Most expensive homes for sale in Oconomowoc, WI

4 days on Rocket

$14,995,000

7 beds • 9 baths • 20,890 sqft

4513 N Hewitts Point Rd, Oconomowoc, WI 53066

#1919354, The Bruce Gallagher Team*, Listing Office: Keller Williams Realty-Lake Country

1 day on Rocket

$5,000,000

4 beds • 4.5 baths • 8,158 sqft

N49W35398 Wisconsin Ave, Oconomowoc, WI 53066

#1920005, Morgan Fleming, Listing Office: Wiesner Real Estate, Inc

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$2,995,000

4 beds • 2.5 baths • 3,736 sqft

36082 N Beach Rd, Oconomowoc, WI 53066

#1911214, JJ Hausmann Team*, Listing Office: Compass RE WI-Lake Country

Tour

$2,990,000

4 beds • 2.5 baths • 3,586 sqft

314 Lac La Belle Dr, Oconomowoc, WI 53066

#1914017, JJ Hausmann Team*, Listing Office: Compass RE WI-Lake Country

2 days on Rocket

$10,000 Closing Credit¹

$2,400,000

4 beds • 2.5 baths • 3,200 sqft

N60W39640 Mary Ln, Oconomowoc, WI 53066

#1919940, Patrick Bolger, Listing Office: Patrick Bolger Realty Group

$10,000 Closing Credit¹

$2,349,999

5 beds • 6.5 baths • 8,500 sqft

N84W36411 Riverwood Ln, Oconomowoc, WI 53066

#1904518, Sharon Tomlinson, Listing Office: Shorewest Realtors, Inc.

$10,000 Closing Credit¹

$1,870,000

3 beds • 2.5 baths • 2,882 sqft

1330 N Dousman Rd, Summit, WI 53066

#1880450, Bonnie Lewis-Tschannen, Listing Office: Stapleton Realty

Room to negotiate?

Median Sold Price

$471.9K

Based on our April 2025 Market Report.

Tour

$10,000 Closing Credit¹

$1,798,000

3 beds • 2.5 baths • 2,384 sqft

W347N5904 Lake Dr, Oconomowoc, WI 53066

#1915571, JJ Hausmann Team*, Listing Office: Compass RE WI-Lake Country

$10,000 Closing Credit¹

$1,500,000

4 beds • 3 baths • 4,108 sqft

W340S2401 County Road C, Oconomowoc, WI 53066

#1912899, Angela Ritonia, Listing Office: First Weber Inc - Delafield

Tour

$10,000 Closing Credit¹

$1,450,000

3 beds • 3 baths • 2,595 sqft

1721 N Waterville Rd, Summit, WI 53066

#1913685, Janette Kosmal, Listing Office: Mahler Sotheby's International Realty

$10,000 Closing Credit¹

$1,200,000

4 beds • 3.5 baths • 3,900 sqft

1620 Saint Andrews Dr Unit 13, Oconomowoc, WI 53066

#1912530, Patrick Bolger, Listing Office: Patrick Bolger Realty Group

$10,000 Closing Credit¹

$1,200,000

3 beds • 4.5 baths • 4,191 sqft

1622 Saint Andrews Dr Unit 14, Oconomowoc, WI 53066

#1909277, J Tweeden & Associates Team*, Listing Office: First Weber Inc - Delafield

$10,000 Closing Credit¹

$1,199,900

4 beds • 2.5 baths • 2,800 sqft

N66W34839 Baltic Pass, Oconomowoc, WI 53066

#1917420, Gary Frankeberger, Listing Office: Keller Williams Realty-Milwaukee Southwest

$10,000 Closing Credit¹

$1,100,000

2 beds • 2 baths • 1,685 sqft

215 E Pleasant St Unit 508, Oconomowoc, WI 53066

#1903835, Patty Strong, Listing Office: Shorewest Realtors, Inc.

$10,000 Closing Credit¹

$1,075,000

2 beds • 2 baths • 2,176 sqft

215 E Pleasant St Unit 301, Oconomowoc, WI 53066

#1914099, Michael Fitzpatrick, Listing Office: First Weber Inc - Delafield

$10,000 Closing Credit¹

$885,000

4 beds • 3.5 baths • 3,224 sqft

628 Sedge Meadow Ct, Summit, WI 53066

#1917063, Robin McCormick, Listing Office: Keller Williams Realty-Lake Country

1 day on Rocket

$10,000 Closing Credit¹

$879,900

4 beds • 3 baths • 4,000 sqft

W341N7120 Northern Lights Dr, Oconomowoc, WI 53066

#1920201, Sarah Steelman, Listing Office: Lannon Stone Realty LLC

$9,499 Closing Credit¹

$799,900

4 beds • 3.5 baths • 3,012 sqft

1421 N Golden Lake Rd, Summit, WI 53066

#1917460, Andrea McHenry, Listing Office: Lake Country Flat Fee

1 day on Rocket

$9,499 Closing Credit¹

$799,900

3 beds • 2 baths • 2,344 sqft

954 N Dousman Rd, Summit, WI 53066

#1920178, Liz Tobolt, Listing Office: First Weber Inc - Delafield

$9,499 Closing Credit¹

$799,900

5 beds • 2.5 baths • 4,500 sqft

W343N7303 N Pole Ln, Oconomowoc, WI 53066

#1917450, Reid Brueser, Listing Office: T3 Realty, LLC

1 day on Rocket

$9,499 Closing Credit¹

$799,900

3 beds • 2 baths • 1,608 sqft

950 N Dousman Rd, Summit, WI 53066

#1920172, Liz Tobolt, Listing Office: First Weber Inc - Delafield

$9,488 Closing Credit¹

$799,000

6 beds • 3.5 baths • 4,311 sqft

909 Old Tower Rd, Oconomowoc, WI 53066

#1915162, Danielle Turer, Listing Office: Coldwell Banker Realty

$9,429 Closing Credit¹

$793,999

3 beds • 3 baths • 2,800 sqft

W389N7112 Pennsylvania St, Oconomowoc, WI 53066

#1906122, Westar Realty Team*, Listing Office: Westar Realty

$9,108 Closing Credit¹

$767,000

2 beds • 3 baths • 1,696 sqft

1835 N Davies Dr, Summit, WI 53066

#1914839, Julie Bushman, Listing Office: List2Sell, LLC

$8,905 Closing Credit¹

$749,900

5 beds • 3 baths • 3,460 sqft

3141 Mineral Springs Blvd, Oconomowoc, WI 53066

#1917852, Heidi Grebe, Listing Office: Shorewest Realtors, Inc.

$8,905 Closing Credit¹

$749,900

3 beds • 3.5 baths • 3,823 sqft

1200 W Mamerow Ln, Oconomowoc, WI 53066

#1919311, Michele Luebke, Listing Office: Real Broker Milwaukee

$8,668 Closing Credit¹

$729,900

3 beds • 3 baths • 4,196 sqft

949 Prairieview Cir, Oconomowoc, WI 53066

#1914298, Anthony McClintock, Listing Office: Shorewest Realtors, Inc.

Tour

$8,301 Closing Credit¹

$699,000

4 beds • 3 baths • 3,576 sqft

1271 Evergreen Trl, Oconomowoc, WI 53066

#1917231, The Elements Realty Team*, Listing Office: Elements Realty LLC

$8,038 Closing Credit¹

$676,900

3 beds • 2 baths • 2,002 sqft

1700 Whalen Dr, Oconomowoc, WI 53066

#1913651, Amy Krieghoff, Listing Office: Coldwell Banker Realty

$7,955 Closing Credit¹

$669,900

2 beds • 2 baths • 1,878 sqft

1382 Prairie Creek Cir Unit 15D, Oconomowoc, WI 53066

#1911533, Danielle Weise, Listing Office: Kings Way Realty, LLC

3 days on Rocket

$7,719 Closing Credit¹

$650,000

3 beds • 2.5 baths • 2,096 sqft

W335N8641 Stone Bank Rd, Oconomowoc, WI 53066

#1919601, Erin Waldron, Listing Office: Property Dynamics/Appraisal Specialists

$7,646 Closing Credit¹

$643,900

3 beds • 2 baths • 1,805 sqft

1746 Whalen Dr, Oconomowoc, WI 53066

#1917405, Jennifer Durand, Listing Office: Bielinski Homes, Inc.

$7,481 Closing Credit¹

$629,990

3 beds • 3 baths • 2,470 sqft

1548 Weston Ridge Rd, Oconomowoc, WI 53066

#1904803, Jennifer Villarreal, Listing Office: Villa Realty

$7,480 Closing Credit¹

$629,900

4 beds • 2.5 baths • 2,312 sqft

1721 Hammock Ln, Oconomowoc, WI 53066

#1909553, Erin Russell, Listing Office: Tim O'Brien Homes

$7,362 Closing Credit¹

$619,990

4 beds • 2.5 baths • 2,484 sqft

1581 Creekview Ln, Oconomowoc, WI 53066

#1898989, Joseph Behmke, Listing Office: Kaerek Homes, Inc.

$7,361 Closing Credit¹

$619,900

3 beds • 3 baths • 2,571 sqft

1588 Weston Ridge Rd, Oconomowoc, WI 53066

#1912046, The Elements Realty Team*, Listing Office: Elements Realty LLC

$7,302 Closing Credit¹

$614,900

4 beds • 2.5 baths • 2,172 sqft

1362 Windwood Rd, Oconomowoc, WI 53066

#1871109, David Hasbani, Listing Office: Shorewest Realtors, Inc.

1 day on Rocket

$7,183 Closing Credit¹

$604,900

2 beds • 2 baths • 1,571 sqft

1626 Belmont Ln Unit 27, Oconomowoc, WI 53066

#1920168, Danielle Weise, Listing Office: Kings Way Realty, LLC

3 days on Rocket

$7,124 Closing Credit¹

$599,900

4 beds • 3 baths • 3,067 sqft

371 Thurow Dr, Oconomowoc, WI 53066

#1919614, Paul Liebe, Listing Office: Lake Country Flat Fee

2 days on Rocket

$7,124 Closing Credit¹

$599,900

2 beds • 2 baths • 1,570 sqft

1766 Derby Ln, Oconomowoc, WI 53066

#1919794, Liana Heun, Listing Office: Priority Property Realtors LLC

Oconomowoc, WI Real Estate Market Overview

There are 58 most expensive homes for sale in Oconomowoc, WI. The following market insights reflect all property types in the Oconomowoc, WI real estate market. In April 2025 in Oconomowoc, WI there were 20.7% more homes for sale than in March 2025. Listings spent 0 days on the market in April 2025, and had a median list price of $471,950 during the same period. While more than 4 listings in Oconomowoc, WI in April 2025 were sold above asking price, there were more than 1 listings sold at asking price, and more than 1 were sold below.

From Rocket Homes Real Estate and based on county public records data

Schools near Oconomowoc, WI

Elementary Schools

Greenland Elementary School
440 Coolidge St
Public District PK-4
Park Lawn Elementary School
300 Parklawn St
Public District PK-4
Summit Elementary School
1680 E Valley Rd
Public District PK-4

Middle Schools

Silver Lake Intermediate School
555 Oconomowoc Pkwy
Public District 5-8
Nature Hill Intermediate School
850 Lake Dr
Public District 5-8

High Schools

Oconomowoc High School
641 E Forest St
Public District 9-12

Data provided by Great Schools

Most expensive homes for sale in Oconomowoc, WI

Oconomowoc, WI Real Estate Market Overview

Schools near Oconomowoc, WI

Housing market reports in Waukesha County

Homes for sale near Oconomowoc, WI

Top real estate cities in Wisconsin