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3 bedsNew constructionWith a pool
Luxury Homes in Oconomowoc, WI
18 listings

Luxury Homes in Oconomowoc, WI

Luxury Homes in Oconomowoc, WI

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18 Listings
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Luxury Homes in Oconomowoc, WI

18 Listings

  1. 215 E Pleasant Street 302 — photo47

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

Call Thomas
Active

$1,299,900

2 bd · — ba · 1,924 sqft

215 E Pleasant Street 302, Oconomowoc, WI

Tina Stapelfeldt · First Weber Inc - Delafield

  • 215 E Pleasant Street 506 — photo59Active

    $1,160,000

    2 bd · — ba · 1,446 sqft

    215 E Pleasant Street 506, Oconomowoc, WI

    Michael Fitzpatrick · First Weber Inc - Delafield

  • W350S3525 Waterville Road — photo65Active

    $1,140,000

    5 bd · — ba · 4,600 sqft

    W350S3525 Waterville Road, Oconomowoc, WI

    Dan Scardino · Point Real Estate LLC

  • 1620 Yardley Court — photo17Active

    $1,599,000

    3 bd · — ba · 3,039 sqft

    1620 Yardley Court, Oconomowoc, WI

    Bill Minett · The Real Estate Company Lake & Country

  • W358N6309 Ennis Road — photo45Active

    $1,249,900

    3 bd · — ba · 3,029 sqft

    W358N6309 Ennis Road, Oconomowoc, WI

    Erin Russell · Tim O'Brien Homes LLC

  • W358N6309 Ennis Rd — photoPrice Reduced46Active

    $1,249,900

    3 bd · 3 ba · 3,029 sqft

    W358N6309 Ennis Rd, Oconomowoc, WI

    Erin Russell · Tim O'Brien Homes LLC

  • W352N5282 Lake Drive — photo58Active

    $1,075,000

    2 bd · — ba · 1,128 sqft

    W352N5282 Lake Drive, Oconomowoc, WI

    Kimberly Stark · First Weber Inc - Delafield

  • W352N5282 Lake Dr — photoPrice Reduced55Active

    $1,075,000

    2 bd · 2 ba · 1,128 sqft

    W352N5282 Lake Dr, Oconomowoc, WI

    Kimberly Stark · First Weber Inc - Delafield

  • N62W35607 Doolan Drive — photo43Active

    $1,150,000

    3 bd · — ba · 2,380 sqft

    N62W35607 Doolan Drive, Oconomowoc, WI

    Thomas Langan · Tom Langan Real Estate

  • 3277 N Canterbury Lane — photo65Active

    $2,695,000

    5 bd · — ba · 10,150 sqft

    3277 N Canterbury Lane, Oconomowoc, WI

    Sewart Group* · Compass RE WI-Northshore

  • N57W34599 Road G - — photo81Active

    $1,674,900

    3 bd · 2 ba · 2,571 sqft

    N57W34599 Road G -, Oconomowoc, WI

    Devin Piehl · First Weber Inc - Delafield

  • N50W35310 Wisconsin Ave — photoPrice Reduced55Active

    $2,450,000

    2 bd · 2 ba · 2,010 sqft

    N50W35310 Wisconsin Ave, Oconomowoc, WI

    Devine Team* · The Real Estate Studio

  • N50W35310 Wisconsin Avenue — photo55Active

    $2,450,000

    2 bd · — ba · 2,010 sqft

    N50W35310 Wisconsin Avenue, Oconomowoc, WI

    Devine Team* · The Real Estate Studio

  • N63W35852 Frederick Dr — photo67Active

    $1,399,900

    4 bd · 4 ba · 3,953 sqft

    N63W35852 Frederick Dr, Oconomowoc, WI

    Jennifer Koutny · Grapevine Realty

  • N84W36411 Riverwood Lane — photo74Active

    $2,349,999

    5 bd · — ba · 8,500 sqft

    N84W36411 Riverwood Lane, Oconomowoc, WI

    Sharon Tomlinson · Shorewest Realtors, Inc.

  • N63W35852 Frederick Drive — photo65Active

    $1,399,900

    4 bd · — ba · 3,953 sqft

    N63W35852 Frederick Drive, Oconomowoc, WI

    Jennifer Koutny · Grapevine Realty

  • 904 W Labelle Ave — photoPrice Reduced48Active

    $2,100,000

    3 bd · 4 ba · 3,380 sqft

    904 W Labelle Ave, Oconomowoc, WI

    Amy Russell · Stapleton Realty

  • 503 N Lake Road 1 — photo24Active

    $3,391,000

    3 bd · — ba · 3,065 sqft

    503 N Lake Road 1, Oconomowoc, WI

    Jeff Scrima · Tenderland Real Estate LLC

  • Explore Oconomowoc homes

    By price

    • Under $300K
    • Under $500K
    • Under $700K
    • Luxury

    By bedrooms

    • 2 beds
    • 3 beds
    • 4 beds
    • 5 beds

    By type

    • Single family
    • Townhomes
    • Condos
    • Manufactured homes
    • Multi-family homes
    • Co-ops

    By feature

    • New construction
    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #58131-90

    Call Thomas

    Listing data & MLS disclosures

    Metro MLS
    Information is supplied by seller and other third parties and has not been verified. The multiple listing data appearing on this website, or contained in reports produced therefrom, is owned and copyrighted by MetroMLS and is protected by all applicable Copyright © 2026 laws. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2026 MetroMLS. All Rights Reserved.
    Wisconsin Real Estate Exchange (WIREX)
    IDX information is provided exclusively for consumers’ personal non-commercial use, may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and is deemed reliable but is not guaranteed by the MLS.

    Oconomowoc, WI community profile

    Population
    18,644
    Median income
    $96,663
    Housing units
    8,169
    People per sq. mi.
    166
    Area
    112.3 sq. mi.

    Source: HJN community data

    Oconomowoc housing market

    August 2026

    Oconomowoc 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 87 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 31, 2026

    Median sale price
    $590,000$432,500–$702,450 typical range
    Sales
    59
    Paid in cash
    33.9%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $649,900
    Homes for sale
    161
    Median days on market
    5 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    5.4%