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6450-6458 S Stony Island Avenue, Chicago

Located at 6450-6458 S Stony Island Ave, Chicago, IL 60637, this 25-unit apartment building with 5 ground-floor retail storefronts offers investors a rare chance to reposition a significant mixed-use property in the heart of Woodlawn, just steps from South Shore. The 25 residential units offer scale for a multi-family repositioning, partially-occupied with 5 vacant retail storefronts. With the right vision and capital, this property has the potential to deliver strong long-term cash flow and become a landmark investment along the Stony Island corridor. Neighborhood highlights: Woodlawn is a hub of transformation, fueled by the upcoming Obama Presidential Center, University of Chicago expansion, and significant public and private investment. South Shore offers lakefront amenities, the South Shore Cultural Center, golf course, and beaches, all minutes away. Excellent access to CTA, Metra, and major thoroughfares position this property for high tenant demand and sustained growth. This is a rare opportunity to acquire a large-scale mixed-use building in a rapidly-appreciating neighborhood. Ideal for value-add investors and developers ready to create a cornerstone asset in one of Chicago's most exciting growth corridors.

12452087 MLS

Located at 6450-6458 S Stony Island Ave, Chicago, IL 60637, this 25-unit apartment building with 5 ground-floor retail storefronts offers investors a rare chance to reposition a significant mixed-use property in the heart of Woodlawn, just steps from South Shore. The 25 residential units offer scale for a multi-family repositioning, partially-occupied with 5 vacant retail storefronts. With the right vision and capital, this property has the potential to deliver strong long-term cash flow and become a landmark investment along the Stony Island corridor. Neighborhood highlights: Woodlawn is a hub of transformation, fueled by the upcoming Obama Presidential Center, University of Chicago expansion, and significant public and private investment. South Shore offers lakefront amenities, the South Shore Cultural Center, golf course, and beaches, all minutes away. Excellent access to CTA, Metra, and major thoroughfares position this property for high tenant demand and sustained growth. This is a rare opportunity to acquire a large-scale mixed-use building in a rapidly-appreciating neighborhood. Ideal for value-add investors and developers ready to create a cornerstone asset in one of Chicago's most exciting growth corridors.

6450-6458 S Stony Island Avenue, Chicago

$775,000

Ultra-contemporary new construction corner residences within a gated 14-home community, designed to elevate daily living while maintaining effortless sophistication. These striking homes feature heated floors-polished concrete or engineered white oak-solid-core flat-panel doors, LED lighting, tall ceilings, and an attached two-car garage. The dramatic two-story main level is anchored by a sun-filled great room and a show-stopping chef's kitchen with Italian flat-panel cabinetry with hidden groove pulls, a Bertazzoni appliance package including panel-ready French-door refrigerator and dishwasher, 36" 36" range, built-in microwave, and externally vented hood. A designer backsplash and island create an ideal gathering space. The second level is light-filled and flexible, offering two spacious bedrooms, a full guest bath, a conveniently located laundry room, and a comfortable family room. The entire penthouse level is dedicated to the primary suite-an impressive retreat with a large walk-in closet and spa-like en-suite featuring dual rain showerheads with handheld, glass enclosure, double-bowl quartz vanity, heated floors, and a dramatic floor-to-ceiling obscured window in the shower. Each corner home includes a private rooftop deck with sweeping north or south views, paver decking, and gas and electric connections-perfect for entertaining or unwinding above the city. INSPIRE Woodlawn seamlessly blends art, architecture, and modern living in the heart of the University of Chicago South Campus, moments from acclaimed cafes and restaurants, cultural destinations, neighborhood markets, the Griffin Museum of Science and Industry, the Obama Presidential Center, lakefront trails, and expansive parks. Live boldly. Live inspired. Schedule your private tour today and choose your corner home at INSPIRE Woodlawn.

3 Beds ⋅ 3 Baths ⋅ 12642180 MLS

Ultra-contemporary new construction corner residences within a gated 14-home community, designed to elevate daily living while maintaining effortless sophistication. These striking homes feature heated floors-polished concrete or engineered white oak-solid-core flat-panel doors, LED lighting, tall ceilings, and an attached two-car garage. The dramatic two-story main level is anchored by a sun-filled great room and a show-stopping chef's kitchen with Italian flat-panel cabinetry with hidden groove pulls, a Bertazzoni appliance package including panel-ready French-door refrigerator and dishwasher, 36" 36" range, built-in microwave, and externally vented hood. A designer backsplash and island create an ideal gathering space. The second level is light-filled and flexible, offering two spacious bedrooms, a full guest bath, a conveniently located laundry room, and a comfortable family room. The entire penthouse level is dedicated to the primary suite-an impressive retreat with a large walk-in closet and spa-like en-suite featuring dual rain showerheads with handheld, glass enclosure, double-bowl quartz vanity, heated floors, and a dramatic floor-to-ceiling obscured window in the shower. Each corner home includes a private rooftop deck with sweeping north or south views, paver decking, and gas and electric connections-perfect for entertaining or unwinding above the city. INSPIRE Woodlawn seamlessly blends art, architecture, and modern living in the heart of the University of Chicago South Campus, moments from acclaimed cafes and restaurants, cultural destinations, neighborhood markets, the Griffin Museum of Science and Industry, the Obama Presidential Center, lakefront trails, and expansive parks. Live boldly. Live inspired. Schedule your private tour today and choose your corner home at INSPIRE Woodlawn.

6218 S Woodlawn Avenue Unit #A, Chicago

$709,500

Nestled in Chicago's vibrant Woodlawn neighborhood, this contemporary new-construction townhome is just moments from the University of Chicago. Thoughtfully designed with four bedrooms and three-and-a-half baths, the residence seamlessly blends sophisticated architecture and elevated finishes with modern functionality. Step inside to an impressive 14-foot-tall living room, where floor-to-ceiling windows flood the space with natural light and create a dramatic sense of volume. An elegant glass-panel staircase leads to the open-concept kitchen and dining level, creating a seamless connection between the home's main living spaces. At the heart of the home, the designer kitchen features Samsung stainless steel appliances and a striking waterfall island. A generous balcony and expansive wall of windows enhance the bright, airy atmosphere, creating an inviting setting for both everyday living and entertaining. The thoughtfully designed floor plan includes a luxurious third-floor primary suite, offering a private retreat with dual walk-in closets, a freestanding soaking tub, and an oversized shower enclosed in floor-to-ceiling glass. Just beyond the primary suite, the private rooftop terrace provides an elevated outdoor setting for morning coffee, evening relaxation, or entertaining guests. Two generously sized bedrooms are located on the second floor, while the versatile lower level can serve as a spacious family room or fourth bedroom, complete with its own ensuite bath. Modern conveniences include dual Nest-controlled HVAC systems, tankless water heaters, and hardwood floors throughout. Full masonry construction, including solid masonry walls between residences, provides enhanced durability and privacy. The home also features an attached, heated two-car garage. Ideally situated near Washington Park, Jackson Park, and the University of Chicago campus, the home offers convenient access to Chicago's cultural, recreational, and educational destinations. The Obama Presidential Center and nearby commercial corridors add to the neighborhood's appeal, while the lakefront, Metra and Lake Shore Drive are easily accessible.

4 Beds ⋅ 4 Baths ⋅ 12773722 MLS

Nestled in Chicago's vibrant Woodlawn neighborhood, this contemporary new-construction townhome is just moments from the University of Chicago. Thoughtfully designed with four bedrooms and three-and-a-half baths, the residence seamlessly blends sophisticated architecture and elevated finishes with modern functionality. Step inside to an impressive 14-foot-tall living room, where floor-to-ceiling windows flood the space with natural light and create a dramatic sense of volume. An elegant glass-panel staircase leads to the open-concept kitchen and dining level, creating a seamless connection between the home's main living spaces. At the heart of the home, the designer kitchen features Samsung stainless steel appliances and a striking waterfall island. A generous balcony and expansive wall of windows enhance the bright, airy atmosphere, creating an inviting setting for both everyday living and entertaining. The thoughtfully designed floor plan includes a luxurious third-floor primary suite, offering a private retreat with dual walk-in closets, a freestanding soaking tub, and an oversized shower enclosed in floor-to-ceiling glass. Just beyond the primary suite, the private rooftop terrace provides an elevated outdoor setting for morning coffee, evening relaxation, or entertaining guests. Two generously sized bedrooms are located on the second floor, while the versatile lower level can serve as a spacious family room or fourth bedroom, complete with its own ensuite bath. Modern conveniences include dual Nest-controlled HVAC systems, tankless water heaters, and hardwood floors throughout. Full masonry construction, including solid masonry walls between residences, provides enhanced durability and privacy. The home also features an attached, heated two-car garage. Ideally situated near Washington Park, Jackson Park, and the University of Chicago campus, the home offers convenient access to Chicago's cultural, recreational, and educational destinations. The Obama Presidential Center and nearby commercial corridors add to the neighborhood's appeal, while the lakefront, Metra and Lake Shore Drive are easily accessible.

6209 S Ellis Avenue Unit #E, Chicago

$700,000

8 Beds ⋅ 7 Baths ⋅ 12719659 MLS

6527 S Drexel Avenue, Chicago

$695,000

Wonderful, well taken care of, updated and improved single family across the street from University of Chicago campus, a short walk to the Lab Schools, and close to the Obama Presidential Center. 4 bed home with tons of space and great light throughout. Fully finished basement with full bath, laundry room, bedroom and storage. Mudroom addition with additional storage underneath; 2 car garage. Home has many upgrades including roof and windows, wainscoting, oak stair treads and railings, crown molding.

3 Beds ⋅ 4 Baths ⋅ 12639798 MLS

Wonderful, well taken care of, updated and improved single family across the street from University of Chicago campus, a short walk to the Lab Schools, and close to the Obama Presidential Center. 4 bed home with tons of space and great light throughout. Fully finished basement with full bath, laundry room, bedroom and storage. Mudroom addition with additional storage underneath; 2 car garage. Home has many upgrades including roof and windows, wainscoting, oak stair treads and railings, crown molding.

1323 E 61St Street, Chicago

$599,000

Beautiful 4-Bed, 3-Bath Chicago Home with Finished Basement & 2-Car Garage right next to Obama Presidential and University of Chicago!This stunning home offers an open-concept layout with a modern kitchen featuring a spacious island, sleek finishes, and ample cabinet space. The cozy family room with a fireplace creates the perfect gathering space. The fully finished basement with 2 bedrooms includes a full bathroom and laundry room. Upstairs, enjoy additional two oversized bedrooms with high ceilings, generous closets, full baths and a hot tub. Two private balconies, including one off the master bedroom, provide the perfect spots to relax outdoors. A detached 2-car garage completes this move-in-ready home. Don't wait-schedule your tour today!

4 Beds ⋅ 3 Baths ⋅ 12734337 MLS

Beautiful 4-Bed, 3-Bath Chicago Home with Finished Basement & 2-Car Garage right next to Obama Presidential and University of Chicago!This stunning home offers an open-concept layout with a modern kitchen featuring a spacious island, sleek finishes, and ample cabinet space. The cozy family room with a fireplace creates the perfect gathering space. The fully finished basement with 2 bedrooms includes a full bathroom and laundry room. Upstairs, enjoy additional two oversized bedrooms with high ceilings, generous closets, full baths and a hot tub. Two private balconies, including one off the master bedroom, provide the perfect spots to relax outdoors. A detached 2-car garage completes this move-in-ready home. Don't wait-schedule your tour today!

6505 S Woodlawn Avenue, Chicago

$559,000

Welcome to 6642 S. Drexel Avenue, a beautifully restored historic residence in the heart of Woodlawn that has been thoughtfully deconverted from a two-flat into a stunning single-family home. Combining timeless character with modern luxury, this home underwent an extensive renovation and restoration completed in 2026. From the moment you enter, you'll appreciate the beautiful hardwood floors that flow throughout the home and the expansive open-concept main level designed for both everyday living and entertaining. The spacious floor plan offers generous living and dining areas, creating the perfect setting for gatherings of any size. The kitchen is truly the heart of the home, featuring backlit cabinetry, abundant storage, and ample space for a large eat-in dining area. Whether hosting guests or enjoying a quiet evening at home, this thoughtfully designed space provides both functionality and style. One of the home's most remarkable features is found on the second level, where you'll discover three spacious ensuite bedrooms-a rare and highly desirable layout seldom found in homes of this caliber. Each suite offers privacy, comfort, and its own dedicated bathroom, creating the ultimate retreat for family members and guests alike. The fully finished basement expands the living space even further, offering two additional bedrooms, a full bathroom, and endless possibilities for recreation, a home office, fitness area, or extended living arrangements. Additional features include a detached two-car garage and countless updates throughout the home that blend historic charm with contemporary finishes. Located in the rapidly growing Woodlawn community near Jackson Park, the University of Chicago, the Obama Presidential Center, and public transportation, this exceptional home offers a unique opportunity to own a piece of Chicago history reimagined for modern living. Zone B for Homegrown program up to $50k downpayment assistance available.

3 Beds ⋅ 5 Baths ⋅ 12746791 MLS

Welcome to 6642 S. Drexel Avenue, a beautifully restored historic residence in the heart of Woodlawn that has been thoughtfully deconverted from a two-flat into a stunning single-family home. Combining timeless character with modern luxury, this home underwent an extensive renovation and restoration completed in 2026. From the moment you enter, you'll appreciate the beautiful hardwood floors that flow throughout the home and the expansive open-concept main level designed for both everyday living and entertaining. The spacious floor plan offers generous living and dining areas, creating the perfect setting for gatherings of any size. The kitchen is truly the heart of the home, featuring backlit cabinetry, abundant storage, and ample space for a large eat-in dining area. Whether hosting guests or enjoying a quiet evening at home, this thoughtfully designed space provides both functionality and style. One of the home's most remarkable features is found on the second level, where you'll discover three spacious ensuite bedrooms-a rare and highly desirable layout seldom found in homes of this caliber. Each suite offers privacy, comfort, and its own dedicated bathroom, creating the ultimate retreat for family members and guests alike. The fully finished basement expands the living space even further, offering two additional bedrooms, a full bathroom, and endless possibilities for recreation, a home office, fitness area, or extended living arrangements. Additional features include a detached two-car garage and countless updates throughout the home that blend historic charm with contemporary finishes. Located in the rapidly growing Woodlawn community near Jackson Park, the University of Chicago, the Obama Presidential Center, and public transportation, this exceptional home offers a unique opportunity to own a piece of Chicago history reimagined for modern living. Zone B for Homegrown program up to $50k downpayment assistance available.

6642 S Drexel Avenue, Chicago

$499,900

Why pay a full mortgage when tenants can cover it? Turnkey East Woodlawn 2-flat with massive income potential. Unit 1: 4BD/2BA duplex with 2 living areas, stainless steel appliances, and in-unit laundry/storage. King-sized beds fit easily, making it ideal for short-term rentals, house hacking, or related living. Unit 2: Bright 3BD/1BA with L-shaped kitchen, in-unit W/D, and a primary bedroom that fits a king. Bonus: The lower level offers flexibility as a plug-and-play short-term rental crash pad or can be converted into a future standalone unit with already existing private entrances. The building has separate utilities, a rear deck for each unit, a yard, and a gorgeous all-masonry 2-car brick garage. Location is a dream. You are minutes from the University of Chicago, Lake Michigan beaches & trails, and within walking distance of public transit - including the Green Line to downtown and all the dining and shopping districts we love in Hyde Park. Driven by $500M+ at the Obama Presidential Center and UofC expansion, Woodlawn home values have outpaced city averages by 12%. 4-bed short-term rentals average $325+/night nearby. Live in one, rent the rest, or collect multiple checks from day one.

7 Beds ⋅ 3 Baths ⋅ 12731749 MLS

Why pay a full mortgage when tenants can cover it? Turnkey East Woodlawn 2-flat with massive income potential. Unit 1: 4BD/2BA duplex with 2 living areas, stainless steel appliances, and in-unit laundry/storage. King-sized beds fit easily, making it ideal for short-term rentals, house hacking, or related living. Unit 2: Bright 3BD/1BA with L-shaped kitchen, in-unit W/D, and a primary bedroom that fits a king. Bonus: The lower level offers flexibility as a plug-and-play short-term rental crash pad or can be converted into a future standalone unit with already existing private entrances. The building has separate utilities, a rear deck for each unit, a yard, and a gorgeous all-masonry 2-car brick garage. Location is a dream. You are minutes from the University of Chicago, Lake Michigan beaches & trails, and within walking distance of public transit - including the Green Line to downtown and all the dining and shopping districts we love in Hyde Park. Driven by $500M+ at the Obama Presidential Center and UofC expansion, Woodlawn home values have outpaced city averages by 12%. 4-bed short-term rentals average $325+/night nearby. Live in one, rent the rest, or collect multiple checks from day one.

6520 S Ellis Avenue, Chicago

$429,900

New Price - New Opportunity. This all-brick 3-story, 6-unit building presents a compelling value opportunity in Chicago's Woodlawn neighborhood. Featuring a consistent unit mix and solid masonry construction, the property offers strong potential for investors seeking to renovate, reposition, or expand their portfolio. Conveniently located just blocks from the 63rd Street Metra Electric/South Shore station and minutes from Jackson Park, the lakefront, the Obama Presidential Center, and the University of Chicago. Offered at an improved price, this is an opportunity to invest in a neighborhood experiencing continued growth and redevelopment.

12702000 MLS

New Price - New Opportunity. This all-brick 3-story, 6-unit building presents a compelling value opportunity in Chicago's Woodlawn neighborhood. Featuring a consistent unit mix and solid masonry construction, the property offers strong potential for investors seeking to renovate, reposition, or expand their portfolio. Conveniently located just blocks from the 63rd Street Metra Electric/South Shore station and minutes from Jackson Park, the lakefront, the Obama Presidential Center, and the University of Chicago. Offered at an improved price, this is an opportunity to invest in a neighborhood experiencing continued growth and redevelopment.

1427 E 66Th Place, Chicago

$395,000

Fee-simple townhome in the heart of Woodlawn, a short walk from the University of Chicago and the medical campus. Three levels, three bedrooms, two baths, an attached garage, and no monthly assessment! Main level has a bedroom and laundry. The second floor opens to living, dining, and a remodeled kitchen with farmhouse sink, tiled backsplash, and opened cabinets, plus a private outdoor deck off the kitchen with a secure shed below. Two bedrooms sit upstairs. Six ION solar panels were added in 2025. Central air, newer water heater and garage shelving. Vacant and ready. A practical home for anyone working at UChicago or the medical campus, or for a buyer who wants a walkable Woodlawn location near campus, parks, and transit.

3 Beds ⋅ 2 Baths ⋅ 12735384 MLS

Fee-simple townhome in the heart of Woodlawn, a short walk from the University of Chicago and the medical campus. Three levels, three bedrooms, two baths, an attached garage, and no monthly assessment! Main level has a bedroom and laundry. The second floor opens to living, dining, and a remodeled kitchen with farmhouse sink, tiled backsplash, and opened cabinets, plus a private outdoor deck off the kitchen with a secure shed below. Two bedrooms sit upstairs. Six ION solar panels were added in 2025. Central air, newer water heater and garage shelving. Vacant and ready. A practical home for anyone working at UChicago or the medical campus, or for a buyer who wants a walkable Woodlawn location near campus, parks, and transit.

1007 E 61St Street, Chicago

6126 S University Avenue Unit #1, Chicago

$370,000

Welcome to this inviting 3-bedroom, 2-bathroom condo in Chicago's Woodlawn neighborhood, ideally situated just a few blocks from the Obama Presidential Center and the University of Chicago. Thoughtfully designed for comfortable everyday living, the home features a convenient mudroom just off the breezeway/patio entrance, offering valuable additional storage and flex space. The spacious layout provides plenty of room to relax and entertain, while the generous back deck creates an inviting setting for outdoor dining, gatherings, or simply enjoying a quiet afternoon. A unique feature of this property is the additional lot, providing an expansive outdoor area for gardening creating your own private green space. Gardeners will appreciate the generous space available for cultivating flowers, vegetables, and more. The location offers convenient access to a variety of educational opportunities, including The University of Chicago Charter School, along with the many cultural, recreational, and educational resources throughout Hyde Park and Woodlawn. Enjoy easy access to the Lakefront, Jackson Park Golf Course, downtown Hyde Park, the University of Chicago, and the historic Obama Presidential Center. Commuting throughout Chicago is also convenient with nearby Metra, CTA bus routes, and the Green Line "L."

3 Beds ⋅ 2 Baths ⋅ 12771208 MLS

Welcome to this inviting 3-bedroom, 2-bathroom condo in Chicago's Woodlawn neighborhood, ideally situated just a few blocks from the Obama Presidential Center and the University of Chicago. Thoughtfully designed for comfortable everyday living, the home features a convenient mudroom just off the breezeway/patio entrance, offering valuable additional storage and flex space. The spacious layout provides plenty of room to relax and entertain, while the generous back deck creates an inviting setting for outdoor dining, gatherings, or simply enjoying a quiet afternoon. A unique feature of this property is the additional lot, providing an expansive outdoor area for gardening creating your own private green space. Gardeners will appreciate the generous space available for cultivating flowers, vegetables, and more. The location offers convenient access to a variety of educational opportunities, including The University of Chicago Charter School, along with the many cultural, recreational, and educational resources throughout Hyde Park and Woodlawn. Enjoy easy access to the Lakefront, Jackson Park Golf Course, downtown Hyde Park, the University of Chicago, and the historic Obama Presidential Center. Commuting throughout Chicago is also convenient with nearby Metra, CTA bus routes, and the Green Line "L."

6126 S University Avenue Unit #1, Chicago

$350,000

Located in the heart of the highly sought-after Woodlawn neighborhood, this property presents an incredible opportunity to own in one of Chicago's fastest-growing communities. Just minutes from the University of Chicago, Jackson Park, the future Obama Presidential Center, and the lakefront, this location continues to attract attention for its growth, convenience, and long-term potential. Surrounded by beautiful tree-lined streets, historic architecture, neighborhood parks, local restaurants, coffee shops, and the amenities of neighboring Hyde Park, Woodlawn has become one of Chicago's most closely watched areas for redevelopment and investment. This spacious property offers approximately 3,500 square feet of living space plus a basement, providing exceptional flexibility for recreation, entertaining, storage, or additional living space. Significant improvements have already been completed, with over $100,000 invested into the property, including a new roof, electrical, plumbing, tuckpointing, and new heating and air conditioning systems. Much of the heavy lifting has already been done, creating an outstanding opportunity for an owner-occupant, investor, or rehabber to complete the finish selections and bring their vision to life. With continued development throughout the surrounding area and substantial improvements already in place, this property offers tremendous upside and the opportunity to capitalize on the ongoing transformation of Woodlawn

4 Beds ⋅ 2 Baths ⋅ 12674525 MLS

Located in the heart of the highly sought-after Woodlawn neighborhood, this property presents an incredible opportunity to own in one of Chicago's fastest-growing communities. Just minutes from the University of Chicago, Jackson Park, the future Obama Presidential Center, and the lakefront, this location continues to attract attention for its growth, convenience, and long-term potential. Surrounded by beautiful tree-lined streets, historic architecture, neighborhood parks, local restaurants, coffee shops, and the amenities of neighboring Hyde Park, Woodlawn has become one of Chicago's most closely watched areas for redevelopment and investment. This spacious property offers approximately 3,500 square feet of living space plus a basement, providing exceptional flexibility for recreation, entertaining, storage, or additional living space. Significant improvements have already been completed, with over $100,000 invested into the property, including a new roof, electrical, plumbing, tuckpointing, and new heating and air conditioning systems. Much of the heavy lifting has already been done, creating an outstanding opportunity for an owner-occupant, investor, or rehabber to complete the finish selections and bring their vision to life. With continued development throughout the surrounding area and substantial improvements already in place, this property offers tremendous upside and the opportunity to capitalize on the ongoing transformation of Woodlawn

6556 S Woodlawn Avenue, Chicago

$325,000

Don't miss this stunning 2 bedroom/ 2 bath penthouse condo. Soaring 20 foot ceilings, windows in all directions, stylish Italian custom cabinetry, huge primary bedroom with fireplace, 3 closets and fabulous spa bath with separate steam shower and deep soaking air bath. Kitchen opens to spacious, airy great room with surround sound speakers and movie projector. New furnace and washer/dryer. Private access to roof top, and parking too! This is Woodlawn's finest, steps from the University of Chicago, the Obama Presidential center, parks and lakefront. Welcome!

2 Beds ⋅ 2 Baths ⋅ 12724127 MLS

Don't miss this stunning 2 bedroom/ 2 bath penthouse condo. Soaring 20 foot ceilings, windows in all directions, stylish Italian custom cabinetry, huge primary bedroom with fireplace, 3 closets and fabulous spa bath with separate steam shower and deep soaking air bath. Kitchen opens to spacious, airy great room with surround sound speakers and movie projector. New furnace and washer/dryer. Private access to roof top, and parking too! This is Woodlawn's finest, steps from the University of Chicago, the Obama Presidential center, parks and lakefront. Welcome!

6640 S Maryland Avenue Unit #3, Chicago

$299,000

Rare development opportunity on an oversized Woodlawn corner lot! Featuring over 80 feet of frontage and 165 feet of depth, this premier parcel offers the ideal canvas for two custom single-family residences. Minutes from UChicago, Jackson Park, lakefront beaches, and the Obama Presidential Center. Enjoy seamless commuting via CTA bus and train options, plus easy, quick access to lakefront beaches, trails, and an array of local shops, cafes, restaurants, and nearby retail.

12735372 MLS

Rare development opportunity on an oversized Woodlawn corner lot! Featuring over 80 feet of frontage and 165 feet of depth, this premier parcel offers the ideal canvas for two custom single-family residences. Minutes from UChicago, Jackson Park, lakefront beaches, and the Obama Presidential Center. Enjoy seamless commuting via CTA bus and train options, plus easy, quick access to lakefront beaches, trails, and an array of local shops, cafes, restaurants, and nearby retail.

6553-6557 S Kimbark Avenue, Chicago

$275,000

Beautifully Renovated 3-Bedroom, 3-Bath Duplex Condo with Private Entrance Experience the comfort of townhome-style living in this beautifully renovated duplex condominium featuring a private entrance and an inviting multi-level layout. The main level offers an open living and dining area with beautifully sanded and stained hardwood floors, creating a warm and welcoming atmosphere. The updated kitchen features contemporary finishes and opens seamlessly to the living space, making it ideal for everyday living and entertaining. Fresh paint, stylish lighting, and thoughtful upgrades continue throughout the home. Recessed lighting enhances the bedrooms and hallway, while all three bathrooms have been updated with new vanities, modern illuminated mirrors, and contemporary fixtures. The spacious primary suite is designed as a private retreat, featuring two walls of closets leading into the en-suite bathroom. Enjoy a dual-sink vanity with clean, modern lines, an oversized Jacuzzi tub, a separate shower, and designer finishes that create a spa-like experience. Step outside to your private balcony with new wood deck planks, perfect for relaxing or enjoying your morning coffee. This spacious home offers three bedrooms and three full bathrooms, providing flexibility for family, guests, or a home office. An additional deeded parking space is available for additional 13,000 and the seller prefers to sell the parking space with the unit. This exceptional Woodlawn comdo combines style, comfort, and convenience.

3 Beds ⋅ 3 Baths ⋅ 12734947 MLS

Beautifully Renovated 3-Bedroom, 3-Bath Duplex Condo with Private Entrance Experience the comfort of townhome-style living in this beautifully renovated duplex condominium featuring a private entrance and an inviting multi-level layout. The main level offers an open living and dining area with beautifully sanded and stained hardwood floors, creating a warm and welcoming atmosphere. The updated kitchen features contemporary finishes and opens seamlessly to the living space, making it ideal for everyday living and entertaining. Fresh paint, stylish lighting, and thoughtful upgrades continue throughout the home. Recessed lighting enhances the bedrooms and hallway, while all three bathrooms have been updated with new vanities, modern illuminated mirrors, and contemporary fixtures. The spacious primary suite is designed as a private retreat, featuring two walls of closets leading into the en-suite bathroom. Enjoy a dual-sink vanity with clean, modern lines, an oversized Jacuzzi tub, a separate shower, and designer finishes that create a spa-like experience. Step outside to your private balcony with new wood deck planks, perfect for relaxing or enjoying your morning coffee. This spacious home offers three bedrooms and three full bathrooms, providing flexibility for family, guests, or a home office. An additional deeded parking space is available for additional 13,000 and the seller prefers to sell the parking space with the unit. This exceptional Woodlawn comdo combines style, comfort, and convenience.

6651 S Drexel Avenue Unit #1E, Chicago

$265,000

Amazing Investor's Opportunity! Don't miss this incredible opportunity to own a legal all-brick two-unit building in a rapidly growing area just minutes from the future Obama Center. Each spacious unit offers approximately 1,500 square feet with 3 bedrooms and 1 full bath, providing an excellent layout for both owner-occupants and investors. With strong income potential and endless possibilities to renovate, update, or expand your portfolio, this property is ready for your vision. Conveniently located near public transportation, parks, shopping, dining, and major expressways. Opportunities like this don't come around often schedule your showing today and unlock the potential of this exceptional investment property! AS-IS

6 Beds ⋅ 2 Baths ⋅ 12725293 MLS

Amazing Investor's Opportunity! Don't miss this incredible opportunity to own a legal all-brick two-unit building in a rapidly growing area just minutes from the future Obama Center. Each spacious unit offers approximately 1,500 square feet with 3 bedrooms and 1 full bath, providing an excellent layout for both owner-occupants and investors. With strong income potential and endless possibilities to renovate, update, or expand your portfolio, this property is ready for your vision. Conveniently located near public transportation, parks, shopping, dining, and major expressways. Opportunities like this don't come around often schedule your showing today and unlock the potential of this exceptional investment property! AS-IS

6646 S Minerva Avenue, Chicago

$250,000

Spacious and beautifully updated 5-bedroom, 3-bath duplex-down in the highly sought-after Woodlawn neighborhood, just minutes from public transportation, the University of Chicago, and the future Obama Presidential Center. Offering exceptional space and flexibility, this home is ideal for homeowners, multigenerational living, or investors seeking additional income potential. The main level features refinished hardwood floors (2024), fresh paint throughout, and a bright open-concept layout designed for comfortable living and entertaining. The sun-filled living room showcases a cozy fireplace and Juliet balcony, flowing seamlessly into the updated kitchen with granite countertops, custom cabinetry, breakfast bar, and newer stainless-steel appliances, including a refrigerator and dishwasher (2024). Three generously sized bedrooms are located on the main level, including a spacious primary suite featuring a spa-inspired bath with dual vanity, jacuzzi tub, and separate shower. Step outside to your private terrace and enjoy the convenience of an assigned parking space. The fully finished lower level expands the living space with a large recreation room complete with a wet bar, two additional bedrooms, and a full bathroom featuring dual sinks, a soaker tub, and separate shower. This level also includes a second kitchen with a newer cooktop and refrigerator (2024), washer and dryer, and a private entrance, creating an ideal setup for extended family, guests, or related living arrangements. Don't miss this unique opportunity to own a versatile and well-maintained home in one of Chicago's fastest-growing communities. Property is being sold as-is and is subject to short sale approval.

3 Beds ⋅ 3 Baths ⋅ 12670318 MLS

Spacious and beautifully updated 5-bedroom, 3-bath duplex-down in the highly sought-after Woodlawn neighborhood, just minutes from public transportation, the University of Chicago, and the future Obama Presidential Center. Offering exceptional space and flexibility, this home is ideal for homeowners, multigenerational living, or investors seeking additional income potential. The main level features refinished hardwood floors (2024), fresh paint throughout, and a bright open-concept layout designed for comfortable living and entertaining. The sun-filled living room showcases a cozy fireplace and Juliet balcony, flowing seamlessly into the updated kitchen with granite countertops, custom cabinetry, breakfast bar, and newer stainless-steel appliances, including a refrigerator and dishwasher (2024). Three generously sized bedrooms are located on the main level, including a spacious primary suite featuring a spa-inspired bath with dual vanity, jacuzzi tub, and separate shower. Step outside to your private terrace and enjoy the convenience of an assigned parking space. The fully finished lower level expands the living space with a large recreation room complete with a wet bar, two additional bedrooms, and a full bathroom featuring dual sinks, a soaker tub, and separate shower. This level also includes a second kitchen with a newer cooktop and refrigerator (2024), washer and dryer, and a private entrance, creating an ideal setup for extended family, guests, or related living arrangements. Don't miss this unique opportunity to own a versatile and well-maintained home in one of Chicago's fastest-growing communities. Property is being sold as-is and is subject to short sale approval.

6328 S Drexel Avenue Unit #1, Chicago

6651 S Maryland Avenue Unit #1E, Chicago

$219,900

Welcome home to this awesome 2-bedroom, 2-bath duplex-up condo in the heart of Woodlawn. This home features hardwood floors throughout the main level, an open layout, and exposed brick that adds character and warmth. The primary suite includes an ensuite bathroom, offering comfort and privacy. Kitchen features stainless steel refrigerator and other appliances will be upgraded to stainless steel prior to closing. Upstairs, enjoy a versatile lofted second level-perfect for a home office, den, or additional living space. Step outside and relax in one of two private outdoor spaces, including a generous deck ideal for entertaining. Located just minutes from Hyde Park, Lake Shore Drive, I-90/94, and the highly anticipated Obama Presidential Library, this home offers the best of city living with neighborhood appeal. Several additional developments are expected in the Woodlawn area, making this home not only a comfortable retreat but an excellent investment. A rare find combining style, space, and a great location-this Woodlawn gem is not to be missed!

2 Beds ⋅ 2 Baths ⋅ 12499133 MLS

Welcome home to this awesome 2-bedroom, 2-bath duplex-up condo in the heart of Woodlawn. This home features hardwood floors throughout the main level, an open layout, and exposed brick that adds character and warmth. The primary suite includes an ensuite bathroom, offering comfort and privacy. Kitchen features stainless steel refrigerator and other appliances will be upgraded to stainless steel prior to closing. Upstairs, enjoy a versatile lofted second level-perfect for a home office, den, or additional living space. Step outside and relax in one of two private outdoor spaces, including a generous deck ideal for entertaining. Located just minutes from Hyde Park, Lake Shore Drive, I-90/94, and the highly anticipated Obama Presidential Library, this home offers the best of city living with neighborhood appeal. Several additional developments are expected in the Woodlawn area, making this home not only a comfortable retreat but an excellent investment. A rare find combining style, space, and a great location-this Woodlawn gem is not to be missed!

6651 S Maryland Avenue Unit #1E, Chicago

$202,500

Large Brick 2 story Single Family located in the Woodlawn neighborhood of the City. Features Hardwood Floors throughout, beautiful Woodwork, Built-ins, Formal Dining Room, 1st floor Family Room, enclosed Porch, full unfinished Basement and a 2.5 Car Garage off the alley. Great location, close to the Obama Presidential Center, University of Chicago, Jackson Park, the Lakefront, Shopping, Dining and Transportation. HUD Case 137-453756, Insured Status: UI (Uninsured). HUD owned Property. The Seller Is selling this property in "AS IS" condition. Seller nor its representatives make any representations or warranties regarding the property. City Code violations, seller disclosure see attached

4 Beds ⋅ 2 Baths ⋅ 12755283 MLS

Large Brick 2 story Single Family located in the Woodlawn neighborhood of the City. Features Hardwood Floors throughout, beautiful Woodwork, Built-ins, Formal Dining Room, 1st floor Family Room, enclosed Porch, full unfinished Basement and a 2.5 Car Garage off the alley. Great location, close to the Obama Presidential Center, University of Chicago, Jackson Park, the Lakefront, Shopping, Dining and Transportation. HUD Case 137-453756, Insured Status: UI (Uninsured). HUD owned Property. The Seller Is selling this property in "AS IS" condition. Seller nor its representatives make any representations or warranties regarding the property. City Code violations, seller disclosure see attached

6625 S Woodlawn Avenue, Chicago

$195,000

Welcome to this spacious 3-bedroom, 2-bath condo offering a bright, open layout with high ceilings and beautiful hardwood floors. The living room features a cozy fireplace and flows into the kitchen with stainless steel appliances and plenty of cabinet space. The primary bedroom includes a private bath, while two additional bedrooms offer plenty of flexibility for guests, a home office or additional living space. Step outside and enjoy the spacious balcony, perfect for relaxing or enjoying your morning coffee. In-unit laundry, generous closet space and dedicated parking add even more convenience. Enjoy a great location near Jackson Park and the new Obama Presidential Center, with easy access to the lakefront, Museum of Science and Industry, University of Chicago, public transportation, dining, shopping and all that the surrounding Woodlawn and Hyde Park neighborhoods have to offer. With three bedrooms, two full baths and plenty of living space, this condo offers a great combination of space, convenience and location!

3 Beds ⋅ 2 Baths ⋅ 12733221 MLS

Welcome to this spacious 3-bedroom, 2-bath condo offering a bright, open layout with high ceilings and beautiful hardwood floors. The living room features a cozy fireplace and flows into the kitchen with stainless steel appliances and plenty of cabinet space. The primary bedroom includes a private bath, while two additional bedrooms offer plenty of flexibility for guests, a home office or additional living space. Step outside and enjoy the spacious balcony, perfect for relaxing or enjoying your morning coffee. In-unit laundry, generous closet space and dedicated parking add even more convenience. Enjoy a great location near Jackson Park and the new Obama Presidential Center, with easy access to the lakefront, Museum of Science and Industry, University of Chicago, public transportation, dining, shopping and all that the surrounding Woodlawn and Hyde Park neighborhoods have to offer. With three bedrooms, two full baths and plenty of living space, this condo offers a great combination of space, convenience and location!

1517 E Marquette Road Unit #2E, Chicago

$150,000

Condominium Association is separating the lot from their common elements and selling AS IS. Property taxes will be determined as a result of the separation.

12606582 MLS

Condominium Association is separating the lot from their common elements and selling AS IS. Property taxes will be determined as a result of the separation.

6422 S Minerva Avenue, Chicago

$119,900

Tucked away on a dead-end street in the Woodlawn School District, this 23x40 manufactured home sits on 1 acre. The setting has a quiet, campground-like atmosphere, making it a great place to relax, enjoy the outdoors, and get away from the noise. The home features a new roof installed in 2026. Inside you will find the interior updated and move-in ready. Outside, you'll find a rear deck overlooking the property, along with a detached 2-car garage that provides plenty of room for parking, storage, hobbies, or workshop space. With its one-acre setting, dead-end location, detached garage, and peaceful surroundings, this property has a lot to offer for anyone looking for space, privacy, and a more relaxed lifestyle.

3 Beds ⋅ 2 Baths ⋅ 12775835 MLS

Tucked away on a dead-end street in the Woodlawn School District, this 23x40 manufactured home sits on 1 acre. The setting has a quiet, campground-like atmosphere, making it a great place to relax, enjoy the outdoors, and get away from the noise. The home features a new roof installed in 2026. Inside you will find the interior updated and move-in ready. Outside, you'll find a rear deck overlooking the property, along with a detached 2-car garage that provides plenty of room for parking, storage, hobbies, or workshop space. With its one-acre setting, dead-end location, detached garage, and peaceful surroundings, this property has a lot to offer for anyone looking for space, privacy, and a more relaxed lifestyle.

12348 N Ring Lane, Woodlawn

6528 S University Avenue Unit #3S, Chicago

$100,000

Sold before being listed. SHORT SALE!

3 Beds ⋅ 2 Baths ⋅ 12417158 MLS

Sold before being listed. SHORT SALE!

6528 S University Avenue Unit #3S, Chicago

6295 E Il Hwy 15 Unit #East Office, Woodlawn

$?

EB455421 MLS

6295 E Il Hwy 15 Unit #East Office, Woodlawn