View All Kenwood Chicago IL Modern Homes Listings

$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

$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

$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

$395,000
4 Beds 3 Baths 11898153 MLS CLOSED Status
This amazing spacious four bedroom-two and a half bath condominium, located on a beautiful treelined street in the heart of Kenwood/Hyde Park. The living room is oversized with a stunning accent wall over the beautifully stoned fireplace, the opposite wall has glass doors leading out to an enclosed balcony. The large entry foyer leads to a grand hallway with closets and ample wall space, perfect for displaying your photographs and artwork. The bedrooms are large, all bathrooms have been exquisitely updated and upgraded for modern taste, while seamlessly blending with the homes vintage character. The formal dining room is spacious and ideal for hosting large dinner parties. The newly renovated kitchen has new hardwood flooring, can lights, new cabinetry, quartz countertops and KitchenAid Stainless Steel appliances. The rest of the home's original hardwood flooring has been refinished and looks great, there is beautiful crown moulding in the living room and dining room. The in-unit laundry has new Chrome (Large) Stackable Washer & Dryer. There are new ceiling fans, updated light fixtures and can-lights throughout the unit. Assessments include heat. There is additional outdoor space, the unit has (3) storage lockers in basement of building. The association backyard has a Koi Pond as well as an outdoor kitchen with pizza oven and grills, all for the enjoyment of the residents. Ideally located steps from Ancona School, University of Chicago, Whole Foods, Metra, CTA, Parks, Bike/Jogging Paths and Lake Michigan.

1348 E 48Th Street Unit #1D, Chicago

$1,790,000
5 Beds 6 Baths 11798319 MLS CLOSED Status
Stunning 5-bedroom 4.5-bath home on one of the most desirable blocks in the South Kenwood historic landmark district. This fully and beautifully renovated 5-bedroom, 4.5-bath home is truly in move-in condition, ready for modern living, with all new electrical, plumbing, and HVAC systems. The first floor features a very versatile open floor plan. The living room, with its imposing wood-burning fireplace with marble surround, has French doors out to a spacious terrace overlooking the historic homes of Kimbark Avenue. The all-new white and stainless kitchen (with room-sized pantry) is fully open to both the living and dining room areas, as well as to a cozy family room, with doors out to the back deck overlooking the charming lawn and flowering garden. Upstairs, the second floor features a wonderful primary suite with enormous walk-in closet, and designer bath with separate vanities, soaking tub, and marble shower. Two more good-sized bedrooms share a hall bath. A full laundry room on this floor is truly a luxury. Completing this level is a private serene outdoor deck, with beautiful views overlooking the yard. The third floor truly adds a new dimension to this home, with two very spacious bedrooms, each with its own beautiful new bath. Either of these suites could easily function as an upstairs play-/media room. The basement, currently unfinished, has great ceiling height and provides endless opportunities for future development. While this impressive property is located on a quiet tree-lined street with little thru traffic, Lake Shore Drive access, the Metra station, and downtown bus stops are just a short distance away.

4812 S Kimbark Avenue, Chicago

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Kenwood, Chicago IL · Curated MLS Search

Modern Homes in Kenwood, Chicago IL

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

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