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5137 S Wabash Avenue, Chicago
$1,031,250
12 Beds ⋅ 8 Baths ⋅ 12651113 MLS
HUGE, legal 4-unit property on an extra-wide lot, now ready for new ownership. Originally built in 2009 as individual condos, this building offers significantly larger units than most 3-4 flats in the area-giving it a clear competitive edge. All four apartments feature spacious 3-bedroom/2-bath layouts with stainless steel appliances, granite countertops, marble baths, fireplaces, and in-unit washer/dryers. The top three units have refinished hardwood floors throughout, while the lower level features newer wood plank vinyl flooring. Major updates include two hot water tanks (2020/21) and three new A/C units (2024/25). The fully gated rear parking lot allows for ample, secure parking spaces. Ideal as a long-term investment or owner-occupant opportunity-live in one unit while tenants help cover your mortgage. Conveniently located near the Metra, Red Line, and Green Line.

5137 S Wabash Avenue, Chicago

5643 S Prairie Avenue, Chicago
$950,000
9 Beds ⋅ 6 Baths ⋅ 12716170 MLS
Turnkey 3 Unit on an oversized lot. Each luxury simplex is an oversized 3-bedroom, 2-bathroom condo-quality unit; each features a beautiful 1,500 sq ft open floorplan, each kitchen with high-end stainless steel appliances, quartz counters, and in-unit laundry. Extra insulation for noise reduction between floors and from the outside. Unbeatable location walking distance to the CTA Green Line station and two blocks from Washington Park. Fully rented at $8,400/month. Developed by Woodlawn's premier New Construction builder, this home is ready for the savvy investor and comes with a one-year builder warranty. This is an opportunity to own a trophy investment property in a rapidly appreciating neighborhood. Schedule a private showing today.

5643 S Prairie Avenue, Chicago

5410 S Indiana Avenue, Chicago
$810,000
12601233 MLS
Nestled in the heart of Chicago's rapidly growing Washington Park neighborhood, this fully occupied, six-unit building offers a blend of stable cash flow and exceptional future potential. Located near the University of Chicago and the expansive Washington Park, this property is positioned to benefit from the area's ongoing development, including the future Obama Presidential Center. With property values steadily rising, this investment represents a rare opportunity for savvy investors. Boasting a classic stone facade and a grand marble entryway, this well-maintained building exudes timeless charm. Each of the six spacious 3-bedroom, 1-bath units spans 1,800 square feet, featuring high ceilings, formal dining rooms, real pantries, private back decks, and beautiful bay windows that flood the interiors with natural light. Hardwood floors and well-kept common areas add to the appeal, ensuring tenant satisfaction and full occupancy. Additionally, the building generates extra income through coin-operated laundry facilities and offers gated parking with a two-car brick garage. With a solid history of long-term tenants, this property is a proven income generator. For investors looking to maximize returns, there is untapped potential in the lower level, where a 7th and possibly 8th unit could be developed, both areas have ingress and egress access. Updates include a 2011 boiler to enhance the property's efficiency. The seller is open to discussing owner financing terms provided the seller is in first position with collateral, thereby expanding this armchair investment opportunity to the widest pool of entrepreneurs. This is your chance to make this Washington Park money maker work for you.

5410 S Indiana Avenue, Chicago

5319 S Indiana Avenue, Chicago
$755,000
14 Beds ⋅ 8 Baths ⋅ 12647110 MLS
Calling all investors and owner-occupants to this rare Washington Park Greystone opportunity! This massive 4-unit property features an impressive 14 bedrooms and 8 bathrooms, offering size, flexibility, and income potential that is rarely available in today's market. Truly nothing else like it around. Located 5 miles from downtown, just 1.5 miles from the University of Chicago and within biking distance to Lake Michigan, the beach, Hyde Park, and the Obama Presidential Center, this property sits directly in the path of continued growth and development. New construction has already been completed throughout the block, additional development has broken ground next door, and values continue trending upward in this rapidly appreciating community. Including accommodating bike lanes. The building features three oversized 4-bedroom, 2-bath units plus a 2-bedroom, 2-bath garden unit, creating strong rental income potential and excellent flexibility for owner-occupants. 2 occupied and 2 vacant, ideal for multigenerational living, or investors seeking long-term cash flow. Units offer spacious layouts, stainless steel appliances, primary bedroom suites with private baths, separate heating systems, and updated finishes throughout. Renovations and improvements were completed in2021, and 2023, including tuckpointing, new roof, hot water heaters, and updated mechanicals. 2026 new back porch. Select units include in-unit laundry room, with additional laundry hookups available. The oversized gated backyard offers room for entertaining and future garage or parking pad potential. Estimated market rents for the main units range from approximately $2,600-$3,000 per month, with the garden unit estimated between $1,700-$2,000 per month, making this an attractive opportunity for both immediate income and immediate/long-term equity growth. Whether you are looking to house hack, expand your portfolio, or secure a large multifamily asset in one of Chicago's evolving investment corridors, this property delivers location, scale, and upside all in one. Schedule your showing today and experience the opportunity for yourself.

5319 S Indiana Avenue, Chicago

5169 S Michigan Avenue, Chicago
$688,776
9 Beds ⋅ 3 Baths ⋅ 12547040 MLS
A LEGAL 3 UNIT! Get up to potentially net a profit over of $1,400 per month After paying PITI and PMI! The annual gross rental income is $77,712. This is the best deal in town. The lot adjacent to this listing will now be two new 3 unit buildings for over $1 million each. There are two other new developments that have recently been built or in the process of being built as well near the property. Get in now before prices sky rocket as the neighborhood is experiencing a rapid revitalization. Zoning Certificate in Agent document folder. Seller needs to sale to close on another property. 5169 S Michigan Ave is a well-maintained 3-unit rehabbed building in vibrant Washington Park. Each of the three spacious units have been updated with modern kitchens featuring quartz countertops and stainless steel appliances, plus larger back decks perfect for everyday use or entertaining. Individualized Central AC and heat was added in 2024, bringing extra comfort for tenants. Roof was replaced by the prior owner in 2022. Permitted Tuckpointing on Front of building in 2023. This unit is close to actual park of Washington Park, University of Chicago/ Hospital, upcoming data Center, Schools, Shopping, and walking distance from the XS Tennis facility. You will be close to public transportation; CTA bus, CTA Green Line stop on 51st, Metra lines, 90/94expressway, and Lake Shore Drive. Only 9 minutes to Hyde Park and a 15 minute drive to downtown Chicago. With public transit steps away, parks nearby, and downtown just a short ride, this property combines convenience, strong rental appeal, and long-term value.

5169 S Michigan Avenue, Chicago

5141 S Wabash Avenue, Chicago
$575,000
4 Beds ⋅ 4 Baths ⋅ 12399632 MLS
Stunningly renovated 4-bedroom, 3.5-bath, three-story brick home that beautifully blends classic Chicago architecture with modern luxury. Step inside to soaring ceilings, abundant natural light, and gleaming hardwood floors that flow throughout the home. The showstopping kitchen features a Scandinavian-inspired modern design with chef-level functionality. Sleek flat-panel cabinetry in warm natural wood pairs seamlessly with crisp white uppers, creating a bright and airy atmosphere. A premium stainless steel appliance package including a professional-grade range and oversized farmhouse sink anchors the space, while the marble-look backsplash, quartz countertops, and contemporary lighting add refined elegance. The open layout provides generous workspace and effortless flow, perfect for daily living or impressive entertaining. Retreat to the spa-inspired primary bathroom, thoughtfully designed with a freestanding soaking tub, custom walk-in shower, floor-to-ceiling marble-style tile, and sophisticated brushed-gold fixtures. Textured accent walls, mosaic flooring, and built-in niches elevate the space, offering a serene environment to unwind. Two additional bedrooms on the upper level share a beautifully updated full bath. A brand-new rear deck extends your living space outdoors ideal for relaxing or hosting gatherings. The large finished attic offers incredible versatility and can serve as a children's playroom, home office, or second family room. The fully finished basement adds even more living options, including a spacious family room, guest bedroom, full bath, laundry area, and ample storage perfect for in-laws, entertaining, or even a private getaway or man cave. Recent upgrades include all-new mechanicals, plumbing, and electrical, ensuring peace of mind and a truly move-in-ready experience. With its timeless style, thoughtful design, and prime location near parks, shopping, dining, and transit, this exceptional brick home is one you won't want to miss.

5141 S Wabash Avenue, Chicago

63 E 56Th Street, Chicago
$550,000
6 Beds ⋅ 4 Baths ⋅ 12586649 MLS
Exceptional Greystone opportunity in Chicago's evolving Washington Park community-ideal for investors and owner-occupants seeking versatility and long-term value. This property features a finished basement with a private 1-bedroom, 1-bathroom mother-in-law suite complete with a full kitchen, creating the perfect setup for multi-generational living, guest accommodations, or potential rental income. Laundry room with coin operated machines. Positioned in a prime South Side location, the property offers convenient access to Washington Park, Hyde Park, the University of Chicago, and the growing cultural and economic corridor surrounding the area. Residents enjoy proximity to shopping, dining, parks, and public transportation, along with easy access to major expressways for a quick commute throughout the city. For investors, the additional living space provides income-generating potential and flexible use options, making this a compelling addition to a rental portfolio or a smart house-hack opportunity. Ideal for multi-generational living or rental income.Located near Washington Park and the University of Chicago.Close to public transportation and major expressways.Strong investment and value-add potential.A rare opportunity to own a property that combines location, flexibility, and investment potential in one of Chicago's historic and steadily developing neighborhoods.

63 E 56Th Street, Chicago

5901 S Indiana Avenue, Chicago
$540,000
10 Beds ⋅ 5 Baths ⋅ 12662903 MLS
Rare and beautifully configured two-unit property in the heart of Chicago's historic Washington Park neighborhood. This spacious building offers a total of 10 bedrooms and 4.5 bathrooms, featuring an incredibly unique layout designed to give each residence the comfort and feel of a single-family home. Both units are duplexes- the first-floor residence duplexes down to the lower level, while the second-floor residence duplexes up-creating two expansive multi-level living spaces with flexible layouts ideal for owner-occupants, multi-generational living, or savvy investors seeking strong rental potential. Perfectly positioned just minutes from the University of Chicago and the highly anticipated Obama Presidential Center, this location places you near world-class education, culture, dining, green space, and continued neighborhood investment. Whether you're looking to live in one unit and rent the other or add a standout property to your portfolio, 5901 S. Indiana Ave offers size, versatility, and long-term upside in one of Chicago's most exciting neighborhoods.

5901 S Indiana Avenue, Chicago

5134 S Indiana Avenue, Chicago
$500,000
11 Beds ⋅ 3 Baths ⋅ 12558337 MLS
Located in the sought after Washington Park neighborhood, this multifamily investment property at 5134 S Indiana Avenue presents an excellent opportunity for investors seeking value and upside potential. The property is conveniently situated near the University of Chicago Hospital and in close proximity to the Obama Presidential Library, adding long-term appeal and neighborhood growth potential. The building features a total of 11 bedrooms and 3 bathrooms, offering generous living space across multiple units. The second and third units include private balconies, providing outdoor space and added tenant appeal. With solid bones and strong rental potential, this property is ideal for an investor willing to add a little TLC to maximize value. Whether for long-term rental income or repositioning, this is a great opportunity to invest in a growing area of Chicago. In addition, the property features a garden-level space with an extra bedroom and bath, presenting a value-add opportunity to renovate and potentially convert into a fourth unit. The Property is being sold AS-IS

5134 S Indiana Avenue, Chicago

5850 S Indiana Avenue, Chicago
$499,000
5 Beds ⋅ 5 Baths ⋅ 12595985 MLS
DRAMATIC PRICE CHANGE!! This stunning Five Bedroom / three-bathroom Colonial Style house with a three bedroom / one-bathroom in-law suite, located in the Washington Park neighborhood. Take advantage of the Super low property taxes and Currently Low interest rates to secure this gorgeous home on a 32X150 Oversized lot. Family moments are best spent at HOME and I'm here to tell you that this is the HOME of your dreams. This expansive residence sits in an oversized lot (32X150) and offers eight generously sized bedrooms (5 above grade and 3 in basement) plus a loft currently serving as an office, and a TV Room/Den along with 4.5 impeccably updated bathrooms (one of them in the basement). The main level flows with effortless elegance, from the formal living and dining areas to the elegant kitchen to the cozy corners made for quiet conversation or lively entertaining outdoors. This storybook Colonial gem's exquisite renovation is a great marriage between timeless architecture and modern comfort. Anchored by a grand spiral staircase worthy of Architectural Digest. Filled with light, grace, and purpose, this home is a stunning tribute to design evolution-a thoughtful preservation of its original intent, now elevated for contemporary living. On the second level, the sprawling master suite complete with a walk-in closet and a spa-like bath, features a soaking tub and separate glass-enclosed shower. But what sets this home apart is the lower, an entertainers oasis, three oversized guest bedrooms, a full bath, and its own private entrance. Whether you're welcoming extended family, housing guests, or exploring rental income, this space offers remarkable flexibility and comfort. It's fascinating how a home can evolve-how each owner leaves a mark. Here, however, the essence has been lovingly preserved, enhanced only to suit the rhythm of today's lifestyle. Moments matter. Family matters. And this is the kind of home that holds them all beautifully. Come see why this hidden Colonial gem isn't just a house-it's the one you've been waiting for.

5850 S Indiana Avenue, Chicago

5168 S Wabash Avenue, Chicago
$431,000
3 Beds ⋅ 3 Baths ⋅ 12656638 MLS
Welcome to this modern, totally rehabbed home in Washington Park neighborhood of Chicago, where everything is NEW, NEW NEW!!! This completely rehabbed property offers 4 bedrooms, bonus room/office, 2 +1/2 spa-like bathrooms, and huge 4 car detached garage! This stunning home combines modern elegance and luxury with a top quality finishes throughout: brand new flooring, custom made wainscot paneling, modern recessed lights and more! Open layout of main floor connects bright living room, spacious kitchen and dining space, with additional quiet office/bonus room in the back of the house. Cozy family room with a wet bar in the basement create an inviting atmosphere for both daily living as well as entertaining. The kitchen is equipped with all ss appliances, shaker style cabinets and quartz countertops. You don't have to worry about anything, since all appliances, plumbing, electric, furnace, AC, HWH, wired security system, windows, roof, siding, garage door, sidewalks - you name it - was replaced in 2023/2024! This homes offers comfort, beauty, abundance of space and piece of mind! Convenient location: train and buss stops nearby, and only a few minutes drive to major expressways! Don't miss the opportunity to make it your own!

5168 S Wabash Avenue, Chicago

5210 S King Drive Unit #C, Chicago
$421,000
4 Beds ⋅ 3 Baths ⋅ 12696080 MLS
Welcome to 8 on The Park in Washington Park! This premier 4 bedroom 2.1 bathroom three-story townhome was rehabbed in 2020 and has LOTS of features and amenities. The main level has an open floor plan with a living room/dining room combo, a gas fireplace in the living room and an eat-in kitchen with an island, custom oak cabinets, granite countertops and stainless steel appliances. The primary bedroom includes an en suite bathroom with double sinks, whirlpool tub and separate shower. There are white oak hardwood floors throughout, zoned heating and cooling, a 2-car attached garage and a second floor laundry area! Entertain and enjoy the city skyline views on your large PRIVATE rooftop deck! Conveniently located across from Washington Park and a short distance from the University of Chicago, Walter H. Dyett High School for the Arts, Metra, Lake Shore Drive, I-90/94, public transportation, schools, restaurants and shopping. This unit is RARELY AVAILABLE and will not last long! Check out the 3D tour!

5210 S King Drive Unit #C, Chicago

5632 S Wabash Avenue, Chicago
$294,000
6 Beds ⋅ 2 Baths ⋅ 12680948 MLS
Ask your broker about terrific grants available! The property is eligible for up to $15,000 in assistance and a home warranty. Welcome to this well-maintained two-unit brick building offering expansive layouts, soaring ceilings, and three spacious bedrooms with one full bathroom in each unit. The upper unit benefits from an oversized layout, with particularly generous bedroom sizes created by the extended stairwell, while both units offer excellent functionality and comfort. The lower unit has previously operated as a successful short-term rental, generating approximately $24,000 annually while being utilized only half of the year. Recent improvements by the current owners include the addition of in-unit laundry in both residences and a fully cleared basement, providing a strong foundation for a potential future garden unit. Both units feature re-stained hardwood floors, with kitchens and bathrooms in superb condition and move-in ready. The property is well suited for an owner-occupant seeking rental income or as a full investment opportunity. The area is poised for continued appreciation, supported by significant nearby development, including multi-billion-dollar investments such as the Obama Presidential Library in adjacent Woodlawn.

5632 S Wabash Avenue, Chicago

5415 S Prairie Avenue, Chicago
$215,000
12603145 MLS
An Exceptional Double Lot Opportunity in the Heart of Bronzeville! Positioned along one of Chicago's most historically rich corridors, 5415 S. Prairie Avenue presents a rare opportunity to shape the future of Bronzeville with a 50 x 180 double lot (approx. 9,147 sq ft) zoned RS-3-perfectly suited for a custom single-family residence with allowed ADU units, thoughtfully designed modern two-flats or upzoning to RT-4 or RM-5 if aiming for 3+ units. Set within the vibrant Bronzeville/Grand Boulevard community, this oversized parcel is surrounded by a dynamic blend of classic Chicago greystones and striking new construction, reflecting the neighborhood's continued growth and strong investment appeal. King Drive anchors the area with a rich mix of local restaurants, cafes, and neighborhood staples, creating a lifestyle rooted in culture, history, and convenience. Location is everything-and this one delivers. Just minutes away, you'll find Washington Park, offering expansive green space, walking trails, and recreational amenities, along with the renowned DuSable Black History Museum and Education Center, a cornerstone of Chicago's cultural legacy. Enjoy easy access to the lakefront with 57th Street Beach, perfect for summer days, bike rides, and scenic relaxation. Daily conveniences are just around the corner, including Whole Foods Market and Trader Joe's, along with the popular dining and shopping corridor along 53rd Street in Hyde Park, known for its vibrant restaurant scene and local boutiques. The property is also ideally located near the prestigious University of Chicago, as well as the world-class Museum of Science and Industry and Chicago's iconic Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Commuting is seamless with nearby access to the CTA Green Line (43rd & 47th Street stations) and the Red Line via Sox/35th, along with multiple CTA bus routes including #3 King Drive and #47 47th Street. For drivers, proximity to Lake Shore Drive and I-90/94 (Dan Ryan Expressway) ensures quick travel throughout the city. This is more than just land-it's an opportunity to build in a location that connects history, culture, education, recreation, and modern living. Whether you envision a timeless residence or a standout new construction project, 5415 S. Prairie Avenue offers the scale, setting, and accessibility to bring your vision to life.

5415 S Prairie Avenue, Chicago

5716 S Indiana Avenue, Chicago
$209,000
3 Beds ⋅ 4 Baths ⋅ 12263122 MLS
Attention developers, investors, and owner-occupants with a vision! Discover the potential of 5716 S Indiana Ave, a prime opportunity in Chicago's thriving real estate market. This RM-5 zoned property is a blank canvas, ready for a complete rehab. Whether you are looking to design a luxurious 3-level mansion, create a single family home with an income-generating garden unit, or convert the property into 3 separate units, the possibilities are endless! The basement already features plumbing and egress, making the addition of a 3rd unit straightforward. With the versatility of RM-5 zoning, this property is a rare find for those ready to transform potential into profit. Situated in a desirable location with access to the Garfield Green Line station, easy access to highways, close to Washington Park, Jackson Park, library, Hyde Park, and 10 minutes from the future site of the Obama Library, and so much more. This is your chance to make an impact! Bring your renovation financing or your developer's dream team and unlock the endless potential of this diamond in the rough! Schedule your showing today and let your imagination run wild! Room sizes and measurements are estimated.

5716 S Indiana Avenue, Chicago

5150 S King Drive Unit #A1, Chicago
$130,000
3 Beds ⋅ 3 Baths ⋅ 12741337 MLS
WELCOME TO THIS BEAUTIFUL SUN BATHED 1ST FLOOR CONDO THAT FEATURES 3 GOOD SIZED BEDROOMS((IT ALSO HAS OFFICE ROOM) AND 3 FULL BATHS. THE CONDO HAS BEEN UPDATED IN 2023 - RE-SANDING OF THE HARDWOOD FLOORING / UPDATED STYLISH BATHROOMS WITH CERAMIC ACCENTS AND VANITIES. UPDATED KITCHEN WITH GRANITE COUNTER TOP/MATCHING STAINLESS STEEL APPLIANCES AND CERAMIC FLOORING. THE ENTIRE UNIT WAS PROFESSIONALLY PAINTED. THE CONDO ALSO FEATURES CENTRAL A/C AND RADIANT HEATING. NOTHING TO DO, THE UNIT IS IN MOVE IN CONDITIONS. WASHINGTON PARK IS ACROSS THE STREET . IT IS ALSO CLOSE TO THE MUSEUM OF SCIENCE AND INDUSTRY AND LAKE MICHIGAN. CALL YOUR AGENT TO SCHEDULE A SHOWING. THIS A TRUE BEAUTY NOTE: THE UNIT IS SELLING CASH ONLY AS IS CONDITIONS.

5150 S King Drive Unit #A1, Chicago

5715 S Calumet Avenue, Chicago
$125,000
12626614 MLS
Multi Site Portfolio Opportunity - This lot is a Prime RM-5 Development Opportunity - Oversized 66' x 178' (11,748 SF) cleared lot with no demolition required. Offering strong multifamily density potential. Preliminary plans drafted for two (2) 3-story buildings totaling 12 units (plans not approved). Ideal for developers-build as designed or maximize density under current zoning. Builder available to assist with any full design/build execution. Sold as-is, where-is. Buyer to verify zoning, plans, and approvals. Portfolio / Opportunity: This Property is part of a multi-lot scattered-site portfolio across the Washington Park and West Woodlawn neighborhoods. Preliminary planning and diligence completed for a proposed 33-unit multifamily scattered site development (plans not approved). Ideal for investors seeking scale in a rapidly developing corridor, with flexibility to execute the current concept or optimize density. Builder and contractor team in place for streamlined execution.

5715 S Calumet Avenue, Chicago

5634 S Calumet Avenue, Chicago
$110,000
12683755 MLS
Unlock the potential of this exceptional double lot in one of the area's most exciting growth corridors. Surrounded by significant development and luxury new construction, this rare offering presents an incredible opportunity for builders, developers, investors, or anyone looking to create a custom dream residence. With ample space and endless possibilities, this expansive parcel provides the perfect canvas to bring your vision to life. Capitalize on the momentum of the neighborhood's transformation and secure a prime piece of real estate before values climb even higher. Whether you're planning a luxury estate, investment project, or future development, opportunities like this are becoming increasingly scarce. Don't miss your chance to own a premier double lot in a rapidly appreciating location. Build today, benefit tomorrow.

5634 S Calumet Avenue, Chicago

222-226 E 56Th Street, Chicago
$110,000
12444278 MLS
Prime Development Opportunity in Rapidly Rising Washington Park! Now is the time to invest in one of Chicago's most exciting and fast-evolving neighborhoods. This excellent development opportunity sits in the heart of Washington Park-surrounded by historic architecture, rich culture, and major neighborhood investments. Close proximity to the University of Chicago, the Green Line Performing Arts Center, the Artists Residences, XS Tennis Village, Park Supper Club, and much more. With easy access to public transportation and I-90/94, this location offers unbeatable connectivity to the rest of the city. Washington Park is undergoing a vibrant transformation, attracting attention from developers, artists, and homebuyers alike. Be part of the neighborhood's resurgence and secure your stake in its future. Opportunities like this are rare-visit the site and submit your offer today!

222-226 E 56Th Street, Chicago



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