Sprinkman Spotlight: Madison’s Near West Side + Agent Jeff Drengler 

We Live Here, We Know Here

At Sprinkman Real Estate, we believe the best agents aren’t just familiar with a neighborhood — they’re part of its fabric. Our team lives where we work, which means we know more than market stats. We know the hidden walking paths, the best patios for a quiet glass of wine, and exactly which street shows off the most spectacular fall colors. That kind of insider knowledge turns a good real estate experience into a great one. Because when you love where you live, you’re naturally better at helping others find their place, too.

One of the best examples of that local love is Sprinkman agent — and proud Near West Side resident — Jeff Drengler. Passionate about the neighborhood he calls home, Jeff shared what makes this corner of Madison so special: an irresistible mix of location, lifestyle, and community spirit that makes it one of the city’s most desirable places to live.

Here’s what he shared:

First things first — where is the Near West Side?

If we’re talking boundaries, the Near West Side is the area of Madison between Monona Bay and Monroe Street, and just south of Regent Street. It’s a collection of cozy, character-rich neighborhoods like Bay Creek, Greenbush, Vilas, and Monona Bay. Bay Creek is bounded by Monona Bay and Wingra Creek, hence its name. I actually live in Monona Bay myself — it’s a smaller neighborhood association, but we share borders and events with the others. This area is very much a place where the lines blur in the best possible way.

 What kind of homes can people expect to find here?

That’s a big part of its charm — there’s something for everyone. The homes near Monona Bay, but not directly on the lake, are some of the most affordable single-family options in Madison, with prices starting in the mid-$300s. Go a few blocks in any direction, and you can find a totally different vibe: classic Craftsman homes in Vilas, lakeside properties on Monona Bay, and historic gems scattered throughout. You could easily spend upwards of $1M for a home with water views or for something truly special. Sprinkman recently listed one over $2M in Vilas. This area has a wonderful mix of price points, styles, and opportunities.

Out of all the areas in Madison, what makes the Near West Side stand out?

Two words: location and community. Location-wise, it’s a dream. You’ve got the UW Arboretum, Vilas Zoo, Camp Randall, Monroe and Regent Streets, and Monona Bay all within walking distance. State Street and Capitol Square are just a short bike ride away. But what really sets it apart is the people. It’s not just friendly — it’s actively welcoming. Weekly neighborhood events, community festivals with music and food trucks, educational workshops, potlucks, you name it. You can’t go for a walk without stopping for a chat with a neighbor. It’s that kind of place.

Are there any exciting changes or developments happening?

Absolutely. South Park Street is undergoing an exciting transformation, with a new grocery store and some excellent new restaurants. There’s also the John Nolen “Lakeway” Project, which will revitalize the eastern edge of the neighborhood and enhance access to the lakefront.

And we can’t forget the Regent Street redesign — still in the planning stages, but making real progress. It’s an exciting time to live in this part of town.

What brought you here and what made you stay?

We bought our home in 2019 and spent almost a year updating it before we moved in. A lot of the time since moving in went into restoring the lawn and gardens for great curb appeal and even better opportunities to meet neighbors out on their walks. We stay because we adore Madison, and this neighborhood encapsulates everything we love about the city. We’ve got diversity – of people, homes, experiences – and a sense of community that’s hard to replicate. Friendly neighbors, great food, and being this close to the lake, parks, and Arboretum? It’s a fantastic place to call home.

How are you involved in the neighborhood community?

Nature is a huge part of my life, and it’s very easy to get involved in meaningful ways in this neighborhood. I’m on the board of the Friends of the Arboretum (FOA), which supports education and fundraising for the UW Arboretum. I also belong to the West Side Garden Club — a wonderful, educational group that supports local nonprofits through annual donations. We’ve also been long-time supporters of the Clean Lakes Alliance, and I volunteer through Sprinkman with them as well. I’m also a member of the Monona Bay Neighborhood Association, and a business sponsor for Bay Creek, Greenbush, and Vilas associations. 

What’s your advice for buyers and sellers as we look ahead to 2026?

For buyers: be ready. Even though the market has cooled slightly, homes in Madison – especially in these neighborhoods – often go under contract within days. Get your financing in place early, and work with an agent who’s responsive and knows how to move fast when your dream home pops up. For sellers: preparation is everything. The earlier you start, the better. Great staging, professional photography, and strong marketing make a huge difference. 

Any tips specific to buying or selling on the Near West Side?

For buyers, I’d say: be flexible. A lot of the homes here have character and some have quirks. Many used to be rentals and need a little TLC, but with the right mindset you can find incredible value. Engage with an agent with strong relationships and resources that can help you set your vision. For sellers: hire a real estate agent who truly knows the area. These neighborhoods each have their own flavor. Whether it’s walkability to Monroe Street, views of Monona Bay, or a particular architectural style, a knowledgeable local agent with ties to the area will know how to tell the story of your home in a way that resonates — so you can take your next step.

Finding the right home – or the right buyer – starts with finding the right agent. Someone who knows the market, but also understands you. At Sprinkman Real Estate, we believe the best fit goes beyond expertise; it’s about connection, trust, and genuine local insight. Ready to find your match? Let’s start the conversation and make your next move feel like coming home.