View All Kenwood Chicago IL Homes with Finished Basement Listings

$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

$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

$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

$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

$910,000
4 Beds 5 Baths 12639055 MLS CLOSED Status
This stately all-brick 4-bedroom, 3.2 bath, two-story residence is ideally situated among historic mansions in prestigious Kenwood on iconic Professor's Row. Kenwood offers a rare suburban feel in the heart of the city and boasts an impressive roster of past and present residents, including Muddy Waters, Muhammad Ali, and the Obamas. Offering over 3,600 square feet of living space, this grand home presents a remarkable opportunity to bring your vision to life and restore it to its former glory. The main level welcomes you with a classical semicircular portico entrance leading into a grand foyer. A massive living room with fireplace flows into an adjacent parlor featuring floor-to-ceiling windows, creating an ideal setting for entertaining. The main floor also includes a sizable kitchen with large breakfast nook, formal dining room, and powder room. The second level features a generous primary bedroom with ensuite full bath and walk-in closet, two additional sizeable bedrooms, and a second full bath. A private landing leads to a second primary suite complete with its own ensuite full bath. The fully finished lower level provides additional living space with a cavernous rec room with bar area, second powder room, laundry area, and ample storage. An attached garage completes this exceptional offering. A rare opportunity to own a distinguished home in one of Chicago's most storied neighborhoods.

4959 S Greenwood Avenue, Chicago

$675,000
3 Beds 3 Baths 12625810 MLS PENDING Status
Move right into this stylish, high-end condo in the heart of Historic South Kenwood and located in desirable Madison Park, renowned for its lush private park and arboretum. This tastefully rehabbed home was redesigned (2020) with a contemporary palette, new central air and high-end modern finishes, yet still retains vintage features with high ceilings, crown moldings, original hardwood floors, handsome doors with original hardware and period woodwork. This home boasts a gracious entertaining layout with a large living room graced with a decorative fireplace, adjacent to a spacious dining room which is directly off a 3 season porch on one end and the 14 foot butler pantry on the other. The newly designed chef's kitchen and butler pantry has a ton of storage. It also features new quartz counters and porcelain backsplash with stylish white cabinets, stainess steel appliances with a chef's stove and vented hood with a charming breakfast nook and balcony. All three bedrooms have ensuite baths and ample closets. The primary bath with its gorgeous tilework and heated floors was enlarged and redesigned with wet and dry rooms. It includes designer double sinks, a stylish large shower with two rain shower heads and separate soaking tub. The primary bedroom has the 2nd and largest balcony overlooking the back garden and brick patio. This home also has a beautifully designed mud room and in-unit laundry, plus a garage space. Additional overnight parking in Madison Park is $500 per year. Super location- walking distance to UC, Whole Foods, shops and restaurants on 53rd and transportation.

1226 E Madison Park Unit #1, Chicago

$1,367,500
4 Beds 4 Baths 12617167 MLS CLOSED Status
Experience a truly rare and unique blend of traditional charm plus modernized conveniences in one of Chicago's most intellectually vibrant and architecturally distinguished neighborhoods. This 19th century Queen Anne Victorian represents an exceptional combination of depth, history, and warmth coupled with extensive updates that will allow you to immediately move in and live comfortably in the space. Set on parts of three oversized city lots totaling 108' x 150', this property provides a quiet sanctuary in the midst of urban sophistication unlike any other property or neighborhood in the city. The property provides multiple areas of outdoor living space with a large multi level bluestone and brick paver patio with; built in brick walls that double as seating ledges, an outdoor kitchen with a built in gas Weber Grill, mature trees, professional landscaping, an extensive nine-zoned sprinkler system that covers the entire property, its huge side yard and multiple vegetable gardening beds which you can enjoy with the frequent bird, and bunny visitors to the property. This 1885 home was painstakingly restored (completed in August 2016) with an all-encompassing professional renovation (copies of specs available for serious buyers) that included all new electrical, plumbing, HVAC (dual zoned), improved insulation, and wired high speed Cat 6 internet capability throughout the home. The extensive renovations retained the appeal and the spaciousness of Kenwood mansions of yesteryear, while at the same time improving the home to accommodate a contemporary and modern sensibility. The home boasts three floors of finished living space in addition to a full unfinished basement that can be used for virtually limitless storage or can be finished for additional living space. The formal living room anchors the home with a stunning tiered crystal chandelier, custom sconces, and a sun-drenched original stained-glass transom window. One set of pocket doors separates the formal living and dining areas from a chef's kitchen, while another original set of pocket doors leads into a side family room that can be used as a study or reading/sitting room. This light-filled property boasts multiple bay and oriel window bays, window seats, and remote controlled custom blinds on the first floor. The upper floors feature window treatments that allow top down operation, which offers all of the benefits of bathing your rooms and yourself in sunlight while also maintaining privacy as desired. The kitchen and bathrooms were professionally and thoughtfully designed. The chef's kitchen features a 48 inch Wolf gas dual oven and range with included grill and griddle/Plancha cooking surface plus a custom commercial grade vent hood, a pot-filler, two large sinks, and a dual temperature zone SubZero wine/beverage fridge. The kitchen also features high end fixtures, including custom Crystal cabinets with leathered granite outer countertops and White Princess Quartzite on the large, custom island. The home boasts four bedrooms including two primary suites, each with an en suite bathroom and large walk in closets. The larger en suite bathroom includes an Oceania air jetted tub, as well as a separate shower with a stone floor. The third bedroom is also oversized and features a working fireplace and bay window. Situated near the border of South Kenwood and Hyde Park, this property is a short 12 minute drive to downtown Chicago, seven minute walk to the Metra, two blocks to Whole Foods and express to downtown CTA bus service, a ten minute walk to the lake front, across the street from the Solon Beman designed Blackstone Library, just over a mile to the center of the University of Chicago campus, and a short walking distance from restaurants, cafes, bookstores, parks, tennis courts, and local shopping. Truly everything you could desire in your urban retreat. Contact us today to schedule a private showing. ***Broker owned property, and broker's primary residence. ***

4916 S Blackstone Avenue, Chicago

$900,000
3 Beds 3 Baths 12618439 MLS ACTIVE Status
The Dorchester Collection is an exclusive, newly constructed gated townhome community nestled in the prestigious Hyde Park/Kenwood neighborhood. Comprising just 13 residences, the development is thoughtfully designed around a beautifully landscaped courtyard, communal garden, and lush front grounds. This exceptional 3-bedroom, 2.5-bath townhome offers a rare blend of modern luxury and historic charm. Spanning three levels, the residence showcases remarkable architectural character, with select elements thoughtfully repurposed from the original 1904 church designed by renowned architect Solo Spencer Beman. The restored facade provides a striking and timeless presence. The main level features an open-concept layout anchored by a chef's kitchen with sleek Zecchinon Italian cabinetry, Bosch appliances, and abundant concealed storage-perfect for both everyday living and entertaining. The primary suite is a true retreat, offering expansive walk-in closets and a spa-inspired en-suite bath complete with a white marble shower, separate soaking tub, and a Restoration Hardware vanity accented by brass and matte black Hansgrohe fixtures. Upstairs, two additional generously sized bedrooms provide flexible space for guests, family, or a home office. This home includes one exterior parking space along with an attached, heated, above-grade oversized garage accommodating one vehicle. Two private outdoor spaces offer additional room to relax and unwind. Ideally located in the vibrant University of Chicago community, this home is just 10 minutes from downtown and moments from the shops, dining, and nightlife along 53rd Street. Enjoy easy access to the lakefront, museums, Kenwood Park, tennis courts, and the Kenwood Public Library-making this exceptional residence a true standout.

4840 S Dorchester Avenue Unit #1, Chicago

$925,000
6 Beds 5 Baths 12605785 MLS ACTIVE Status
Looking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Single Family Home in the Hyde Park/Kenwood Community, where historical elegance is seamlessly integrated with contemporary living. This rare gem has been updated on the 1st level only to offer both classic charm and modern amenities perfect for short-term rentals generating great annual income. Bring your own touches for units 2. Step through the front portico (with 4 tall columns), and see how 3 units, (1,300 ft on each floor) exude cozy living space with historic charm flooded with natural light from brand new windows, featuring many vintage details including solid mahogany doors, molding throughout, as well as oak and antiqued pine flooring. The 1st floor duplex unit has 1700+sf living space with various new updates including stainless steel appliances, cortz countertops, refurbished original hardwood floors, new fixtures, freshly painted and a fully height semi-finished basement, and so much more. The 3rd floor features an updated kitchen with new cortz countertops, laminate flooring mixed with the original oak wood, and freshly painted. This property is zoned as RM5 w/two city lots (25 ft x 200 ft), offering the new owner an opportunity for growth, with a shared driveway connected to a gated luxury townhome community, a new construction project converted from the original building constructed by the architect, Solon Spencer Beman. Don't miss your chance to own a piece of history that caters to today's lifestyle needs, and steps from Chicago's Beautiful Lakefront and shuttle service to the University of Chicago. Please note, this building can be easily converted to a single family home if wanted.

4836 S Dorchester Avenue, Chicago

$2,900,000
7 Beds 5 Baths 12540892 MLS CONTINGENT Status
New on Woodlawn Avenue. Located in the heart of the South Kenwood Historic Landmark District, this imposing and gracious three-story brick residence is a rare architectural offering. Originally designed and constructed in 1904 by noted architect George Beaumont for prominent Chicago industrialist and philanthropist Bernard E. Sunny, the home was thoughtfully and comprehensively updated in 1937 with striking Art Deco era finishes, seamlessly blending historic character with modern livability. The light-filled interior is ideally suited for today's lifestyle, featuring an open and expansive floor plan across all three upper levels. A welcoming entrance opens to a dramatic oval reception hall, anchored by a sweeping curved staircase leading to the second floor. From this impressive entry, gracious rooms flow into a grand living room, formal dining room, designer kitchen with butler's pantry, and a cheerful breakfast room overlooking a private backyard with patio and garden areas. A true standout is the library off the living room, complete with distinctive leather-clad walls and a hidden bar, perfect for entertaining. The second and third floors open on to substantial landings and each features three bedrooms, two full baths, and additional flexible rooms ideal for offices or dens. Each bedroom is generously sized and uniquely detailed, with special features such as a sun porch, private terrace, or semi-enclosed reading nook. Abundant closet space is found throughout the home. The full-height basement provides excellent recreation and work-out space along with ample storage. Adding exceptional value, the rear of the property includes a recently renovated two-story coach house featuring a three-car garage on the main level and a beautifully appointed one-bedroom apartment above, complete with new windows, central air conditioning, in-unit laundry and up-to-date kitchen and bath, ideal for guests, in-law living, a nanny suite, or rental income. Conveniently located near The University of Chicago campus (including the Lab Schools), Lake Shore Drive, Metra stations, and downtown bus routes, this remarkable home offers historic elegance, modern comfort, and outstanding accessibility.

4933 S Woodlawn Avenue, Chicago

$2,050,000
5 Beds 6 Baths 12541443 MLS CLOSED Status
A true rarity in historic Kenwood, this move-in-ready urban estate was meticulously restored during a multi-year renovation, reemerging as a masterful blend of early 20th-century elegance and modern luxury. Set on an expansive 50 x 300-foot lot within the historic district, the 1904 J.B. Cole residence was once praised by The Economist as "a picturesque structure in old English style of architecture"-a distinction it proudly maintains today. Regal stone lions still guard the original ornamental iron doors, opening to a dramatic foyer with a paneled fireplace and built-in seating. A sweeping circular staircase, illuminated by a period chandelier, sets an immediate tone of grandeur. The reimagined main level unites the home's two original parlors into elegant open-concept living and dining spaces, ideal for entertaining. Pocket doors lead to a chef's kitchen featuring stainless steel appliances, quartzite countertops, and generous banquette seating. French doors open to a sunroom and expansive deck overlooking the beautifully landscaped, fully fenced backyard. The second floor is anchored by a luxurious primary suite offering a huge custom walk-in closet, marble spa bath with steam shower, and a sun-filled, heated porch with serene backyard views. Two additional bedrooms, each with decorative fireplaces, share a thoughtfully updated bath. The third level provides two generously sized en-suite bedrooms with custom closets and steam showers. Wide-plank wood floors and custom windows are throughout, while the fully finished lower level lives like a home of its own. Heated with radiant flooring, it includes a spacious family/media room, large laundry room, fifth bedroom with walk-in closet, abundant storage, and a wine cellar tucked beneath the front porch. Completing the property is a Coach House with a four-car garage and a spacious flex space above-ideal for guests, office or gym. Ideally located near the University of Chicago, the Laboratory Schools, and Kenwood's dining, shopping, and cultural amenities, this is more than a home-it's a lifestyle. A rare opportunity to own a meticulously restored piece of Kenwood history, exquisitely reimagined for modern living.

4730 S Greenwood Avenue, Chicago

$1,089,500
5 Beds 3 Baths 12412880 MLS CLOSED Status
North Kenwood Living at Its Finest! This beautiful 5 bedroom, 2.1 bath home offers everything you're looking for, beginning with an exquisite front entry that opens into a refreshingly functional and elegant layout. The main level is ideal for both entertaining and everyday living, featuring a formal living room, a private parlor, a spacious dining room, and a gourmet chef's kitchen with a butler's pantry that leads to a gorgeous back deck and a serene, lushly landscaped private yard. A 2+ car garage completes the outdoor space. Upstairs, the second floor offers four generously sized bedrooms and a full bath. The top level is dedicated to a luxurious primary suite with space for a king-sized bed, a cozy sitting area, and a newly designed, lovely bath. The lower-level recreation room is perfect for games, movie nights, or gatherings, and includes multipurpose space ideal for a home gym, studio, or workshop. Set in one of Chicago's most architecturally rich and welcoming neighborhoods, this North Kenwood gem is moments from Lake Shore Drive, Lake Michigan's 43rd and 57th Street Beaches, the University of Chicago, the Griffin Museum of Science and Industry, and an excellent selection of grocery stores including Whole Foods, Trader Joe's, and Hyde Park Produce. You'll also enjoy easy access to Metra, CTA, and an array of dining and entertainment options. Don't miss the opportunity to call this timeless and spacious home your own. Schedule your private showing today.

4923 S Blackstone Avenue, Chicago

$1,600,000
5 Beds 5 Baths 12421410 MLS CLOSED Status
Custom renovation in Historic Kenwood! Sophisticated single-family home offers a perfect blend of mid-century charm and modern living. Large garden is a lovely oasis which includes a private pergola and formal dining area. Dine al fresco with family and friends using the large outdoor cooking area and expansive front yard. The home was completely reconstructed to the studs by the owner. The home features an open floor plan with intimate spaces filled with natural light and pre wired for entertainment through the house. Upon entering, you are welcomed by an elevated family room with a room-sized skylight, complemented by custom shelving and built-ins for both comfort and organization. This room boast floor-to-ceiling windows, creating a bright and airy atmosphere. The sunken living room features a vaulted ceiling, dual skylight, and modern double crystal chandeliers with pairing wall sconces. The dining room is adorned with a crystal chandelier and double archway doors. The room includes a built in custom wet bar and comfortably seats 12-14. Enjoy after-dinner wine or tea on the private enclosed patio. The sophisticated kitchen is a chef's dream, equipped with double ovens, microwave drawer, ample cabinetry, and a custom-designed built in armoire housing a Subzero refrigerator and pantry space. An oversized porcelain island and Wolf appliances complete this stunning culinary space, making it perfect for entertaining and cooking. On the second level, four of the five bedrooms are spacious and filled with natural light, with three featuring elegantly designed attached bathrooms. Custom closets are thoughtfully configured for optimal space usage. The primary bedroom is a standout, boasting a luxurious walk-in shower for two, a separate modern Victoria & Albert tub, a generous custom walk-in closet, and a private toilet room. The lower level offers 10-foot ceilings and contemporary spaces designed for relaxation and fun, including a game room, gym, guest bedroom, half bath, and a laundry room. Two attached heated garages provide convenient access from a gated, private entryway and heated driveway. A custom outdoor porch to patio perfect for outdoor cookouts, garden parties, and relaxation. Boasting white hydrangeas and other blooming flowers and trees all spring and summer long. Additional features include remotely operated skylights and custom door coverings, heated floors throughout, and numerous built-in custom closets for ample storage. This exquisite home seamlessly combines luxury and functionality, making it a must-see for discerning buyers.

1150 E 49Th Street, Chicago

$2,085,000
5 Beds 4 Baths 12415335 MLS CLOSED Status
Luxury Living in the Kenwood Historic District - Award-Winning Design, Massive Yard! Nestled in the heart of the prestigious Kenwood Historic District, this luxurious residence is a true architectural gem, boasting a massive, beautifully landscaped yard that spans nearly half the length of a football field. Designed by award-winning architect, Anthony Akindele in 1999, this home blends timeless elegance with modern comfort, highlighted by a striking turret staircase, soaring ceilings, and walls of windows that bathe the interiors in natural light. Step inside to a formal foyer adorned with custom stonework that sets the tone for the craftsmanship throughout. The main level features an expansive living room with a wall of windows and a cozy double-sided fireplace that opens to the formal dining room-perfect for entertaining guests, holiday dinners, and family gatherings. A stylish powder room adds convenience, while the gourmet kitchen is a chef's dream with top-tier appliances, granite countertops, abundant cabinetry, double ovens, a cooktop with a vented hood, and an oversized refrigerator. The kitchen's serene view of the backyard makes it a tranquil space to cook, gather, and unwind. Ascend the gracefully curved turret staircase to the second floor, where you'll find three spacious bedrooms, two full bathrooms, and a utility room. The highlight of this level is the sprawling primary suite, featuring custom closets and a spa-like bathroom complete with granite floors and walls, a dual-sink vanity, an walk-in shower with body sprays, and an oversized luxurious elevated whirlpool tub-your personal sanctuary. The grand lower level offers high ceilings and a large family room with a fireplace and wet bar, two additional bedrooms, a full bathroom, and an impressive laundry room with tons of storage space. Whether you're hosting game nights or housing extended guests, there's room for everyone. The lower level does have an exterior door. But the crown jewel is the yard-truly breathtaking. From the elevated deck to the custom stone patio and the expansive grassy field lined with privacy trees, lush plants, and vibrant flowers, this outdoor oasis is ideal for everything from backyard parties to family sports tournaments. It's rare to find this kind of outdoor space in such a coveted urban setting. Additional features include a 3-car garage and a prime location within walking distance of Hyde Park's shops and restaurants, the lakefront, and the University of Chicago. Meticulously maintained and in pristine condition, this home is a one-of-a-kind masterpiece in one of Chicago's most storied neighborhoods. Welcome home!

925 E 49Th Street, Chicago

$1,200,000
4 Beds 4 Baths 12321987 MLS CLOSED Status
Nestled in the heart of the sought-after Kenwood Historic District on a tree-lined street, this beautifully renovated rowhouse blends timeless charm with modern comfort. Perfectly positioned across from the neighborhood's large scenic park, the gracious home is bathed in natural light and offers picturesque views year-round. Step inside to the flowing floor plan where the vestibule opens to a formal living room with gleaming hardwood floors, classic wainscoting, and a cozy fireplace. A handsome staircase provides a graceful separation between the living area and the spacious dining room adjacent to the chef's kitchen - complete with a wall of windows overlooking the lush backyard. The outdoor space is ideal for entertaining or relaxing, with an oversized deck and elegantly landscaped yard featuring a flagstone patio, perfect for play or gatherings. Upstairs, the second floor hosts a luxurious primary suite with a spa bath and walk-in closet, along with two additional bedrooms and a stylishly renovated bathroom. The top floor offers incredible flexibility, featuring a bright, open space with a panoramic view. There is a ton of natural light and the space is ideal as a fourth bedroom, family room or guest suite, with a full bath and a charming loft space for an office or creative nook. The walk-out basement has been upgraded with new drainage, houses the laundry area, and offers abundant storage with potential for future finishing to add even more living space. Additional features include zoned air conditioning, newer windows throughout, and classic details preserved with care. A rare opportunity to own a piece of history, updated for modern living, within walking distance to amenities and schools and is located in one of the city's most beloved neighborhoods - welcome home!

1329 E 50Th Street, Chicago

$1,125,000
4 Beds 4 Baths 12390654 MLS CLOSED Status
Welcome to this spectacular and fully renovated luxury residence nestled among the historic mansions of Kenwood, located on the picturesque and iconic Drexel Boulevard. One of the few completely upgraded homes in the neighborhood, this stately property blends timeless architecture with modern elegance, offering over 4,200 square feet of refined living space. Renovated just five years ago, the home features FIVE spacious bedrooms, three and a half bathrooms, a full finished basement, and an oversized three-car garage-all behind a secure gated entrance. The main floor offers a perfect layout for both formal entertaining and comfortable everyday living, featuring a sophisticated sitting room with a fireplace and a formal dining area that easily accommodates a table for eight. The stunning gourmet kitchen is equipped with top-of-the-line Monogram appliances, quartz countertops, under cabinet lighting, a custom butler's pantry, striking custom wood ceiling beams and an adjacent family room with a fireplace. The second floor houses four full bedrooms and a full sized laundry room on one floor! Featuring the huge primary suite with a walk-out balcony, customized walk-in closet, and a gorgeous bathroom that looks like it is in a 5 star hotel! Both bathrooms on the second floor have heated floors. The fully finished basement with high ceilings offers even more space to enjoy, including a full bathroom, wet bar, and large recreation room and a fifth bedroom, ideal for guests, a home gym, or a private office. Additional highlights include custom window treatments through-out, a spacious fenced backyard, a dual-zoned HVAC system, modern designer light fixtures, RING alarm system and an advanced camera surveillance system for added peace of mind. A rare luxury in the city, this home offers a 3-car garage with ample space for vehicles and storage. All of this within walking distance to the lake front, the shops/restaurants in Hyde Park, and the University of Chicago. Combining luxury, comfort, and historic charm in one of Chicago's most coveted neighborhoods, this home is truly a rare find. It's more than a home-it's a legacy. Welcome to Drexel Boulevard.

4741 S Drexel Boulevard, Chicago

$868,800
5 Beds 5 Baths 12361780 MLS CLOSED Status
MOTIVATED SELLER! PRICED TO SELL! This stately Greystone home is on the market for the first time in 51 years. Built in 1892, the current owner has thoughtfully updated the home while retaining the original elegance. A sense of grace and grandeur is felt upon entering into the large entry hall-gallery space which highlights a sweeping staircase. This main level is the perfect entertainment space. The open floor plan hosts an expansive living room area with woodburning fireplace leading into the spacious dining room and open kitchen. The kitchen was updated in 2018 and has a copious amount of cabinetry, quartz countertops, stainless steel appliances and a wonderful island. The kitchen leads to the spacious 170 sq. ft. back deck. There is a powder room on this level as well as laundry with full size washer and dryer. Originally a 6 bedroom home, one of the bedrooms on the second floor has been opened and a skylight has been added, providing extra natural light. This open concept room is perfect for a family room or open office. There are 3 bedrooms on this level - one with a woodburning fireplace- and 2 updated baths. The third floor has 2 additional bedrooms with a bath. The full finished basement, with powder room, offers additional space for multiple uses: an area for a recreation room, an area for a playroom and an area for a workroom! The rear stairway leading to the kitchen remains, the hardwood floors on the main level have been replaced, the windows have been replaced, roofs have been replaced, the kitchen and baths have been updated, the carpeting is all new AND the home has a parking pad that accommodates two cars! The location of this home in the Hyde Park/Kenwood neighborhood is amazing! Only steps to transportation, parks, the lake, schools, shopping, restaurants, the Museum of Science & Industry, the Obama Center and to the University of Chicago.

5034 S Blackstone Avenue, Chicago

$415,000
3 Beds 2 Baths 12317457 MLS CLOSED Status
A very beautiful true 3 bedroom and 2 full bathroom PENTHOUSE find in East Hyde Park in this Beaux Arts fully restored 1920 built 6 unit building with double beveled brick tiers. Very low turnover in this professionally managed condominium building. Approximately 1800+ square feet, Residence 3 offers exquisitely restored vintage details of the period including and English fireplace with the original mantle with dental moldings, miniature brick hearth and surround, decorative summer grate, leaded glass paned side to side bookcases, high 7" baseboards, crown moldings, well preserved original closet and room doors and hardware hallway, vertical piers framing each doorway and a well-featured double parlor for modern day family and living rooms. Residence 3 features a gracious foyer with gallery space for art display, third bedroom with authentic 1920 pocket doors for open flexibility, real "tongue and groove" original oak hardwood floors throughout and original "tongue and groove maple floors in the kitchen. Primary bathroom features vanity with cabinet storage, shower/tub combination with shelving, built in medicine cabinet. Hallway office niche. Installed new double, thermal paned windows by Scientific Windows throughout this Residence. Sumptuous separate dining room. Large kitchen, 42" all wood cabinetry, contemporary stainless steel long cylinder handler pulls, white counter tops, mosaic backsplash, all stainless steel appliance, culinary hood, butler pantry for additional storage an counter space, walk-in door pantry with horizontal freezer. Maid's quarter turned utility room with full size stackable, front loading LG washer and dryer, utility sink, second full bathroom, plenty of additional storage and cabinetry. Private terrace of kitchen that measures 26'3" by 7'9" facing east. NO SPECIAL ASSESSMENTS. $41,040 in RESERVES. Very generous additional storage on lower level of building. Rental parking on the block for $150 or easy street parking on Dorchester which is not permitted. Easy access to public transportation. Enjoy all retail, grocery, restaurant/food life on 53rd/Harper. Convenient to University of Chicago. Close to parks and green space, LSD, Museum of Science and Industry, Lakefront. Pristine condition and the utmost level of pride of ownership. A true "turnkey" Residence.

5009 S Dorchester Avenue Unit #3N, Chicago

$2,300,000
5 Beds 6 Baths 12318091 MLS CLOSED Status
This stunning Kenwood home seamlessly blends historic charm with contemporary comforts, making it a perfect sanctuary for families and entertainers alike. The grand entryway welcomes you into a spacious living area adorned with refined finishes and an abundance of natural light. The chef's kitchen, equipped with high-end appliances and ample counter space, is a culinary enthusiast's dream, ideal for both casual breakfasts and lavish dinner parties. The outdoor living space is equally impressive, featuring a well-designed patio that is perfect for open air dining or simply enjoying the serene surroundings. The lush garden, complete with blooming white floral pear trees, adds a touch of nature's beauty, creating a peaceful retreat right at home. The second and third levels provide ample space for privacy and relaxation. The second level includes a luxurious private suite which boasts a private sitting area and fireplace, a multi-party shower and generous closet space. The additional two bedrooms include private bathrooms and spacious closets, making this home suitable for families of all sizes. The third level includes fourth and fifth bedrooms, an additional full bathroom, a full wet bar, office and a large second family room. A roof deck with panoramic views of historic Kenwood tops this lovely third-floor retreat. The lower level is a perfect hang-out space for the kids, with two game rooms and a full bath. A dedicated gym and storage room cap off this space. The home is tri-zoned cooling and heating. Two car parking is available in the front driveway. With its thoughtful renovations, exceptional outdoor amenities, and spacious layout, this Kenwood home is truly a rare find. Experience the perfect blend of elegance and modern living in this exquisite residence, where every detail has been meticulously crafted for both comfort and style. Don't miss the opportunity to make this stunning home your own.

4816 S Kenwood Avenue, Chicago

$3,645,000
6 Beds 7 Baths 12216908 MLS CLOSED Status
This magnificent residence is located on a verdant tree-lined street in the heart of the Kenwood Historic District. While constructed after the turn of the last century, the house has been elegantly and thoroughly updated for life in the current one. Horatio R. Wilson was a well-respected architect of his time, and his work is known for structural integrity and quality of materials - each of which are apparent decades after he first conceived of the design. Sited on a ridge that once ran across the Kenwood landscape, the impressive house had been meticulously maintained by former owners, and that stewardship continues. Behind the handsome facade of the nearly 8,000 square foot house is a wide array of aesthetic and mechanical improvements recently completed. The latest renovation (following an earlier gut rehab) included extensive masonry work, new windows, floors sanded and refinished, fireplaces relined and chimneys tuckpointed, new lighting, new bathrooms; all combine to make this a home that is a rarity in the neighborhood - truly move in ready. The quality of the residence is apparent the moment one enters the foyer, with an elegant carved stairway that rises the full three levels, capped by a dramatic skylight. The refined layout of the main level offers a formal living and dining rooms, a library (each with a fireplace) and a kitchen that was transformed by John Vinci, a living legend of Chicago architecture. The stunning space offers Bulthaup cabinetry, with vistas that extend to the lush exterior through a glass wall to covered porch framed by commercial grade railings and staircase, accented by recessed lighting in the warmth of a wood slat ceiling. The second and third levels of the house each feature three bedrooms and multiple baths, of which the Primary Bath is truly a room with a view. Large welcoming landings, hardwood floors, walk-in closets, vintage woodwork, crown moldings, leaded glass - the amenities are too numerous to list! And they continue on the lower level, with a mud room complete with dog spa, exercise room, additional full laundry, game room, family room and storage. The coach house was fully renovated and accommodates two cars (with EV charger) below the contemporary one-bedroom apartment. Kenwood is a short 8-minute drive from the Loop, near the University of Chicago, Laboratory Schools and all the Hyde Park community has to offer. A stunning property where you can with the next chapter of its extraordinary history.

4943 S Woodlawn Avenue, Chicago

$300,000
4 Beds 3 Baths 12191021 MLS CLOSED Status
Welcome to a once-in-a-lifetime opportunity to renovate a piece of Chicago history into your dream home. Superbly situated in a boutique, elevator building off of historic Madison Park, a serene oasis located in highly desirable Kenwood, your spacious 4 bedroom, 3 bathroom mansion condo offers unparalleled potential. Sprawling across approximately 3,200 square feet on one level, the condo boasts a very functional layout with ample room for creative redesign and expansion. Upon entering, you will be warmly greeted by your grand entry foyer that overlooks your massive living room. Your living room flows seamlessly into your separate, huge dining room that can easily accommodate a dining table for 8 or more. Your condo is saturated with natural sunlight and features a sun room with dual entry off of the living and dining rooms. The kitchen features a sizable pantry and is a canvas for culinary creativity awaiting your vision to transform it into a chef's paradise. Your condo truly lives like a single family home and makes it easy for you to maintain your privacy while also enjoying all of the pleasures of city living! This blend of suburban tranquility and urban convenience is a rare find. Welcome to "Suburban Living in the City." Conveniently located close to multiple parks, Trader Joe's, Starbucks, Whole Foods, Marshall's, Michael's, public transportation, the lake, Lake Shore Dr., downtown Hyde Park, countless restaurants, shopping and a 10-15 minute drive downtown. Embrace the opportunity to preserve and restore a piece of Madison Park's history. Storage space included. Solid association. No upcoming special assessments. Pet-friendly building. This condo requires a complete renovation, allowing you to customize every detail to your taste and specifications. Please don't miss this opportunity. Schedule your showing today.

1227 E Madison Park Unit #2, Chicago

$1,495,000
8 Beds 5 Baths 12128447 MLS CLOSED Status
Welcome to historic Kenwood, where yesterday's grandeur meets today's elegance. Nestled on a scenic double lot, this grand three-story home formerly known as The Duchisois Residence and designed by F.R. Schock is located in the South Kenwood Historical District. This stunning 8-bedroom, 5-bathroom home exudes vintage charm with its original oakwood floors, trim, solid core doors, and three original fireplaces. Offering nearly 6500 sq ft of luxurious living space, it features recessed lighting throughout, updated electric and plumbing, a new roof installed in 2014, a newly installed boiler, and separate central air systems. The grand foyer entry with parlor showcases gorgeous stained glass. The formal living and dining spaces and main level family room provide ample space for entertaining. The master bedroom suite includes a spa bath, while spacious bedrooms on the 2nd and 3rd floors offer comfort and style, including a large cedar closet. The modern gourmet kitchen boasts built-in custom appliances, and updated baths enhance the home's appeal. The lower recreational space has a wet bar and a second functional kitchen adding versatility. Outside, a huge detached 2-car garage with a 1000 sq ft coach house on top complements the incredible gated yard featuring a luxurious patio and mature landscaping. Walking distance to Lake Michigan, shopping, and museums. Easy to show with occupancy upon closing. This is a rare opportunity to own a piece of Kenwood history.

4800 S Kenwood Avenue, Chicago

$1,600,000
9 Beds 6 Baths 12100303 MLS CLOSED Status
Welcome to a rare gem on one of historic Kenwood's most desirable tree-lined streets. The Alonzo Fuller House and Coach House, built in 1890, offer approximately 9,550 sq. ft., 8250 sq. ft. in the main house, and 1,300 sq. ft. in the coach house, all situated on a generous half-acre lot. This extraordinary property features three stories, an unfinished basement, and a four-car garage with a coach house. Step inside to discover a wealth of historic charm and character, including oak and parquet flooring, original trim and millwork, arched windows, turret rooms, coiffured ceilings, and magnificent original fireplaces. Designed by architect Federick W. Perkins, this expansive Queen Anne-style home welcomes you with a grand foyer and an exquisite staircase adorned with oak spindles and banisters. Entertain in style with a parlor, formal living room, and dining room featuring a bay window and a butler's pantry. The light-filled kitchen, with original maple floors and large windows, offers serene views of the picturesque backyard and coach house. The second floor features five spacious bedrooms with generous closets and two full bathrooms. The third floor offers the primary bedroom with an ensuite bath and walk-in closet, a versatile study/family room/ballroom with a fireplace, two additional bedrooms, a full bathroom, and the remnants of a convenient kitchenette, ideal for formal entertaining or everyday enjoyment.The unfinished basement presents endless possibilities, whether you envision a wine cellar with a tasting room, a hidden speakeasy, recreation room, full in-home gym, or game room. Outside, the property boasts a striking exterior of limestone and red brick, a driveway, a slate roof, and a heated four-car garage with storage, a workroom, and a coach house. The coach house includes two bedrooms, a bath, living and dining areas, and a sitting room, perfect for accommodating guests or multi-generational living. Experience Kenwood living in this exceptional residence. This magnificent home awaits your vision to carry it through the next several decades.

4832 S Ellis Avenue, Chicago

$775,000
6 Beds 5 Baths 12048392 MLS CLOSED Status
An incredible opportunity to invest in the potential of an historic home the Kenwood neighborhood. House requires work - but is gracious, spacious and is priced to move. At the time this home was constructed there were only four houses on the 4800 block of Greenwood Avenue; Kenwood was then a bucolic suburban retreat. The catalysts fostering the growth of the neighborhood (the founding of the University of Chicago and the 1893 World's Columbian Exposition) were years away. For a century and a half this home has stood proudly as the world evolved around it - a new century dawned (twice) and houses by architectural innovators including Frank Lloyd Wright and Burnham & Root rose nearby. A resurgence occurred as the community was landmarked, and a neighbor elected president. And through it all 4849 endured. The ambience of those earlier years remains: a handsome staircase, leaded windows, high ceilings, warming fireplaces and a verdant yard. This welcoming, spacious home offers a layout that can be reconceived for the 21st century, including space for a large kitchen and family room. With six bedrooms, four full and one-half baths, enclosed porches and lovely formal rooms on the main level, this house provides ample space indoors, and out. Hyde Park and Kenwood are vibrant communities - enhanced by the University of Chicago, adjacent to the city's magnificent lakefront and located a mere ten-minute drive from the Loop. This is an amazing opportunity to write the next chapter of this home's enduring legacy. Property is sold AS-IS.

4849 S Greenwood Avenue, Chicago

$455,000
7 Beds 6 Baths 12020593 MLS CLOSED Status
**Captivating Investment Opportunity: 1880's Victorian & Brick Coach House** Welcome to a rare gem in the Kenwood/Hyde Park Community. Nestled on a sprawling 19,000+ square feet lot, this property presents an exceptional investment opportunity for savvy investors seeking prime real estate for development. **Property Highlights:** - **Historic Charm:** Built in the 1880s, the Victorian residence exudes timeless elegance, while the brick Coach House adds character and versatility to the property. - **Expansive Lot:** Spanning over 19,000 square feet, this sizable lot boasts a length of 284 feet, offering ample space for various development possibilities. - **Premier Location:** Situated in a coveted location, the property enjoys easy access to major amenities, renowned schools, and vibrant entertainment hubs, making it an ideal choice for prospective buyers. - **Alley Access:** With alley access on the entire east side and north end of the lot, developers have the convenience of easy ingress and egress for construction purposes, enhancing the appeal for potential projects. **Development Potential:** The generous lot size and strategic location make this property an excellent canvas for development projects such as: - **Row-Homes:** With the lot's dimensions, there's potential for the creation of row-homes, catering to the demand for upscale urban living. - **Condo Building:** Explore the possibility of constructing a modern condo building, offering luxury residences that capitalize on the area's desirability. - **Multi-Unit Development:** Utilize the vast space to develop a multi-unit residential complex, accommodating the growing demand for rental properties in the area. **Property Details:** - **Victorian Residence:** Offering approximately 5500 square feet of living space, the Victorian residence awaits restoration, presenting an opportunity to breathe new life into its historic charm. - **Brick Coach House:** Comprising approximately 3000 square feet, the Coach House provides additional space and potential for renovation or repurposing to suit your vision. **Renovation Opportunity:** While the Victorian and Coach House are in need of renovation, this presents a blank canvas for investors to reimagine and revitalize these structures, adding significant value to the property. **Don't Miss Out:** Rarely does an opportunity of this caliber present itself. Whether you're an experienced developer or an investor seeking to diversify your portfolio, this property offers endless potential and promises substantial returns on investment. Contact us today to schedule a viewing and unlock the possibilities that await with this remarkable real estate opportunity.

Chicago

$2,280,000
7 Beds 7 Baths 12005667 MLS CLOSED Status
Welcome to 4857 S Kimbark - a spacious stone and red slate house in a desirable South Kenwood location. This home has completely updated mechanicals and wiring, and offers all the modern amenities you expect, yet it retains a wealth of original details such as a stately wrap around porch, inviting wood paneled foyer, carved mantel pieces, built in cabinets and pocket doors in Birdseye maple, cherry and quartersawn oak. Step through the front door into a grand entry foyer with original staircase, wainscoting, fireplace and inlaid floors. Perfect for entertaining and large gatherings, this level offers several rooms and open spaces that can accommodate more or less formal living. New eat-in kitchen with white custom cabinets, quartz counter tops and Miele, Bosch and Thermidor appliances. There is also a sizeable pantry and a powder room on this level. Ascend the stairs to the second floor where you will find 4 very spacious bedrooms with custom built in closet interiors and high-end blinds and shades. There are three bathrooms on this level, two are ensuite. Primary bath has separate steam shower and a laundry room conveniently adjacent. There is a balcony which has just been completely rebuilt. On the third floor there are three additional bedrooms, two bathrooms, large storage closets and a family room with built in entertainment center, speakers, gas fireplace and wet bar with beverage fridge. The basement is finished and features an additional bedroom/ workout or office space, a full bathroom, storage, family/ entertainment room and a wine cellar with cork walls and built in wine racks and wine fridge. The house has 400 amp electric service, all new wiring, smart home wiring, three zone heating and two zone cooling systems, all new copper plumbing, new gas lines, new water service and drains. The inlaid gutters have been rebuilt and the house was fitted with insulation and new red slates in 2007. All 6 bathrooms have been recently remodeled and most feature designer tile, heated floors and Toto, Grohe, Kohler and Kallista fixtures. The gardens are custom designed and are automatically irrigated. The outdoor kitchen with piped gas grill and wood burning pizza oven sits in a peaceful corner of the garden. Thousands of bulbs await spring. There is a wrought iron electric side gate that allows two cars to park on the property. A car port could likely be fitted under the back porch to create more parking, however there is ample street parking. South Kenwood is a historic landmark neighborhood, and the home is designated under the preservation easement with landmarks. Welcome!

4857 S Kimbark Avenue, Chicago

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Kenwood, Chicago IL · Curated MLS Search

Homes with Finished Basement in Kenwood, Chicago IL

An editorially curated view of every active homes with finished basement listing in Kenwood, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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