Old Town Homes for Sale

Welcome to Old Town, a vibrant neighborhood located in the heart of Chicago, Illinois. Situated in Cook County, Old Town is a charming community known for its rich history, diverse culture, and lively atmosphere.

Old Town is a sought-after destination for homebuyers, offering a wide range of residential options to suit various preferences and budgets. Whether you're looking for a historic brownstone, a modern condo, or a spacious single-family home, you'll find an array of homes for sale in this neighborhood.

One of the appealing aspects of Old Town is its prime location. With its proximity to downtown Chicago, residents can enjoy easy access to the city's bustling business district, world-class dining, shopping, and entertainment options. Additionally, Old Town boasts excellent transportation links, making it convenient for commuters and those who love to explore the city.

Living in Old Town means immersing yourself in a vibrant community with a unique character. The neighborhood is known for its charming tree-lined streets, historic architecture, and a thriving arts scene. Residents can explore a variety of local galleries, theaters, and music venues, showcasing the area's creative spirit.

When it comes to amenities, Old Town has plenty to offer. From trendy boutiques and specialty shops to cozy cafes and renowned restaurants, there's something for everyone. The neighborhood also boasts beautiful parks and green spaces, providing opportunities for outdoor recreation and relaxation.

Whether you're a first-time homebuyer or looking to upgrade your current living situation, Old Town is a fantastic place to call home. With its rich history, vibrant culture, and diverse real estate options, this neighborhood offers a unique and fulfilling living experience. Explore the homes for sale in Old Town and discover your perfect place in this thriving community.

Newest Old Town Homes for Sale

$1,450,000

3 Beds ⋅ 4 Baths ⋅ 12713927 MLS ⋅ NEW Status

One of the defining features of this home is its setting within Old Town Village East - a private, tree-lined horseshoe street that offers guest parking, a rarity in Chicago, and a gated alley where neighbors gather and children play. It is a neighborhood that offers an uncommon sense of community while remaining just minutes from the heart of the city. The home has been thoughtfully renovated with an emphasis on both design and functionality. The first floor was completely reconfigured to improve the original layout, including a remodeled kitchen, relocated powder room, and the addition of a walk-in pantry, creating a more practical and cohesive living space. The main level features custom millwork and wainscoting, while updated lighting, fixtures, switches, outlets, and integrated recessed lighting throughout provide a clean, contemporary aesthetic. Hardwood floors were added to the upstairs bedrooms, and the finished lower level includes two additional bedrooms and a spacious spa-inspired bath, offering exceptional flexibility for guests, extended family, or work-from-home needs. Ideally situated within walking distance of Old Town's restaurants and several of Chicago's most respected schools, including Latin, Walter Payton College Prep, Catherine Cook School, and Immaculate Conception/St. Joseph School (ICSJ), this home combines thoughtful renovations with an exceptional neighborhood setting. A private deck and landscaped outdoor space extend the living area outdoors, complemented by a detached two-car garage. Extensive recent capital improvements further enhance the home's appeal (Roof, Gutters, HVAC (2025/2026).

344 W Scott Street, Chicago

$5,200,000

7 Beds ⋅ 6 Baths ⋅ 11755660 MLS ⋅ ACTIVE Status

Nestled on the prestigious North Park Avenue, Significant Mansion stands as a remarkable architectural gem in the vibrant Old Town/Gold Coast neighborhood. This custom-built residence, constructed from exquisite masonry brick and limestone, spans an impressive 8,000 square feet and occupies a generous double lot measuring 50 feet in width. The property boasts an expansive side yard and entrance, multiple balconies, and a covered rooftop deck, crowned by a magnificent turret tower that presents breathtaking panoramic views of the city skyline and the lush, tree-lined surroundings. Featuring seven bedrooms and five and a half bathrooms, this home is a testament to meticulous design and thoughtful attention to detail. Inside, the residence showcases soaring 12-foot ceilings, rich hardwood flooring, a coffered ceiling in the living room, elaborate crown moldings, and stately 8-foot doors. The ambiance is further enhanced by three elegant wood-burning fireplaces, a five-stop elevator, and a well-appointed gym on the top floor that overlooks an impressive professional indoor basketball court. The spacious chef's kitchen is a culinary enthusiast's dream, equipped with a Wolf range cooktop and custom copper hood, built-in Wolf convection ovens, a commercial Thermador refrigerator, and luxurious granite countertops. Custom cabinetry, a large center island with counter seating, and a separate dining area create a seamless flow into the grand family room, which features yet another wood-burning fireplace. The spectacular three-season room invites relaxation with its own wood-burning fireplace and provides access to an outdoor grilling patio complete with a built-in DCS chef's grill. The home also includes a convenient mudroom with laundry facilities and direct access to the stunning side yard. The expansive primary suite is a private retreat, featuring a walk-out balcony, a dedicated staircase leading to a unique turret office, and two generous walk-in closets. The en suite bathroom is a luxurious haven, offering a double vanity, a spacious steam shower, and a jetted bathtub. Additional bedrooms are equally generous, each equipped with walk-in closets, en suite baths, and walk-out balconies. The lower level is designed for entertainment, featuring a cozy fireplace and a potential wine storage room, alongside two sizable bedrooms with walk-in closets and a full bath. Additional highlights of this extraordinary residence include a spacious attached 2.5-car garage, an automated privacy gate, a snowmelt driveway, a central vacuum system, geothermal radiant heating, Marvin windows, multiple laundry rooms, and a Sonos multi-room sound system throughout the home. Perfectly suited for entertaining large families, this unique property is ideally located near a wealth of entertainment options, exquisite dining, top-tier schools (including Latin and Parker), parks, and the picturesque lakefront. This is truly a one-of-a-kind home that promises an unparalleled living experience.

1515 N North Park Avenue, Chicago

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