West Woodlawn Real Estate

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Newest Listings in West Woodlawn

$850,000

12634033 MLS ⋅ NEW Status

This fully renovated 6-unit building in Woodlawn has been strategically repositioned to maximize income and provide long-term stability for its next owner. With strong in-place cash flow and major updates already completed, this is a true turnkey investment. Each unit is exceptionally spacious, offering 3 generously sized bedrooms along with a formal living room, separate dining room, and full kitchen-an increasingly rare layout that supports premium rents. Four of the six units feature front balconies, and all units include rear decks, adding valuable outdoor space for tenants. The property is designed for efficiency, with individual heating systems that shift a significant portion of expenses to tenants, helping to reduce owner overhead. Additional features include a full-building camera system for security and on-site laundry in the basement for tenant convenience. Located in rapidly growing West Woodlawn-one of the South Side's most promising investment corridors-the building is just minutes from the lakefront and a short bike ride to University of Chicago. Hyde Park is also just minutes away, offering tenants convenient access to dining, shopping, entertainment, and everyday essentials. Downtown Chicago is accessible in under 15 minutes by car, making this an ideal location for renters seeking space, value, and connectivity. With large 3-bedroom units driving strong rental demand, this property offers an excellent opportunity to step into immediate cash flow, continued appreciation, and long-term upside-all without the burden of renovation.

6140 S Eberhart Avenue, Chicago

$500,000

5 Beds ⋅ 4 Baths ⋅ 12703114 MLS ⋅ NEW 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, 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. OpenHouses August 8th from 10am-1pm & August 9th from 12pm-3pm.

6552 S Evans Avenue, Chicago

$410,000

3 Beds ⋅ 4 Baths ⋅ 12710425 MLS ⋅ ACTIVE Status

Welcome to this newly renovated two-story home in the desirable Woodlawn community. Thoughtfully updated throughout, this residence offers 4 bedrooms and 2.1 baths with a bright, open-concept layout and stylish designer finishes. The main living area flows seamlessly into a chef-inspired kitchen featuring solid wood cabinetry, quartz countertops and backsplash, stainless steel appliances, a hidden vent, a large center island, and a dedicated eating area. A versatile den provides the perfect space for a home office, playroom, or additional living area. Upstairs, the spacious primary suite includes a spa-like bath, walk-in closet, and generous room dimensions. Two additional bedrooms and a full bath complete the second level. The fully finished, light-filled basement offers an additional bedroom, full bath, family room, laundry area, and storage closet. Additional updates include a new oversized two-car garage with 220v line to charge your EV, roof, mechanicals, windows, and more. With too many improvements to list, this move-in-ready home is a must-see. Come make it yours!

6627 S Saint Lawrence Avenue, Chicago

$450,000

5 Beds ⋅ 3 Baths ⋅ 12708799 MLS ⋅ ACTIVE Status

Exceptional legal 3-unit greystone in the heart of rapidly growing Woodlawn! This beautifully updated investment property features two spacious 2-bedroom units, each with a bonus room ideal for a home office, den, or flex space, plus a large 1-bedroom garden unit. Additional highlights include on-site coin laundry, a 2-car garage, and a finished enclosed porch. Ideally located just minutes from the Obama Presidential Center, the University of Chicago and public transportation. Perfect for an owner-occupant looking to house hack or an investor seeking a strong addition to their portfolio. Don't miss this outstanding cash flowing opportunity in one of Chicago's most dynamic neighborhoods!

6524 S Eberhart Avenue, Chicago

$575,000

4 Beds ⋅ 4 Baths ⋅ 12710393 MLS ⋅ ACTIVE Status

Welcome to WOODLAWN "SAME AS" NEW CONSTRUCTION 3-STORY, 5 BEDROOM 3.5 BATH SINGLE FAMILY HOME. WITH OVER 2,000 OF ADDITIONAL NEWLY BUILT SQUARE FOOTAGE, FOR A TOTAL OF 3,808 SQFT - THIS IS A BRAND NEW HOME! This exquisite modern-style home has been completed with over 350k in expansion, redesign, renovation and is ready for the discerning Buyer seeking luxury, comfort and convenience. This is a well curated floor plan with an expansive main level, featuring new hardwood flooring throughout, 10ft ceilings, plenty of natural sunlight, separate living/dining room combo, Butler's pantry with wine cooler, walk-in kitchen pantry, half bath and storage room! However, that's not it! Keep walking and you'll notice a beautiful chef kitchen with custom-built soft close cabinetry, over-sized 11ft waterfall island with breakfast bar overhangs, Calacatta white quartz countertops with ceramic tile backsplash, professional series stainless steel appliances with double oven, eat-in breakfast nook large enough for 6-chair table, and a spacious family room! The entire second floor is a family oasis that includes primary bedroom with walk-in closet, spa-like master suite with separate soaker tub, massive shower and double vanity sinks. 3 additional bedrooms and another full bath with double vanity sinks for all the kids, laundry has been added to the 2nd floor for your convenience, dual controlled heating and cooling, and hardwood floors throughout. Can't wait to see your face drop with all the space in the basement! Drain-tile zero flooding system, vinyl flooring, an additional bedroom, full bath with more storage and utility room. The wrought iron fence and wood fenced yard provides privacy and professional landscaping brings urban oasis to life. New cement patio and sidewalk and new 2.5 car garage. This home is surrounded by new construction, The Obama Library, University of Chicago, Jackson Park Golf Course, Children's Hospital, Museum of Science & Industry and Lake Shore Beaches ALL are within a few miles away! Come take a tour and fall in love!!

638 E 65Th Street, Chicago

$610,000

9 Beds ⋅ 3 Baths ⋅ 12707833 MLS ⋅ ACTIVE Status

A rare opportunity to own a beautifully updated Greystone. 3 legal units (basement ADU) in one of Chicago's most exciting growth corridors. This stately building commands immediate attention. With freshly tuckpointed stonework, stonewashed exterior, and updated landscaping, it delivers curb appeal that stands apart on the block. Brand new kitchens, bathrooms, and flooring throughout, complemented by fresh paint and newer windows that flood each space with natural light. The fully permitted garden-level ADU adds a legal 3rd income stream and significantly boosts overall yield. Live in one, rent two, or maximize all three. Woodlawn is in the midst of a remarkable transformation. With a wave of new construction in the pipeline and steadily climbing rental rates, savvy investors are moving in early. This property puts you ahead of the curve. Secured in a neighborhood whose trajectory is unmistakably upward, with the bones, the beauty, and the bottom line to match.

6506 S Saint Lawrence Avenue, Chicago

$1,050,000

9 Beds ⋅ 6 Baths ⋅ 12706879 MLS ⋅ ACTIVE Status

Modern Luxury Meets Timeless Craftsmanship in the Heart of Woodlawn Welcome to 6150 S. Saint Lawrence Avenue, an exceptional new construction luxury 3-unit building where sophisticated design, expansive living spaces, and premium finishes come together to create one of Woodlawn's most compelling residential opportunities. Each residence offers an impressive 1,700 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2 designer bathrooms, and wide-open floor plans that live like single-family homes. From the moment you enter, you'll be captivated by the abundance of natural light, soaring ceilings, rich hardwood flooring, and carefully curated finishes that deliver both elegance and functionality. The chef-inspired kitchens are the centerpiece of each home, showcasing custom cabinetry, quartz countertops with waterfall-edge islands, premium stainless steel appliances, designer lighting, and ample space for entertaining. Every detail has been selected to create a seamless blend of luxury and modern convenience. Retreat to spacious primary suites featuring spa-inspired bathrooms, contemporary fixtures, and finishes typically reserved for much more expensive homes. Throughout each residence, you'll find condo-quality craftsmanship, modern architectural details, and an elevated aesthetic designed to impress even the most discerning buyer. The striking contemporary exterior creates an unforgettable first impression with its dramatic floor-to-ceiling windows, sleek architectural lines, and bold modern design. Residents will also enjoy the convenience of rear parking area with three dedicated parking spaces and EV charging capability, a highly sought-after feature that future-proofs the property for years to come. Perfectly positioned in the rapidly transforming Woodlawn neighborhood, just minutes from the University of Chicago, Jackson Park, Lake Michigan, the Obama Presidential Center, and downtown Chicago, this property offers the rare combination of luxury living, long-term appreciation potential, and modern urban convenience. Luxury. Design. Space. Location. 6150 S. Saint Lawrence Avenue represents a unique opportunity to own a premier new construction residence in one of Chicago's most exciting and evolving neighborhoods.

6150 S Saint Lawrence Avenue, Chicago

$99,900

2 Beds ⋅ 1 Baths ⋅ 12705485 MLS ⋅ ACTIVE Status

Great investor/buyer opportunity with this condo which is 4 blocks walking to the University of Chicago. Located in West Woodlawn. First floor with 2 bedrooms 1 bathroom. Newly painted, new laminate flooring throughout except 2 bedrooms which have new carpeting. Bathroom has new vanity and tub is re-glazed. Jewel Food Store is nearby. Conveniently located near public transportation on Cottage Grove and King Drive. Great location next door to Hyde Park. Across the street from Washington Park. Plenty of street parking. , 1 miles from the new Obama Presidential Library, short drive to the Museum of Science and Industry. This bright and inviting unit features abundant natural light, hardwood floors, in-unit laundry, separate living and dining rooms. Ideal for students, healthcare professionals, or investors, with no rental cap offering excellent income potential. Hard money lender, cash or DSCR loan! Quick closing! No FHA or conventional.

541 E 60Th Street Unit #1A, Chicago

$210,000

4 Beds ⋅ 3 Baths ⋅ 12702142 MLS ⋅ ACTIVE Status

Move-in ready!

6521 S Saint Lawrence Avenue, Chicago

$525,000

3 Beds ⋅ 4 Baths ⋅ 12683860 MLS ⋅ ACTIVE Status

Welcome to this four-bedroom, three-and-one-half bathroom home in West Woodlawn. This home was rehabbed in 2019 with classic materials that continue to showcase its elegance. The main level of the house is designed with an open concept; a cozy living room with bay windows is warmed by a fireplace and opens to a formal dining area and kitchen with stainless steel appliances and quartz countertops. A powder room and glass doors opening up to a spacious deck and the backyard make it easy to entertain guests. Upstairs are three generously sized bedrooms that include the primary with its en-suite bathroom and another full bathroom with a walk-in shower. The fully finished basement has a comfortable recreation room, a fourth bedroom, another full bathroom, laundry, mechanical room, and additional storage. This property has a two-and-a-half car garage and is surrounded by a privacy fence. The University of Chicago campus and hospitals are four blocks away; arrive within minutes to explore the Obama Presidential Center. Walk to grab coffee or have breakfast at Daley's (Chicago's oldest restaurant) before taking the CTA to the loop.

6351 S Evans Avenue, Chicago

$359,000

2 Beds ⋅ 3 Baths ⋅ 12696189 MLS ⋅ ACTIVE Status

Modernist Gem in the Heart of Woodlawn! Creative, cool, and highly functional, this impeccably updated Woodlawn bungalow offers a refreshing departure from the everyday. Blending Modernist aesthetics with Prairie-inspired details, 6334 S. Saint Lawrence is a move-in-ready sanctuary designed for the art-forward homeowner. The front entry opens into a voluminous, vaulted-ceiling great room, creating a gallery-like atmosphere perfect for showcasing a curated collection of furniture & art. Feel happy thanks to strategic skylights, the interior remains bright and airy even on the grayest Chicago winter days. The Chef's Alcove kitchen features a smart U-shaped design with brand-new appliances and sleek, minimalist lines. The main level hosts two spacious bedrooms and two full bathrooms, including a light-filled primary suite with a private en suite, that opens to the massive rear deck. Frank Lloyd Wright would approve of the custom-crafted oak staircase leads to the fully realized, walk-out lower level, which offers a generous family room and a private third bedroom with its own en suite bath-the perfect setup for guests or a quiet home office. Enjoy year-round comfort and peace of mind with zoned central heating and air conditioning. Outside, the massive gated rear yard is an entertainer's dream, featuring a massive rear deck with dramatic full-width stairs that invite you down to the grassy lawn and brand-new gated parking pad. Located just blocks from the Cottage Grove Green Line station and surrounded by the rapid development defining the Woodlawn corridor, this is a rare opportunity to own a uniquely designed, right-sized single-family home for the price of a local condo. Every detail has been carefully considered-now it's yours to enjoy.

6334 S Saint Lawrence Avenue, Chicago

$365,000

5 Beds ⋅ 2 Baths ⋅ 12666296 MLS ⋅ ACTIVE Status

Discover a beautifully proportioned two-flat in the heart of Chicago's historic Woodlawn neighborhood, offering a rare blend of architectural charm and modern potential. This classic Chicago two flat has strong investment appeal creating an ideal opportunity for owner-occupants or savvy investors seeking rental income. Each residence features generous living spaces filled with natural light, high ceilings, and timeless character typical of Chicago's traditional multi-family homes. Unit 1 offers 2 bedrooms and 1 bath, while Unit 2 includes 3 bedrooms and 1 bath. The property includes a full basement with additional storage and expansion possibilities, plus convenient on-site parking. Perfectly positioned near the University of Chicago, Jackson Park, and the rapidly transforming Woodlawn corridor, this residence offers access to cultural landmarks, green spaces, and the highly anticipated Obama Presidential Center. A refined opportunity for those seeking elegance, character, and future potential in one of Chicago's most evolving neighborhoods. This property presents an excellent opportunity for investors seeking to expand their portfolio in one of Chicago's most actively revitalized communities. Whether you're looking for a buy and hold asset, value add project, or house hack opportunity, this property offers strong fundamentals and long term appreciation potential in a high growth market.

6602 S Marquette Road, Chicago

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