $2,500 appliance credit, allowing the new owner or future occupant to update the appliances to their personal preference while adding value to the property. A professionally managed, investor-friendly building that allows rentals, making this a rare opportunity to acquire a turnkey asset with immediate income and future upside.

4537 S Drexel Boulevard Unit #203, Chicago

$535,000

4 Beds ⋅ 3 Baths ⋅ 12703019 MLS ⋅ ACTIVE Status

Set along the iconic boulevard of historic Kenwood, this expansive and character-filled residence at 5036 S. Drexel Blvd. #3N blends timeless architectural detail with thoughtful modern updates. Located in a distinguished 1910 building designed by renowned architect Frank B. Jobson, this beautifully preserved home offers exceptional scale, rich craftsmanship, and a layout that lives comfortably for both everyday living and entertaining. With ~2,600 square feet, this space truly lives like a single family home. Inside, original details take center stage: from quarter-sawn oak wall paneling and pocket doors to coffered ceilings, leaded glass built-ins, Honduras mahogany paneling, original sconces and French doors. Hardwood flooring runs throughout featuring maple in the kitchen and oak throughout the remaining living spaces, while original wood doors and hardware further preserve the home's historic charm. The spacious living and dining areas offer elegant entertaining space filled with warmth and character. The dining room showcases stunning original built-ins, quarter-sawn oak detailing, coffered ceilings and lush park views, while the living and family rooms feature striking Honduran mahogany paneling, stunning gas fireplaces with original mantels and tile work. Completed in 2026, the updated kitchen combines functionality and design with granite countertops, full wall marble tile backsplash, Bosch appliances, LG dishwasher, outside venting Bosch hood, abundant cabinetry, and a custom movable island with extensive storage. The charming butler's pantry provides additional storage and workspace and a separate lovely beverage center are an extension to your kitchen. The home offers four spacious bedrooms, including a newly updated fourth bedroom and half bath completed in 2026. The hallway bathroom was renovated in 2021 with marble finishes, Kohler and Grohe fixtures, custom vanity inserts and a custom medicine cabinet. This unit provides two private outdoor spaces: an enchanting front balcony off of the family room, accented with stone arches and overlooking the boulevard and the rear deck off of the kitchen complete with original glass French doors. Additional highlights include generous closet space, in-unit laundry, replacement windows throughout most of the home, beautifully restored radiators and new energy-efficient, quiet window AC units. The building has a parking lot with five spaces which are available on a first arrival basis. Street parking is very accommodating, as Drexel Boulevard is not designated as either a snow or bus route. Residents enjoy close proximity to the University of Chicago, University of Chicago Medicine, the new Northwestern outpatient facility, Hyde Park stores and restaurants, lakefront access, and multiple transportation options nearby.

5036 S Drexel Boulevard Unit #3N, Chicago

$149,900

1 Beds ⋅ 1 Baths ⋅ 12701256 MLS ⋅ ACTIVE Status

Updated one bedroom condo in an investor-friendly building across the street from the green oasis of Kenwood Community Park. This top floor condo features hardwood floors, combined living/dining space, spacious bedroom, and updated kitchen with stainless steel appliances and granite counters. The low monthly assessment of $301 includes heat and cooking gas. Access to the CTA #6 bus, University of Chicago UGo shuttle and #172 bus, and Metra Electric train station is within a short walking distance. Dog-friendly Kenwood Community Park, spanning 7 expansive acres, features tennis courts, baseball fields and athletic field for soccer or football. There is a wait list for onsite parking and ample street parking along Dorchester Ave.

4939 S Dorchester Avenue Unit #5F, Chicago

$259,000

3 Beds ⋅ 1 Baths ⋅ 12699647 MLS ⋅ ACTIVE Status

Spacious 3-bedroom condo in the heart of Hyde Park/Kenwood! Set within a charming 1905 vintage brick building, this sun-filled second-floor home offers timeless character, generous living space, and exceptional value in one of Chicago's most vibrant neighborhoods. Inside, you'll find hardwood floors throughout, abundant natural light, generously sized rooms, an eat-in kitchen, and a private back deck perfect for grilling, relaxing, or enjoying your morning coffee. The functional floor plan provides flexibility for everyday living, working from home, or entertaining guests. Move right in or bring your ideas-this home offers a fantastic opportunity to personalize and build equity over time. The building features private storage and shared laundry, with the possibility of adding in-unit laundry for added convenience. Easy street parking makes city living even more manageable. With no rental restrictions, this investor-friendly building offers excellent flexibility, whether you're searching for a primary residence, University of Chicago housing, or an income-producing property. Enjoy an unbeatable location just steps from Whole Foods, Trader Joe's, Target, neighborhood restaurants, coffee shops, parks, and public transportation. You're also minutes from the University of Chicago, the Museum of Science and Industry, Jackson Park, the lakefront, and the shopping and dining along 53rd Street. Combining vintage Hyde Park charm, generous living space, and an outstanding location, this home presents an exceptional opportunity to own in one of Chicago's most sought-after neighborhoods.

5052 S Blackstone Avenue Unit #2, Chicago

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