Old Town Real Estate Guide 2026: Lincoln Park's Best-Value Neighbor

Hazel Mae
May 16
4 min read

Updated: 4 days ago

By Jason Rowland | Founder & Managing Broker, Rowland Group at Compass | May 2026

Old Town sits directly south of Lincoln Park — separated by a few blocks, a price differential, and not much else. It has the same tree-lined residential streets, excellent dining, and proximity to the lakefront that define its more famous neighbor. But it remains meaningfully less expensive, and that gap has been closing. For buyers who have been priced out of Lincoln Park or who recognize where value lies, Old Town is the answer. Here is the complete picture for 2026.

Why Old Town Is Having Its Moment

Old Town has always had the bones — the 19th-century architecture, the neighborhood fabric, the location. What it has lacked historically is the critical mass of amenities and the market recognition that drives Lincoln Park prices. Both are changing. The restaurant scene along Wells Street has strengthened significantly over the past five years. The Second City comedy club remains a cultural anchor. And as Lincoln Park inventory has tightened, buyers are discovering that Old Town offers a comparable experience at lower entry costs.

Old Town Real Estate Prices in 2026

Single-Family Homes

Old Town's single-family market is one of the more compelling value propositions in Chicago. Solid homes on good blocks start around $900K-$1.2M — significantly below the Lincoln Park floor for comparable product. Renovated or new construction homes on premium streets, particularly the historic blocks near North Park Avenue and Wieland Street, reach $2M-$3M. The spread between unrenovated and renovated is wide, creating opportunity for buyers willing to take on a project.

Condos & Townhomes

Old Town's condo market is more modest in scale than Lincoln Park's but offers solid value. One-bedrooms range from $275K-$450K. Two-bedrooms run $400K-$750K. Townhomes — which are plentiful in Old Town's historic building stock — typically range from $700K-$1.5M depending on size and condition.

Historic Architecture

Old Town contains one of Chicago's most significant concentrations of pre-Fire architecture — Victorian cottages and Italianate row houses that survived the 1871 Great Chicago Fire because they lay just north of its path. The Old Town Triangle Historic District designation protects much of this character. Historic properties carry their own premium and their own considerations for renovation — work with an agent who understands both.

The Old Town Market in 2026

Old Town is a competitive but not frenzied market in 2026. Unlike Lincoln Park, where multiple-offer situations on well-priced single-family homes are nearly routine, Old Town buyers typically have more room to conduct due diligence and negotiate. This is the practical benefit of buying in a neighborhood that is still being 'discovered' rather than one that is fully arrived.

That said, the best properties — especially renovated single-family homes in the historic district and well-located condos near Wells Street — do move quickly and attract multiple buyers. Pre-approval and decisiveness remain essential.

What It's Like to Live in Old Town

Old Town is quieter than Lincoln Park but shares much of its character. Wells Street between Division and North Avenue is the commercial heart — a mix of restaurants, bars, and neighborhood retail that has improved markedly in recent years. The Second City, one of America's great comedy institutions, has been an Old Town fixture for decades. The lakefront is a 10-15 minute walk east. Lincoln Park proper — the park — is immediately accessible from the neighborhood's northern edge.

Frequently Asked Questions: Old Town Real Estate

How does Old Town compare to Lincoln Park?

Old Town offers a very similar lifestyle to Lincoln Park at prices typically 15-20% lower for comparable properties. The primary differences are the depth and maturity of the retail/dining scene (Lincoln Park has more) and school options. For buyers without school-age children prioritizing Lincoln Park, Old Town deserves serious consideration.

Is Old Town appreciating?

Yes, and the appreciation story is compelling precisely because the market is still in the process of being fully recognized. As Lincoln Park inventory tightens and prices rise, buyer spillover into Old Town accelerates. I expect the price gap between Old Town and Lincoln Park to continue narrowing over the next 3-5 years.

Are there good investment properties in Old Town?

Yes. Old Town has solid multi-family inventory at more accessible price points than Lincoln Park, and the renter population is large and stable. It is an underappreciated investment market relative to its northern neighbor.

About the Author

Jason Rowland is the Founder and Managing Broker of Rowland Group at Compass, Chicago's top-producing real estate team. With $400M+ in closed transactions and over 15 years of experience, Jason is consistently ranked in the Top 1% by the Chicago Association of REALTORS®. Contact: jason.rowland@compass.com | 312-927-1942 | rowlandgroupre.com