West Woodlawn Real Estate

West Woodlawn Real Estate

West Woodlawn: A Hidden Gem in Chicago

Located in the heart of Chicago, West Woodlawn is a vibrant neighborhood that offers a unique blend of urban living and community charm. Situated in Cook County, Illinois, this area is known for its rich history, diverse culture, and close-knit community.

One of the standout features of West Woodlawn is its convenient location. With easy access to downtown Chicago and major highways, residents can enjoy the best of both worlds - a peaceful suburban atmosphere and the bustling city life just a short drive away. This makes it an ideal choice for those who seek a balance between work and leisure.

The neighborhood boasts a variety of housing options, ranging from historic brownstones to modern condominiums. Whether you're a young professional looking for a trendy apartment or a growing family in search of a spacious home, West Woodlawn has something for everyone.

In addition to its prime location and housing options, West Woodlawn is home to a thriving community. The area is known for its strong sense of unity and active neighborhood associations. Residents can engage in various community events, such as farmer's markets, festivals, and block parties, fostering a sense of belonging and camaraderie.

West Woodlawn also offers a plethora of recreational opportunities. Beautiful parks, like Washington Park and Jackson Park, provide ample space for outdoor activities, including picnics, sports, and leisurely strolls. Additionally, the neighborhood is dotted with local shops, restaurants, and cafes, giving residents plenty of options for shopping and dining.

With its rich history, diverse culture, and a strong sense of community, West Woodlawn is truly a hidden gem in Chicago. Whether you're looking for a place to call home or simply exploring the city, this neighborhood should be on your radar.

Newest Listings in West Woodlawn

$650,000
5 Beds ⋅ 4 Baths ⋅ 12755646 MLS ⋅ NEW Status
WHY BUY ONE LIVING SPACE WHEN YOU CAN HAVE TWO? BRAND-NEW CONSTRUCTION WOODLAWN DUPLEX designed for luxury living, house hacking, and income potential! Live upstairs and let the garden unit help reduce your mortgage-or maximize the property's rental potential in one of Woodlawn's most exciting locations. UNIT 1 offers 3 spacious bedrooms and 2.5 baths with HARDWOOD FLOORS THROUGHOUT. Enjoy an impressive overly sized open layout with quartz countertops, waterfall island, custom wet bar with glass rinser, fireplace, smart toilets, and high-end washer and dryer per unit. The spacious primary suite features its own private bath with double vanities. The GARDEN UNIT features 2 bedrooms and 1 bath with its own open modern open kitchen, living area, and high end washer/dryer in unit. Ideal for long-term rental income, extended family, or potential short-term rental use where permitted. Short-term rentals in the surrounding area can command strong rates, with demand supported by nearby attractions and institutions. LOCATION MATTERS! Minutes from the OBAMA PRESIDENTIAL CENTER, University of Chicago, Jackson Park, Museum of Science and Industry, Hyde Park, the lakefront, and convenient transportation. More upgrades include SOLAR PANELS that you ACTUALLY OWN to help reduce utility expenses, tankless hot water, a HUGE REAR DECK built for entertaining, and a BRAND-NEW 2-CAR GARAGE. NEW CONSTRUCTION. TWO LIVING SPACES. INCOME POTENTIAL. PRIME WOODLAWN LOCATION. GRANTS ASSISTANCE MAY BE AVAILABLE for qualified buyers. Schedule your private showing today!

6547 S Evans Avenue, Chicago
$335,000
4 Beds ⋅ 2 Baths ⋅ 12753199 MLS ⋅ NEW Status
Opportunity meets flexibility in this classic Chicago two-flat in Woodlawn. Offering five total bedrooms and two full baths, the property has historically been configured with a two-bedroom first-floor residence and a three-bedroom second-floor residence, making it an attractive option for owner-occupants, extended-family living or investors. Inside, you'll find hardwood flooring, spacious living areas, functional kitchens with updated cabinetry and appliances, and plenty of room to make the property your own. A full unfinished basement provides valuable storage and additional possibilities, while the building's distinctive masonry exterior adds timeless Chicago character. With convenient access to public transportation and neighborhood amenities, this property offers the chance to move in, generate income and add value over time. Whether you're house hacking, expanding your rental portfolio or seeking flexible multi-generational living, 6620 S Marquette Rd presents a compelling opportunity.

6620 S Marquette Road, Chicago
$365,000
6 Beds ⋅ 2 Baths ⋅ 12753109 MLS ⋅ NEW Status
Rarely Available Greystone 2-Flat! This Gem has the original wood work thru-out along with gorgeous hardwood flooring. The built-in on the first level adds character that blends with the remodeled upgrades perfectly. All units feature remodeled kitchen and baths with stainless steel appliances, dishwasher and granite countertops with ceramic style modern flooring and new vinyl windows (2022)Newer roof with silver coating. Seperate heat in all units. First floor has 3 bedrooms and Second floor has 3 bedrooms. Partially finished basement with laundry and storage. Detached 2 Car Garage and conveniently located near transportation and the Obama Presidential Library.

6525 S Vernon Avenue, Chicago
$325,000
5 Beds ⋅ 2 Baths ⋅ 12748855 MLS ⋅ ACTIVE Status
Positioned in the heart of Chicago's historic Woodlawn neighborhood, this classic two flat presents an attractive opportunity for investors, owner occupants, and buyers seeking long-term value in an evolving South Side market. The property combines the enduring appeal of a traditional Chicago multifamily with multiple avenues to enhance income, improve value, and build equity. The building features two residential units: a 2 bed /1 bath first floor unit and a 3 bed /1 bath second floor unit. Both apartments offer generous living areas, abundant natural light, high ceilings, and the architectural character associated with Chicago's classic two flats. A full basement provides valuable storage and potential for future expansion or additional usable space, while on site parking adds convenience and enhances tenant appeal. From an investment perspective, the property offers several compelling strategies, including buy and hold, value add renovation, rental income optimization, and owner occupant house hacking. Investors have the opportunity to capitalize on the property's existing two units while exploring improvements that could increase rents, strengthen tenant demand, and enhance long term asset value. The property is situated near the University of Chicago, Jackson Park, and the Obama Presidential Center, as well as the ongoing redevelopment and investment throughout the Woodlawn corridor. Continued neighborhood revitalization, proximity to major institutions, transportation, parks, and cultural amenities provide a strong foundation for future demand and potential appreciation. For investors looking to acquire a multifamily asset in a neighborhood undergoing significant transformation, this Woodlawn two flat offers a compelling combination of income potential, value add upside, and long term appreciation prospects. Tenant on 1st floor pays $1650/month for rent plus utilities.

6602 S Marquette Road, Chicago
$1,369,000
14 Beds ⋅ 8 Baths ⋅ 12741726 MLS ⋅ PRICE CHANGE Status
EXCEPTIONAL, MASSIVE, EXTRA WIDE, ARCHITECTURALLY SIGNIFICANT 4 UNITS BUILDING ON A DOUBLE LOT AND IN MOST HOT, DESIRABLE LOCATION. IT WAS CONVERTED FROM 8 SMALLER UNITS TO HUGE 4 UNITS. ALL NEW ROOF, WINDOWS, PLUMBING, ELECTRIC, MECHANICALS, ETC. 4TH SMALL BEDROOM IS OPTIONAL OFF LIVING ROOM. IN UNIT LAUNDRY. 2 CAR GARAGE, 3 EXTERIOR PARKING SPOTS OFF ALLEY AND 3 EXTERIOR SPOTS ON SIDE DRIVE. TONS OF NEW CONSTRUCTION AND REHABS ON THE BLOCK. UNBEATABLE LOCATION. VERY CLOSE TO GREEN LINE AND ALL PUBLIC TRANSPORTATION. ACT NOW !!!

6418 S Vernon Avenue, Chicago
$200,000
8 Beds ⋅ 3 Baths ⋅ 12737026 MLS ⋅ ACTIVE Status
This property is located in a prime area, close to the Newly opened Obama Center and is already totally gutted. It is ready for Your personal taste and flare to make it your own.

6321 S Rhodes Avenue, Chicago
$679,000
8 Beds ⋅ 5 Baths ⋅ 12721912 MLS ⋅ ACTIVE Status

Chicago
$1
10 Beds ⋅ 4 Baths ⋅ 12732123 MLS ⋅ AUCTION Status
Listing price $405,600 Great opportunity on this 4-unit building. It offers approximately 3,858 square feet of living space with 10 bedrooms and 4 bathrooms. Built in 1925 repairs and updates are needed but has potential. Property sold "AS-IS" without contingencies, repairs, warranties, guarantees or representation as to listing accuracy, property information, photo or other depiction included or described herein. Inspect prior bidding.

Chicago
$899,000
9 Beds ⋅ 6 Baths ⋅ 12724368 MLS ⋅ ACTIVE Status
Your home should work harder for you. This brand-new construction Three Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by an award-winning home builder this high-performance, all-electric, three-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the designer interior and gated intercom security, is crafted for effortless, low-maintenance living. All three units offer a condo-quality 3 Bedroom + 2 Bath layout upstairs with a with East facing great rooms with a glimpse of the new Obama Presidential Library from the top floor primary unit. Each unit also features a chef's kitchen with custom cabinetry, quartz countertops, and a premium induction ranges. Three Parking spaces in the rear. Live in one unit and generate high-value rental income to enhance your affordability.Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy ultra low utility costs without compromising on lifestyle. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6312 S Champlain Avenue, Chicago
$589,000
4 Beds ⋅ 3 Baths ⋅ 12724342 MLS ⋅ ACTIVE Status
Your home should work harder for you. This brand-new construction Two Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by award-winning Greenline Homes, this high-performance, all-electric, two-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is crafted for effortless, low-maintenance living. The primary unit on the second floor offers a condo-quality 2 Bedroom + 2 Bath layout The unit features a chef's kitchen with custom cabinetry, quartz countertops, and a premium Induction range. An expansive private balcony extends from the great room, offering a seamless indoor/outdoor living experience.The stunning grade-level accessible first-floor offers a easy to rent 2 Bedroom + 1 Bath Layout that interfaces well with the private rear yard. This unit provides a spacious retreat, perfect for multi-generational living or generating high-value rental income to enhance affordability. Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy near-zero utility costs without compromising on style. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6553 S Rhodes Avenue, Chicago
$850,000
12634033 MLS ⋅ ACTIVE 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
$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
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