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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 ⋅ CONTINGENT Status

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

$1,000,000

Six-unit property featuring four-bedroom two-bathroom apartments. A portion of units have received updated including refreshed kitchens and modern cabinets. Additionally, some units feature updated quartz countertops and stainless-steel appliances. Building located less than two blocks from University of Chicago and within walking distances of both Jackson Park and the Metra Electric 63rd St. station. Building sold as-is.

12785457 MLS ⋅ CONTINGENT Status

Six-unit property featuring four-bedroom two-bathroom apartments. A portion of units have received updated including refreshed kitchens and modern cabinets. Additionally, some units feature updated quartz countertops and stainless-steel appliances. Building located less than two blocks from University of Chicago and within walking distances of both Jackson Park and the Metra Electric 63rd St. station. Building sold as-is.

6221 S Kimbark Avenue, Chicago

$700,000

8 Beds ⋅ 7 Baths ⋅ 12719659 MLS ⋅ CONTINGENT Status

6527 S Drexel 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 ⋅ CONTINGENT Status

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 ⋅ PENDING Status

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 ⋅ CONTINGENT Status

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

$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 ⋅ CONTINGENT Status

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 ⋅ CONTINGENT Status

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 ⋅ CONTINGENT Status

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 ⋅ CONTINGENT Status

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

$260,000

First-Floor Beauty Near University of Chicago - Move-In Ready! Available now! This bright and beautiful first-floor condo offers the perfect blend of historic charm and modern updates in the heart of Woodlawn. This 3-bedroom, 2-bath condo features gleaming hardwood floors, fresh paint, and an elegant kitchen with granite countertops and upgraded cabinets. Prime Location! Just minutes from the University of Chicago, the Obama Presidential Library, Lake Shore Drive, and Jackson Park, with easy access to shopping, dining, and public transportation. Enjoy all the best of city living, with Hyde Park, the Museum of Science and Industry, and scenic lakefront trails just moments away. Don't miss this incredible opportunity to own a piece of history with modern conveniences! MOTIVATED SELLER!

3 Beds ⋅ 2 Baths ⋅ 12775617 MLS ⋅ CONTINGENT Status

First-Floor Beauty Near University of Chicago - Move-In Ready! Available now! This bright and beautiful first-floor condo offers the perfect blend of historic charm and modern updates in the heart of Woodlawn. This 3-bedroom, 2-bath condo features gleaming hardwood floors, fresh paint, and an elegant kitchen with granite countertops and upgraded cabinets. Prime Location! Just minutes from the University of Chicago, the Obama Presidential Library, Lake Shore Drive, and Jackson Park, with easy access to shopping, dining, and public transportation. Enjoy all the best of city living, with Hyde Park, the Museum of Science and Industry, and scenic lakefront trails just moments away. Don't miss this incredible opportunity to own a piece of history with modern conveniences! MOTIVATED SELLER!

6137 S Kimbark Avenue Unit #1, 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 ⋅ CONTINGENT Status

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

$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 ⋅ PENDING Status

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

$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 ⋅ PENDING Status

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

6528 S University Avenue Unit #3S, Chicago

$100,000

Sold before being listed. SHORT SALE!

3 Beds ⋅ 2 Baths ⋅ 12417158 MLS ⋅ CONTINGENT Status

Sold before being listed. SHORT SALE!

6528 S University Avenue Unit #3S, Chicago

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