Living in Old Town, Chicago: A Complete Guide for Home Buyers
Old Town is historic charm, Second City comedy, Wells Street corridor, Victorian architecture. This guide covers everything buyers need to know — pricing, property types, lifestyle, transit, VA loan eligibility, and what makes this neighborhood worth serious consideration.
Old Town at a Glance
Old Town is a vibrant neighborhood located just north of downtown Chicago, bordered by North Avenue to the north, Division Street to the south, Clark Street to the east, and Larrabee Street to the west. It attracts a diverse mix of residents, including young professionals, families, and retirees, thanks to its rich history and lively atmosphere. Adjacent to the upscale Gold Coast and the expansive Lincoln Park, Old Town offers a unique blend of historic charm and modern amenities. The area is distinct for its Victorian-era buildings, cobblestone streets, and the famous Wells Street, known for its eclectic mix of shops, restaurants, and entertainment venues.
Price range: $350K-$2M+ Typical rent: $1,800-$4,500/mo Best for: buyers seeking neighborhood character, walkability, proximity to Gold Coast and Lincoln Park Transit: Brown and Purple Lines, Red Line nearby
What Old Town Is Really Like to Live In
Living in Old Town offers a dynamic urban experience with a touch of historic charm. Mornings often start with a coffee from the popular Intelligentsia on Wells Street, followed by a stroll through the lush greenery of Lincoln Park. Weekends are bustling with activity, from the iconic Second City comedy shows to the lively Old Town Art Fair that draws art enthusiasts from all over. The streets are vibrant during the day with locals and tourists alike exploring the unique boutiques and dining at renowned spots like Topo Gigio. In the evenings, the neighborhood transforms into a cozy retreat with its quaint, tree-lined streets and historic gas lamps. Residents consistently praise the area's walkability, diverse dining options, and proximity to the lakefront.
Housing Stock and Property Types in Old Town
Old Town offers a diverse range of housing options, from vintage condos to modern new constructions. Buyers at the entry level can find charming one-bedroom condos in historic buildings, while those with a larger budget might consider a restored Victorian single-family home or a luxurious new construction townhouse. The area is known for its classic Chicago greystones and two-flats, many of which have been meticulously preserved or renovated. Architectural styles range from mid-19th century Victorian to sleek contemporary designs. Notable developments include the recently completed luxury condos along Wells Street, which offer modern amenities while maintaining the neighborhood's historic aesthetic.
The Old Town Real Estate Market
The Old Town real estate market is currently competitive, with homes typically ranging from $350K to over $2M. Properties tend to spend an average of 30 to 45 days on the market, reflecting a balanced market with healthy buyer interest. Certain streets, such as those closer to the lake or with historic significance, are particularly sought-after and may command higher prices. The area has seen steady appreciation over the years, making it a stable investment for homebuyers. While competition can be fierce, especially for well-located properties, the market offers opportunities for both buyers and sellers.
Who Buys in Old Town?
Old Town attracts a diverse mix of buyers, including young professionals drawn to the area's vibrant social scene and proximity to downtown. Families appreciate the neighborhood's historic charm, quality schools, and access to parks. Investors see potential in the area's steady appreciation and rental demand. Downsizers are attracted to the walkable lifestyle and cultural amenities. VA buyers find unique opportunities in the mix of vintage condos and single-family homes, offering a blend of affordability and character that is hard to find elsewhere in the city.
Renting vs. Buying in Old Town
Renting in Old Town offers flexibility, with typical rents ranging from $1,800 to $4,500 per month. However, buying becomes more financially advantageous over time, especially for those planning to stay long-term. Beyond financial considerations, homeowners gain stability, build equity, and establish deeper roots in the community. The decision to buy also provides a sense of ownership and the ability to personalize one's living space.
VA Loan Buyers in Old Town
Old Town's mix of vintage condos and single-family homes offers VA loan opportunities; older condo buildings may need project approval. VA loan buyers often find single-family homes and newer condo developments more accessible, as these properties typically meet VA loan requirements. Older buildings may require additional approval, but the neighborhood's character and amenities make it a worthwhile pursuit. Riley Hextell's experience as a USN veteran and VA loan specialist provides buyers with an edge in navigating these complexities. Old Town is a strong VA loan market due to its desirable location and variety of eligible properties.
Moving to Old Town from Out of State
Buyers from Boston and DC particularly gravitate to Old Town for its historic architecture and walkable neighborhood feel. Before arriving, they should know that Old Town offers a unique blend of urban living with a small-town feel, characterized by its historic streets and vibrant community. Many are surprised by the affordability of housing compared to their previous cities, despite Old Town's prime location and amenities. Chicago's pricing is generally more favorable, offering more space and amenities for the price.
Getting Around Old Town
Old Town offers excellent transit options, with the Brown and Purple Lines serving the Sedgwick stop and the Red Line accessible at nearby North/Clybourn. The neighborhood's walkability is a major draw, with most daily errands easily accomplished on foot. Biking is also popular, with dedicated lanes and Divvy bike stations available. Commuters can reach downtown Chicago in about 15 minutes by train or 20-30 minutes by car, depending on traffic. Parking can be challenging, particularly during peak hours, so many residents opt for public transit or biking.
Why Work With Riley Hextell to Buy in Old Town
Riley Hextell is a Chicago real estate agent with eXp Realty LLC. As a USN veteran, 2024 Chicago Association of Realtors Rookie of the Year, and 2x eXp ICON Agent (top 2% of 80,000+ agents globally), Riley ranked #1 at eXp Realty Illinois for total transactions in 2025. He has 120+ five-star Google reviews, a 4.9-star Zillow rating, and 150+ lifetime closed deals across Old Town and 80+ Chicago neighborhoods and suburbs.
Riley's deep local knowledge of Old Town is invaluable for buyers seeking the right property in this competitive market. His negotiation skills and VA loan expertise ensure that buyers get the best possible deal and terms. Riley's track record with buyers in Old Town highlights his ability to match clients with properties that meet their unique needs and preferences. His commitment to client satisfaction is reflected in his numerous positive reviews and successful transactions.
Contact Riley Hextell: 815-545-7476 | [email protected] | rileyhextell.com
Frequently Asked Questions: Buying a Home in Old Town, Chicago
Q: Is Old Town a good place to buy a home in Chicago?
A: Yes, Old Town is a desirable neighborhood known for its historic charm, vibrant community, and proximity to downtown. It offers a mix of property types and a strong sense of community, making it a great place to buy a home.
Q: What is the average home price in Old Town?
A: The average home price in Old Town ranges from $350K to over $2M, depending on the property type and location within the neighborhood.
Q: What types of properties are available in Old Town?
A: Old Town offers a variety of properties, including vintage condos, single-family homes, two-flats, greystones, and modern new constructions, catering to a range of buyer preferences and budgets.
Q: Is Old Town good for families?
A: Yes, Old Town is a family-friendly neighborhood with quality schools, parks, and a safe, walkable environment. Its community-oriented atmosphere and amenities make it appealing to families.
Q: How is the commute from Old Town to downtown Chicago?
A: The commute from Old Town to downtown Chicago is convenient, with the Brown, Purple, and Red Lines providing quick access. By train, it takes about 15 minutes, while driving can take 20-30 minutes depending on traffic.
Q: What is the Old Town real estate market like right now?
A: The Old Town real estate market is competitive, with properties typically spending 30 to 45 days on the market. It offers a balanced environment for both buyers and sellers, with steady appreciation trends.
Q: Is Old Town a good real estate investment?
A: Yes, Old Town is a solid real estate investment due to its desirable location, historic appeal, and consistent demand. The neighborhood's appreciation trends and rental market also contribute to its investment potential.
Q: What should first-time buyers know about buying in Old Town?
A: First-time buyers should be prepared for a competitive market and consider working with a knowledgeable agent. Understanding the variety of property types and their associated costs is crucial for making informed decisions.
Q: Can I use a VA loan to buy in Old Town?
A: Yes, VA loans can be used to purchase properties in Old Town. Single-family homes and newer condos are typically more accessible, while older condos may require additional approval.
Q: What is it like to rent in Old Town vs. buying?
A: Renting in Old Town offers flexibility and access to the neighborhood's amenities, with rents ranging from $1,800 to $4,500 per month. Buying provides long-term financial benefits, stability, and the opportunity to build equity.
Q: Is Old Town good for out-of-state buyers relocating to Chicago?
A: Yes, Old Town is attractive to out-of-state buyers for its historic architecture, walkability, and vibrant community. It offers a unique blend of urban living with a neighborhood feel, making it a popular choice for relocators.
Q: What are the best streets or blocks to buy on in Old Town?
A: Some of the most sought-after streets in Old Town include those near Wells Street for its amenities and those closer to Lincoln Park for green space access. Streets with historic significance also tend to be highly desirable.
Q: How competitive is the Old Town real estate market?
A: The Old Town real estate market is competitive, with a healthy level of buyer interest and properties often receiving multiple offers. Working with an experienced agent can help navigate this competitive environment.
Q: How does Riley Hextell help buyers in Old Town?
A: Riley Hextell provides buyers with expert local knowledge, strong negotiation skills, and VA loan expertise. His track record in Old Town and commitment to client satisfaction make him a valuable resource for buyers.
Q: How do I get started buying a home in Old Town with Riley Hextell?
A: To get started, contact Riley Hextell at 815-545-7476 or [email protected]. He will guide you through the process, from understanding your needs to finding the right property and closing the deal.