18

Oconomowoc, WI Homes for Sale under $500,000

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  • N73W36308 S Shore Dr, Oconomowoc, WI 53066
    N73W36308 S Shore Dr, Oconomowoc, WI 53066
    N73W36308 S Shore Dr, Oconomowoc, WI 53066
    /23

    $499,900

    • Land
    • 2.98 Acres
    • $167,752 per Acre

    N73W36308 S Shore Dr, Oconomowoc, WI 53066

    Rare opportunity to own lake frontage property w/gorgeous sunset views & mature trees on almost 3 acres! Enjoy peaceful Ashippun Lake & 114 ft of frontage as per GIS map. Bids available for demolish/removal of existing abandoned cottage & 2 car GA. Buildable portion of lot & lake frontage zoned R-2 Residential- is approx 161 ft long with 75 ft shore setback and 75 ft wetland setback with 20 ft

    Suzy Osum Shorewest Realtors, Inc.

    N73W36308 S Shore Dr, 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
  • 435 E Harvard St, Oconomowoc, WI 53066
    435 E Harvard St, Oconomowoc, WI 53066
    435 E Harvard St, Oconomowoc, WI 53066
    /26

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    435 E Harvard St, Oconomowoc, WI 53066

    This is your chance to call a beautifully updated and conveniently located 4-bedroom, 2-bathroom Cape Cod home! Located in a quiet cul-de-sac, this home has been fully renovated, including a newer roof, siding, furnace and landscaping. The property backs up to a school, offering a serene and private setting with no rear neighbors, where you can enjoy the spacious, fully fenced backyard and deck.

    Kelly Trezek Shorewest Realtors, Inc.

    435 E Harvard St, Oconomowoc, WI 53066
  • 704 Thackeray Trail, Oconomowoc, WI 53066
    704 Thackeray Trail, Oconomowoc, WI 53066
    704 Thackeray Trail, Oconomowoc, WI 53066
    /54

    $449,900

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    704 Thackeray Trail, Oconomowoc, WI 53066

    Classic ranch home with an ideal, functional layout! The bright & spacious living room opens to dining area-perfect for dinners & game night. A built-in cabinet provides a stylish spot to display your treasures. The kitchen features abundant storage & open-concept to a stunning family room w/ built-ins, beams, & gas fireplace. Enjoy the outdoors while being inside the 3-season room. This home

    Lisa Nevinski Lannon Stone Realty LLC

    704 Thackeray Trail, Oconomowoc, WI 53066
  • 914 W Wisconsin Ave, Oconomowoc, WI 53066
    914 W Wisconsin Ave, Oconomowoc, WI 53066
    914 W Wisconsin Ave, Oconomowoc, WI 53066
    /46

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,512 Sq Ft

    914 W Wisconsin Ave, Oconomowoc, WI 53066

    Take an easy stroll to everything vibrant downtown Oconomowoc has to offer, plus live steps from Lake Lac La Belle and City Beach Park. This charming home blends classic character with smart updates. Recent upgrades per seller: dishwasher (2025), living room flooring (2024), hot water heater (2023), washer/dryer (2023), exterior paint (2023), trash compactor (2023), built-in oven/microwave

    Gregg Willich Logan Marshall Realty LLC

    914 W Wisconsin Ave, Oconomowoc, WI 53066
  • N51W34681 W Wisconsin Ave Unit 3116, Oconomowoc, WI 53066
    N51W34681 W Wisconsin Ave Unit 3116, Oconomowoc, WI 53066
    N51W34681 W Wisconsin Ave Unit 3116, Oconomowoc, WI 53066
    /26

    $494,900

    • 2 Beds
    • 2 Baths
    • 1,642 Sq Ft

    N51W34681 W Wisconsin Ave Unit 3116, Oconomowoc, WI 53066

    One of the best and largest units at Mission Lakes condominiums in Okauchee Village!This corner unit-top level condo provides sweeping views of clean spring fed Florence lake from every room. Open kitchen /dining /great room with vaulted ceilings, gas FP, and balcony deck. Quality finishes include custom Maple cabinetry and millwork, granite countertops, wood and ceramic floors. A split bedroom

    Lawrence Burger Lightning Realty LLC

    N51W34681 W Wisconsin Ave Unit 3116, Oconomowoc, WI 53066
  • 954 N Dousman Rd, Oconomowoc, WI 53066
    954 N Dousman Rd, Oconomowoc, WI 53066
    954 N Dousman Rd, Oconomowoc, WI 53066
    /77

    $499,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 2,344 Sq Ft

    954 N Dousman Rd, Oconomowoc, WI 53066

    Lake Country best lake front value with 383' (+/-) frontage on Lower Genesee Lake. Enjoy lake front living including boating, water skiing, kayaking, fishing and swimming in clean water. Sandy frontage in a private setting. Bring your decorating ideas to this 4 bedroom, 2 full bath home. Family room with vaulted ceiling, and wood burning stove for those cozy winter nights. Large park like lot to

    Liz Tobolt First Weber Inc - Delafield

    954 N Dousman Rd, Oconomowoc, WI 53066
  • 1420 Arrowwood Circle West St Unit 38120301, Oconomowoc, WI 53066
    1420 Arrowwood Circle West St Unit 38120301, Oconomowoc, WI 53066
    1420 Arrowwood Circle West St Unit 38120301, Oconomowoc, WI 53066
    /3

    $495,100 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    The Weston Plan at Arrowood, Oconomowoc, WI 53066

    FROM THE MOMENT YOU WALK THROUGH the front door of The Weston, it feels like home. The open floor plan is perfect for evenings entertaining friends or for simply snuggling into the couch with popcorn during movie night. Picture yourself in the owner’s suite sleeping in on those lazy Saturdays. And that charming front porch – it’s the perfect place to press pause and sip some freshly squeezed

    Veridian Homes Builder
    1420 Arrowwood Circle West St Unit 38120301, 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 37164486, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 37164486, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 37164486, Oconomowoc, WI 53066
    /5

    $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
  • 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
    /5

    $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
  • 1420 Arrowwood Circle St W Unit 36733408, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733408, Oconomowoc, WI 53066
    /2

    $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
  • 1420 Arrowwood Circle St W Unit 36733399, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733399, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733399, Oconomowoc, WI 53066
    /3

    $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
  • 1420 Arrowwood Circle St W Unit 36733391, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733391, Oconomowoc, WI 53066
    1420 Arrowwood Circle St W Unit 36733391, Oconomowoc, WI 53066
    /3

    $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
  • 1011 Elderberry Rd, Oconomowoc, WI 53066
    1011 Elderberry Rd, Oconomowoc, WI 53066
    /2

    $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
  • 997 Elderberry Rd, Oconomowoc, WI 53066
    997 Elderberry Rd, Oconomowoc, WI 53066
    /2

    $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
  • 1117 Elderberry Rd, Oconomowoc, WI 53066
    1117 Elderberry Rd, Oconomowoc, WI 53066
    /2

    $449,900 New Construction

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

    1117 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
    1117 Elderberry Rd, Oconomowoc, WI 53066
  • 1121 Elderberry Rd, Oconomowoc, WI 53066
    1121 Elderberry Rd, Oconomowoc, WI 53066
    /2

    $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
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 31 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
$567,800
Median 2 Bedroom Sale Price
$482,400
Median 1 Bedroom Sale Price
$519,900
Average Price Per Sq Ft
$307
Number of Homes for Sale
270
Last 12 months Home Sales
525
Months of Supply
6.20
Median List Price
$575,000
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 18 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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