14

Oconomowoc, WI Homes for Sale under $500,000

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  • N566 Westview Dr, Oconomowoc, WI 53066
    N566 Westview Dr, Oconomowoc, WI 53066
    N566 Westview Dr, Oconomowoc, WI 53066
    /15

    $475,000

    • 3 Beds
    • 2 Baths
    • 3,298 Sq Ft

    N566 Westview Dr, Oconomowoc, WI 53066

    Fantastic split ranch home on over 1/2 acre lot. Vaulted ceiling in living room with lovely stone gas fireplace, open to dinette and kitchen with loads of cabinet space, breakfast bar, hardwood floors and pantry. Huge primary suite with walk-in closet. Two nice sized bedrooms, full bathroom, formal dining room/office space, and laundry room complete the main level. Finished lower level with

    Craig Schmitz Redefined Realty Advisors LLC

    N566 Westview Dr, Oconomowoc, WI 53066
  • 909 York Imperial Dr, Oconomowoc, WI 53066
    909 York Imperial Dr, Oconomowoc, WI 53066
    909 York Imperial Dr, Oconomowoc, WI 53066
    /37

    $495,000 Open Fri 5PM - 6:30PM

    • 3 Beds
    • 2 Baths
    • 2,158 Sq Ft

    909 York Imperial Dr, Oconomowoc, WI 53066

    Welcome to your new home located in the beautiful Orchards neighborhood in the heart of Oconomowoc. This stunning 3 Bed, 2 bath cozy family floor plan is sure to be the perfect place to make the happiest memories. Plenty of updates, private yard, 2 car garage and more. You must see to appreciate. The location is prime, close to everything that creates joy in life. Schedule your showing today.

    Corienne Walek Keller Williams Realty-Lake Country

    909 York Imperial Dr, Oconomowoc, WI 53066
  • 1420 Arrowwood Circle St W Unit 36788963, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36788963, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36788963, Oconomowoc, WI 53066
    /4

    $485,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,575 Sq Ft

    The Harlequin Plan at Arrowood, Oconomowoc, WI 53066

    Work and play. Play and work. The kitchen island in The Harlequin is fully equipped for both. Mix up your mother’s red velvet cake recipe. Chat with your friends over coffee and scones. Prepare your financials. Store your new pots and pans in the cabinets below. Toast to a happy home. This kitchen island allows you to do it all, within the comfort of your own home. Meet The Harlequin. All prices,

    Veridian Homes Builder
    1420 Arrowwood Circle St W Unit 36788963, Oconomowoc, WI 53066
  • W277 Madison Ave, Oconomowoc, WI 53066
    W277 Madison Ave, Oconomowoc, WI 53066
    W277 Madison Ave, Oconomowoc, WI 53066
    /23

    $409,900

    • 3 Beds
    • 1.5 Baths
    • 1,288 Sq Ft

    W277 Madison Ave, Oconomowoc, WI 53066

    This charming ranch is nestled on a generous lot and is conveniently located to downtown Oconomowoc and Lac La Belle. Many recent updates including a newly replaced furnace (2024), air conditioning (2024), water heater (2023), new carpeting, newly remodeled bathroom, updated kitchen cabinets, roof shingles replaced on home only (2018) and new fence (2023) make this ready to move in. It will not

    Anthony Alesci Alesci Realty

    W277 Madison Ave, Oconomowoc, WI 53066
  • 1420 Arrowwood Circle St W Unit 36733391, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733391, Oconomowoc, WI 53066
    /2

    $496,700 New Construction

    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft

    The Julian(Twin Home) Plan at Arrowood, Oconomowoc, WI 53066

    This year, it’s your turn to host the holidays. And with The Julian, you’ve got this. The island has been lined with all of your favorite fixings. The table is set. You’ve dressed the guest bed in new linens. It’s time to make beautiful memories in home that is so perfectly you. Welcome to The Julian. All prices, promotions and specifications are subject to change at any time without notice based

    Veridian Homes Builder
    1420 Arrowwood Circle St W Unit 36733391, Oconomowoc, WI 53066
  • 1420 Arrowwood Circle St W Unit 36733399, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733399, Oconomowoc, WI 53066
    /2

    $467,400 New Construction

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft

    The Olivia Twin Home Plan at Arrowood, Oconomowoc, WI 53066

    SAY HELLO TO EASY LIVING. Open, airy and all on one floor, The Olivia was designed to take a few things off your plate. Get lost preparing your favorite recipe in the kitchen while the fireplace crackles in the corner. Curl up with that memoir you’ve been meaning to devour in the flex room, then retreat to the owner’s suite for your very own private oasis. Enjoy a life of rest and relaxation in

    Veridian Homes Builder
    1420 Arrowwood Circle St W Unit 36733399, Oconomowoc, WI 53066
  • 1121 Elderberry Rd, Oconomowoc, WI 53066
    1121 Elderberry Rd, Oconomowoc, WI 53066
    1121 Elderberry Rd, Oconomowoc, WI 53066
    /18

    $464,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    1121 Elderberry Rd, Oconomowoc, WI 53066

    Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1121 Elderberry Rd, Oconomowoc, WI 53066
  • 997 Elderberry Rd, Oconomowoc, WI 53066

    $484,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft

    997 Elderberry Rd, Oconomowoc, WI 53066

    Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    997 Elderberry Rd, Oconomowoc, WI 53066
  • 1007 Elderberry Rd, Oconomowoc, WI 53066
    1007 Elderberry Rd, Oconomowoc, WI 53066
    1007 Elderberry Rd, Oconomowoc, WI 53066
    /5

    $444,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,317 Sq Ft

    1007 Elderberry Rd, Oconomowoc, WI 53066

    Move-in Ready 77 ARW Wyatt Cottage Unit B - TWIN HOME. Available 12/23/25 Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes with private yards. Monthly association fee of $245 covers lawn mowing, fertilization, and snow removal; plus a la carte seasonal services are available for a separate rate. Built by Wisconsin's leading homebuilder, you can expect

    Tamra Litzau Shorewest Realtors, Inc.

    1007 Elderberry Rd, Oconomowoc, WI 53066
  • 1420 Arrowwood Circle St W Unit 36733408, Oconomowoc, WI 53066

    $439,700 New Construction

    • 2 Beds
    • 2 Baths
    • 1,304 Sq Ft

    The Wyatt Twin Home (Haven) Plan at Arrowood, Oconomowoc, WI 53066

    WHOEVER SAID LIVING WITHIN YOUR MEANS HAS TO BE DULL? The Wyatt provides convenience, innovation and satisfaction all in one intelligently designed package. Friends, neighbors and relatives alike will marvel at your gleaming custom built cabinetry. They’ll likely turn green with envy if they get a peek at your energy bills. They could even get too comfortable. Buyers beware: guests may tend to

    Veridian Homes Builder
    1420 Arrowwood Circle St W Unit 36733408, Oconomowoc, WI 53066
  • 1011 Elderberry Rd, Oconomowoc, WI 53066

    $444,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,304 Sq Ft

    1011 Elderberry Rd, Oconomowoc, WI 53066

    Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1011 Elderberry Rd, Oconomowoc, WI 53066
  • 1498 Olde Highlander Dr, Oconomowoc, WI 53066
    1498 Olde Highlander Dr, Oconomowoc, WI 53066
    1498 Olde Highlander Dr, Oconomowoc, WI 53066
    /30

    $400,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,490 Sq Ft

    1498 Olde Highlander Dr, Oconomowoc, WI 53066

    NEW CONSTRUCTION Buildable Floor plan - The Quentin! Discover The Quentin, a thoughtfully laid out 2 bedroom, 2.5 bath townhome featuring an open-concept first floor ideal for modern living and entertaining. The spacious Great Room flows seamlessly into a beautifully appointed Kitchen complete with a large center island and a corner walk-in pantry. The upstairs, offers two private suites, each

    Paige Sederberg Harbor Homes Inc

    1498 Olde Highlander Dr, Oconomowoc, WI 53066
  • 1420 Arrowwood Circle St W Unit 37164486, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 37164486, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 37164486, Oconomowoc, WI 53066
    /4

    $493,600 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    The Astoria Plan at Arrowood, Oconomowoc, WI 53066

    The Astoria, with an open, airy floor plan and an abundance of natural light – it’s the perfect place to call home. Grab the popcorn for family movie night in the great room. Gather around the large kitchen island while you make blueberry pancakes on Saturday morning. Wave hello to neighbors from your farmhouse front porch. You can already see the memories being made. Welcome home to The Astoria.

    Veridian Homes Builder
    1420 Arrowwood Circle St W Unit 37164486, Oconomowoc, WI 53066
  • W355N5745 Lisbon Rd, Oconomowoc, WI 53066
    W355N5745 Lisbon Rd, Oconomowoc, WI 53066
    W355N5745 Lisbon Rd, Oconomowoc, WI 53066
    /38

    $489,000

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    W355N5745 Lisbon Rd, Oconomowoc, WI 53066

    Remarkable home in the popular Misty Meadows neighborhood has a spacious yard that adjoins 22 acres of expansive green space dotted with towering trees. Enjoy the views and the summer fireworks show from the deck or the adorable screened in gazebo. The lovely interior features hardwood floors, new matte black door hardware, new ceiling lights and fans, and tons of windows. The kitchen sparkles

    Nicole Gillette The Real Estate Company Lake & Country

    W355N5745 Lisbon Rd, Oconomowoc, WI 53066
Wisconsin Waukesha County Oconomowoc

Real Estate & Homes in Oconomowoc, WI under $500,000

Home Trends in Oconomowoc, WI

On average, homes in Oconomowoc, WI sell after 32 days on the market compared to the national average of 53 days. The median sale price for homes in Oconomowoc, WI over the last 12 months is $560,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$560,000
Median Single Family Sale Price
$559,900
Median 2 Bedroom Sale Price
$520,000
Median 1 Bedroom Sale Price
$460,000
Average Price Per Sq Ft
$300
Number of Homes for Sale
80
Last 12 months Home Sales
523
Months of Supply
1.80
Median List Price
$569,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Oconomowoc, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 14 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Oconomowoc, WI and find the perfect fit for your homeownership goals.

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