Old Town Condos for Sale Chicago
Based on it's popularity, you'd never guess that Old Town is a relatively small Chicago neighborhood. For that reason, condos for sale in Old Town are always in demand. As usual in Chicago, the taller high rise condos in Old Town can be found along the lake. Smaller buildings including duplex condos typically have lower HOA fees and dominate the interior streets of the neighborhood. For luxury Old Town condos, I've highlighted a few listings below. For the more affordable options, I filtered the condos by price. Whatever you're seeking, reach out and I'm sure I can help.
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Selling in Old Town?
Pricing it right is an important first step
Old Town Condos for Sale by Price
- All Listings
- $300,000 - $400,000
- $400,000 - $500,000
- $500,000 - $600,000
- $600,000 - $700,000
- $700,000 - $800,000
- Over $1,000,000
Old Town Chicago Condos For Sale
Old Town, nestled just north of downtown Chicago, is one of the city’s most iconic and charming neighborhoods, known for its rich history, preserved architecture, and vibrant cultural scene. With tree-lined streets, Victorian-era homes, and an eclectic mix of shops and restaurants, Old Town offers an unmatched blend of historic character and modern urban living. For those seeking condos for sale in Chicago, Old Town presents a diverse inventory, including classic three-flats, sleek high-rises, boutique mid-rises, and unique loft conversions—each reflecting a different aspect of the neighborhood’s timeless appeal.
Old Town Condos - Curated
The Best of Old Town Real Estate
Mid-rise condo buildings are also a prominent part of Old Town’s real estate market. These buildings usually span four to six stories and often combine classic architectural facades with contemporary interiors. Many mid-rises in Old Town offer boutique living experiences, with fewer units per building and amenities like rooftop decks, secure entryways, and garage parking. The scale of these developments complements the neighborhood’s village-like feel, making them attractive to buyers who want convenience and comfort without sacrificing community and charm.
Although high-rises are more characteristic of nearby neighborhoods like Gold Coast or Streeterville, Old Town does feature a number of high-rise condominium towers, particularly along its eastern edge near Lake Shore Drive and Lincoln Park. These high-rises cater to those seeking sweeping views of Lake Michigan or the downtown skyline and typically include a wide range of amenities such as doorman service, fitness centers, pools, and expansive balconies. These properties often appeal to professionals, downsizers, and investors looking for full-service living in a highly walkable neighborhood.
Lofts, while less common than in industrial areas like the West Loop or River North, do appear in Old Town, especially in converted commercial buildings or newer developments that embrace the aesthetic of exposed brick, high ceilings, and open floor plans. These loft-style condos offer a unique option for buyers who desire a modern, minimalist interior with character and space.
Whether you're ready to make a move or simply exploring your options, reach out below and let's start the conversation!
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More on Old Town Chicago
The origins of Old Town date back to the mid-19th century when German immigrants settled in the area and built homes, churches, and businesses. The neighborhood was one of the few parts of Chicago that survived the Great Chicago Fire of 1871, which means that many of its buildings date back well over a century. Old Town’s architectural charm is defined by its narrow streets, vintage row houses, ornate ironwork, and cobblestone alleys, giving it a distinct personality within the broader cityscape. It gained further recognition in the mid-20th century as a bohemian enclave, home to artists, writers, musicians, and counterculture movements. Landmarks like the famed Second City comedy club and the Old Town Art Fair helped to cement its cultural reputation.
Today, Old Town’s architectural diversity continues to make it a favorite among homebuyers. Traditional Chicago three-flats remain a mainstay, especially on the quieter, residential streets west of Wells Street. These low-rise brick or greystone buildings typically house three separate condo units stacked vertically, each with its own floor. Many of these three-flats have been lovingly restored or updated, offering hardwood floors, original millwork, and charming front porches. Some have been fully modernized inside, blending old-world craftsmanship with new fixtures, finishes, and open layouts.
Living in Old Town comes with a long list of benefits that go far beyond the walls of any condo. The neighborhood’s location is one of its greatest assets. Residents are just minutes from the lakefront, Lincoln Park, and North Avenue Beach, as well as a short commute to downtown via CTA buses or the Brown and Red Line trains. Old Town’s walkability is unmatched; daily errands, weekend brunches, or late-night comedy shows are all easily accessible on foot.
The shopping and dining scene in Old Town is as vibrant as its streetscape. Wells Street, the neighborhood’s main commercial corridor, is lined with boutique clothing stores, art galleries, fine dining establishments, and cozy cafes. Whether you're in the mood for sushi, steak, gelato, or cocktails on a rooftop patio, you’ll find a spot that satisfies your cravings. The neighborhood also hosts seasonal events and festivals, with the Old Town Art Fair being one of the most celebrated cultural events in the city.
Old Town’s charm also lies in its ability to balance its rich history with a modern lifestyle. Families, young professionals, and retirees alike are drawn to the area’s sense of community, architectural beauty, and easy access to both nature and city life. The presence of high-performing schools, nearby medical facilities, and cultural institutions further enhances the livability of the neighborhood.
For those considering purchasing a condo in Chicago, Old Town represents a rare opportunity to live in a place where heritage and progress coexist seamlessly. Whether it’s the elegance of a restored three-flat, the convenience of a boutique mid-rise, the luxury of a high-rise with lake views, or the uniqueness of a loft, Old Town offers an array of housing choices within a neighborhood that feels like home the moment you arrive.
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