Woodlawn Real Estate

Woodlawn Real Estate

Welcome to Woodlawn, a charming community nestled in the heart of the United States, where small-town warmth meets urban convenience. Located just a stone's throw from the bustling city of Chicago, Woodlawn offers residents the best of both worlds—easy access to city life while maintaining a tranquil suburban atmosphere.

Rich in history and culture, Woodlawn is home to a diverse population and a vibrant arts scene. The neighborhood boasts beautifully preserved architecture, with historic homes that tell the story of the area’s past. Strolling through the tree-lined streets, you’ll find a mix of quaint shops, local eateries, and community parks, creating a welcoming environment for families and individuals alike.

One of the highlights of living in Woodlawn is the strong sense of community. Residents take pride in their neighborhood, often coming together for local events, farmers' markets, and festivals that celebrate the unique culture of the area. The community is also home to several educational institutions, making it an ideal place for families seeking quality schooling options.

For outdoor enthusiasts, Woodlawn offers ample green spaces for recreation and relaxation. With nearby parks and access to Lake Michigan, residents can enjoy activities like hiking, biking, and picnicking, all while soaking in the natural beauty of the region.

Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Woodlawn presents a variety of real estate options to suit your needs. Discover the charm and character of Woodlawn today—where your dream home awaits!

Newest Listings in Woodlawn

River Oaks Dr, Woodlawn

River Oaks Dr, Woodlawn

Discover a unique investment opportunity with this expansive 1.65-acre parcel of land, perfectly positioned for future development or personal retreat. This generous lot offers a blank canvas for visionary investors looking to capitalize on the growing demand for residential properties in the area. Imagine the possibilities: build your dream home, create a serene getaway, or develop multiple residences to maximize your return on investment. The ample space allows for creative landscaping, outdoor amenities, or even sustainable living options, appealing to a wide range of potential buyers or renters. Located in a tranquil setting, this land provides a peaceful escape while remaining conveniently accessible to local amenities and services. The surrounding area is ripe for growth, making this an ideal time to invest. With the potential for appreciation in value, this property is not just a piece of land; it's a strategic investment in your financial future. Whether you're an experienced developer or a first-time investor, this property offers the flexibility and potential to meet your goals. Don't miss out on the chance to secure a prime piece of real estate that promises both comfort and opportunity. Embrace the potential of this land and turn your vision into reality!

River Oaks Dr, Woodlawn

Listing courtesy of Charis Realty Group. Contact:

1906 Park Pl, Woodlawn

1906 Park Pl, Woodlawn

4 Beds ⋅ 4 Baths

Seller may consider a closing-cost credit with an acceptable offer. The amount and terms are negotiable and subject to seller approval. Beautifully renovated from top to bottom, this spacious 4-bedroom, 3.5-bath home offers modern finishes, flexible living spaces, and an inviting open floor plan. The cozy living room features an electric fireplace and flows seamlessly into the beautifully updated kitchen, complete with quartz countertops, stainless-steel appliances, a large entertaining island, and a built-in wine refrigerator. Step directly from the kitchen onto the stone patio—perfect for outdoor dining, entertaining, or relaxing while enjoying the oversized backyard. Just off the living room is a versatile bonus space with French doors, ideal for a private home office, studio, playroom, or den. The main level also includes a convenient laundry hookup and half bath. Upstairs, you’ll find two additional bedrooms and an impressive owner’s suite featuring a private full bathroom, walk-in closet, and access to a huge private balcony overlooking the expansive lot—a peaceful retreat for morning coffee or evening relaxation. The fully finished lower level offers even more living space, including a fourth bedroom and full bathroom—perfect for guests, extended family, or a private living area. An oversized driveway, generous backyard, and beautiful details throughout complete this move-in-ready home. Every space has been thoughtfully remodeled to combine comfort, style, and functionality. This exceptional property is a must-see!

1906 Park Pl, Woodlawn

Listing courtesy of Redfin Corp. Contact:

1454 Barrett Rd, Woodlawn

1454 Barrett Rd, Woodlawn

3 Beds ⋅ 2 Baths

Welcome to 1454 Barrett Rd, a beautifully maintained brick townhome in the desirable Edmondson Heights community. This move-in ready home offers three bedrooms and one and a half baths, with hardwood floors throughout the main and upper levels and abundant natural light filling the bright, inviting living spaces. The main level features a spacious living room, separate dining area, and a great kitchen with new appliances. Just off the kitchen, step out into a yard, perfect for outdoor dining or relaxing and a parking pad. The lower level provides additional living space with brand new flooring, ideal for a rec room, home office, or guest area, along with a laundry/mudroom with rear access and a convenient half bath. Upstairs, you’ll find three well-sized bedrooms with ample closet space, a nicely updated full bath, and additional hallway storage. This is a move-in ready ...you don't want to miss it!

1454 Barrett Rd, Woodlawn

Listing courtesy of JS Realty LLC. Contact:

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Kathleen McMahan

For Kathleen McMahan, real estate has always been about more than buying and selling homes. It’s about people, relationships, and helping clients feel confident during some of the biggest transitions of their lives. With more than a decade of experience in Maryland and Washington, D.C. real estate, Kathleen has built her business around a simple philosophy: stay positive, work hard, communicate honestly, and treat every client’s move as if it were her own. Positivity has long been Kathleen’s “north star,” both personally and professionally. When her oldest son spent time in the NICU, she focused on learning everything she could from his nurses so she would feel prepared when it was finally time to bring him home. That experience reinforced something she carries into her work today: even during stressful and uncertain moments, knowledge, preparation, and the right perspective can make all the difference. That mindset has helped Kathleen build a successful real estate career based largely on relationships, referrals, and clients who return to her as their lives and real estate needs evolve. Now, as the agent behind McMahan Homes at Real Broker, she brings the experience of more than a decade in the industry together with the personal attention and flexibility of an independent real estate business. Originally from New Jersey, Kathleen came to Maryland to attend Salisbury University. Her studies in sociology and marketing helped spark a lasting curiosity about people—what motivates them, what matters to them, and what makes a place truly feel like home. Today, that curiosity is one of her greatest strengths as an agent. Kathleen takes the time to understand not just what her clients are looking for on paper, but what they want their lives to look like. Whether she’s preparing a home for the market, negotiating on behalf of a seller, helping a buyer find the right community, or simply answering the questions that come up along the way, her goal is to make the process feel informed, personal, and manageable. Kathleen lives in Maryland with her husband and two sons. When she isn’t working, you’ll most likely find her spending time with her family, dreaming about her next trip to the Florida Keys, or planning her next home project.

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