Woodlawn Homes under $300,000

Gorgeous 2 bedrooms, 2- bathrooms condo located in hot Woodlawn area. This spacious unit features 10 inch ceilings, updated kitchen with granite counter tops, stainless steel appliances, island, hardwood floors, fireplace, and in-unit washer/dryer. Master suite with private bath. 2 separate balcony areas with one in the living room and another off the master. In unit washer & dryer. Gated

Tokela Brown Heart My Home Chicago Inc

Charming Updated Brick Bungalow in Booming East Woodlawn! Welcome to this beautifully updated solid brick bungalow nestled on a quiet, tree-lined block in the heart of East Woodlawn-one of Chicago's fastest-growing neighborhoods. Thoughtfully maintained and updated as recently as August, this home is truly move-in ready. Recent upgrades include a brand-new roof, new heater, updated 100 amp

Carlos Matos Core Realty & Investments Inc.

First-Floor Beauty Near University of Chicago - Move-In Ready! Available now! This bright and beautiful first-floor condo offers the perfect blend of historic charm and modern updates in the heart of Woodlawn. This 3-bedroom, 2-bath condo features gleaming hardwood floors, fresh paint, and an elegant kitchen with granite countertops and upgraded cabinets. Prime Location! Just minutes from the

Jarrie Lesure Keller Williams Infinity

***CALLING INVESTORS! RENTED $2300 per month 8/1/25 - 7/31/26. $170,000 of the loan is assumable at a 4% with PHH. *** Beautifully updated 3bed/2.5bath Duplex Up in Historic Woodlawn! Walk up the exposed brick hallway stairs into the living area where you will be greeted by a gorgeous gas fireplace in the foyer, high ceilings, hardwood floors, and plenty of sunshine from the oversized windows!

Kimberly Chang Realty ONE Group Karmma

Welcome to Kimbark Estates, where Vintage Charm Meets Modern Comfort in the Heart of Woodlawn! This spacious and well-appointed top-floor condo seamlessly blends vintage character with contemporary updates. Saturated with natural light, this bright unit features captivating views from all windows, gleaming hardwood floors and new lighting that accentuates its timeless appeal. The

Tracey Hill EXIT Strategy Realty

This 3 bedroom, 2 bath Woodlawn condo has upgraded amenities. The unit features generous natural light filled living spaces, hardwood floors throughout and high-end finishes like a private balcony, crown molding and gourmet kitchen and stainless steel appliances, granite counter-tops and 42" cabinets. The master suite bathroom includes a whirlpool tub and double vanity. A washer and dryer is

James Bohannon Enterprise Realty Power Broker

Winsome Woodlawn, 1,789 sq. ft., 3 BD/3 BA duplex down. Easy access to the University of Chicago, Jackson Park, 63rd St Beach, the Obama Presidential Center, and Lake Michigan. Entertain in the sun-filled living room with bay windows and crown molding overlooking Beehive Park and the 62nd & Dorchester Community Garden. There is an upgraded kitchen featuring solid surface countertops, ample

Robert Mehney @properties Christie's International Real Estate

Beautiful Victorian house features 4 bedrooms and 2.5 bathrooms, living room, dining room, kitchen, unfinished basement.

Steve Meeker Meeker Real Estate Inc