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

$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

$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

$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

$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

$949,000

4 Beds ⋅ 4 Baths ⋅ 12698231 MLS ⋅ ACTIVE Status

Move-in ready new construction at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences on a quiet, tree-lined cul-de-sac in historic Kenwood. Designed as a full masonry build to deliver lasting quality, timeless curb appeal, and long-term value, this thoughtfully planned three-level residence offers the scale and privacy of a single-family home with the ease of modern new construction, featuring expansive living spaces, refined designer finishes, private outdoor living, and a 2-car garage included for added convenience and storage. Sun-filled interiors feature clean architectural lines and timeless finishes throughout. The beautifully appointed kitchen is designed for everyday living and effortless entertaining, with custom dark wood Studio 41 cabinetry, stainless steel appliances, an oversized quartz island, and ample storage. Limited opportunity remains for buyer customization and select finish selections. The open-concept main living spaces are designed for seamless indoor-outdoor living, with sliding glass doors opening directly to a private backyard retreat. Ideal for entertaining, dining al fresco, relaxing, or everyday enjoyment, this rare outdoor space adds a true single-family feel within a boutique new-construction setting. With no monthly HOA assessment, The Kenwood Reserve offers a rare combination of privacy, autonomy, and low-maintenance luxury. The lower level provides a warm and versatile secondary living space, perfect for a media room, lounge, playroom, fitness area, or home office, along with a private fourth bedroom ideal for guests. Located moments from Hyde Park, the University of Chicago, lakefront parks, dining, and major cultural institutions - including the Obama Presidential Center in nearby Jackson Park - The Kenwood Reserve offers full masonry new-construction living in one of Chicago's most historic and architecturally distinguished neighborhoods. Preferred lender program available. Only three residences available. Private tours now offered.

4719 S Ingleside Avenue, Chicago

$80,000

2 Beds ⋅ 1 Baths ⋅ 12661988 MLS ⋅ ACTIVE Status

Experience timeless Chicago living in this beautifully remodeled 2-bedroom, 1-bath condo set within a highly desirable lakefront co-op community. Perched above the shoreline, this home offers uninterrupted views of Lake Michigan and the iconic downtown skyline, creating a daily backdrop that feels both serene and cinematic. Every inch of the residence has been meticulously maintained and thoughtfully updated, blending modern finishes with classic co-op charm. The open living and dining space is framed by expansive windows that flood the home with natural light and showcase the sweeping vistas. A fully renovated kitchen and refreshed bath add comfort and style, while both bedrooms offer generous space and flexibility. This is a rare opportunity to own a turnkey home in a wellrun, soughtafter building known for its community feel, architectural character, and unbeatable lakefront access.

4800 S Lake Park Avenue Unit #2005, Chicago

$585,000

4 Beds ⋅ 3 Baths ⋅ 12679414 MLS ⋅ ACTIVE Status

5054 S Woodlawn Avenue Unit #3C, Chicago

$425,000

4 Beds ⋅ 2 Baths ⋅ 12675404 MLS ⋅ ACTIVE Status

For the first time in 47 years, a rare value-add opportunity in the heart of historic Kenwood Mansion District. This spacious 4-bedroom, 1.1-bath townhome offers three levels of living space, including a partially finished basement and a large private fenced yard. Solid brick and concrete construction provides the perfect foundation for renovation, with tremendous upside for investors or owner-occupants looking to build equity. Featuring 4 bedrooms on one level, this home offers a functional layout that can easily be reimagined for modern living. Ideally located just blocks from the neighborhood gem, Kenwood Community Park, and close proximity to Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the recently finalized Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this property presents a unique chance to renovate and live in one of the South Side's most sought-after neighborhoods.

4753 S Woodlawn Avenue, Chicago

$55,000

3 Beds ⋅ 1 Baths ⋅ 12649015 MLS ⋅ ACTIVE Status

Seller is highly motivated and looking for a serious buyer ready to move into this beautifully maintained unit located in the heart of Hyde Park - one of Chicago's most sought-after neighborhoods. This home offers the perfect blend of comfort, convenience, security, and affordability with access to premium building amenities and city living near downtown Chicago. Featuring modern updates, a spacious layout, and the added convenience of a gas stove and appliance coverage included in the monthly fee, this unit is ideal for a buyer seeking low-maintenance living in a secure, well-managed building. Property Details * Monthly Carrying Charges: $1,523 * Shares / Refundable Deposit: $6,240 * Garage Parking: Starting at $75/month Monthly Fee Includes * Heat, water, and cable (HBO, Showtime, and STARZ included) * Gas stove and appliance coverage * All unit maintenance * Common area amenities Additional Highlights * 24/7 building and garage security * Only electricity is excluded from the monthly fee * Owner-occupancy required for at least one year before resale * All renovations or changes require board approval Located in desirable Hyde Park, this unit presents a rare opportunity to own an affordable, secure, and low-maintenance home in one of Chicago's most vibrant and growing communities. Perfect for buyers looking for value, convenience, and move-in-ready living. CASH DEAL ONLY

4850 S Lake Park Avenue Unit #2111, Chicago

$2,475,000

8 Beds ⋅ 5 Baths ⋅ 12485443 MLS ⋅ ACTIVE Status

Distinguished by its striking crow-stepped gable, this remarkable residence stands proudly in the heart of historic Kenwood. Built in 1896 for Edith and Laurence Carton, the home was designed by noted architect William Otis, a graduate of Paris's prestigious Ecole des Beaux-Arts and a protege of William LeBaron Jenney. At the height of Chicago's fascination with revival architecture, Otis looked to the canals of Amsterdam for inspiration, creating a residence that beautifully captures the elegance and craftsmanship of 17th-century Dutch design. Commissioned for the treasurer of Swift & Company, the home remains an exceptionally preserved example of architectural artistry and enduring quality. Beyond its richly detailed brick facade lies a grand yet welcoming interior filled with natural light. Original woodwork, art glass, and decorative tile have been meticulously preserved and thoughtfully complemented by modern updates. Expansive formal living and dining rooms flow effortlessly into a warm, inviting kitchen and a sunlit family room that opens onto a spacious deck-ideal for both elegant entertaining and everyday living. Offering eight bedrooms, multiple fireplaces, and a dramatic third-floor family room with soaring 15-foot ceilings, the residence provides extraordinary scale, character, and versatility. Set on a beautifully landscaped, tree-lined lot, the property also includes a charming coach house with a two-bedroom apartment-perfect for guests, extended family, or supplemental income. Timeless, sophisticated, and well maintained, this extraordinary home offers a rare opportunity to own a treasured piece of Kenwood's architectural heritage.

4923 S Greenwood Avenue, Chicago

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