Woodlawn Real Estate

Woodlawn Real Estate

Welcome to Woodlawn, a vibrant neighborhood located in the heart of Chicago, Illinois. Known for its rich history and strong sense of community, Woodlawn offers residents a unique blend of urban amenities and small-town charm.

Situated in Cook County, Woodlawn is a diverse and culturally rich neighborhood that has been undergoing a revitalization in recent years. With its tree-lined streets, historic architecture, and close-knit community, Woodlawn is a popular choice for those looking to live in a dynamic and evolving area.

Woodlawn is home to a variety of housing options, from historic brownstones to modern condominiums, making it an attractive destination for individuals and families alike. The neighborhood also boasts an array of local businesses, restaurants, and shops, providing residents with everything they need right at their doorstep.

For those who enjoy the outdoors, Woodlawn is just a short distance from beautiful parks and green spaces, perfect for leisurely strolls or picnics on a sunny day. With easy access to public transportation and major highways, getting around the city is a breeze for Woodlawn residents.

Whether you're a young professional looking for a lively urban environment or a family seeking a tight-knit community to call home, Woodlawn has something to offer everyone. Come discover all that this charming neighborhood has to offer and find your perfect place in the heart of Chicago.

Newest Listings in Woodlawn

$299,800
3 Beds ⋅ 3 Baths ⋅ 12711975 MLS ⋅ NEW 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 $20,000, 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
$930,000
9 Beds ⋅ 6 Baths ⋅ 12712761 MLS ⋅ NEW 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
$600,000
4 Beds ⋅ 4 Baths ⋅ 12696617 MLS ⋅ ACTIVE Status
Welcome to 1506 E. Marquette Rd., Chicago, IL, a beautifully designed home offering the perfect combination of space, comfort, and modern living. This spacious residence features 4 bedrooms, 2 full bathrooms, and 2 half bathrooms, making it ideal for growing families or those who love to entertain! The impressive primary suite serves as a private retreat, complete with a double vanity, relaxing soaking tub, and separate walk-in shower. Thoughtfully designed living spaces provide both functionality and comfort throughout the home! Enjoy outdoor living with two private balconies-one located on the first floor and another on the third floor-perfect for morning coffee, evening relaxation, or entertaining guests! The fully finished basement expands your living space and includes an additional half bathroom, making it ideal for a family room, recreation area, home office, fitness room, or guest space! With its generous layout, desirable amenities, and move-in-ready appeal, this home offers everything today's buyers are looking for. Schedule your private showing today and experience all that 1506 E. Marquette Rd. has to offer!

1506 E Marquette Road, Chicago
$290,000
3 Beds ⋅ 2 Baths ⋅ 12710724 MLS ⋅ ACTIVE Status
Spacious and beautifully appointed 3-bedroom, 2-bath condominium offering approximately 1,700 square feet of comfortable living space in a highly desirable location. This sun-filled home features an open-concept floor plan designed for modern living and entertaining, complemented by rich hardwood flooring throughout the main living areas and a private balcony directly off the living room, perfect for enjoying your morning coffee or unwinding after a long day. The thoughtfully designed kitchen is equipped with stainless steel appliances and flows seamlessly into the expansive living and dining areas, creating an inviting space for gatherings of any size. The generously sized bedrooms provide exceptional comfort, while the oversized primary suite serves as a true retreat, featuring a massive en-suite bathroom and a spacious walk-in closet. Additional highlights include the convenience of in-unit laundry, abundant storage, and one exterior parking space. Ideally situated just minutes from the future Obama Presidential Center and close to parks, dining, shopping, public transportation, and the lakefront, this home offers the perfect blend of space, style, and location. Whether you're looking for your next primary residence or a smart investment opportunity, this move-in-ready home delivers exceptional value and lifestyle. Schedule your private showing today!

6526 S Kimbark Avenue Unit #2S, Chicago
$539,000
7 Beds ⋅ 3 Baths ⋅ 12710583 MLS ⋅ ACTIVE Status
Move right into this beautifully updated East Woodlawn two-unit offering the perfect blend of immediate income potential and comfortable owner-occupancy. The spacious first-floor duplex features 4 bedrooms, 2 full baths, two separate living areas, an updated kitchen with stainless steel appliances and a dishwasher, private laundry with storage, and a private entrance-ideal for related living, guests, or a short-term rental opportunity. Two of the bedrooms easily accommodate king-size beds with nightstands. The second-floor simplex offers 3 bedrooms, 1 bath, an L-shaped kitchen, in-unit laundry, and a spacious primary bedroom that comfortably fits a king-size bed. A rare find in Chicago multifamily homes, each unit has separate utilities, generous closets, and individual laundry. Step outside to enjoy a spacious rear deck, backyard, and a 2-car brick garage. Live in one unit and rent the other, or add a turnkey investment to your portfolio. Ideally located just minutes from the University of Chicago, the Obama Presidential Center, Jackson Park, Lake Michigan, public transportation, neighborhood restaurants, coffee shops, and the vibrant Hyde Park corridor. Surrounded by historic architecture, tree-lined streets, and ongoing redevelopment, this property is perfectly positioned for long-term appreciation in one of Chicago's most sought-after investment neighborhoods. Whether you're an investor seeking strong cash flow or an owner-occupant looking to offset your mortgage with rental income, this is an exceptional opportunity in the heart of Woodlawn.

6520 S Ellis Avenue, Chicago
$299,990
6 Beds ⋅ 2 Baths ⋅ 12697314 MLS ⋅ PRICE CHANGE 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
$699,000
3 Beds ⋅ 3 Baths ⋅ 12706953 MLS ⋅ ACTIVE Status
New construction single-family home in Woodlawn featuring 3 bedrooms and 2.5 baths. Open-concept main level with spacious living room, dining area, and a modern kitchen with quality finishes. Inviting family room with an electric fireplace, perfect for everyday living and entertaining. The second floor offers generously sized bedrooms, including a primary suite with a private bath. 2-car garage with rooftop deck, ideal for outdoor entertaining and relaxation. Quality craftsmanship throughout with thoughtful design and functional layout

6538 S Kimbark Avenue, Chicago
$469,000
3 Beds ⋅ 2 Baths ⋅ 12706715 MLS ⋅ ACTIVE Status
Stunning townhome located right next to the University of Chicago campus, directly across the street from the dorms. This tri-level home features an open-concept main level with fresh paint throughout. The kitchen boasts newer stainless steel appliances and opens to a private deck-perfect for entertaining. The home includes 3 bedrooms, 2 updated bathrooms, and a 1-car attached garage. Enjoy an incredibly convenient location within walking distance of university buildings, the medical center, local restaurants, and the lakefront. Parking is a breeze with corner lot resident parking, street parking, and permit parking available. NO HOA, NO HOA, NO HOA. Close to the Metra and CTA. The roof was newly replaced. Harwood flooring was recently installed. the windows were newer. A new range hood with vent out was installed last year. Whole house repainted last year. Come check it out for yourself-you don't want to miss this one!

1009 E 61St Street, Chicago
$199,500
3 Beds ⋅ 1 Baths ⋅ 12686271 MLS ⋅ ACTIVE Status
Welcome to this charming, vintage courtyard co-op. This freshly painted 3-bedroom, 1-bath co-op is filled with natural light and offers a spacious open-concept living and dining area, plus a bright sunroom ideal for a home office, reading nook, or morning coffee. Set in a classic courtyard building, this co-op combines timeless character with an unbeatable location near the University of Chicago, parks, restaurants, coffee shops, the local farmers market, and a variety of cultural attractions. Enjoy walking access to the Obama Presidential Center, along with convenient Metra and CTA bus service for an easy city commute. Monthly assessments INCLUDE TAXES, heat and gas.Co-op requires board approval.

6108 S Kimbark Avenue Unit #2E, Chicago
$444,900
12702000 MLS ⋅ PRICE CHANGE Status
NEW PRICE - motivated seller! Exceptional value on this solid all-brick 3-story 6-unit in booming Woodlawn. Unbeatable rental-demand location just blocks from the 63rd St Metra Electric/South Shore station and minutes to Jackson Park, the lakefront, the Obama Presidential Center, and the University of Chicago. Solid masonry construction and a consistent unit mix make this a smart hold in one of the South Side's most closely watched neighborhoods. Priced to move - investors, don't wait.

1427 E 66Th Place, Chicago
$299,000
3 Beds ⋅ 2 Baths ⋅ 12701088 MLS ⋅ ACTIVE Status
Welcome home to this sun-drenched 3-bedroom, 2-bath condo perched on the top floor of a brick walk-up in the heart of Woodlawn. Freshly painted throughout in timeless White Dove, this beautifully maintained home offers soaring vaulted ceilings, abundant natural light, and an airy, inviting feel from the moment you step inside. Brand new stainless steal refrigerator and stove! The spacious living room and primary suite are filled with sunlight, creating warm and comfortable spaces to relax and unwind. The primary bathroom has been thoughtfully updated, while brand new carpeting in all three bedrooms adds a fresh, cozy touch throughout the home. Rear deck freshly coated! Located in the vibrant Woodlawn community, this home offers close proximity to neighborhood staples and green spaces including Jackson Park Golf Course, Robust Coffee Lounge, and the lakefront. Conveniently situated near the newly opened Obama Presidential Center and the many local businesses, parks, and cultural institutions that make this neighborhood so special.

6534 S Kimbark Avenue Unit #3, Chicago
$239,560
4 Beds ⋅ 3 Baths ⋅ 12698203 MLS ⋅ ACTIVE Status

6619 S Ellis Avenue, Chicago
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