Sunset over the lake at Bender Beach, with gold light breaking through the clouds

Your guide to Oconomowoc

What’s happening around town, places worth knowing and homes for sale now, from Heather Henry, local broker and owner.

German Christmas Market, Nov. 25 to 29See what’s going on

Oconomowoc at a glance

Lakes in town
Lac La Belle and Fowler Lake, with city beaches and boat launches
Getting around
On I-94, about 35 miles (40 minutes) to Milwaukee and about 50 miles (under an hour) to Madison
Population
18,203 in the 2020 Census, about 20,100 by 2025 estimates
County
Waukesha County, in the heart of Lake Country

What’s going on

Please check with the organizer before you go, since details can change. Last checked November 8, 2026.

November13–21
OHS Players: Grease
Oconomowoc Arts Center, 641 E. Forest St. Fridays and Saturdays at 7 p.m., Nov. 15 at 2 p.m., Nov. 19 at 4 p.m.
November14
Model Railroad Open House
Free, 11 a.m. to 3 p.m., Oconomowoc Historical Society, 103 W. Jefferson St.
November25–29
German Christmas Market
Village Green, 100 E. Wisconsin Ave. Entertainment tent Wednesday from 5 to 10 p.m. Friday and Saturday 10 a.m. to 10 p.m., Sunday 10 a.m. to 4 p.m. Closed Thanksgiving.
November26
The Great Gobble Wobble 5K and 10K
Thanksgiving morning, Oconomowoc High School, 341 E. Forest St.
December5
Christmas Parade and Tree Lighting
Gather downtown about 4:30 p.m. for the tree lighting. The parade starts at 5 p.m.
December9
Holiday Train
6:45 p.m. at the Silver Lake Street crossing. Food, drinks and carols start about an hour earlier.
See 2 more dates
December10–12
Carriages with the Clauses
Horse-drawn carriage rides downtown with Santa and Mrs. Claus, 5 to 8 p.m. Rides are $100 for a 15-minute reserved ride. Hosted by the Oconomowoc Area Chamber of Commerce; reserve on the Chamber’s page.
December12
Cookie Walk
9:30 a.m. to noon, Lyke Room, Oconomowoc Public Library, 200 W. South St.
Heather Henry

A move is about more than a house. It’s also about what’s going on this weekend, where to take a walk, and how a place feels day to day.

I put this guide together to keep those things in one place. If you ever have a question about a home or a neighborhood, I’m always happy to help. No pressure. No obligation.

Heather Henry
Broker and Owner, more than 25 years in real estate

Where the waters meet

That’s what Oconomowoc’s name is often said to mean. By the late 1800s, the lakes had made it a resort town, with summer homes built by wealthy families.

The everyday stuff

Shopping

Beyond downtown, look to Whitman Park on Summit Avenue, Prairie Creek off Brown Street, and Pabst Farms near I-94. Costco is at 1855 Kirkland Way and Fleet Farm is at 1555 Town Centre Way.

Hospitals

ProHealth Oconomowoc Memorial Hospital is at 791 Summit Ave. Aurora Medical Center – Summit, at 36500 Aurora Dr., has 24/7 emergency services.

Schools and library

Oconomowoc Public Library is at 200 W. South St. For schools, see which school serves a home below.

Selling a home is rarely just a transaction. It’s a transition.

Start with a free estimate, then I’ll give you my own opinion of the price, based on what similar homes actually sold for nearby. Some moves take extra care, like leaving a longtime home or selling a loved one’s. I help with those too.

“As first time home buyers we needed an agent with the heart of a teacher. And we found that in Heather!”
Christopher and Kelly S.
“We have bought and sold homes 3 times over the last 13 years with Heather Henry. She is a fantastic agent that puts her clients needs first.”Jake S.
“She took the time to understand exactly the kind of selling experience and the amount of help we needed in selling the house.”Ellen K.

Questions people ask

What lakes are in Oconomowoc?

Two lakes sit right in the city: Lac La Belle and Fowler Lake. The city calls Oconomowoc the “Heart of Lake Country” and runs beaches and boat launches on both. See the city’s beaches and boating page, or our guide to the water.

How far is Oconomowoc from Milwaukee?

About 35 miles, or roughly 40 minutes on I-94 without traffic. Madison is about 50 miles west, just under an hour.

Which school district serves Oconomowoc?

The main district is the Oconomowoc Area School District. Which school serves a home depends on its exact address. Check the district’s boundary map, and call Student Services at 262-560-2155 to be sure, since the district says the map may not be exact in newer neighborhoods.

What do homes cost in Oconomowoc right now?

Here’s the current list of Oconomowoc homes for sale. For recent sales and average prices, see our Oconomowoc home values and market report. And for a price on your own home, start with a free home value estimate.

In September 2026, the median sale price for a single-family home in Oconomowoc was $641,300. Homes sold for about 99.8% of their asking price, after a median of 38 days on the market. With about 3.8 months’ supply of homes for sale, RPR rated it a seller’s market. Source: Realtors Property Resource (RPR), based on MLS listings.

Let’s talk

262-617-2725

Call or text. You work directly with me, from the first consultation to closing day.

Local details checked November 1–8, 2026, using the U.S. Census Bureau, the German Christmas Market, Oconomowoc Arts Center, Oconomowoc Historical Society, Visit Oconomowoc, the Oconomowoc Area Chamber of Commerce, Oconomowoc Public Library, the Wisconsin DNR, Aurora Health Care and the Oconomowoc Area School District. Drive times are estimates without traffic. Lake and town photos © 2026 Henry Real Estate Company. Please ask before using them.