Kenwood Homes for Sale

Welcome to Kenwood, one of Chicago's most cherished neighborhoods, where historic charm meets modern living. Nestled along the picturesque shores of Lake Michigan, Kenwood is known for its tree-lined streets, stunning architecture, and a rich cultural heritage that tells the story of its vibrant community.

Kenwood boasts a diverse array of homes, from magnificent vintage mansions to contemporary condominiums, catering to a variety of lifestyles and preferences. Many properties are adorned with exquisite details, such as ornate woodwork and grand staircases, reflecting the neighborhood's storied past. As you explore the homes for sale in Kenwood, you'll discover spacious layouts, lush gardens, and breathtaking views that make this area truly unique.

Beyond the beautiful homes, Kenwood offers an abundance of amenities that enhance the quality of life for its residents. The neighborhood is home to several parks, including the scenic Washington Park, perfect for leisurely strolls, picnics, or enjoying a sunny afternoon. The vibrant local scene also features a selection of shops, cafes, and restaurants, where you can savor delicious cuisine and connect with your neighbors.

Education is a priority in Kenwood, with access to top-rated schools and educational institutions, making it a desirable location for families. Additionally, its proximity to downtown Chicago ensures that residents can easily enjoy the hustle and bustle of the city while returning to the tranquility of their suburban oasis.

If you're looking to find your dream home in a community that embodies both elegance and warmth, Kenwood is the perfect place to call home. Explore the homes for sale today and discover the charm that awaits you in this exceptional neighborhood!

Newest Kenwood Homes for Sale

$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

$2,295,000

8 Beds ⋅ 6 Baths ⋅ 12702363 MLS ⋅ ACTIVE Status

Located in the heart of the South Kenwood historic landmark district, 4901 S Kimbark Avenue offers a rare opportunity to own a distinguished residence in one of Chicago's most architecturally significant neighborhoods. Surrounded by stately homes, mature trees, and picturesque streets, this exceptional property combines timeless character with an unbeatable location just moments from the University of Chicago campus, Jackson Park, the Museum of Science and Industry, and the lakefront. The imposing 3-story home has impressive curb appeal, including an inviting wrap-around porch and mature plantings. A private side yard provides a verdant refuge for play and outdoor dining. The new 2+ car garage is a real plus. Inside, the 8-bedroom, 5.5 bath home showcases generous living spaces, abundant natural light, and classic architectural details that reflect Kenwood's rich heritage. Spacious formal rooms are complemented by comfortable everyday living areas, creating an ideal setting for both entertaining and daily life. Among the many outstanding features is the beautifully designed modern eat-in kitchen with top-of-the-line appliances and the fully-finished lower level with a spacious recreation room, separate work-out room, and a new full bath. New water service, zoned a/c, and updated systems throughout. The location is second to none. Residents enjoy easy access to acclaimed restaurants, neighborhood cafes, shopping, cultural institutions, Metra and CTA transportation downtown, and the scenic paths and beaches along Lake Michigan. Jackson Park's ongoing improvements and the renowned Obama Presidential Center further enhance the appeal of this vibrant community. Whether you're seeking a remarkable historic residence or an elegant home in one of Chicago's most desirable neighborhoods, 4901 S Kimbark Avenue offers an exceptional blend of architectural character, urban convenience, and enduring value.

4901 S Kimbark Avenue, Chicago

$1,675,000

4 Beds ⋅ 4 Baths ⋅ 12711971 MLS ⋅ ACTIVE Status

Designed by renowned modernist architect Tony M. Grunsfeld, this mid-century gem highlights architect's love for clean lines, minimalist design and above all, natural flow from inside to the outside world. This house built in 1965, has been recently fully renovated. When entering the house one is immediately drawn to the expansive living room with its' three floor-to-ceiling double glass doors that open the space onto a lush, oversized backyard full of blooming flowers. Spacious chef's kitchen, features lots of counter space and storage, beautiful cabinets and high end appliances . This delightful space is flooded with light from a set of floor-to-ceiling glass doors and opening to the light filled living room. First level features also an office/guest bedroom and a half bath. Four spacious bedrooms are all located on the second floor. Primary bedroom has en-suite bathroom with double sink and two large walk-in closets. Additional two bedrooms and one office (originally a bedroom) share a beautiful bathroom with a bathtub. Comfortable family room and a gym are located in the basement. In addition, there is a large storage space, mechanical area and laundry as well as additional half bath on the lower level. All wooden floors are oak, while the entry hall floor is covered with stone ties. This is a unique home with simple beauty, inviting, light filed space and a very comfortable interior. Recent major updates: HVAC system 2022, new sewer line to the street, direct vent gas fireplace 2024.

1203 E 50Th Street, Chicago

$2,175,000

8 Beds ⋅ 5 Baths ⋅ 12752094 MLS ⋅ ACTIVE 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 ⋅ ACTIVE Status

4801 S Kimbark Avenue, Chicago

$1,695,000

6 Beds ⋅ 6 Baths ⋅ 12705893 MLS ⋅ ACTIVE Status

Offering more than 6,000 square feet of living space, this grand Kenwood greystone pairs remarkable original craftsmanship with the scale and flexibility of a 7-bedroom, 6-bath home. Rich hardwood floors, exceptional millwork, handcrafted built-ins, pocket doors and seven fireplaces create architectural character increasingly difficult to find. Designed by noted Chicago architect Horatio Wilson, the home reflects the craftsmanship found throughout many of Kenwood's significant historic residences. Generously proportioned living and dining rooms provide impressive spaces for entertaining while remaining comfortable for everyday living. Just beyond the dining room, an intimate lounge with a dramatic built-in banquette creates one of the home's most memorable spaces-perfect for morning coffee, cocktails or conversation. The adjoining butler's pantry leads to the kitchen, while the original servant's staircase provides a second connection to the upper level. The spacious primary suite offers a private retreat with a walk-in closet and ensuite bath featuring a steam shower, soaking tub and dual vanities. Additional bedrooms provide exceptional flexibility for guests, home offices or creative space. The finished lower level expands the possibilities even further with a second full kitchen, dining area, recreation space, bedroom and full bath-ideal for guests, extended stays or a more independent living arrangement. Outside, a private garden surrounded by mature landscaping provides a peaceful escape in the city. Set on a beautiful tree-lined block near Hyde Park and the University of Chicago, the home offers a rare combination of exceptional space, remarkable original craftsmanship and the flexibility to make a significant Kenwood residence your own.

4942 S Ellis Avenue, Chicago

$2,325,000

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

SPECIAL FINANCING INCENTIVE! Seller is offering assistance toward a mortgage interest rate buydown for qualified buyers, subject to lender approval and loan terms. Contact listing agent for additional details. Experience the privacy of single-family-style living with the convenience of move-in-ready new construction at The Kenwood Reserve, an exclusive collection of just three full-masonry residences on a quiet, tree-lined cul-de-sac in historic Hyde Park-Kenwood area. This thoughtfully designed four-bedroom, three-and-a-half-bath home offers three levels of modern living, a private outdoor retreat, two-car garage, secured, PRIVATE entry and no monthly HOA assessment. The main living level features sun-filled interiors, clean architectural lines, and sophisticated finishes designed for both everyday comfort and entertaining. At the heart of the home, the designer kitchen showcases custom dark wood Studio 41 cabinetry, an oversized quartz island, and a generous pantry, with an open-concept layout connecting the kitchen, dining, and living spaces. Step outside to your own private outdoor retreat, offering space to relax, entertain, garden, or enjoy indoor-outdoor living in the heart of the city. Upstairs, thoughtfully arranged bedrooms provide privacy and flexibility, while the finished lower level offers an additional living area ideal for a media room, home office, playroom, or fitness space, along with a fourth bedroom perfect for guests or extended family. An additional approximately 230 SF of unfinished space provides valuable flexibility for future customization, whether envisioned as a wine cellar, creative studio, wellness space, or additional storage. Two separate HVAC systems, each with its own furnace and central air-conditioning unit, provide greater control over comfort throughout the home. Limited opportunities remain for select finish customization, allowing buyers to incorporate their personal style into this newly constructed residence. Conveniently located near Hyde Park, the University of Chicago, lakefront parks, public transportation, restaurants, and cultural attractions, The Kenwood Reserve combines quality masonry construction, modern functionality, private outdoor space, and garage parking in one of Chicago's most established neighborhoods. A distinctive opportunity to enjoy new-construction living with the independence of fee-simple ownership and no monthly HOA assessment.

4721 S Ingleside Avenue, Chicago

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Kenwood Homes for Sale

Newest Kenwood Homes for Sale

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