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$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

$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

$5,100,000
12685129 MLS ACTIVE Status
Exceptional opportunity to acquire a large multifamily asset featuring approximately 38 beds and positioned for shared housing, student housing, workforce housing, co-living, or short-term rental strategies. Located within close proximity to the University of Chicago and other major educational, healthcare, and employment centers, this asset presents a unique opportunity for investors seeking to capitalize on the growing demand for housing in one of Chicago's most active and rapidly evolving markets. The property's layout and scale make it particularly attractive for operators focused on shared housing initiatives, student accommodations, workforce housing, or alternative residential investment models. Its location near a world-renowned Ivy League-caliber institution and major neighborhood redevelopment activity creates multiple pathways for revenue generation and long-term value creation. This offering is being marketed confidentially. Financial information, property details, and exact location will be provided to qualified buyers upon request. Please contact the listing agent for additional information, financials, and access to the offering package.

Chicago

$1,695,000
6 Beds 6 Baths 12705893 MLS ACTIVE Status
An extraordinary Kenwood greystone where historic craftsmanship takes center stage. Designed by celebrated Chicago builder Horatio Wilson, this remarkable 7-bedroom, 6-bath residence showcases more than 5,000 square feet of gracious living space, blending the grandeur of Chicago's architectural past with the comforts of modern living. Rich hardwood floors, extraordinary original millwork, handcrafted built-in cabinetry, decorative columns, pocket doors, and intricate wood detailing reflect a level of craftsmanship rarely found today. Formal living and dining rooms provide elegant spaces for entertaining and everyday living. Just beyond the dining room, a cozy lounge invites morning coffee or evening cocktails, while the adjoining butler's pantry offers a timeless transition into the kitchen. Tucked discreetly behind the kitchen, the original servant's staircase provides a charming connection between the home's first and second floors. Throughout the residence, seven fireplaces further celebrate its architectural heritage. The spacious primary suite serves as a private retreat with abundant closet space and a spa-inspired ensuite featuring a steam shower, soaking tub, dual vanities, and a walk-in closet. A finished lower level lives like a residence of its own with a second full kitchen, dining area, expansive family room, additional bedroom, and full bath-ideal for extended family, guests, or flexible living. Outside, a lush private garden offers a peaceful escape with mature landscaping and seasonal blooms. Ideally situated on a picturesque, tree-lined block in Kenwood near Hyde Park and the University of Chicago, this exceptional residence places you among one of Chicago's most architecturally significant neighborhoods, surrounded by historic homes, cultural institutions, acclaimed dining, and everyday conveniences. Homes of this caliber rarely become available, offering the opportunity to own not simply a remarkable residence, but an enduring chapter in Chicago's architectural story.

4942 S Ellis Avenue, Chicago

$2,371,500
5 Beds 6 Baths 12711888 MLS ACTIVE Status
An exceptional expression of architectural elegance and refined living, this distinguished 6-bedoom, 5.5-bath Kenwood residence offers the rare combination of grandeur, scale, and gracious comfort. Set on one of the neighborhood's most beautiful, tree-lined streets, this magnificent early 20th-century home is distinguished by its handsome brick facade, generous proportions and timeless craftsmanship, along with many significant modern upgrades. Spanning approximately 6,700 square feet, the residence unfolds across an impressive and thoughtfully designed floor plan, with soaring ceilings, exquisite hardwood floors, elegant millwork, and a wealth of original architectural character. The gracious entry leads to beautifully proportioned formal rooms, including an expansive living room anchored by a fireplace and an elegant dining room designed for memorable entertaining. The sophisticated yet inviting kitchen features top-quality stainless-steel appliances, a substantial center island, farmhouse sink, and abundant cabinetry, creating a refined setting for both intimate meals and large-scale gatherings. A private den offers an ideal retreat for work or relaxation. The sumptuous primary suite is a true sanctuary, featuring generous proportions, two large walk-in closets, and a luxurious marble bath with dual vanities, a deep soaking tub, and separate shower. Additional bedrooms are also generously sized and complemented by beautifully appointed baths, offering exceptional comfort and privacy. The lower level further enhances the home's remarkable livability, with an expansive finished recreation room featuring built-in shelving, and recessed lighting -- an ideal setting for casual entertaining, recreation. A separate guest room with private full bath completes this level. Outside, meticulously landscaped grounds create a private and serene urban oasis, complemented by a spacious backyard and a concrete drive from the street leading to a detached two-car garage. Perfectly positioned near the lakefront, parks, premier schools, downtown transportation, and the cultural and academic institutions of the greater Hyde Park community, 4900 S. Kimbark Avenue represents a rare opportunity to experience the grandeur of a classic Chicago residence with the comfort and sophistication of modern living. The home is truly in move-in condition, having undergone extensive mechanical & structural renovations from sub-foundation to roof, including multi-zone radiant heat and air conditioning, continuous hot water, 400 AMP electrical service, and replaced water, gas and sewer lines.

4900 S Kimbark Avenue, Chicago

$999,000
3 Beds 4 Baths 12706221 MLS ACTIVE Status
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

$399,500
4 Beds 2 Baths 12675404 MLS PRICE CHANGE Status
For the first time in 47 years, a rare value-add opportunity in the heart of the historic Kenwood Mansion District. This 4-bedroom, 1.1-bath townhome offers a functional three-level layout, including a partially finished basement, a private fenced yard, and access to a shared private community park-providing exceptional outdoor space in the city. Solid brick and concrete construction provides a strong foundation for renovation, with potential for owner-occupants looking to build equity. All four bedrooms are conveniently located on one level, however, some owners have reimagined the space and combined two bedrooms to make a large primary suite. Ideally located near Kenwood Community Park, Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this is a unique opportunity to renovate and create a home of your own in one of the Chicago's most sought-after neighborhoods.

4753 S Woodlawn 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

$665,000
3 Beds 3 Baths 12625810 MLS CLOSED 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 PENDING 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

$987,500
5 Beds 5 Baths 12453495 MLS CLOSED Status
Spacious is the word that comes to mind as you view this solid brick residence in the well sought after Hyde park area. This property has a connection to the 44th president Barack Obama as the family grew up with them & shared a backyard. The 2 1/2 garage was leased to the secret service detail assigned to protect the Obama's. The former garage, now two story coach house, was rehabbed to suit their needs and can be used as separate dwelling with its own HVAC, bath & kitchen or perhaps rented out for income or simply used as a guest house. As you enter into the residence you will notice the 10 ft beamed ceilings, dark woodwork, stained glass and hardwood floors throughout. This property features two fireplaces, two jacuzzi tubs, two stairways and a 2nd floor rear balcony. The 1st floor features a huge kitchen/dining room combo, pocket doors, kitchen nook, bathroom, & spare room. Front of basement is finished and boast a family room, game room, two bedrooms etc. Rear has mechanicals with newer furnace & hot water heaters, laundry room and walkout to yard. Second floor has master bedroom & 3 additional bedrooms. Third floor has 1 bedroom & two rooms that share a large hall closet. Did I mention the shed and long driveway? Showings for qualified buyers will be by appointment only. Come & see this Jewel and make it your own or invest and resale at a profit. "AS IS"

1036 E Hyde Park Boulevard, 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

$712,500
5 Beds 5 Baths 12419808 MLS CLOSED Status
Welcome to this stunning brick single-family home located in Chicago's architecturally rich and historic Kenwood District. Spanning an impressive 4,458 square feet, this timeless residence presents a rare opportunity-a versatile canvas for your next inspired design. Thoughtfully reimagined with a focus on both aesthetics and infrastructure, the home blends classic character with modern updates. Newly installed windows flood the interiors with natural light, while a carefully applied brick veneer overlay on the rear exterior of the home enhances the original masonry, offering both durability and a refined finish. A distinctive decorative brick line near the top of the rear wall adds a subtle architectural flourish and unique visual detail. The spacious basement, with its high ceilings, provides exceptional potential-ideal for creating additional living space, an entertainment area, or a custom creative studio. Step outside to a private backyard, a cozy retreat awaiting your landscape vision-perfect for relaxing, entertaining, or crafting your own urban oasis. Whether you're looking to restore, reimagine, or simply admire the craftsmanship of a classic Chicago row home, this property is rich with inspiration and possibility.

5028 S Blackstone Avenue, 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

$400,000
4 Beds 3 Baths 12403863 MLS CLOSED Status
Historic Kenwood neighborhood! Live among the notable and iconic homes in South Chicago. Just 3 blocks to Metra Train, walk to Lake Michigan and the walking trails, and close to Lake Shore Drive. Fabulous Opportunity to own this 4 Bedroom (all on 2nd floor), 2.1 Bath, large end unit. "True" townhome with ownership to the building and the land! The property includes over 2,550 SF with 1,725 SF above ground and a partially finished basement of 863 SF. Well-built structure with brick and concrete construction. Solid concrete divides each floor. The townhomes are in the neighborhood of notable historic homes valued over $2 million. It is located just 1 block from the Mohammed's Ali's home/museum and walking distance to the future Barack Obama's Presidential Library, Jackson Park and the University of Chicago campus. With some sweat equity, there is HUGE POTENTIAL and incredible upside on this amazing 4 Bedroom home. It includes a huge private, completely fenced-in yard. New fencing is in the plans by the HOA. Low HOA Assessment is only $600 per year. Owner is responsible for maintaining the entire structure and yard. ** New Furnace, A/C, and Hot Water Heater 2022. Home needs work and is being sold "AS IS". Structure is solid. Access to home is by appt only.

4741 S Woodlawn Avenue, Chicago

$960,000
4 Beds 4 Baths 12401489 MLS CLOSED Status
The historic greystone homes that line the north side of the highly desirable Madison Park community are truly special and seldom come on the market. The listing of this stately property therefore represents a rare opportunity for a discerning buyer seeking a gracious 4-bedroom, 3.5-bath home with garage parking in that very special location. The rooms are all spacious and retain many original architectural details including high ceilings, beautiful crown moldings, and hardwood floors throughout. The eat-in kitchen has been thoroughly renovated with high-end stainless appliances. Bathrooms have likewise all been brought up to date. Mini-split a/c units are in all of the major rooms. Almost all windows have been replaced. The large open basement is currently unfinished, but is ready for renovation if desired. A charming private backyard with a two-car garage completes the property. Though located in a quiet park-like setting on a tree-lined street with little thru traffic, Lake Shore Drive access, the Metra station, and downtown bus stops are just a short distance away.

1344 E Madison Park Avenue, 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

$1,300,000
6 Beds 6 Baths 12286341 MLS CLOSED Status
SOUTH KENWOOD BEAUTY IN THE HEART OF THE HISTORICAL DISTRICT-this elegant, historical Greystone was designed by Architects Wilson and Marshall and built in 1896. The craftsmanship of its day is noticed from the exterior of the building, past the wrought iron fence and once you step inside. This elegant home features three levels of living above grade, 6 bedrooms and 5 1/2 baths has the bonus of a large three-bedroom coach house with 2 full bathrooms above the 3-car garage. Coach house is great for extended family stays or as added income. First floor has second staircase to the second floor. Other features are arched doorway, built-ins, tons of light. Coach house is so sweet and is large and homey. Home sits on 50' x 150' lot which allows for the side lot to be used to garden, read, party, play, relax, etc. With its high ceilings, original wood moldings, original inlaid rift-sawn oak floors, uniquely crafted staircase, fireplaces, stained glass windows, multiple ensuite bedrooms, and so much more. Full semi-finished high-high ceiling basement adds for more living space. Separate HVAC systems for house and coach house. Lake, university, museums, restaurants, and so much more. This masterful built home is awaiting your furniture. A REAL GEM!!!

4950 S Ellis Avenue, Chicago



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