Kenwood Real Estate

Kenwood is a vibrant and historic neighborhood nestled in the heart of Chicago, Illinois. Located in Cook County, this charming area offers a perfect blend of urban convenience and a peaceful residential atmosphere.

Known for its rich history and architectural beauty, Kenwood boasts a variety of stunning homes, ranging from stately mansions to cozy bungalows. Many of these properties showcase exquisite craftsmanship and unique design elements, reflecting the neighborhood's past as a hub for Chicago's elite.

In addition to its architectural gems, Kenwood is also home to several beautiful parks and green spaces. Residents can enjoy leisurely strolls along tree-lined streets or take advantage of the numerous recreational activities available in the area. The neighborhood's proximity to Lake Michigan provides an added bonus, allowing residents to enjoy waterfront views and access to the lakefront trail.

Kenwood is also known for its cultural diversity and vibrant community spirit. The neighborhood is home to a diverse mix of residents, including professionals, artists, and families, creating a welcoming and inclusive atmosphere. Local businesses, restaurants, and shops add to the neighborhood's charm, offering residents a range of amenities within walking distance.

With its prime location, rich history, and strong sense of community, Kenwood is a highly desirable neighborhood for those seeking an ideal blend of urban living and suburban tranquility. Whether you are looking for a historic home or a modern apartment, Kenwood offers something for everyone.

Newest Listings in Kenwood

$40,000

2 Beds ⋅ 1 Baths ⋅ 12741378 MLS ⋅ NEW Status

A well-maintained residence offering excellent value and strong long-term potential. Located on the 7th floor, this unit provides bright natural light and pleasant open views. The building features a fully renovated marble lobby, 24hour reception, and onsite security, creating a secure and welcoming environment for residents and guests. The home includes 2 bedrooms, 1 bathroom, and a functional combined living/dining/kitchen layout that offers flexibility for updates or customization. Ideal for buyers seeking an affordable entry into the Hyde Park/Kenwood market or investors looking for a value-add opportunity. Close to the lakefront, parks, public transit, and neighborhood amenities.

4850 S Lake Park Avenue Unit #709, Chicago

$2,729,000

12755416 MLS ⋅ NEW Status

1209 E. Madison Park and 1210 E. Hyde Park Blvd. are two back-to-back 4-unit buildings with 8 units, 37 bedrooms, and 19 bathrooms on the border of Hyde Park and Kenwood. Unit sizes are exceptional for the submarket: four and five-bedroom layouts averaging 1,800 square feet with in-unit laundry, renovated kitchens and baths, and original vintage detail throughout. The property is fully occupied, with every lease running through late 2026 and 2027. Five units are supported by Housing Choice Voucher contracts, pairing a government-backed rent component with a deep private renter pool. At $317,064 in annual scheduled rent, the offering combines immediate cash flow with clear near-term upside as a utility reimbursement program already in place on recent leases rolls out building-wide, one remaining original unit awaits renovation, and below-market units convert to market rent on turnover. This property is ideally suited for investors seeking a core Kenwood / Hyde Park position with strong in-place income and durable long-term value growth. The location drives consistently high demand, making this an outstanding opportunity in one of the most resilient and historically stable multifamily submarkets in Chicago.

1209 E Madison Park Boulevard, Chicago

$229,999

2 Beds ⋅ 2 Baths ⋅ 12755276 MLS ⋅ NEW Status

BEAUTIFUL TOP-FLOOR 2-BEDROOM, 2-BATH CONDO IN KENWOOD! This bright and spacious home features a desirable open-concept living and dining area with soaring ceilings and rich cherry hardwood floors throughout. The primary suite offers a private bath and a generous walk-in closet, creating the perfect retreat. The updated kitchen is equipped with stainless steel appliances, ample cabinetry, and an in-unit washer and dryer for added convenience. Low HOA assessments make this home an exceptional value. Ideally located in the heart of Kenwood, you'll enjoy easy access to the University of Chicago, shopping, restaurants, public transportation, Lake Shore Drive, and the expressway. Just minutes from downtown Chicago, this home offers the perfect combination of comfort, convenience, and location. Don't miss the opportunity to make this exceptional condo your new home!

4731 S Ingleside Avenue Unit #A3, Chicago

$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

$445,000

4 Beds ⋅ 2 Baths ⋅ 12754001 MLS ⋅ NEW Status

Beautifully updated 4-bedroom home in the heart of Hyde Park featuring timeless hardwood floors, soaring ceilings, and an impressive vaulted foyer upon entry. The home has a dramatic 36 ft gallery hallway creating an elegant flow to spacious bedrooms. Sun-filled south-facing exposure pours natural light throughout the home, charming sunrooms at both the front and rear of the property offering the perfect spaces to relax, work, or entertain. Thoughtfully updated while maintaining character and warmth, this home combines classic architecture details and modern comfort in one of Hyde Park's most desirable areas. Enjoy easy access to local coffee shops, restaurants, whole foods, and neighborhood favorites along 53rd Street. Convenient transportation options include Metra, CTA, and easy access to Lake Shore Drive. Garage Parking and large storage space included. This home will not disappoint!

1140 E Hyde Park Boulevard Unit #3D, Chicago

$1,775,000

6 Beds ⋅ 5 Baths ⋅ 12753755 MLS ⋅ NEW Status

4801 S Kimbark Avenue, Chicago

$40,000

2 Beds ⋅ 1 Baths ⋅ 12747823 MLS ⋅ ACTIVE Status

Welcome home to an abundance of natural light in this renovated south-facing 2 bed, 1 bath co-op, offering approximately 1,000 square feet of comfortable living space with sunny south-facing views that take in the lake from this upper-floor vantage point. This unit has been thoughtfully updated with a new kitchen, new flooring throughout, and a new vanity in the bathroom. Located just minutes from everything that sought-after Hyde Park has to offer, including easy access to the University of Chicago, Metra, lakefront trail, Museum of Science and Industry, shopping, and award-winning restaurants. Assessments at this fully owner-occupied co-op include heat, AC, water, cable, real estate taxes, 24-hour door staff, party room, laundry room, fitness center, and interior and exterior maintenance. Covered parking is available for $80 per month. Please note that in addition to the purchase price, $4,640 in transfer shares are required to be deposited with Harper Square Cooperative prior to move in. This transaction is cash only, and rentals are not permitted.

4850 S Lake Park Avenue Unit #2109B, Chicago

$399,900

3 Beds ⋅ 2 Baths ⋅ 12685740 MLS ⋅ ACTIVE Status

Nestled in the heart of the historic South Kenwood Landmark District, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of timeless neighborhood charm and modern comfort. Overlooking the green spaces of Madison Park, this second floor home enjoys peaceful treetop views. 5041 S Dorchester is a boutique building of just five residences. The property 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. Rare for the neighborhood, the home includes two deeded parking spaces (one of the spaces is covered) in a secure gated lot. 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

$899,000

4 Beds ⋅ 4 Baths ⋅ 12743333 MLS ⋅ ACTIVE Status

APPRAISED AT $999,000-NOW OFFERED AT $899,000, A FULL $100,000 BELOW APPRAISED VALUE, WITH A PRIVATE TWO-CAR GARAGE INCLUDED. An exceptional new-construction opportunity at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences tucked along a quiet, tree-lined cul-de-sac in historic Kenwood. This full-masonry, three-level, 4-bedroom, 3.5-bath residence delivers the space and privacy of a single-family home with the convenience, efficiency, and refined finishes of modern construction. Sun-filled interiors feature clean architectural lines, generous room proportions, and thoughtfully selected finishes throughout. The beautifully appointed kitchen is designed for both everyday living and effortless entertaining, with custom dark-wood Studio 41 cabinetry, stainless steel appliances, an oversized quartz island, and abundant storage. Select opportunities for buyer customization may still remain. Sliding glass doors extend the open-concept living space directly into a private backyard retreat-an exceptional feature ideal for dining outdoors, entertaining, relaxing, or creating a garden oasis. Combined with the included two-car garage and no monthly HOA assessment, the home offers a rare level of privacy, autonomy, and long-term value. The versatile lower level provides a warm secondary living space suited for a media room, lounge, playroom, fitness area, or home office, along with a private fourth bedroom ideal for guests or extended living. Moments from Hyde Park, the University of Chicago, lakefront parks, dining, and major cultural destinations, including the Obama Presidential Center in nearby Jackson Park, The Kenwood Reserve presents a compelling opportunity to own full-masonry new construction in one of Chicago's most architecturally distinguished neighborhoods. Preferred lender program available. Private tours now offered.

4719 S Ingleside Avenue, Chicago

$585,000

4 Beds ⋅ 3 Baths ⋅ 12741279 MLS ⋅ ACTIVE Status

Welcome to Woodlawn Manor. Stay in the Chicago that shaped history. The Obama Presidential Center opens this summer. We're handing you the keys to the neighborhood that started it all. Steps away from the Obama Presidential Center, this four-bedroom "penthouse" sits in the heart of historic Kenwood, minutes from the brand-new Obama Presidential Center and steps from the University of Chicago. It's a 1908 residence with the kind of grandeur you can't rebuild: mahogany walls and beams restored to a glow, original leaded glass framing the treetops, and rooms big enough for the whole crew to spread out and still find a quiet corner. The kitchen is a cook's dream with Sub-Zero and Wolf appliances, granite surfaces and two walk-in pantries. Whether you bring in a chef or prefer DIY meals, this space is built for long dinners, slow mornings, and the feeling of waking up where history is being made. Formal dining room designed for the ultimate host; it comfortably accommodates a table for 12 or more, making it the perfect stage for holiday gatherings and elegant dinner parties. Sleeps your family or your group in comfort. An added perk: in-unit laundry. Walk to everything. Beyond your front door, you are steps away from the University of Chicago, lush parks, and the vibrant dining and shopping scene of Hyde Park. Come for the opening. Stay for the neighborhood.

5054 S Woodlawn Avenue Unit #3C, Chicago

$36,900

1 Beds ⋅ 1 Baths ⋅ 12728372 MLS ⋅ ACTIVE Status

Find yourself at home in an abundance of natural light in this south facing 1 bed 1 bath co-op minutes from everything that sought-after Hyde Park has to offer. Easy access to University of Chicago, Metra, lakefront trail, Museum of Science and Industry, shopping, and award-winning restaurants. Assessments at this fully owner-occupied co-op include heat, AC, water, cable, real estate taxes, 24 hr. door staff, party room, laundry room, fitness center, interior and exterior maintenance. Parking available for additional per month cost. Rentals are not allowed.

4850 S Lake Park Avenue Unit #903, Chicago

$299,900

2 Beds ⋅ 3 Baths ⋅ 12723335 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

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