Working With Jen

Woman in a greenhouse wearing patterned wide-leg trousers and large gold earrings.

I'm hands-on with my clients and direct with them. I enjoy the analytical side of real estate: pricing, why one property outperforms another, and what the market is telling us at any given moment. But what I love most is helping people make the right move, whether that means finding a home they love or figuring out the best way to sell one. Many of my clients are repeat clients, and I always enjoy hearing how they're doing long after closing.

I've worked in Chicago real estate since 2011 and lead The Romolo Group at @properties | Christie's International Real Estate. I've closed more than 440 sales, have ranked in the top 1.5% of Chicagoland brokers since 2021, and have been recognized annually as a Chicago Association of REALTORS® Top Producer. I was also voted Best Realtor in the Chicago Reader's Best of Chicago 2025.

My clients make the decisions, but they don't hire me just to present options. They hire me for my professional opinion, and I give it to them directly.

I'm also not interested in closing a deal for the sake of closing it. I want my clients to feel good about their decision after the excitement and stress of the transaction are over. With sellers, that sometimes means advising them to wait to list, skip a project they won't get their money back on, or rethink the price they had in mind. With buyers, I've talked clients out of plenty of homes, including ones they loved at first sight.

Modern kitchen with a marble island, dark cabinets, wood backsplash, and skylight.

For Sellers

Pricing is one of the most important decisions we'll make, so I don't set a list price until I've seen the property. Comps tell me a lot, but what I really want to understand is why buyers paid more for one home than another, whether those differences apply to yours, and how your property compares with what buyers can choose from right now.

Condition, layout, outdoor space, parking, location and competing inventory all matter, but they don't always matter in the way people expect. Sometimes a seemingly small difference has a real effect on value. Other times, something a seller is worried about matters far less to buyers than they think. Seeing the property in person gives me the context to make that distinction.

Before we list, I'll help you decide what's worth doing: where spending money is likely to improve the sale, what we can solve through presentation and marketing, and what I'd leave alone. Positioning matters a lot to me, but knowing what not to do is part of the job too.

From there, we build the launch around the property, with professional photography and video, print and digital marketing, social media, direct outreach to agents, and open houses when they make sense.

Once we're live, I'm looking for the pattern, not just collecting feedback. I'm watching showings, online engagement, competing inventory, conversations with other agents and how buyers are responding. The goal is to understand whether the market is confirming our original assumptions or telling us something different.

I don't get attached to being right about our original strategy. When the market gives us new information, I respond to it, and I keep my sellers updated not only on what I'm seeing, but on what I think it means for us.

When offers come in, I look at the whole picture: price, financing, contingencies, timing, buyer strength and how likely the deal is to close. I'll tell you where we have leverage, where I think we should push, and where pushing harder could cost you an otherwise good deal.

Red-brick house with a steep gable, arched entry, and iron fence.

For Buyers

I love house hunting, and I want my clients to enjoy it too. It can be fun! Figuring out the right fit for someone is a puzzle, and it's one of my favorite parts of the job.

I go through the inventory myself and send you the properties I think are worth a look. I'll also tell you which ones I'd skip and why, but the final call is always yours. The more homes we see together, the better I understand what you're really after, which isn't always exactly what you thought you wanted at the start.

There's no reason to force it. Sometimes we find the right place immediately; sometimes it takes a lot of showings before something clicks. Every showing teaches us something, and I'd much rather keep looking than watch you talk yourself into a house because you're tired of searching.

When you love a house, I get excited with you, but I'm still looking at it critically: condition, value, the compromises you're making, whether those compromises make sense for you, and how what we notice now could affect you when you eventually sell.

Sometimes that means pointing out something that changes how you feel. Other times I'm the one telling you to go for it because we've found something special. I don't want fear to keep you from the right house any more than I want excitement to push you into the wrong one.

With condos, I look past the unit to the association itself: reserves, capital projects, special assessments, litigation and the overall financial health of the building. These aren't the exciting part of a showing, but they can matter a lot after closing.

When we find the right place, I'll tell you what I think it's worth, how aggressive I think you should be, where I see potential issues, and when I think you should let one go.

Historic Chicago townhouses with ornate gables and bay windows, backed by downtown skyscrapers.

Perspective From Both Sides

Working both sides of transactions shapes how I approach each one.

When I represent a buyer, I'm also thinking like the listing agent who may someday have to sell that property: what will future buyers notice, what will they forgive, and what could make resale harder?

When I represent a seller, years of working with buyers tell me what gets their attention, what they'll pay more for, and what they tend to care about far less than sellers expect.

I've worked in neighborhoods all over Chicago and across the housing stock that makes this city interesting: vintage condos, bungalows, two-flats, lofts, high-rises, new construction, single-family homes and multi-unit buildings. After more than a decade, you start to see how much one block, one building, one floor plan or one small detail can change both a property's value and the way buyers respond to it.

I've also been through plenty of deals that went off script: low appraisals, difficult inspections, financing problems, association issues, cold feet, and deals that had to be put back together.

Experience doesn't mean problems stop happening. It means you get better at knowing which ones truly matter, which ones can be solved, and what the realistic options are when something goes sideways.

Jen in an olive-green shirt and dark denim skirt, standing in an office.

Why I Still Love Doing This

I love this city. I'm endlessly curious about Chicago's neighborhoods, architecture, history and all the small details that give different parts of the city their own character.

That curiosity is a big part of why real estate has stayed interesting to me for so long, and it's also what I get to explore as a host and segment producer for ADTV, where I feature Chicago neighborhoods, architecture and the people who know the city best.

We're intentionally a small team. I'm hands-on with my clients from the first meeting through closing, and the judgment you're hiring me for doesn't get handed off. I love my job, and I want to do my job.

I also own and manage property in Chicago, so I've made many of the same decisions I advise clients on with my own money.

When I'm not working, I'm usually reading, at a show, riding my bike, or staring at an old building for longer than necessary.

For Sellers

For Buyers

Perspective From Both Sides

Why I Still Love Doing This

Guiding You With Clarity

Get in Touch

Get in Touch

Get in Touch