View All Oakland Chicago IL Homes with Main Floor Primary Listings

5 Beds ⋅ 3 Baths ⋅ 12671795 MLS ⋅ CLOSED Status

Rarely available Lake Park Avenue duplex! This property offers exceptional flexibility for owner-occupants, multigenerational living, or investors in a sought-after Bronzeville location near the lakefront and downtown. The property features a 3-bedroom, 1.5-bath owner's duplex and a private 2-bedroom, 1-bath garden unit with strong rental potential. The main duplex boasts hardwood floors throughout, a kitchen with stainless steel appliances, updated bathrooms, and a separate laundry room. The primary suite includes a private balcony with seasonal lake views and a walk-in closet with the potential to add a second full bath. Enjoy seamless indoor-outdoor living with an oversized patio deck and a large backyard. The potential for additional space, such as an office or studio, is found within the separate 2-bedroom, 1-bath garden unit, in-unit laundry. This unit features its own private entrances and offers this additional living space for the owner's use, related living, guests, or as a source of strong rental income. Outdoor space includes a landscaped side yard and patio area. The property is conveniently located near the lakefront, Oakwood Beach, Mandrake Park, public transportation, shopping, and nearby neighborhoods, including Hyde Park, Kenwood, and South Loop. Easy access to Lake Shore Drive, parks, bike trails, and downtown Chicago completes this opportunity to own a solid, well-cared-for property. The property is being sold as is, and the price reflects the garage requiring repair or replacement. The property has two addresses (3761-3763). The lower-level unit's most recent rental income (2022) was $1,900. Agent owned/interest.

3761 S Lake Park Avenue, 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

$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

$649,900

5 Beds ⋅ 4 Baths ⋅ 12505205 MLS ⋅ CLOSED Status

First time ever on the market! Welcome to 3769 S Lake Park Ave, a beautifully maintained 2-unit property offering comfort, function, and opportunity in an ideal location. The lower level unit features 2 bedrooms, 1 bathroom, in-unit laundry, and a warm, inviting layout perfect for extended family, guests, or steady rental income.The main level unit offers 3 bedrooms, 2.5 bathrooms, a gas fireplace in the living area, a bright open kitchen with walkout deck access, and a private balcony off the primary suite for indoor-outdoor relaxation. Recent updates throughout include fresh interior paint, new flooring, upgraded lighting, a stylish barn door, quartz countertops, and new carpet, along with a freshly painted exterior deck. Natural light fills each space, highlighting generous room sizes and thoughtful design. Nestled in a desirable location near the lakefront, parks, schools, shopping, transportation, and just minutes to downtown. This is an exceptional opportunity for both owner-occupants and investors seeking a well-cared-for and versatile property in a prime area.

3769 S Lake Park 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

$475,000

3 Beds ⋅ 4 Baths ⋅ 12327646 MLS ⋅ CLOSED Status

Newer Construction, 4 Bedroom, 2 Full Bath, 2 Half Bath Single Family Home in the Oakland/Kenwood Neighborhood with close proximity to the Lake, Hyde Park and Bronzeville. The residence is situated on a lovely tree lined, one way street on an oversized city lot with a two car garage and huge backyard. The main floor is open floor plan and features hardwood flooring, a gas fireplace in the living room, high ceilings and a modern kitchen with granite countertops and wonderful built in shelving. Three of the bedrooms and two of the bathrooms are located on the second floor. A skylight brightens up the second floor and floods it with natural light. Primary is bright and spacious with ample closet space. The finished basement features a very generous sized family room, large bedroom, half bath and laundry room. Outdoors, enjoy a large yard, deck off the kitchen and a two car garage. Close proximity to the new pedestrian bridge, shopping/ dining District on 43rd Streeet, University of Chicago/Hospitals and Lake Shore Drive. A wonderful place to call home!

4134 S Ellis Avenue, 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

$260,000

3 Beds ⋅ 2 Baths ⋅ 12338200 MLS ⋅ CLOSED Status

Wonderful condo off historic Drexel Blvd. just blocks to the 39th St. beach/DuSable LSD with open floor plan, patio and a garage space. The spacious main living space features a corner gas log fireplace, breakfast bar, SS appliances, granite counters and newer laminate flooring. The ensuite primary bedroom has a walk-in closet and steam shower. Two more bedrooms provide space for a home office and guests. Central AC and in-unit laundry. Freshly painted. Total privacy.

844 E 40Th Street Unit #A2, Chicago

$375,000

3 Beds ⋅ 2 Baths ⋅ 12172251 MLS ⋅ CLOSED Status

Discover urban living at its finest with this expansive 3-bedroom, 2-bath condo! Spanning 1,850 sq ft, this modern residence features a bright, open floor plan with gleaming hardwood floors in the main areas and cozy carpet in the bedrooms. Enjoy two private balconies and an abundance of natural light throughout the home. The heart of this condo is its fully renovated kitchen, completed in 2022-23, boasting sleek quartz countertops, a huge waterfall island, and ample drawer storage. Stainless steel appliances add a touch of sophistication and functionality. Additional highlights include a new water heater (June 2023), new carpet in the primary and middle bedrooms (August 2021), and recent building updates such as a new roof (Spring 2021), lintel repair (Fall 2022), masonry repair (Fall 2023), and back deck/porch repair (Spring 2024). Enjoy easy access to Oakwood Beach just a short walk away and a nearby dog park within a 2-minute stroll. With in-unit laundry and an exterior parking space included, convenience and comfort are at your fingertips. Don't miss out on this exceptional blend of modern amenities and prime location!

3862 S Lake Park Avenue Unit #3N, Chicago

$186,900

1 Beds ⋅ 2 Baths ⋅ 12052795 MLS ⋅ CLOSED Status

BEAUTIFUL GREYSTONE GATED BUILDING IN ONE OF THE HOTTEST AREAS IN THE CITY. UNIT FEATURES IN UNIT LAUNDRY, GLEAMING HARDWOOD FLOORS, MAIN PRIMARY SUITE WITH SPA TUB AND WALK IN CLOSET. RELAX IN THE OPEN LIVINGROOM FEATURING A FIREPLACE AND GREAT SUNLIGHT. THE UNIT HAS A BALCONY GREAT FOR ENTERTAINMENT AND INCLUDES A ONE CAR ASSIGNED PARKING SPOT. SELLER DOES NOT PROVIDE SURVEY, TAXES PRORATED AT 100%.

4105 S Drexel Boulevard Unit #1NR, Chicago

$745,000

4 Beds ⋅ 3 Baths ⋅ 11998335 MLS ⋅ CLOSED Status

This is your opportunity to own this new construction (2021) Brick Multi-level Row Home w/ unobstructed terraces and spectacular downtown/lake views. This breathtaking corner home is located in the Oakland/North Kenwood neighborhood. This home offers an open concept layout; you enter into the ground level foyer that leads you to the 1st bedroom that can also be used as office/guestroom/playroom etc. w/ sliding doors into outdoor patio area. As you walk up to main level you will notice the custom railings that flow into a gourmet island kitchen with quartz rainfall countertops and backsplash to match, stainless steel Bosch appliances. Open living/dining room combo, stone media wall with electric fireplace, powder room with wainscoting detailed walls. On the second level you will find the 2nd & 3rd bedroom, full bath, sitting loft area with small balcony and laundry closet. The 3rd level offers you the private primary suite level with sitting area that walks out to your balcony with panoramic city views, wet bar, a spa like bathroom with a soaring vaulted ceiling and walk in closet. Hardwood floors throughout, modern finishes, custom cabinetry. Enjoy the convenience of being in a walkable neighborhood within minutes from the city, world class Museum of Science and Industry, Newark Street dog park, which is across the street, 31st Street Harbor (Pier), McCormick Place which is the largest convention center, and the Historical University of Chicago & IIT. Your backyard consists of the scenic bike and nature trails, award winning bridges, blocks from the lakefront, Lake Shore Drive and the spectacular views of the skyline of Chicago. Brand NEW, never lived in, little to no maintenance, Low HOA, Low property taxes! Nothing to do but move in and enjoy. Schedule your showing today!!

3901 S Lake Park Avenue, Chicago

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Oakland, Chicago IL · Curated MLS Search

Homes with Main Floor Primary in Oakland, Chicago IL

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