Old Town Homes for Sale

Located in the heart of Chicago, Old Town is a vibrant and historic neighborhood that offers residents a unique blend of charm, culture, and convenience. Situated in Cook County, Illinois, Old Town is known for its tree-lined streets, beautiful Victorian-era architecture, and a thriving arts and entertainment scene.

Old Town is a highly sought-after area for homebuyers, thanks to its prime location and diverse housing options. From historic brownstones and vintage apartments to modern condos and townhouses, there is something for everyone in this neighborhood. Whether you're a young professional looking for a trendy loft or a growing family in search of a spacious single-family home, Old Town has it all.

In addition to its beautiful homes, Old Town boasts an array of amenities and attractions. Residents can enjoy shopping at unique boutiques, dining at world-class restaurants, and exploring the neighborhood's vibrant nightlife. The famous Second City comedy club, renowned for launching the careers of many comedic legends, is also located in Old Town.

For outdoor enthusiasts, there are several parks and green spaces nearby, including Lincoln Park, which offers jogging paths, sports fields, and a zoo. The neighborhood's proximity to Lake Michigan also provides opportunities for boating, fishing, and enjoying the beach during the summer months.

Old Town is well-connected to the rest of Chicago, with easy access to public transportation and major highways. This makes commuting to downtown or other parts of the city a breeze.

If you're looking for a neighborhood that combines history, culture, and a vibrant community, Old Town is the perfect place to call home. With its diverse housing options and convenient location, it's no wonder that homes for sale in Old Town are in high demand.

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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