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6450-6458 S Stony Island Avenue, Chicago
$2,150,000
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

6016 S Saint Lawrence Avenue, Chicago
$1,100,000
16 Beds ⋅ 8 Baths ⋅ 12773057 MLS ⋅ CONTINGENT Status
16 BEDROOMS | 8 BATHROOMS | 4-UNIT MULTIFAMILY Welcome to 6016 S. St. Lawrence Avenue, an exceptional four-unit multifamily property offering an impressive combination of scale, modern updates, and prime Chicago location. Recently rehabbed, this expansive property features 16 bedrooms and 8 bathrooms across four spacious units, providing substantial residential capacity and multiple potential rental income streams within one investment. Each unit features updated interiors, modern kitchens and bathrooms, and refreshed living spaces designed for comfortable, contemporary living. Located just blocks from the University of Chicago and near the Obama Presidential Center, the property is surrounded by major institutions, restaurants, shopping, transportation, and cultural attractions. Investment Highlights * 16 Bedrooms * 8 Bathrooms * 4 Residential Units * Recently Rehabbed * Updated Kitchens & Bathrooms * Modernized Interiors * Multiple Potential Rental Income Streams * Near University of Chicago * Near Obama Presidential Center * Convenient Access to Hyde Park & Washington Park With its four-unit configuration, impressive bedroom count, recent rehabilitation, and sought-after location, 6016 S. St. Lawrence presents a compelling opportunity for investors looking to acquire a substantial multifamily asset in Chicago. A remarkable property with the scale, location, and potential to stand out in any investment portfolio. 6016 S. ST. LAWRENCE AVENUE - FOUR UNITS. SIXTEEN BEDROOMS. ONE EXCEPTIONAL INVESTMENT.

6016 S Saint Lawrence Avenue, Chicago

6402 S Vernon Avenue, Chicago
$779,000
8 Beds ⋅ 5 Baths ⋅ 12696280 MLS ⋅ PENDING Status
Experience elevated living and exceptional investment potential with this stunning new-construction three-unit property in the heart of Woodlawn. Thoughtfully designed to deliver both modern luxury and lasting value, this turnkey building presents an outstanding opportunity for investors and owner-occupants alike. The first and second-floor residences each offer spacious three-bedroom, two-bathroom layouts with open-concept living spaces, beautiful white oak hardwood floors, and an abundance of natural light. The garden-level unit features two bedrooms and one bathroom, providing excellent flexibility for additional rental income, multigenerational living, or an owner-occupied investment strategy. Every chef-inspired kitchen is designed to impress, featuring a dramatic 7-foot waterfall-edge island, a 36-inch undermount stainless steel sink, 42-inch shaker-style cabinetry, stainless steel appliances, and elegant Calacatta quartz countertops-creating the perfect space for everyday living and effortless entertaining. The spa-inspired bathrooms offer sleek, contemporary vanities and glass-enclosed showers, providing a relaxing retreat in every residence. Built with quality and efficiency in mind, the property is equipped with a robust 600-amp electrical service and a high-efficiency 50-gallon water heater to support today's modern lifestyle. Durable Hardie siding wraps the entire exterior, enhancing both curb appeal and long-term durability. A professionally installed drain tile system and sump pump provide added protection for the foundation and peace of mind year-round. Ideally situated just minutes from the University of Chicago, the Obama Presidential Center, Woodlawn Central-an exciting 8.5-acre mixed-use development near the 63rd Street Metra station-lakefront parks and trails, and major public transportation, this property is perfectly positioned in one of Chicago's most dynamic and rapidly growing neighborhoods. Eligible buyers may also benefit from valuable down payment assistance programs, including up to $20,000 through the University of Chicago Employer-Assisted Housing Program and up to **$20,000** through the Cook County Land Bank program. These programs are available on a first-come, first-served basis and are subject to funding availability. Whether you're looking to build long-term wealth through rental income or enjoy luxury living while offsetting your mortgage, this exceptional new-construction property offers the best of both worlds.

6402 S Vernon Avenue, Chicago

6637 S Evans Avenue, Chicago
$689,900
5 Beds ⋅ 4 Baths ⋅ 12677666 MLS ⋅ CONTINGENT Status
Introducing Deux on Evans, where qualified buyers automatically receive a $20,000 grant that may be applied toward eligible closing costs and qualifying funds needed to purchase the home. Qualified buyers may also be eligible for up to $70,000 through the City of Chicago's grant programs. Together, these grants create one of the most compelling opportunities to own a new construction home in Chicago. Welcome to Deux on Evans, a striking new construction two-unit residence where contemporary design, sophisticated living, and long-term opportunity converge in the heart of West Woodlawn. Bold modern architecture, expansive windows, and thoughtfully curated finishes immediately distinguish this exceptional property. Inside, soaring ceilings, wide-plank flooring, oversized windows, and an open-concept design create bright, inviting spaces that are equally suited for everyday living and effortless entertaining. The designer kitchen serves as the heart of the home, featuring rich wood-toned cabinetry, quartz countertops, dramatic pendant lighting, premium appliances, and an oversized island that naturally brings family and friends together. Sophisticated finishes and clean architectural lines continue throughout, creating a timeless aesthetic that blends modern luxury with everyday comfort. What truly sets Deux on Evans apart is the beautifully appointed garden residence, offering exceptional flexibility and income-producing potential. Whether utilized as a long-term rental, furnished executive residence, corporate housing, or a short-term rental where permitted by applicable laws and regulations, the additional residence creates an outstanding opportunity to generate supplemental income while building long-term wealth. Its location makes it especially appealing to visiting professors, physicians, researchers, graduate students, medical professionals, and families visiting the University of Chicago, as well as guests traveling to experience the highly anticipated Obama Presidential Center, Jackson Park, and Chicago's vibrant South Side. It also serves as an ideal home away from home for executives, consultants, traveling medical professionals, and others working in Chicago on temporary assignments who appreciate the comfort, privacy, and space that a luxury residence offers over a traditional hotel. Perfectly positioned near the University of Chicago, the Obama Presidential Center, Jackson Park, the South Shore lakefront, the Museum of Science and Industry, golf courses, neighborhood restaurants, parks, and convenient transportation, this home is located in one of Chicago's most exciting and rapidly evolving communities, where continued investment is shaping the future. Deux on Evans offers something increasingly rare: a luxury residence that elevates your everyday lifestyle while creating meaningful financial opportunity. Whether you're searching for an exceptional place to call home, a residence with built-in income potential, or both, this extraordinary property delivers an unmatched combination of contemporary design, flexibility, and lasting value. Luxury without compromise. Opportunity without limits. Welcome to Deux on Evans.

6637 S Evans Avenue, Chicago

6552 S Evans Avenue, Chicago
$630,000
5 Beds ⋅ 4 Baths ⋅ 12776774 MLS ⋅ CONTINGENT Status
Rare Opportunity: Anyone INCLUDING Non-Veterans Can Assume This 2.487% VA Mortgage & Save Over $418,000 in Interest! Save $1,373 Every Month by Locking In This Historically Low, Fixed-Rate Loan Instead of Today's ~7.25% Market Rate! Ideal for Owner-Occupants or Savvy Investors - Only a Handful of Multi-Units in All of Illinois Qualify for a Rate This Good! This New Construction (Built 2021) 2-Unit Brick-and-Frame Building in the Heart of Chicago's Booming Hyde Park / West Woodlawn Corridor is FULLY LEASED and Cash-Flowing from Day One! Minutes From the Obama Presidential Center, the University of Chicago (#6 University in the Nation), and Hyde Park's Dining & Entertainment Scene! Unit 1 is a Spacious 3 Bed / 2.5 Bath Duplex-Up with Flowing Open-Concept Living, Quartz Countertops, a Walk-In Pantry, and a Spa-Inspired Primary Suite w/ Rain Shower! Unit 2 is a Well-Designed 2 Bed / 1 Bath Layout with High Windows and a Bright, Comfortable Interior. Both Units Feature In-Unit Washer/Dryer, Modern Shaker Cabinetry, Quartz Counters & Hardwood Floors & 1 Assigned Parking Space Apiece Inside Included Two-Car Detached Garage! Tenants Pay ALL Utilities! Unit #1 Rented for $2,615/Month (Incl. Parking), Lease Through 5/2027. Unit #2 Rented for $1,800/Month Beginning 10/2026 - Combined Rent of $4,415/Month! You Could Acquire This Cash-Flowing Asset for as Little as $7,466 to Close by Assuming the Seller's Fixed 2.487% VA Loan and Financing the Remaining Gap w/ a Securities-Backed Line of Credit, Cash or a 2nd Mortgage - an 8.47% Cap Rate and a Cash-on-Cash Return of up to 211% (depending on purchase structure)! Don't Miss This Once-in-a-Cycle Chance to Lock In 2021-Era Financing in a 2026 Rate Environment! Security System Included. For Information on Qualifying for 2nd Mortgages on Mortgage Assumptions, Contact Dan Fray of Barrett Financial.

6552 S Evans Avenue, Chicago

6747 S Langley Avenue, Chicago
$579,000
3 Beds ⋅ 3 Baths ⋅ 12746871 MLS ⋅ PENDING Status
Built for the next 100 years, not the last. This brand-new two-unit building offers a superior living experience with enhanced comfort and library-quiet interior, enhanced affordability, a low-maintenance lifestyle, and a promising return on investment. Constructed by the renowned Greenline Homes, this brand-new all-electric two-flat delivers. The larger, primary, upstairs unit boasts a dining room-sized private rear balcony, an expansive great room with 10-foot ceilings, and seamless indoor-outdoor living, a perfect fit for your needs or a perfect opportunity to get peak market rental income. The stunning backyard-level first-floor rear unit provides a generous one-bedroom retreat, perfect for multi-generational living or an owner occupant seeking high-value rental income to improve affordability. Additionally, it's ADA accessible, featuring a zero-threshold bath. Enjoy designer-coordinated custom cabinetry, beautiful quartz countertops, and chef's-choice induction cooking in a home engineered for the next 100 years, not the last. Triple-pane windows and an enhanced building envelope ensure optimal thermal comfort, while a fully paid-for solar PV system results in ultra-low utility costs without compromising style. From the premium James Hardie fiber cement exterior to camera intercom with electronic front gate, every detail is meticulously considered and crafted for effortless, low-maintenance living. High-quality appliances like Frigidaire Gallery, Mitsubishi HVAC, and an EPA Air Quality Plus Certification cater to your lifestyle and wellness. Transform your experience into a healthier, wealthier, and far more comfortable home-your best life begins here. This building has been third-party certified, and performance verifications, including the HERS Score, are available for review. Save over $3,345 a year over a typical new construction building... enough to help buy that EV you can plug into the ready to go level 2 charger in the extra wide 2.5 car garage!

6747 S Langley Avenue, Chicago

6642 S Drexel Avenue, Chicago
$559,000
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

608 E 64Th Street, Chicago
$360,000
12 Beds ⋅ 4 Baths ⋅ 12759677 MLS ⋅ CONTINGENT Status
Woodlawn 4-Unit Brick - Gutted, Framed, and Priced to Move. Motivated seller is stepping away from this Woodlawn rehab, leaving a rare opening for a developer to take over a project that's ready to move to completion. This solid two-story brick 4-flat on a corner lot is sold strictly AS-IS. Classic Chicago construction: red pressed-brick facade, limestone belt courses, arched window openings, and an original ornamental cornice. New black double-hung windows have been installed throughout. Inside, the building has been fully gutted and re-framed. New wall framing, HVAC trunk lines, electrical panels, conduit, and recessed lighting boxes are in place, with plumbing rough-in started. Exposed brick and original timber joists throughout give the next owner a strong canvas for a high-end finish. Layout per plans: two duplex-down units on the first floor/garden level and two single-level units on the second floor. Architectural plans and permits are available. Corner location with open side yard and mature trees. Easy to show. Bring your crew and your vision. Experienced and qualified developers only. Property sold strictly AS-IS - please inspect prior to submitting an offer. Proof of funds required for access and for offers to be considered.

608 E 64Th Street, Chicago

6334 S Saint Lawrence Avenue, Chicago
$359,000
2 Beds ⋅ 3 Baths ⋅ 12696189 MLS ⋅ CONTINGENT Status
Discover a great value in Woodlawn with this updated bungalow, perfect for buyers seeking affordability and investment potential. This home combines modern style with practical features, making it a smart investment. The spacious great room with a vaulted ceiling offers plenty of room and feels expansive with its skylights keeping the space bright even on cloudy days. The kitchen is modern and efficient, equipped with new appliances and a smart layout. The main level includes two large bedrooms and two full bathrooms, with a primary suite that opens to a big rear deck. The custom oak staircase leads to a lower level with a family room and a third bedroom, ideal for guests or a home office....OR the building also has a separate entrance to the lower level, and the front half of the basement could be enjoyed as a Airbnb rental, with its en suite bathroom! The recently opened Obama presidential Center is nearby with limited hotels in the area. Enjoy comfort with zoned heating and air conditioning. Outside, the large fenced yard is perfect for gatherings, with a deck and new parking pad. Located near the Cottage Grove Green Line station, this home offers a unique opportunity to own a single-family house at a condo price, with plenty of room for growth and enjoyment.

6334 S Saint Lawrence Avenue, Chicago

539 E 68Th Street, Chicago
$350,000
6 Beds ⋅ 3 Baths ⋅ 12769283 MLS ⋅ CONTINGENT Status
Excellent opportunity to own a spacious 2-unit brick multifamily property on Chicago's South Side. This property offers an attractive combination of immediate rental income and flexibility for an owner-occupant or investor. The first-floor residence features a spacious 3-bedroom, 2-bath duplex-down and is currently vacant and ready for occupancy. The second-floor unit offers 3 bedrooms and 1 bath and is occupied by a long-term tenant. With one unit already generating income and the duplex-down available for immediate occupancy or lease-up, the property provides multiple options for its next owner. Live in one unit while collecting rent from the other, or lease both units to maximize the property's income potential. The full lower level incorporated into the duplex-down provides additional living space and a highly desirable unit configuration. Conveniently located with access to public transportation, neighborhood amenities, and major thoroughfares. A great opportunity for buyers looking for a multifamily property with existing income and additional upside. Do not disturb tenants. Easy to show.

539 E 68Th Street, Chicago

6556 S Woodlawn Avenue, Chicago
$350,000
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

6651 S Drexel Avenue Unit #1E, Chicago
$275,000
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

6137 S Kimbark Avenue Unit #1, Chicago
$260,000
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

6328 S Drexel Avenue Unit #1, Chicago
$250,000
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

6359 S Rhodes Avenue, Chicago
$249,999
7 Beds ⋅ 4 Baths ⋅ 12652369 MLS ⋅ CONTINGENT Status
This spacious 2-flat in West Woodlawn is designed with open layouts, modern updates all in a prime location. The building does need some TLC but is a great starter investment property! Both units offer good natural light that fills both units, creating a warm and inviting atmosphere. Vinyl plank flooring throughout, adding a modern touch. Unit 1 features 3 bedrooms and 1 full bath. Unit 2 offers an expansive 4 bedrooms and 1.5 baths-ideal for owner-occupants or savvy investors alike. Each unit boasts an open-concept living, dining, and kitchen layout, perfect for entertaining or everyday living. The generously sized bedrooms provide flexibility for home offices, guest rooms, or personal retreats, all with ample storage. Both kitchens and full bathrooms are enhanced with granite finishes, bringing a refined, upscale feel to daily living. Enjoy close proximity to a beautiful community garden-perfect for relaxing or cultivating your green thumb. Located near public transit, shopping, and the historic Jackson Park, as well as the scenic Museum Campus, this home offers convenient access to everything Chicago has to offer. Whether you're looking to invest or occupy, this exceptional property delivers on space, style, and location. Don't miss the opportunity to make it yours! Property is being Sold As Is.

6359 S Rhodes Avenue, Chicago



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