View All Oakland Chicago IL Homes with Finished Basement Listings

$2,150,000
12673900 MLS ACTIVE Status
Once in a Generation, The Crown Jewel of Oakland set on a botanical campus spanning 70 feet of frontage. If you seek the best, if you have exquisite taste, if you want a one of a kind with an elevator that opens directly into most apartments with grand terraces, you have arrived. Located in an exclusive community alongside million dollar homes & within 1/4 block of Mandrake Park, 5 minute walk to the lakefront at the very north end of Drexel Blvd, with its idyllic fountain & cul-de-sac is a magical whimsical storybook setting offering 5 Massive full-floor units ultra-luxurious 3-4 Bed/2-3 Bath residences set in a made for TV boutique, elegant, Gothic Greystone. Be inspired by the grand, formal lobby with inlaid stone floors, intricate woodwork, stunning modern art, a crystal cut chandelier & super "mod" LED wall sconces. The elevator opens directly into most residences' private foyer, which leads to a massive great room, with soaring ceilings & 7' tall window bays that capture phenomenal sun soaked south & west vistas up & down lush & forested Drexel Boulevard. Gorgeous plank hardwood floors, which contrast with sleek 7" crown & baseboard moldings, 8' tall solid core doors, polished chrome door handles & accessories, a custom designed & built fireplace with glass, stone & quartz mantel + gorgeous lighting with Decora switches & dimmers. Adjacent to the great room, cook, entertain & eat in a true & REAL gourmet kitchen with 1 1/4" thick quartz countertops, a massive work island with bar stool seating, state-of-the-art stainless appliances, a multi burner stove, tunnel exhaust hood, dishwasher, 36" refrigerator with ice & water dispensers, built-in microwave drawer & brilliant porcelain full height backsplashes. Other features include strategically placed cable & electric for flat screen televisions, Hi Efficiency HVAC, high tech LED lighting & many other features. Gracious jaw dropping primary bedroom suite with an infusion of natural light from tall south facing windows, enormous walk-in closet is ready to house a large wardrobe, with custom double hanging SS organizers some which include 20 lineal feet of hanging & 55 lineal feet of shelves. Resort Luxury spa bathroom with heated porcelain tile heated floors, steam shower, quartz bench, a custom designed floor to ceiling glass wall & door system, a rain shower, handheld shower & separate body washes, 6' air bath, a wall mounted floating double bowl vanity & two large mirrored medicine cabinets. Numerous oversized rear terraces offer respite to enjoy cocktails, read a book or have breakfast through dinner, private & spacious with sweeping downtown views. Full Laundry Center complete with full size washer & dryer, countertops & cabinetry cabinets. Enjoy fully curated exotic botanical gardens fully with specimen trees & bushes, many grafted, from around the world, including Japan, various countries in Eastern Europe, Canada & the USA ( all irrigated controlled by app) topped off with 9 car garage (2 of 9 Tandem). Fully stabilized with exceptional longer term tenants, this stunning, unique, trophy property offers a rare hybrid opportunity pairing investment with legacy. Full financials, floorplans, survey, and extensive pictures available. Actual Annual Income $213,045/NOI $141,525 / 6.5CAP Pre Approved buyers only. 48-72 hours' notice to show M-F (no weekend showings)

3967 S Drexel Boulevard, Chicago

$799,000
5 Beds 3 Baths 12680626 MLS ACTIVE Status
What you've been waiting for in Bronzeville-an extraordinary residence on picturesque Lake Park Avenue that seamlessly blends timeless vintage character with sophisticated modern updates. Far from a cookie-cutter home, this one-of-a-kind residence offers over 4,000 square feet of thoughtfully designed living space across three levels plus a finished basement, creating a floorplan that is as distinctive as it is functional. From the moment you arrive, the stately red-brick exterior and impressive custom solid-wood double doors make a lasting first impression. Step through the private vestibule foyer and into a home filled with architectural details, warm finishes, and captivating design elements rarely found in today's newer construction. A dramatic staircase anchors the home, while the open-concept main level effortlessly balances grandeur and comfort, making it ideal for both everyday living and entertaining. The inviting living room features, soaring ceilings, a striking stone accent wall and cozy fireplace, creating the perfect gathering space. The expansive kitchen serves as the heart of the home, offering abundant cabinetry, stone countertops, stainless steel appliances, and generous space for dining and hosting family and friends. The second level showcases three spacious bedrooms, a full bath, and a versatile family room-an uncommon and highly desirable layout that provides flexibility for growing households, guests, or work-from-home needs. Occupying much of the third floor, the luxurious primary suite serves as a private retreat. The oversized bedroom is complemented by a spa-inspired bath featuring a custom walk-in shower, distinctive tile flooring, dual vanities, and a relaxing whirlpool tub. An additional bedroom on this level is currently configured as a home office, offering endless possibilities. A skylight illumates the stunning staircase. The finished, walk-out, basement extends the living space even further with another family room, a full bathroom, an oversized laundry room, and a private sauna-your own personal wellness retreat. Outdoor living is equally impressive, featuring a large rear deck, yard space, and garage parking. Perfectly situated on one of Bronzeville's most desirable blocks, this home is within walking distance of neighborhood parks and the pedestrian bridges that connect you to Chicago's stunning lakefront. Rich in character, architectural charm, and modern comfort, this is a rare opportunity to own a truly distinctive home in one of the city's most vibrant and historic neighborhoods. Welcome home!

4126 S Lake Park Avenue, Chicago

$344,900
3 Beds 3 Baths 12685324 MLS ACTIVE Status
Welcome to this marvelous over-sized duplex condo in the picturesque sought after neighborhood of historic Bronzeville. Featuring 3 bedrooms and 3 full bathrooms, this beautifully updated duplex offers an abundance of space that is drenched with natural light. The gleaming luxury hardwood floors welcome you in the spacious living room with a grandiose patio door that offers wonderful views of the beautiful tree lined streets. The living room guides you into the spectacular kitchen with amazing high end cabinets, elegant quartz countertops that boast a breakfast bar and stainless steel appliances. The living room offers a serene setting that features a breathtaking fireplace. The main floor also offers a conveniently located full bathroom and a guest bedroom, perfect for when entertaining family and friends. The lower level features two expansive master bedrooms with new carpet, new light fixtures, large walk-in closets and full master baths. The unit also offers plenty of storage space throughout and in-unit laundry room. Enjoy some fresh air on those spring and summer days on your own private balcony. Updates include: New paint throughout, new light fixtures, refinished hardwood floors, new carpet, new kitchen faucet, and new cabinet pulls. The unit includes 1 parking space conveniently located steps away from the backdoor entrance, intercom system, and a private storage locker. Walking distance to the beautiful Oakwood Beach. The proximity to golfing, parks, shopping and dining is outstanding. Pets are welcome.

4105 S Drexel Boulevard Unit #1SR, Chicago

$680,000
4 Beds 3 Baths 12530301 MLS CLOSED Status
Live by the Lake, Earn by the Month! A Rare Find! Stunning, Beautiful, exceptionally renovated 2-unit Brownstone home in a gated community of the Historic North Kenwood/Bronzeville Neighborhood that's Income Producing! This home offers modern living at its finest. Walk into the first unit which is a 2-story home with Gorgeous Oak Hardwood floors, High ceilings, and perfectly placed recess lighting. Open style designer kitchen with Custom Quartz Countertops and Stainless-Steel Top of the Line Appliances. Enjoy quiet cozy evenings with a full fireplace and outdoor deck. The primary bedroom allows for great comfort in a King Size Bed and an en-suite with double access. The perfect packaged, totally renovated garden apartment, with a beautiful designer kitchen, stainless steel appliances and washer and dryer hook up, giving the homeowner the perfect opportunity to generate income and cash flow. This home comes with an Agricultural Gift offering a great platform for Gardening Enthusiast with its growing Peachtree and Grape Vines. A 2 1/2 Car Garage completes this home! Conveniently located walking distance from Lake Michigan, Chicago's Oakwood beach, 5 minutes from downtown and University of Chicago. Enjoy easy access to scenic waterfront views, a fountain park directly across the street, and beautiful historic vintage homes. Located near public transportation, Lake Shore Drive and interstate 90/94. Minutes away from some of Chicago's most iconic attractions: Millennium Park and The Bean, McCormick Place, Soldier Field, The Shed Aquarium Guaranteed Rate Field (White Sox Stadium), The Arie Crown Theater and Dusable Museum. Live in one unit and rent the other. This magnificent Legal 2-unit home will not last! Schedule Your Private Showing Today!

4055 S Ellis Avenue, Chicago

$800,000
3 Beds 4 Baths 12513856 MLS CLOSED Status
Experience refined luxury and modern sophistication in this impeccably designed four-level Windsor Row home, where timeless architecture meets contemporary comfort and craftsmanship in every detail. Spanning approximately 3,000 sq. ft. of beautifully finished living space, this elegant residence welcomes you with a soaring 14-foot foyer that opens into a grand living room featuring 8-foot doors, coffered ceilings, and a cozy fireplace. The formal dining room offers an inviting space for both intimate dinners and lively gatherings. At the heart of the home lies the gourmet 21x21 chef's kitchen - a true showpiece featuring Bosch stainless steel appliances, including a 5-burner cooktop, designer hood, and drawer microwave. The oversized island, pantry, and spacious private deck-perfect for BBQs, alfresco dining, or relaxing outdoors-make this kitchen ideal for both entertaining and everyday living. The primary suite is a serene retreat, offering elegant detailing, a spa-inspired bathroom with a jacuzzi tub, rain shower, heated floors, and a walk-in closet. Additional highlights include a large main-level family room and a versatile lower-level recreation suite with a full bathroom and walk-in closet-ideal for a guest suite, entertainment area, or the ultimate man cave. The home also features dual furnaces, integrated sound and internet wiring, ample storage, and a comprehensive security system for year-round comfort and peace of mind. A rare find in the City of Chicago, the property includes a two-car attached garage with a gated private driveway, offering convenience and comfort-especially during the winter months. Location, location, location! Ideally situated in the sought-after Oakland/Kenwood neighborhood, just steps from the community park, 7 minutes to Downtown Chicago, and close to Hyde Park's premier shopping, dining, and entertainment. Enjoy a five-minute walk to the 39th Street Beach and scenic Lake Shore Drive's picturesque lakefront. View our video and photos - once you step inside, you'll be captivated by every thoughtful detail of this exceptional home!

4065 S Ellis Avenue, Chicago

$947,000
6 Beds 5 Baths 12471948 MLS CLOSED Status
Where timeless architecture meets modern ease, this exquisitely renovated greystone offers room to live, entertain, and unwind in style. With six bedrooms, four-and-a-half baths, and a thoughtful three-level layout, every corner invites you to stay a little longer. On the main floor, natural light flows through gracious living and dining spaces, anchored by a designer kitchen and a dining room crowned with a striking fluted light fixture-an art piece in its own right. Wide doorways lead to a rear deck that's perfect for summer dinners or a quiet morning coffee. The second floor is a sanctuary. The primary suite features customized closets and a charming step-up window niche that begs for a built-in seat or meditation perch. An additional ensuite bedroom shares the level, while a private balcony off another bedroom offers a quiet retreat in the treetops. Up on the third floor, the home takes a playful turn: a dedicated Snack Lounge-complete with mini fridge, microwave, and cabinetry-sits among three more bedrooms, ideal for late-night treats or weekend movie marathons. A fully finished lower level provides a guest bedroom, flexible exercise or hobby space, and a convenient exterior entrance. Three separate furnaces deliver zoned heating and cooling for comfort on every floor. Outside, a classic one-car brick garage completes the picture. Set on a serene, short street just blocks from the lake and the pedestrian bridge, this home blends elegance and everyday function. From the statement lighting to the inviting outdoor spaces, 922 E 42nd Place is designed for the way you live-and the way you love to entertain.

922 E 42Nd Place, Chicago

$725,000
4 Beds 4 Baths 12222630 MLS CLOSED Status
Stately Vintage 3 story Greystone. Current owner a long time Chicago architect has loving restored the home maintaining much of the original charm and character. The home features a sprawling open floor plan full of character at every turn. Patterned mahogany wainscoting wrap 3 stunning levels of stairs, intricate ornamental plaster ceiling inlays, turret rooms, 7 fireplaces, and a turn of the century entry & foyer that will transport you to the golden age of the Chicago Greystone. What a beautiful home! Main level features large updated kitchen adjacent to dining room and set at the rear of the home so perfect for outdoor entertaining. An open parlor connects the dining room to the enormous living room and eventually to the formal entry. The second floor features a large primary suite complete with turret room, enormous walk in closet, and separate water closet/shower & makeup station/sink. Two additional bedrooms with large walk-in closets, a full hall bath, and gracious open space atop the stairs complete the floor. The third floor contains a large open recreation room with lake views! Also additional bedroom and multiple storage/walk-in closets that would be ideal for work from home space. Lower level is partially finished with large open room, kitchenette, potential bedroom, and storage abound but does need some attention for proper use. Substantial work has been done to the home over the past 10 years including but not limited to... entirely new roof including structural elements; newer electrical & plumbing; various windows replaced or repaired; new sewer and water supplies; addition of zoned HVAC systems & new hot water heater; refinished wood, doors, and trim; various tuck pointing & chimney work; and the list goes on. Massive 20 x 40 garage with an open lofted room above. Above grade square footage estimated at 3300sf but total square footage is over 5000sf including basement & garage loft. Superb Bronzeville/Oakland location with new construction in every direction. Close to IIT, UIC, University of Chicago, lake front & trail, 15 minutes to the loop, 8 minutes to Hyde Park, and close to so much more. A rare find in a city of extraordinary homes! Any questions regarding this listing please contact Norbert Mika - Text or email preferred.

3982 S Lake Park Avenue, Chicago

$659,000
5 Beds 4 Baths 12310541 MLS CLOSED Status
This extensively renovated 3-story, 5-bedroom, 3.5-bath Graystone is located on a landmark block in Chicago's Oakland neighborhood -- an architecturally rich enclave between Kenwood and Bronzeville. Ideally situated near parks, Lake Shore Drive, and the 41st Street Pedestrian Bridge, it offers easy access to lakefront recreation and an effortless commute to downtown or Hyde Park. After an award-winning four-year rebuild by its artist owners, this home is in pristine move-in condition. The main level is thoughtfully designed for family living and entertaining, featuring a fully outfitted eat-in kitchen with stainless steel appliances and quartz countertops. Upstairs, four spacious bedrooms include custom closets, complemented by two beautifully renovated full baths and a cozy office. The lower level adds versatility with a rec room, an ensuite bedroom, and a spacious laundry room with a full-sized GE washer and dryer. Notable features include a double-door entry foyer, two wood-burning fireplaces, a wood-burning stove, zoned HVAC with central humidification, and multiple outdoor spaces-including decks on every level and fenced front and rear yards. The historic embankment across the alley is a part of the former Kenwood Branch rapid transit line and the proposed site of the Bronzeville Trail, a planned two-mile pedestrian and bike path reminiscent of the North Side's Bloomingdale (606) Trail. Additionally, the adjacent side lot at 1032 E. 41st Place is city-owned and may be available for purchase, providing potential expansion opportunities. Ample street parking completes this exceptional offering. Marianos, Whole Foods, and Trader Joe's are close by.

1034 E 41St Place, Chicago

$550,000
7 Beds 4 Baths 11993102 MLS CLOSED Status
In the heart of the storied Oakland community, nestled proudly overlooking the Boulevard, stands a majestic relic of the past, awaiting its renaissance. The ME Team brings you an exclusive insight into the magnificent Greystone at 4123 S Drexel Avenue, an architectural masterpiece waiting to be reborn. This three-unit Greystone, a testament to the grandeur of yesteryears, beckons investors, dreamers, and visionaries alike. With its stately gray stone facade casting an imposing silhouette against the skyline, this property is a timeless symbol of elegance and potential. What sets this property apart is not just its historical significance, but the myriad of opportunities it presents. In need of total rehabilitation, this blank canvas offers the chance to transform and revitalize, breathing new life into its 5260 square feet of living space. With four majestic fireplaces lending an air of opulence, and the possibility to duplex down, the potential for grandeur is limitless. Imagine the opportunity to offset your mortgage with the rental income from the other two units, or to craft a singular haven, a sprawling single-family mansion befitting of royalty. The choice is yours, limited only by the bounds of your imagination. Venturing below, discover an additional unit awaiting transformation in the lower level, offering even more potential for expansion or rental income. And with the property boasting both forced air and a boiler system, modern amenities can seamlessly meld with the historic charm, ensuring comfort and efficiency for generations to come. But perhaps the most compelling aspect of this property lies not just in its bricks and mortar, but in its enviable location. Oakland, a community steeped in history and culture, offers more than just a place to live - it offers the promise of generational wealth. In the equation of Location + Land, the sum is far greater than its parts, promising a legacy that transcends time.

4123 S Drexel Boulevard, Chicago

$685,000
4 Beds 4 Baths 11809513 MLS CLOSED Status
This contemporary and elegant home is a true masterpiece. It has four bedrooms, three and a half bathrooms, and is located steps away from Chicago's beautiful Lakefront. From the moment you lay eyes on this property, you'll be impressed by its remarkable features, including a statement making mural garage and side drive. The interior is just as impressive with beautiful white oak hardwood floors throughout the upper levels, a spacious and modern Marfa chef's kitchen with quartz counters, a huge island, and a sleek fireplace that's both stylish and eco-friendly. The en-suite bedroom is a peaceful retreat with impressive tall ceilings, a bold contemporary bathroom, and ample closet space. This thoughtful design offers many unique and practical amenities, including a "real" laundry room in the basement, abundant storage, a second laundry on the bedroom floor, automatic fresh air intakes, mudroom area, a full pantry, and a hidden exhaust fan in the kitchen. The spacious back deck off the kitchen is perfect for grilling or relaxing while overlooking the yard with a custom-painted mural on the garage door, providing a beautiful backdrop to any entertaining. Located in the desirable Bronzeville area, this home is just down the block from the stunning 35th Street Bridge crossover and offers easy access to Lake Meadows shopping center, Gallery Guichard, Two Fish Restaurant, Simply Soups Salad and Sandwiches, Mariano's, Bronzeville Winery and more. Enjoy the convenience of the city with access to bike trails, jogging paths, CTA trains and buses, the Metra, LSD and 90/94. Don't miss your chance to experience this exceptional home - call us today to schedule a private tour.

3625 S Ellis Avenue, Chicago

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Oakland, Chicago IL · Curated MLS Search

Homes with Finished Basement in Oakland, Chicago IL

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

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