Multiple Offers Received. Requesting Highest & Best by 6/8/2026 Monday 3 p.m. Rarely available and full of character, this beautifully maintained single-family home offers three finished levels of living space on one of Bridgeport’s most desirable tree-lined streets. Welcome to this truly one-of-a-kind single-family home in the heart of Bridgeport, perfectly situated on picturesque, tree-lined Union Avenue. Brimming with character, charm, and exceptional living space, this beautifully maintained residence is sure to impress from the moment you arrive. Outstanding curb appeal sets the stage for what awaits inside. Spanning three finished levels, the home offers a versatile and spacious floor plan with hardwood floors throughout the main and second levels. The sun-filled main floor features a welcoming living room, a generously sized bedroom, a den/home office nook, and a beautifully updated kitchen complete with abundant cabinetry and granite countertops. Additional living spaces include a cozy sitting area or study, an expansive dining/family room perfect for gatherings, and a full bathroom. Upstairs, you’ll find three comfortable bedrooms and a second full bath. The spectacular 20′ x 17′ primary bedroom is a true retreat, featuring a wall of closets and a charming Juliet balcony overlooking the private backyard oasis. The finished lower level adds even more functional living space with a warm and inviting family room anchored by a fireplace, a second kitchen, a full bathroom, a laundry area (washer conveyed AS-IS condition), and ample storage-ideal for entertaining, extended living arrangements, or everyday convenience. Step outside and discover a private backyard designed for relaxation and entertaining. Whether hosting summer gatherings or enjoying a quiet evening outdoors, this space is sure to become a favorite. Additional highlights include central air conditioning, dual heating systems – gas forced heat & baseboard hot water heat, and a detached two-car garage providing convenient off-street parking. Lovingly cared for and thoughtfully maintained, this special home is ready for its next chapter. Property is being conveyed AS-IS. Enjoy an unbeatable Bridgeport location just steps from public transportation, neighborhood restaurants, parks, coffee shops, and shopping. Conveniently located near Chicago White Sox Park, downtown Chicago, and major expressways, this home offers the perfect blend of neighborhood charm and city accessibility. Taxes do not include home owner’s or Senior exemption credits. New Complete Tear Off Roof and gutters on house and garage 2022.