Leigh Marcus, one of Chicago’s leading real estate agents and FastExpert partner, provides unique insight into the North Side Chicago neighborhoods. Not only does the Leigh Marcus Team operate here, but Leigh also raises his family here, making this a must-read for everyone!

Chicago neighborhoods offer a diverse tapestry of residential communities, each with its own unique charm and character. Among these, Bucktown, Roscoe Village, and Old Irving Park stand out as desirable neighborhoods for homebuyers seeking a blend of urban amenities and suburban tranquility.

For me, Roscoe Village became home, not only for my family but also for my team’s headquarters, because it has a little piece of what aligns all of these communities closely together.

As you embark on your journey to find the perfect home in these vibrant communities, check out these insights and tips to guide you through the process.

Roscoe Village

Nestled on the North Side of Chicago, Roscoe Village exudes a warm, family-friendly atmosphere with tree-lined streets and quaint storefronts.

Known for its cozy cafes, boutique shops, and local eateries, Roscoe Village appeals to those seeking a tight-knit community vibe within the bustling city. The housing options range from charming vintage homes to modern condos, offering something for everyone.

Bucktown

Adjacent to Wicker Park, Bucktown epitomizes urban chic with its trendy boutiques, art galleries, and hip dining spots.

The neighborhood boasts a mix of historic architecture and contemporary lofts, attracting young professionals and families alike. With easy access to public transportation and a thriving cultural scene, Bucktown embodies the dynamic spirit of Chicago’s creative class.

Old Irving Park

Steeped in history and architectural charm, Old Irving Park offers a tranquil retreat from the urban hustle.

Lined with majestic Victorian homes, lush green spaces, and picturesque streetscapes, this neighborhood exudes timeless elegance and suburban allure. Residents enjoy a sense of community camaraderie while relishing the convenience of nearby amenities and transportation options.

Insights for Home Buyers

When looking at a new home in these areas (or any community, really), it’s important to keep several behaviors on the top of your mind.  

1. Define Your Priorities

Before diving into the home buying process, take time to outline your priorities and preferences.

Consider factors such as proximity to schools, commute times, neighborhood vibe, and housing budget. By clarifying your must-haves and deal-breakers, you can streamline your search and focus on properties that align with your lifestyle goals.

2. Research Market Trends

Stay informed about the current real estate market trends in these North Side Chicago neighborhood communities.

Monitor property prices, inventory levels, and days on market to gauge the overall competitiveness and affordability of each neighborhood. Working with a knowledgeable real estate agent can provide valuable insights and help you make informed decisions throughout the buying process.

3. Explore Financing Options

Explore various financing options and mortgage rates to determine the most suitable solution for your financial situation.

Get pre-approved for a mortgage to strengthen your purchasing power and demonstrate your seriousness as a buyer. Keep in mind that securing financing early can expedite the closing process and give you a competitive edge in a competitive market.

4. Attend Open Houses and Neighborhood Events

Immerse yourself in the local community by attending open houses, neighborhood events, and farmer’s markets. Engage with residents, explore different areas within each neighborhood, and envision yourself as part of the community fabric.

Pay attention to school districts, parks, and amenities that align with your lifestyle preferences and family needs.

5. Conduct Due Diligence

Prioritize due diligence when evaluating potential properties in the community.

Schedule home inspections to assess the condition of the property and uncover any potential issues or repairs. Familiarize yourself with local zoning laws, building codes, and property taxes to avoid any surprises down the road.

6. Think Long-Term Investment

Consider the long-term investment potential of your prospective home in Chicago’s residential real estate market. Assess factors such as property appreciation, neighborhood development projects, and future resale value.

A strategic approach to homebuying can yield both personal satisfaction and financial growth over time.

Find Your Ideal Chicago Neighborhood

Navigating the residential real estate landscape in Roscoe Village, Bucktown, and Old Irving Park requires careful consideration, research, and patience. These are the steps that I followed in selecting Roscoe Village as a family and business base of operations.

By understanding the unique characteristics of each neighborhood and leveraging valuable insights and tips, you can embark on your homebuying journey with confidence and clarity. Whether you’re drawn to the vibrant energy of urban living or the tranquility of suburban bliss, Chicago offers a diverse array of housing options to suit every lifestyle and preference.

Work with the best real estate agent who can guide you along the way and help you find your ideal home!

Happy house hunting!

Key takeaways

• The Chicago housing market slightly favored sellers in May, but the balance of power was nearly even.
• Home prices, sales, and listings all rose as activity returned to the market.
• The city’s seasonal trends acted more “normal” than they have in years, in line with the national market’s slow reset. 

Chicago housing market snapshot

Spring housing season was in full swing in May, and Chicago’s market followed suit. Sales increased, homes moved faster, and prices climbed. The typical listing took about seven weeks to sell, but those that were well-priced moved more quickly than in previous springs. The market was nearly perfectly balanced, but strategy still mattered.

Learn everything you need to know about the Chicago, IL, housing market as we edge closer to summer, and what buyers and sellers can do to succeed.

U.S. housing market snapshot

Nationally, prices are rising, inventory is growing, and pending sales are up. The prolonged slow and expensive buyer’s market that has defined the post-pandemic market is finally showing signs of thawing—but buyers are still firmly in charge.

“Housing has been stuck in a rut for years, with buyers and sellers priced out and too few homes to go around,” said Chen Zhao, Redfin’s head of economics research. “While conditions are still difficult, many cities are undergoing a yearslong reset from the pandemic, with price growth easing and inventory climbing—helping affordability improve as wages rise. Pending home sales have increased over the last three months, which is an early sign that buyers and sellers are beginning to reenter the market. But volatility tied to the Iran War is keeping everyone on edge.”

Let’s dive into the Chicago housing market.

Chicago’s housing market slightly favored sellers

In Chicago, buyers outnumbered sellers by just 0.5% in May, giving the market a slight tilt toward sellers. The number of buyers rose 5% year over year in May, while the number of sellers was essentially flat. Nationally, it was essentially the opposite; there were 47% more sellers than buyers. 

Homes moved relatively quickly. The median home sat on the market for 51 days, and 44% of listings went under contract within two weeks. Meanwhile, 37% of homes sold above their original list price, compared to just 26% nationally. 

Active buyers should move quickly on well-priced listings—homes that are priced right are still drawing multiple offers. Sellers can be confident in the demand but shouldn’t overprice; the data shows buyers are active but not desperate, and overpriced homes are sitting.

Prices rose at a less frenzied pace

The median sale price in Chicago reached $379,900 in May, up 5.4% year over year. That was a continued upward trend, but a deceleration from the 8.3% year-over-year growth at this time in 2024 and the 6.1% gain last year. Chicago’s appreciation outpaced the nation as a whole (where prices rose just 1.9%), but the gap narrowed. 

To put this data into context, Chicago’s median sale price has nearly doubled from its post-recession lows. The sharpest growth came during the pandemic, when prices jumped by $50,000 in under two years. The current pace of growth is far more sustainable, averaging roughly 5–6% annually since mid-2024.

Home searchers shouldn’t wait for price drops from sellers, though. Only 11% of active listings in Chicago have had a price reduction, compared to 20% nationally. That said, sellers who do cut their price are cutting by an average of 4% of their list price. Sellers should price to the market, and buyers should make competitive offers.

Inventory held steady

Active listings held steady at 26,679, up less than 1% year over year—essentially flat after several months of modest growth. New listings climbed 4%, a sign that more homeowners chose to sell. Combined with months of supply at 3.1 (compared to 3.5 nationally), Chicago remained a tighter market than the U.S. as a whole.

The data painted a picture of a market that was unevenly normalizing: inventory plateaued near its multi-year rebuild level, but demand absorbed much of it before supply could accumulate meaningfully. For buyers, that meant a similar number of options as last year and still limited leverage on price.

All data is a Redfin analysis of MLS, U.S. Census Bureau, and/or county record data. Check the Redfin Data Center for additional in-depth housing market data.