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$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

$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

$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

$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

$962,000
9 Beds 6 Baths 12050216 MLS CLOSED Status
LAST ONE OF TWO REMAINING! Welcome 6340-42 S Drexel Discerning Designed Residences. Set in exceptionally well located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Magazine Caliber Simply Stunning, Expansive footprint, set on 25 x 132 deep lot with 3 car garage. New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Custom Back splash, Engineered floors, Fireplace, Curated Gallery of Cohesive Design Offering relief from ordinary, Sequestered Primary Suite with walk in closet, lifestyles primary bathroom offer Opulent over sized Shower w/ Frame less Glass, Double Vanity, Custom Mirrors and Designer Plumbing fixtures. Professional closet organizers throughout, 3 car Garage. Urban Intimacy w/ Hyper Convenience Experience excellence. Veteran developers of 25 + years, 1 year warranty included. Hyper Convenient, AAA Trophy Piece Perfect Turn key, Owner Occupied, Investor or 1031. This is part of a 2 building series. This is an exceptional property and location. Show and sell. Delivery end of April 2024 - Pictures of Similar Building. All showings will start at model location @ 4228 S Langley then Looping Back through Drexel.

6340 S Drexel Avenue, Chicago

$949,000
9 Beds 6 Baths 12022430 MLS CLOSED Status
Welcome 6340-42 S Drexel Discerning Designed Residences. Set in exceptionally well located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Magazine Caliber Simply Stunning, Expansive footprint, set on 25 x 132 deep lot with 3 car garage. New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Custom Back splash, Engineered floors, Fireplace, Curated Gallery of Cohesive Design Offering relief from ordinary, Sequestered Primary Suite with walk in closet, lifestyles primary bathroom offer Opulent over sized Shower w/ Frame less Glass, Double Vanity, Custom Mirrors and Designer Plumbing fixtures. Professional closet organizers throughout, 3 car Garage. Urban Intimacy w/ Hyper Convenience Experience excellence. Veteran developers of 25 + years, 1 year warranty included. Hyper Convenient, AAA Trophy Piece Perfect Turn key, Owner Occupied, Investor or 1031. This is part of a 2 building series. This is an exceptional property and location. Show and sell. Delivery end of April 2024 - Pictures of Similar Building. All showings will start at model location @ 4228 S Langley then Looping Back through Drexel.

6342 S Drexel Avenue, Chicago

$385,900
8 Beds 3 Baths 11908620 MLS CLOSED Status
Introducing this exceptional 2 flat Graystone with Garden unit, composed of a 4 bed/1 bath on 2nd floor, 3 bed/1 bath on main floor and a 1 bed/1 bath garden. Each unit features a private entrance to the residence and a beautiful fully fenced in backyard perfect for relaxing & enjoying the outdoors or ample entertaining space. With updated and extremely spacious units, every level can enjoy hardwood floors, high ceilings, abundance of natural light, and potential to have a home office, fitness room, guest room, art studio, game room, craft room...the possibilities are endless! This property presents an incredible investment opportunity (projected rent of $1,000+ for the 1st and 2nd floor units and $875+ for the Garden unit) while tenants can enjoy everything Woodlawn and Hyde Park have to offer. Or seamlessly blend owner occupant convenience, income generating potential, and equity building for the future! Perfectly located along the developing 63rd Street corridor, walking distance to The University of Chicago and The Obama Presidential Library, nearby gorgeous Lake Michigan & beaches including Jackson Park Harbor, Downtown Chicago, CTA and Metra stations, expressways, shopping, restaurants, entertainment, and museums! Detached 2 car garage and permitted street parking are available.

6147 S Drexel Avenue, Chicago

$867,500
11 Beds 7 Baths 11882076 MLS CLOSED Status
Located in prime Woodlawn location, rarely available Legal 4 Flat was renovated in 2016 by a reputable rehabber. Purchase as an investment or to live in. The 3 above ground oversized units each feature 3 bed/2 bath configurations & 1 lower level features an oversized 2 bed/bath configuration. Property renovations were completed in 2016 and feature new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAV infrastructure and drywall. The floorplan layout was reworked to have open concept Kitchens in the front area of the units with 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 rear staircase & maintenance fee vinyl siding wrapped porch. 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. This property is located walking distance to University of Chicago Hospital & University of Chicago, University of Chicago Law School, University of Chicago Charter School, Toyota Technological Institute of Chicago, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Parks, multiple grocery & eating locations.

6638 S Woodlawn Avenue, Chicago

$131,900
7 Beds 2 Baths 11858076 MLS CLOSED Status
East Woodlawn is one of the fastest appreciating neighborhoods in the entire nation! This 2-unit is available for an absolute steal! There is so much upside for an investor looking to make a large profit or a homeowner looking to plant their feet in an area that will continue to aggressively appreciate for years to come! This solid 2-flat includes two residential units, a full walkout basement and a private enclosed back yard! Unit #1 has 3-bedrooms, and 1 full bathroom and Unit #2 has 4-bedrooms and 1 full bathroom. Updated 4-bedroom apartments can rent for $2,000+ per month and updated 3-bedroom apartments can rent for $1,700+ per month in this neighborhood! The strategy that will yield the maximum equity or profit margin will be achieved by converting this 2-unit into a legal 3-unit by digging down the large unfinished basement 3-5 inches and cooperating with the city of Chicago to improve the zoning from a 2 to 3-unit residential property. This strategy was effective at 6235 S. Eberhart which was sold in December of 2022 for $585,000. The after-repair-value for non-new construction 3-units or 2-units with legal garden apartments is $570,000, based on comparable sales within the past 6 months! With the right construction strategy there is an approximate $170,000 - $200,000 profit margin available! In 2020 the city of Chicago passed the Additional Dwelling Unit Ordinance which provides owners of multi-units with up to $35,000 in funds in the form of a forgivable loan to create additional living space in the basement or attic! For more ambitious investors, there is also potential to dormer the attic to create additional living space or build a coach house in the back yard which the ADU ordinance also supports in the effort to achieve an even higher valuation ($600,000+). For the traditional retail buyer that wants to convert this multi-unit into a single-family home, the approximate after-repair-value for this strategy is $700,000+ based on comparable SFH sales! The retail buyer has the equity available to significantly invest in the conversion project and enjoy a great home with $100,000+ in equity upon completion or an investor can enjoy an approximate $75,000 - $150,000 profit with the right construction strategy implemented. There are a plethora of new construction projects on Maryland Ave with many multi-units that have recently sold for a little under 1-million dollars each! A+ location! Walking distance from Washington Park, Minutes from the Lakefront, proximity to The University of Chicago, the Obama Presidential Library, Dan Ryan, Red Line and Jackson Park! Priced to sell so please act swiftly! ***This property is already hard money approved with our lender that requires 7% down and will finance 100% of the renovation***

6605 S Maryland Avenue, Chicago



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