Why Buyers Continue to Fall in Love with Chicago's Vintage Homes

Illustrations hand-drawn by: @katiebodnar.art

Chicago's vintage homes, especially those built between the 1860s and 1940s, represent the golden age of the city's residential architecture. Crafted by skilled tradespeople and rich in detail, these homes tell the story of Chicago's resilience and creativity.

At Redden + McDaniel, we love homes and we love Chicago. We appreciate the city's vintage homes and the role they play in defining the character of our communities.

Features We Commonly See in Vintage Homes

Original details do more than add beauty. They tell a story. These preserved features reflect craftsmanship, character, and the care a home has received over generations.

Stained Glass Windows

Because of its delicate nature, stained glass is often one of the first original features lost in a vintage home. Intact stained glass creates an emotional connection and suggests the home has been well cared for.

Pocket Doors

Pocket doors are one of those original features buyers love to discover. Their extra width creates separation between living and dining spaces while preserving the home's character and craftsmanship.

Dining Buffets

Many dining buffets have disappeared under layers of latex paint over the years. An untouched, well-preserved buffet reflects the care and stewardship found throughout the home.

Original Floors

Original old-growth floors are valued for the beautiful variation and warmth they bring to a home. Their healthy patina reflects decades of character that simply cannot be replicated.

What We Hear from Buyers 

We asked homeowners what first drew them to their vintage homes and which details continue to matter most.

Garrett + Taylor

Owners of a Craftsman Cottage in Albany Park

What originally drew you to your home? When we were looking for a home, we knew we wanted something with character. We weren’t originally looking in this neighborhood, but the floors and wooden built-ins made us want to tour it immediately.

What characteristics or craftsmanship stood out to you?

This house is over 100 years old. It had a life before us, and it will have a life after us. The craftsmanship has withstood the test of time. There is a warmth and attention to detail in our home that I don’t think you could get in a new build. They truly don’t build them like they used to.

Joe + Kimberly

Owners of a Brick Two-Flat in Roscoe Village

What originally drew you to your home? We knew brick buildings and greystones go for a premium, but the beauty of the greystone was captivating. It was hard to go a different direction once we started looking at them.

What features made you fall in love with your home? Original built-ins are still intact and functional in the units.

Were there any details you were willing to pay a premium for? Original wood frame around doorways (ideally not painted), original frame details and original built-ins.

What characteristics or craftsmanship stood out to you? Two things: 1) Boiler heat. It just feels a lot better, and I love putting my feet on the radiator in the morning during the winter, looking out our bay window. 2) Structural integrity. The building is a fortress. It'll last another 100+ years.

What advice would you give someone considering a vintage home today? There's less and less supply every day. You can always buy a new home, but there are limited opportunities to buy a vintage home. Chicago architecture has such a history, and I feel like we're helping preserve the history.

Michelle

Owner of a Vintage Multi-Unit Building in Avondale

What features made you fall in love with your home? It was the stained glass windows that immediately spoke to me. Definitely not something you find these days. That coupled with how many original features remain throughout the building. Those details are special.

What characteristics or craftsmanship stood out to you? Obviously the stained glass, the built-ins, all the beautiful trim work, original doors and hardwood floors. The mosaic tile in the entry is a nice little reminder of my old condo, like I got to take a piece of it with me. It has so much character and charm. And it's kind of cool that I get to be the person who really is bringing the building back to life. Just giving it the breath of fresh air it needs to really shine.

What advice would you give someone considering a vintage home today? It's a lot of work, but it's worth it. It becomes about more than just ownership. You become a steward for the neighborhood and community by preserving the roots of the city. I'm becoming a part of the story which is really cool.

Kay

Former Owner of a Vintage Wicker Park Condo

What originally drew you to your home? I was looking for a home with some character that reflected the architectural design Chicago is so well-known for. I wanted to be on a block that still had much of the original architecture, not one where most of the homes had been replaced with new, modern construction.

What features made you fall in love with your home? The original pine floors and trim and molding. It was so rare to see trim that wasn’t coated in multiple layers of paint. I fell in love immediately.

Were there any details you were willing to pay a premium for? The leaded glass windows. They created amazing shadows across the ceilings and walls.

What characteristics or craftsmanship stood out to you? To name a few: heavy wood doors, unique brickwork on the facade, leaded windows, long-plank floors.

What advice would you give someone considering a vintage home today? Go for it! I’ve found the vintage homes I’ve owned to be really well-built and relatively easy to maintain, as most tradespeople in Chicago are familiar with working on older homes and know how to handle their quirks. Take advantage of Chicago’s incredible vintage shops to find furnishings appropriate for the space!

Color Traditions of Craftsman Homes

Arts & Crafts and early Craftsman influences can be found throughout many historic Chicago homes, often featuring warm neutrals, muted greens, and deeper accent colors drawn from nature. When selecting colors today, staying close to these traditional palettes can help preserve the character and charm of the home.

*Arts & Crafts color palette shown for historical reference. Colors adapted from the Sherwin-Williams® Historic Arts & Crafts Collection.

Redden + McDaniel is an independent local real estate brokerage dedicated to its clients and Chicago. As part of Chicago’s vibrant small business community, we believe our neighborhoods are best served through transparency and cooperation. We love homes, Chicago, and history, and we are grateful to be your neighbor.