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$849,000
7 Beds ⋅ 6 Baths ⋅ 12755888 MLS ⋅ NEW Status
Legal 3 fla.Total gut Rehab to the studs with new constructions permits, all mechanicals are brand new. New water lines B Box and meters, windows, insulations, GE appliances, sump pump & ejector pump. Everything you see is NEW. 3300 sqft living space.LUXURY-DESIGNED LAYOUT WITH THREE MASTER SUITES ON THE 2ND FLOOR DUPLEXED TO THE MAIN LEVEL WITH COMPLETE OPEN CONCEPT FLOOR PLAN!!! GREAT FOR OWNER WITH OPTION TO RENT OR AIRBNB LOWER LEVEL. OVER 2,500SF OF LIVING SPACE WITH 4 BEDROOMS AND 3.5 BATHS DUPLEX WITH SEPARATE LARGE LOWER LEVEL APARTMENT WITH 2 BEDROOMS AND 1 FULL BATH EQUIPPED FOR AIRBNB OR RENTAL THAT WILL HELP WITH THE MORTGAGE! ALL NEW ROUGH FRAMING, SUPPORT BEAMS AND STAIRCASE IS COMPLETED. ALL NEW DUCTWORK COMPLETED. ALL NEW ROUGH ELECTRICAL COMPLETED WITH DUAL 200AMP SERVICE AND PANELS INSTALLED. ALL NEW CEMENT BASEMENT FLOOR POURED WITH OVER 7FT CEILING HEIGHT. NEW ROOF HAS BEEN INSTALLED. GARAGE ROOF, OVERHEAD DOOR AND TUCKPOINTING COMPLETED. EVERYTHING HAS BEEN DONE UP TO CITY CODE. THE VALUE IS ENDLESS AS EAST WOODLAWN IS ONE OF THE MOST PRIME REAL ESTATE IN CHICAGO WITH THE PROXIMITY TO ALL AMENITIES: NEW OBAMA LIBRARY, UNIVERSITY OF CHICAGO, MUSUEM OF SCIENCE AND INDUSTRY, LAKE SHORE BEACHES, JACKSON PARK GOLF COURSE, CTA GREEN LINE, HYDE PARK AND SO MUCH MORE.

6627 S Maryland Avenue, Chicago
$419,900
6 Beds ⋅ 2 Baths ⋅ 12750297 MLS ⋅ ACTIVE Status
Smart buy, attainably priced! Cool & dramatic, First floor three bedroom, one bath apartment with hardwood floors throughout, a modern kitchen, beautiful bath and hookup for laundry in unit. It is already setup for a duplex. Stable income from a long term tenant in the first floor. It's perfect for an owner occupant buyer. Second floor is a vacant three bedroom, one bath apartment. Separate gas and heat with forced air in each unit. Central air in the first floor unit. A fenced yard, enclosed rear porch, brick two car garage and tall unfinished basement round out this perfect investment.

6611 S Maryland Avenue, Chicago
$1,198,988
8 Beds ⋅ 4 Baths ⋅ 12749117 MLS ⋅ ACTIVE Status
This beautiful, rare, and meticulously maintained vintage greystone is a fantastic, solid investment opportunity and an investor's dream! An ideal turnkey operation, it features two 3BR rentals plus a fully-furnished, top-rated, 2BR Airbnb, allowing several options for the buyer: enjoy income from the popular Airbnb and the fully-rented units; reside in a unit (or two) and reduce your mortgage payments through value-added rentals; or transform the entire building into your single family dream home! This spacious and sun-drenched beauty retains its vintage charm with 10' ceilings, hardwood floors, huge double hung windows, built-ins, and some original moldings. The main level 3BR, 1 bath features a wood burning fireplace with built-in mantel and bookshelves, full kitchen, in-unit W/D hookup, and window blinds. The second level 3BR, 1.5 bath was fully rehabbed in late 2019 with all new kitchen and baths, refinished floors, new in-unit W/D, built-out closets, new light fixtures, new wood blinds, new HVAC. The open plan, inviting 2BR, 1 bath, garden-level Airbnb (since July, 2018) with private entrance is fully furnished and has all the extra amenities guests expect, making it a top-rated (4.9/5) destination with Superhost designation. First and second level units open onto private decks with newly-rebuilt and sealed back stairs, including easy access to the roof via pull-down stairs on the second level deck, plus 15' x 8' secured storage area under the stairs. The Airbnb opens out the private back door to a storage area featuring full-size washer and dryer, then into the huge, secure and private backyard. Enjoy a green, urban oasis with mature landscaping, two large patios, and path leading to the masonry 2.5 car garage with extra storage space above (or retain the current garage renter for the extra income). The new roof (7/2019) is fitted with 9.0 kW Roof Mount Solar PV Array solar panels, offsetting utility costs. The location is the icing on the cake! Just steps from the University of Chicago law school and the Renee Grossman Residential Commons, and a stone's throw from the Green Line and Jewel-Osco, this property offers community, connectivity, and convenience. Only 3/4 mile from Jackson Park, the transformative Obama Presidential Center, and the vibrant lakefront, this location offers investment stability and exciting growth potential. Schedule your private showing now!

6109 S Greenwood Avenue, Chicago
$930,000
9 Beds ⋅ 6 Baths ⋅ 12747729 MLS ⋅ ACTIVE Status
Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6508 S Ingleside Avenue, Chicago
$1,200,000
11 Beds ⋅ 7 Baths ⋅ 12726785 MLS ⋅ ACTIVE Status
Turnkey cash flowing Rarely Available 4 Flat Building Located in prime East Woodlawn desirable community just steps from Obama Presidential Library, University of Chicago Campuses including Medical School, Law School, University of Chicago Hospital, Charter School, Museum of Science and Industry, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Grocery Stores, Multiple Eatery's including the South Shore Cultural Center. A true gem for investors and or owner occupant alike. The 3 above ground oversized units each feature 3 bed/2 Full baths configurations & 1 lower level features an oversized 2 bed 2bath configuration. Property features new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAC infrastructure and drywall. Open floorplan concept layout within each unit with the top floor unit giving a penthouse vibe. Kitchens positioned in the front of each unit 42' Maple shaker style cabinets, granite & laminate countertops, stainless steel appliances & recessed lighting. Meticulously preserved & refinished woodwork architecture & hardwood flooring in the property was blended with new upgrades to keep the charm & character of this historic property. Exterior upgrades include new vinyl windows, concrete parking pad with rear wrought iron gated fence, front wrought iron gated fence with intercom system, treated wood The lower level was renovated by excavating the floor & creating higher head space & upgrading to a new sump pump rainwater drainage system & concrete slab. The property shares a common area laundry with washer/dryer owned by Landlord. Each unit is individually metered & has separate HVAC & Hot Water Heater tanks.

6638 S Woodlawn Avenue, Chicago
$499,900
7 Beds ⋅ 3 Baths ⋅ 12731749 MLS ⋅ CONTINGENT 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
$265,000
6 Beds ⋅ 2 Baths ⋅ 12725293 MLS ⋅ CONTINGENT Status
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
$885,000
9 Beds ⋅ 7 Baths ⋅ 12723988 MLS ⋅ ACTIVE Status
Prime Woodlawn Investment Opportunity! Invest in the growth of Chicago's historic Woodlawn neighborhood with this meticulously maintained, condo-quality 3-unit building. Perfectly positioned just blocks from the Obama Presidential Center, this turn-key property is an exceptional opportunity to owner occupy or invest, offering high-end rental income and significant long-term appreciation potential. Property Highlights: Optimal Unit Mix: Three highly desirable, spacious units, each featuring a 3-bedroom, 2-bathroom layout. Premium Floor Plans: The first-floor unit is a sprawling duplex-down, providing massive living space that lives like a single-family home. Condo-Quality Finishes: Beautiful interior details, including exposed brick walls, add character and charm to attract premium tenants while minimizing upkeep. Turn-Key Mechanicals: All major systems-including plumbing, electrical, HVAC have been modernized, and recent tuckpointing, ensuring low maintenance and peace of mind for the next owner. Unmatched Location & Upside: Situated at the epicenter of a multi-billion dollar neighborhood transformation, this building sits directly across the street from a brand-new 8-unit development, signaling strong and continuous local investment. Residents enjoy an incredible quality of life with seamless access to DuSable Lake Shore Drive, the lakefront recreation trail, the renowned Jackson Park Golf Course, the beach, and the harbor. Plus, the vibrant shopping, dining, and entertainment of nearby Hyde Park are just minutes away. Don't miss this rare chance to own a strategic, cash-flowing piece of Woodlawn's exciting future!

1527 E 66Th Place, Chicago
$980,000
9 Beds ⋅ 6 Baths ⋅ 12626647 MLS ⋅ ACTIVE Status
Welcome to this exceptional 3-flat multi-unit property with a 3-car detached garage, located in the desirable Woodlawn neighborhood, just minutes from the University of Chicago and the Obama Presidential Center. Solid brick building with high-end finishes throughout, ideal for strong rental income and long-term appreciation. Each unit features 42" cabinetry, quartz countertops, custom backsplash, recessed lighting, and a fireplace. Spacious layouts include primary suites with walk-in closets and spa-style baths with frameless glass showers and double vanities. In-unit laundry in all units. Top-floor unit offers vaulted ceilings and additional storage with a large pantry. Professionally organized closets maximize space and tenant appeal. Perfect for investors or owner-occupants-high-demand location with excellent income potential. Don't miss this opportunity to add a quality asset to your portfolio.

6621 S Drexel Avenue, Chicago
$930,000
9 Beds ⋅ 6 Baths ⋅ 12712761 MLS ⋅ ACTIVE Status
Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Photos are of the model unit at 6508 S. Ingleside Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6506 S Ingleside Avenue, Chicago
$680,000
9 Beds ⋅ 6 Baths ⋅ 12687847 MLS ⋅ CLOSED Status
Rarely does an opportunity like this come along at this price point. Priced at $665,000, this 3-unit sits just steps from the future Obama Presidential Center and near the rapidly transforming 63rd Street corridor. The $800M Woodlawn Central development, an 8-acre mixed-use project, is expected to bring a hotel, theater, technology center, retail, restaurants, residential towers, and a vertical farm to the neighborhood. Each unit features a generously sized primary bedroom with en-suite bath, a private balcony, and a cozy fireplace in the living room. With two units vacant, you have immediate flexibility to set market rents or design your ideal living setup. This property offers a clear value-add opportunity for buyers looking to build equity in a rapidly appreciating market. Live in one unit while generating rental income from the others, or hold as a long-term investment in one of Chicago's most closely watched growth corridors. Each unit has its own PIN, offering a potential path to future condo conversion. Gated rear parking for three vehicles and tenant-paid utilities add to the appeal. Conveniently located near Mt. Carmel High School and the Metra line. Sold as-is.

6500 S Dorchester Avenue, Chicago
$730,000
8 Beds ⋅ 6 Baths ⋅ 12676628 MLS ⋅ CLOSED Status
Exceptional investment opportunity in the heart of Woodlawn! This fully occupied, income-producing 3-unit building offers a rare combination of strong cash flow, modern amenities, and significant future upside. Currently generating $5,931 per month in rental income with below-market rents (3rd floor tenant vacating in July), the property presents an excellent opportunity for increased revenue through future rent adjustments. Renovated in 2018, the building features an attractive unit mix of two spacious 2-bedroom, 2-bathroom units (2nd floor includes bonus room) and one oversized 3-bedroom, 2-bathroom unit. Each apartment is equipped with central air conditioning, in-unit washer and dryer, and separately metered utilities; tenants pay all utilities except water which minimizes operating expenses for ownership. Additional features include a detached 2-car garage, security camera system, and a private backyard entertainment area ideal for gatherings and outdoor enjoyment. The full unfinished basement offers exceptional value-add potential and may be suitable for a duplex-down conversion or additional dwelling unit (ADU), subject to zoning and city approval. Ideally situated within walking distance of the transformative Obama Presidential Center development, the property is positioned to benefit from continued neighborhood investment, rising property values, and growing rental demand. Convenient access to public transportation, parks, shopping, restaurants, and the University of Chicago further enhances its appeal. Whether you're seeking a turnkey investment with immediate income or a value-add asset with future expansion potential, this property delivers both stability and opportunity in one of Chicago's most rapidly evolving neighborhoods. ***Property is Agent Owned

6504 S Maryland Avenue, Chicago
$659,000
5 Beds ⋅ 4 Baths ⋅ 12673209 MLS ⋅ ACTIVE Status
Attainable, comfortable, healthy, and cool! Award-winning, Greenline Homes Two Flat in Southeast Woodlawn! Greenline Homes has made Woodlawn the destination for high-performance homes in Chicago. We're thrilled to offer a resale of a groundbreaking two-unit building that showcases cutting-edge construction and high-performance materials and design throughout. Unit 1 is a bright, modern garden unit with two bedrooms. Unit 2 is a spacious and modern 3-bedroom/2.5-bath duplex. Sustainable without compromise. Both units boast beautiful and durable quartz countertops, custom cabinetry, and energy-efficient appliances. Own your energy. The building includes a solar photovoltaic system on the roof, which produces much of the building's energy needs and reduces the building's carbon footprint with clean, free renewable energy. Efficiency by design. Engineer-designed and sized zoned Mitsubishi heating and cooling provide extreme comfort and efficiency to both units. Comfort is built right in. Incredible engineered insulation, triple-pane glass, and an air-sealed building envelope make this building quieter and more comfortable than any standard building on the market. Healthy air is standard. Energy return ventilators and Panasonic whisper-quiet exhaust fans ensure consistent, high-quality indoor air while maintaining peak efficiency. The low-maintenance lifestyle. Well-designed exteriors with high-quality materials like James Hardie siding and commercial-grade roofing reduce maintenance, allowing your home to work harder for you, instead of you working hard for it. Greenline Homes is making sustainable, green homes more accessible, and now you can own a sustainable green home with income! Plus, a 2-car garage is included. The home is currently leased, and access for showing is limited. Located steps to Metra Electric Trains, Jackson Park, and the Obama Presidential Center.

1221 E Marquette Road, Chicago
$315,000
5 Beds ⋅ 2 Baths ⋅ 12675346 MLS ⋅ CLOSED Status
Welcome to 6619 South Maryland Avenue, a recently rehabbed gem in the East Woodlawn neighborhood near the University of Chicago! This versatile property features two distinct units, making it perfect for a variety of living arrangements or investment opportunities. Step into Unit 1, where you'll find a cozy layout with 2 bedrooms and 1 bathroom, offering a comfortable space to unwind. Unit 2 boasts 3 bedrooms and 1 bathroom, providing ample room for all your needs. Both units have been thoughtfully updated to blend modern charm with classic touches. Below, a full unfinished basement awaits your creativity, providing endless potential for storage or future expansion. Additionally, the unfinished attic offers even more space to customize to your liking. Whether you're looking to occupy one unit and rent out the other, or seeking a spacious home with rental potential, this property is a fantastic opportunity.

6619 S Maryland Avenue, Chicago
$350,000
4 Beds ⋅ 2 Baths ⋅ 12674525 MLS ⋅ RE-ACTIVATED 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
$410,000
6 Beds ⋅ 2 Baths ⋅ 12663098 MLS ⋅ CLOSED Status
Stunning Greystone two-flat in SIZZLING hot Woodlawn! This is an exceptional opportunity in one of Chicago's fastest-growing neighborhoods. This classic multi-unit property offers two spacious 3-bedroom residences with soaring ceilings, original woodwork, and beautiful vintage details, including decorative fireplaces and charming built-ins that showcase timeless character. The partially finished basement already includes a bathroom and offers incredible potential-create a garden unit, duplex down, or reimagine the entire property as a grand single-family home. The options here are truly endless, so bring your vision, your creativity, and your contractor. Ideal for a 203K loan and surrounded by exciting new development. The location is unbeatable-minutes from the Obama Presidential Library, Griffin Museum of Science and Industry, University of Chicago, beaches, golf courses, parks, top-rated schools, and a vibrant dining scene. Schedule your showing today and explore the possibilities. Property is being sold **AS-IS**.

6418 S Drexel Avenue, Chicago
$930,000
9 Beds ⋅ 6 Baths ⋅ 12649597 MLS ⋅ CONTINGENT Status
Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6500 S Ingleside Avenue, Chicago
$520,000
5 Beds ⋅ 3 Baths ⋅ 12586088 MLS ⋅ CLOSED Status
Multiple Offers Received. Highest & Best due by Tues 4/7 at 6 pm. Rare opportunity to own a beautifully maintained, turn-key legal two-unit in the heart of East Woodlawn, one of Chicago's fastest-growing neighborhoods. Ideally located just blocks from the transformative future Obama Presidential Library, this property offers both long-term stability and exciting growth potential. The first-floor unit features 2 bedrooms and 1 full bath, offering flexibility for owner occupant, tenants or multigenerational living. The second unit is a spacious duplex-up that lives like a single-family home, offering 3 bedrooms and 2 full baths. A newer addition provides extra living space that can be used as a family room or home office, with double doors leading to a private deck, perfect for relaxing or entertaining. In 2026, the property received several key updates including two new furnaces with a 10-year warranty, a new roof with warranty, fresh interior paint throughout both units, updated lighting fixtures, and new stainless steel appliances with granite countertops in the upper duplex kitchen, creating a clean, refreshed, and move-in-ready environment. Hot water heaters were replaced in 2019. Both units offer in-unit laundry, separate utilities, and gas forced-air heat, providing convenience for residents and efficiency for ownership. A private fenced backyard and two-car garage complete the property. Enjoy exceptional access to neighborhood amenities, including the vibrant redevelopment corridor near the historic Stony Island Hotel at 64th and Stony Island. Commuting is easy with the Metra Electric line at 63rd Street just one block away. The location is also minutes from the University of Chicago, the Museum of Science and Industry, Hyde Park, lakefront beaches, boating and golf at Jackson Park, and convenient access to Lake Shore Drive. Lovingly owned by the same owner since construction, this solid property reflects pride of ownership and long-term care. Property is being sold AS-IS. Don't miss the opportunity to own in one of Chicago's most dynamic and rapidly developing neighborhoods.

6419 S Kenwood Avenue, Chicago
$255,000
5 Beds ⋅ 3 Baths ⋅ 12580265 MLS ⋅ CLOSED Status
Experience the momentum of Woodlawn with this polished twostory 2flat, perfectly positioned near the anticipated Obama Presidential Center. Surrounded by high-end new construction and active redevelopment, this property offers the rare blend of immediate cashflow potential and long-term appreciation. Thoughtfully updated with a new roof, new tuckpointing, select new windows, and a striking wrought iron fence, the building delivers strong curb appeal and low future maintenance. Both units are exceptionally spacious with fully functioning utilities, and the full basement adds valuable expansion or storage options. A 2car detached garage and generous backyard complete the package. A standout opportunity for investors seeking a solid, well located asset in one of Chicago's fastest rising neighborhoods. Located just moments from the University of Chicago, this property sits in one of the area's most dynamic and academically driven corridors. Classic, Chicago brick 2-flat + basement in BOOMING Woodlawn. Occupants to take advantage of rapid appreciation in the area. Imagine the possibilities of a full, unfinished basement - just waiting for your personal touches. Although the property has been well-cared for over many years, it is being conveyed AS-IS.

6513 S Maryland Avenue, Chicago
$529,000
8 Beds ⋅ 3 Baths ⋅ 12575940 MLS ⋅ CLOSED Status
Set in the heart of Woodlawn, this classic Chicago three-flat blends solid construction with modern upgrades and an unbeatable location. The building features two generously sized three-bedroom, one-bath units on the first and second floors, along with a two-bedroom, one-bath garden unit. The first-floor unit is currently vacant, offering immediate options for an owner-occupant or value-add investor, while the garden and second-floor units are occupied. All units showcase updated kitchens with granite countertops, stainless steel appliances, and the convenience of in-unit laundry. Central air and heat throughout the building add comfort and efficiency, making these residences attractive, functional, and easy to maintain. Woodlawn continues to see meaningful momentum, and this property sits just blocks from major neighborhood anchors including The University of Chicago, Jewel grocery store, and the green expanses of Jackson Park, soon to be home to the Obama Presidential Center. Commuters will appreciate quick access to Lake Shore Drive, as well as nearby CTA Green Line and Metra stations connecting to downtown and beyond. Whether you're looking to live in one unit while generating income or add a strong asset to your portfolio, this property offers a compelling combination of location, updates, and long-term upside in one of Chicago's most closely watched neighborhoods.

6522 S Ellis Avenue, Chicago
$240,000
5 Beds ⋅ 2 Baths ⋅ 12541042 MLS ⋅ CLOSED Status
Highest and Best DUE Monday, January 19th, 2025 at Noon. Exciting Investment Opportunity in Woodlawn | 2-Flat Brick Building Located on the east side of Cottage Grove in the heart of Woodlawn, this classic 2-flat brick building presents an exceptional opportunity for investors, developers, or owner-occupants ready to bring a vision to life. The property is in need of a full gut renovation, making it a true blank canvas with tremendous upside in a rapidly improving area. The second-floor unit offers a generous layout featuring four bedrooms, a spacious living room, a separate dining room, a full-size bathroom, and a kitchen with a pantry. Original hardwood floors are in place and ready for restoration, and select electrical upgrades have already been completed. A skylight above the second-floor staircase floods the interior with natural light, adding character and architectural charm. The first-floor unit includes two bedrooms, one full bath, and a large kitchen, offering flexible living arrangements or strong rental potential. The full-height basement features approximately 7-foot ceilings with ingress and egress, making it ideal for an impressive in-law suite, duplex-down, or additional living space. The building will require a new roof and rear porch, allowing the next owner to design and build to modern standards With its solid brick construction, generous room sizes, and endless configuration possibilities, this property is perfectly positioned for a value-add renovation. Whether you envision a duplex-down, an owner's unit with rental income, or a fully rehabbed income-producing asset, the potential here is truly limitless.

6351 S Drexel Avenue, Chicago
$185,000
EB460760 MLS ⋅ CLOSED Status

606 N Main Street, Woodlawn
$755,000
7 Beds ⋅ 7 Baths ⋅ 12496714 MLS ⋅ CLOSED Status
Join Woodlawn before the grand opening of the Obama Presidential Center, right around the corner. Newer construction 3-unit in pristine condition. All units have updated open concept kitchens and living spaces, hardwood floors throughout, ceramic tile baths, primary bedrooms that can accommodate a king-sized bed, walk-in closets and en-suites, large balconies, and a designated off-street parking space. The first floor is a 3-bed/2.1-bath duplex; the second and third floors are 2-bedroom/2-bathroom units. Bonus: Units 1 and 2 are on a MTM lease.

6433 S Drexel Avenue, Chicago
$730,000
9 Beds ⋅ 7 Baths ⋅ 12498493 MLS ⋅ CLOSED Status
A ROOF OVER YOUR HEAD AND MONEY IN YOUR POCKETS..........RECENTLY RENOVATED 3 UNIT IN EAST WOODLAWN. 1ST FLOOR DUPLEX FEATURES 3 BED/3 BATH, PERFECT FOR OWNER'S UNIT. 2ND AND 3RD FLOORS HAVE 3 BED/2 BATH. HARDWOOD FLOORS THROUGHOUT. LAUNDRY IN EACH UNIT. INDIVIDUAL MECHANICALS. SECURED GATED PARKING. PERFECT INVESTMENT: RENT NOW AND SELL AS CONDOS LATER, OR LIVE-IN AND LET TENANTS PAY THE MORTGAGE. STEPS TO HYDE PARK, MUSEUM OF SCIENCE AND INDUSTRY AND OBAMA LIBRARY.

6406 S Ingleside Avenue, Chicago
$462,000
9 Beds ⋅ 3 Baths ⋅ 12497078 MLS ⋅ CLOSED Status
Fully Rehabbed 2-Unit in Prime East Woodlawn! Welcome to this spacious two-unit building in East Woodlawn, near the University of Chicago and the Obama Presidential Center. Tons of new construction on Maryland Ave. The property has 9 bedrooms and 3 bathrooms, offering great living space and rental potential. Each unit has separate utilities. While there's no central air, both units have HVAC furnaces for heating. The first-floor unit is duplexed with the finished basement, providing a large living area with laundry hookups. The second unit is upstairs, offering privacy. Surrounded by new construction, this is a great opportunity for investors or owner-occupants. Schedule a showing today!

6605 S Maryland Avenue, Chicago
$680,000
8 Beds ⋅ 3 Baths ⋅ 12493562 MLS ⋅ CLOSED Status
Brick 3 flat on over-sized 171' lot in Woodlawn/Hyde Park. One 2 bedroom 1 bathroom unit and two 3 bedroom 1 bathroom units. All oversized units with newer rehabs. Each unit has separate living and dining rooms with balconies, individual furnaces, fireplaces and hardwood floors. Units also include side by side washer/dryer and exterior parking. Unit 2 is vacant allowing for owner occupant buyer. New roof in 2022.

6239 S Ellis Avenue, Chicago
$727,500
8 Beds ⋅ 3 Baths ⋅ 12464172 MLS ⋅ CLOSED Status
$15,000 seller credit and a low interest rate! A Greystone rebuilt with permits in vibrant Woodlawn. This 2023 gut-rehab blends historic elegance with modern upgrades. Potential rental income of up to $6,000/month. With the seller's credits you can reduce your mortgage payment to around $4,000, offering up to a potential $2,000 in monthly profit. The property features tall ceilings, hardwood floors, and condo-quality finishes like quartz countertops, shaker cabinets, and stainless steel appliances. Each unit has in-unit laundry and oversized decks. The first-floor includes a 2 bed/1 bath setup and is duplexed down with $60K in structural basement enhancements, providing future living space potential. Updates include new electrical, plumbing, main water line, main sewer line, and a 2-car garage. Located steps from the 63rd Green Line, near the University of Chicago, and close to the Obama Presidential Center, Hyde Park, and the lakefront. A unique opportunity to own a turnkey multi-unit in one of Chicago's most dynamic neighborhoods.

6347 S Drexel Avenue, Chicago
$360,000
5 Beds ⋅ 3 Baths ⋅ 12461858 MLS ⋅ CLOSED Status

6547 S Drexel Avenue, Chicago
$550,000
6 Beds ⋅ 2 Baths ⋅ 12391850 MLS ⋅ CLOSED Status

6630 S Drexel Avenue, Chicago
$170,000
5 Beds ⋅ 5 Baths ⋅ 12349312 MLS ⋅ CLOSED Status
Located in the hotter than hot East Woodlawn community this building provides a unique opportunity to a buyer who has vision for finishing a project! The home is a brick two unit which was in the midst of renovations, the home can be kept as a two unit or very easily turned into a single family residence! The main level unit has been duplexed to the second floor to create a single family like feel with the basement being the second unit. Keep this intended layout and live in one unit while renting the other or convert to a single family and watch your equity soar! The main unit in the home offers roughed out set up for 3 bedrooms/3 1/2 baths, all three bedrooms offer en-suite bathrooms! All of the big ticket items have been started, interior is framed out, rough plumbing is completed, electric is in place, rough plumbing is laid out. Just need to come in and finish the project while reaping huge rewards! The location should not be overlooked, East Woodlawn is a hot market, close to Lakefront, Obama Library, Dan Ryan and much more! Get inside today to really take advantage of this unique oppertunity!

Chicago



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