Kenwood Real Estate

Welcome to Kenwood, one of Chicago's most cherished neighborhoods, where historic charm meets modern vibrancy. Nestled along the picturesque shores of Lake Michigan, Kenwood is not only known for its stunning tree-lined streets and beautiful architecture but also for its rich cultural heritage and diverse community.

As you stroll through Kenwood, you'll be captivated by the stately homes, many of which date back to the early 20th century, showcasing a variety of architectural styles from classic greystones to elegant mansions. This neighborhood boasts a unique blend of historic significance and contemporary living, making it an ideal place for families, professionals, and anyone looking to embrace the best of city life.

Kenwood is also home to the renowned University of Chicago, which brings a vibrant academic atmosphere and a host of cultural amenities. Residents enjoy easy access to world-class museums, art galleries, and theaters, all just a stone's throw away. For those who appreciate the outdoors, the nearby Washington Park and the scenic Lakefront Trail offer ample opportunities for recreation, from jogging and biking to picnicking by the water.

In Kenwood, community spirit thrives. Local shops, cafes, and restaurants provide a warm, welcoming atmosphere where neighbors become friends. With excellent public transportation options and proximity to downtown Chicago, Kenwood combines convenience with a tranquil suburban feel.

Whether you're seeking a place steeped in history or a lively community with a bright future, Kenwood is a neighborhood that truly has it all. Come and discover the charm of Kenwood—your dream home awaits!

Newest Listings in Kenwood

$999,000

4 Beds ⋅ 4 Baths ⋅ 12792798 MLS ⋅ NEW 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. 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.

4717 S Ingleside Avenue, Chicago

4850 S Lake Park Avenue Unit #308B, Chicago

$47,500

2 Beds ⋅ 1 Baths ⋅ 12790698 MLS ⋅ ACTIVE Status

Beautifully updated and move in ready 2 bed, 1 bath co-op in sought-after Hyde Park has custom closets throughout. North-facing unit offers peaceful tree-top views over the courtyard. Unbeatable location just steps to the University of Chicago, Lakefront Trail, Whole Foods, Trader Joe's, Metra Electric Line, CTA buses, and Michelin-starred restaurants. Cash transactions only; rentals not permitted. In addition to the purchase price, a $5,620 transfer shares deposit to Harper Square Cooperativ is required.

4850 S Lake Park Avenue Unit #308B, Chicago

4840 S Dorchester Avenue Unit #11, Chicago

$1,150,000

4 Beds ⋅ 4 Baths ⋅ 12790678 MLS ⋅ ACTIVE Status

The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A courtyard, a communal garden, and a landscape front yard support a total of 13 townhouses. This 4 bedroom, 3.5 bath townhome is a dream for anyone looking for something a little extra from their home. This stunning facade is restored, a 1904 church designed by nationally famed architect Solo Spencer Beman. The main level is an open-concept chef's kitchen featuring custom two-tone cabinetry, a quartz countertop/backsplash, and a Bosch appliance package. There is still an opportunity for the buyer to select finishes. The primary suite, located on the top floor, includes 2 walk-in closets and an en-suite bathroom highlighting a stunning white marble shower and a separate soaking tub. The second floor features 3 spacious bedrooms and two full bathrooms. All bathrooms feature porcelain tiles, custom cabinetry, quartz countertops, and Hans Grohe plumbing fixtures. The unit has an attached, heated, above-ground, oversized garage that fits 4 cars. This University of Chicago community is ideally located just 10 minutes from downtown and a short distance to grocery stores, nightlife, distinctive restaurants, and cafes on 53rd street. Access to the lake and museums, and immediately next to the tennis court, Kenwood Park, and Kenwood public library, make this townhouse development a must-see.

4840 S Dorchester Avenue Unit #11, Chicago

4716 S Ingleside Avenue Unit #2N, Chicago

$324,900

2 Beds ⋅ 2 Baths ⋅ 12786114 MLS ⋅ ACTIVE Status

Welcome to 4716 S. Ingleside Avenue Unit 2N, where generous proportions, sophisticated updates, and abundant natural light come together in an exceptionally spacious 1,800-square-foot, 2-bedroom, 2-bath condominium. Featuring a kitchen and baths renovated in 2023, gleaming hardwood floors throughout, in-unit laundry, and remarkably generous living spaces, this residence offers the scale and comfort of a single-family home with the ease of condominium living. The expansive living and dining room combination is the home's centerpiece, an impressive, light-filled space that offers tremendous flexibility for everyday living and entertaining. Generous windows welcome abundant natural light, while a handsome fireplace anchors the room, creating an inviting focal point and adding character to the home's gracious proportions. The kitchen, renovated in 2023, combines contemporary style with everyday functionality. Stainless steel appliances, updated finishes, and a dedicated eating area create an inviting setting for casual dining, while ample workspace makes everyday cooking and entertaining effortless. The oversized primary suite offers exceptional space and privacy, a true retreat within the residence. A generous walk-in closet plus a secondary closet provide abundant storage, while the beautifully renovated primary bath adds modern comfort. The suite is completed by a private balcony, offering a personal outdoor escape for fresh air, relaxation, or unwinding at the end of the day. The generously proportioned second bedroom provides flexibility for family, overnight guests, or an executive home office. A second renovated full bathroom adds convenience while maintaining the home's cohesive, updated presentation. In addition to generous in-unit closet space and the convenience of an in-unit washer and dryer, the condominium includes assigned storage for seasonal belongings and everyday essentials. Perfectly positioned in South Kenwood, just minutes from Hyde Park and the University of Chicago, this residence places shopping, dining, education, culture, recreation, and the lakefront within easy reach. Enjoy convenient access to Whole Foods Market, Trader Joe's, and Hyde Park's vibrant 53rd Street shopping and dining district. Nearby lakefront and cultural destinations include Promontory Point, Lake Michigan, the Lakefront Trail, Jackson Park, Jackson Park Golf Course, the Obama Presidential Center, the Griffin Museum of Science and Industry, Washington Park, and the Midway Plaisance. The surrounding South Kenwood and Hyde Park community offers convenient access to a variety of educational institutions, including the University of Chicago Laboratory Schools, Kenwood Academy, Ariel Community Academy, and Shoesmith Elementary School, along with additional public and private educational options throughout the area. The University of Chicago and UChicago Medicine are also just minutes away. DuSable Lake Shore Drive is just moments away, providing convenient access to downtown Chicago and the lakefront. Nearby Metra Electric service, CTA bus routes, and CTA rail connections provide additional transportation options throughout the city. This is more than a condominium; it is gracious city living on a scale rarely found today, combining exceptional space, beautifully updated interiors, a private outdoor retreat, and an enviable South Kenwood location.

4716 S Ingleside Avenue Unit #2N, Chicago

$1,595,000

5 Beds ⋅ 4 Baths ⋅ 12786855 MLS ⋅ ACTIVE Status

Beautifully updated and move-in ready, this exceptional 3-story brick home on a coveted Kenwood block offers over 4,700 square feet of living space, 5+ bedrooms, 3 1/2 baths, and a fully finished and thoughtfully designed basement. A spacious, covered front porch welcomes you home, offering multiple seating areas and a ceiling fan for comfortable outdoor enjoyment even on the warmest days. Inside, the inviting entry hall opens seamlessly into the gracious living room, featuring a beautiful gas fireplace and built ins. The elegant separate dining room, with its handsome built-in cabinetry, is perfectly positioned between the living room and kitchen, connecting to the kitchen through an open butler's pantry. The spacious eat in kitchen is outfitted with a 2025 premium appliance package, including a Sub-Zero refrigerator, Viking cooktop, Wolf double oven and microwave, and Bosch dishwasher. Just off the kitchen, a large newly refinished deck overlooks the beautiful professionally landscaped yard and leads down to a full-size sport court -- an incredible amenity for recreation and entertaining. A conveniently tucked-away powder room is located beneath the staircase on the main floor. Up the grand staircase, the 2nd floor features a beautifully renovated custom office (with a discreetly integrated full-size washer and dryer), 2 generously sized bedrooms, a cozy family room, and a newly updated full bath. The 3rd floor offers a private primary suite with a newly renovated spa-like bath including radiant heated floors and a large walk in closet. Also on this level are another large bedroom, a fully renovated hall bath, and a versatile 2nd office or 5th bedroom. The fully finished lower level provides an expansive recreation room with endless possibilities-as a family room, play area, craft space, home gym, or whatever best suits your needs. A separate laundry area with sink, large walk-in pantry, second refrigerator and abundant additional storage add to the functionality of this level, which also offers convenient walk-out access to the backyard. Newer mechanicals include heat pump and space pack and 2 water heaters. The flat roof lining was replaced around 2017. This exceptional home combines beautiful original character with thoughtful updates, generous living space, and an impressive array of indoor and outdoor amenities. Truly move-in ready, it offers everything you have been looking for in a beautiful Kenwood home. Easy access to Lake Michigan, downtown transportation, and the University of Chicago campus.

4941 S Kimbark Avenue, Chicago

5041 S Dorchester Avenue Unit #2N, Chicago

$394,900

3 Beds ⋅ 2 Baths ⋅ 12786353 MLS ⋅ ACTIVE Status

Located in the historic South Kenwood Landmark District, this beautifully maintained 3-bedroom, 2-bath residence at 5041 S. Dorchester offers a blend of historic charm and modern comfort. Situated on the second floor of a boutique five-unit building, the home overlooks Madison Park with peaceful treetop views and includes TWO deeded parking spaces in a secure gated lot. The building was completely renovated and modernized in 2001, including all new building systems. Inside, you'll find a thoughtfully designed open-concept layout featuring hardwood floors throughout, a contemporary kitchen with stainless steel appliances, granite countertops, and the perfect amount of space for both everyday living and entertaining. The spacious floor plan includes three generous bedrooms, two outdoor spaces, elegant marble tile baths, and the convenience of in-unit laundry along with central heat & air conditioning. The primary bedroom leads to its own private balcony for relaxing or morning coffee. The primary bath has dual entry access to the primary and second bedrooms. The third bedroom opens to a second outdoor space and leads down to the parking area. Enjoy an unparalleled Hyde Park lifestyle just steps from Whole Foods, Madison Park, neighborhood dining and shopping, the lakefront, and the vibrant cultural and academic amenities of the University of Chicago. Nearby Metra and CTA transportation provide quick access to downtown Chicago. A happy and spacious home in one of Chicago's most architecturally significant and sought-after neighborhoods.

5041 S Dorchester Avenue Unit #2N, Chicago

4800 S Lake Park Avenue Unit #306, Chicago

$49,999

2 Beds ⋅ 1 Baths ⋅ 12784601 MLS ⋅ ACTIVE Status

AFFORDABLE HYDE PARK LIVING WITH 2 COVERED GARAGE SPACES!!! Just Minutes away from the OBAMA PRESIDENTIAL COMPLEX!!! Large Recently renovated 2 Bedroom Co-op Unit with an Open Floor Plan. A Few of the Many Amenities Include Granite Counter Tops, Stainless Steel Appliances, Bamboo Flooring, 42 Inch Maple Cabinets With Crown Molding, Large Breakfast Bar and Island Combination, Custom Real Flame Fireplace, Contemporary Bathroom with 2 Oversized spacious bedrooms. The Monthly Carrying Charge Of $1,311.00 Includes, Taxes, 24 Hour Door Person, Lawn Care, Snow Removal, Heat, Central Air, Basic Cable, Water, Interior Maintenance and On-Site Management. You only pays for Lights. Cash Buyers Preferred. Unit Must Be Owner Occupied. Board Approval Required. Must Go Through Credit, Income and Back Ground Check With Management Office. Buyer Pays The Purchase Price, and additional $5,420 For The Share, and The Monthly Carrying Charge Of $1,311.00. SOLD AS-IS. A Property To Live In And Relax!

4800 S Lake Park Avenue Unit #306, Chicago

4800 S Lake Park Avenue Unit #2102, Chicago

$60,000

3 Beds ⋅ 2 Baths ⋅ 12776233 MLS ⋅ ACTIVE Status

Experience elevated living situated on the 21st floor, this spacious three-bedroom residence offers an impressive combination of natural light, beautiful hardwood floors, and expansive windows framing sweeping southern views of the surrounding neighborhood and Chicago skyline. The generously proportioned living room flows into a separate dining area, creating an inviting setting for everyday living and entertaining. Enjoy remarkable lakefront and park views, along with an ever-changing urban landscape, from this distinctive high-rise setting. The thoughtfully arranged floor plan includes three bedrooms, a functional kitchen with warm wood cabinetry and ample counter space, and a full bathroom with a separate additional half bath. Conveniently located in Hyde Park near Lake Michigan, parks, shopping, dining, cultural attractions, and transportation. Discover the space, scenery, and possibilities of 21st-floor living.

4800 S Lake Park Avenue Unit #2102, Chicago

$385,000

3 Beds ⋅ 2 Baths ⋅ 12774294 MLS ⋅ ACTIVE Status

Over 2,000 SQ FT | KENWOOD LEGACY ASSET | Experience the power of scale and heritage in this sprawling 2,000 sq. ft. second-floor condo, perfectly positioned in Chicago's Kenwood neighborhood. This is more than a home. Boasting soaring 12-foot ceilings and intricate architectural details, this 3-bedroom, 2-bath offers the volume and character that modern construction cannot replicate. The expansive floor plan features a grand foyer, a living room anchored by a classic fireplace, and custom-built bookshelves by Arthur Levin. The primary bedroom features a unique vanity transition and shutter-door privacy. With an entertainer's floor plan, you will enjoy a grand foyer, massive formal dining room with bay windows and a large private rear porch overlooking the backyard. In-unit laundry included. Steps from the lakefront and elite dining like Virtue and 14 Parish. Seize this rare opportunity for wealth arbitrage in Chicago's most culturally significant corridor. Position yourself in the heart of Kenwood, schedule your private tour today. Monthly HOA includes:Heat, Water, Common Insurance, Security, Lawn Care, Scavenger, Snow Removal

1354 E 48Th Street Unit #2E, Chicago

$314,000

3 Beds ⋅ 2 Baths ⋅ 12771807 MLS ⋅ ACTIVE Status

4710 S Ellis Avenue Unit #3N, Chicago

4939 S Dorchester Avenue Unit #5F, Chicago

$147,000

1 Beds ⋅ 1 Baths ⋅ 12767252 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

$1,925,000

12758275 MLS ⋅ ACTIVE Status

Finally available! Where the Hot Bronzeville/Woodlawn/Kenwood/Hyde Park Neighborhoods intersect sits this "Value-Add" 7 Unit investment opportunity. 4 Units, now vacant, have been Occupied by family members for several decades with the 3 remaining units on MTM/ below market rentals. Many of the original features are still intact: Pocket Doors, Paneled Walls, Butlers Pantry, Built in China Cabinets and Bookcases, French Doors, Cofferred Ceilings, Decorative Fireplaces, Tile floor staircases, Sunrooms, Jack and Jill Baths, Crown Molding! With a newer roof, central stairwell skylight and updated circuit breakers, the Building has 'Great Bones', making it a fabulous candidate for Value Add updates and cosmetic work, optimizing rentals to current market rates. Easy Access to Public Transportation, University of Chicago and the University of Chicago Medical Center, the Obama Library and the Lakefront.

4711 S Greenwood Avenue, Chicago

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Kenwood Real Estate

Newest Listings in Kenwood

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