Oconomowoc truly embodies the spirit of Lake Country. As one of only two cities in all of Wisconsin to have not one, but two lakes accessible from the downtown area, Oconomowoc has become a premier living destination for young families and professionals alike. Located on the Interstate 94 corridor, living in Oconomowoc makes for an easy commute to either Milwaukee or Madison, while maintaining a friendly, small-town atmosphere. Home to several unique shops, restaurants, recreational opportunities, and a wealth of residential services, it’s no wonder this area is fast-growing.
Oconomowoc has a long history of delighting its residents with a healthy downtown and several points of interest. In fact, following the arrival of the railroad, Oconomowoc became a favorite summer retreat for tourists and wealthy vacationers from all major Midwest cities, including several well-known beer barons. Some of the nation’s most affluent families were drawn to the excitement of the area and built stately summer homes on the lakes, most still present today. In the 1880’s Oconomowoc featured six luxury resorts and from then until the Great Depression, it was fondly known as the “Newport of the West.”
See all that Oconomowoc has to offer:
Single-Family
631 Wilson St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
50Picture(s)
2,400Sqft
Located in the Presidents District neighborhood makes for a leisurely stroll to downtown Oconomowoc, Fowler Park, or one of the nearby schools. The solid 4-bedroom boasts a large yard, backyard deck and enough green space to toss around a football. Beautiful living room with loads of natural light with hard wood floors, natural fireplace and open to a formal dining room.
$550,000
Single-Family
N67W34613 County Hwy K -, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
52Picture(s)
3,000Sqft
Here is your opportunity to enjoy all Okauchee Lake living has to offer, 1.7 acres & the main lake! Southern exposure tree lined property gives you the privacy & serenity not found on many lake homes. Tennessee marble stone exterior, property has been in the family for over 70 years, complete remodel in 1992.
$2,299,000
Single-Family
1222 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,879Sqft
Move-In Ready 107 ARW Sawyer Craftsman - Available 4/24/26All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, much better than a typical used home. As your local home builder, you can expect the best local brands and trades for your home as well.
$562,900
Single-Family
1855 S River Lakes Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3/1Bathroom(s)
40Picture(s)
2,480Sqft
Beautifully Updated Pabst Farms Ranch! This 3BR, 3.5BA home feels like new with extensive upgrades throughout. Enjoy all-new windows, refreshed Kitchen with stainless steel appliances, gleaming hardwood floors, updated lighting, and newly finished organized closets. Soaring ceilings and crown molding elevate the open, airy Great Room featuring a gas fireplace and adjoining formal Dining Room.
$705,000
Single-Family
743 Royal Troon Ct, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
97Picture(s)
4,738Sqft
Tucked away on a quiet cul-de-sac, this custom-built residence offers an exceptional blend of elegance, privacy, & timeless design. From your arrival, the dramatic roofline & stately presence create a lasting first impression, setting the tone for the quality & craftsmanship found throughout the home.
$899,900
Single-Family
1525 River Highlands Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
40Picture(s)
2,027Sqft
Live That Lake Country Life Without the Lake Country Price! Less than 2 miles from City Beach & Veterans Memorial Park on Lac La Belle, this 3BR 3BA Mid-Century Ranch delivers convenience & comfort throughout. Generous living space, elegant bay window & recessed lighting will be a few initial impressions.
$449,900
Single-Family
1364 Periwinkle Pass, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
37Picture(s)
2,021Sqft
Remarkable new construction ranch home in Oconomowoc's Prairie Creek Ridge! This beautiful home offers a vaulted open concept living area, split bedroom design, and an exposed lower level with full size windows. LVP flooring though main living areas. Great room has gas fireplace. Kitchen features quartz countertops, island breakfast bar, and large walk-in pantry.
$649,900
Vacant Land
W343N6205 Bayview Rd, Oconomowoc, Wisconsin 53066
14Picture(s)
0Sqft
OKAUCHEE LAKE. This is a once in a lifetime opportunity to build your dream home on one of Lake Country's most coveted properties. It sits on the Gold Coast of Okauchee Lake and was once the original and famous Breezy Point. This parcel features 250 feet of level shoreline frontage with a southern exposure for full sun all day and views of the entire lake.
$3,700,000
Single-Family
987 Prairieview Cir, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3Bathroom(s)
59Picture(s)
3,426Sqft
Tucked into sought-after Longmeadow on rare lot backing to green space, this well-maintained ranch delivers flow that simply make sense. Vaulted ceilings & southeast-facing windows flood the home w/light & airiness. Kitchen is both functional and elevated, with generous counter space and an oversized pantry.
$650,000
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
40Picture(s)
1,485Sqft
Experience elevated living in this exceptional 2 bed, 2 bath 3rd floor end unit residence. Filled with natural light from expansive windows and enhanced by soaring cathedral ceilings, this home showcases upscale cabinetry, granite countertops and premium appliances. Enjoy an in-unit washer and dryer, 2 deeded underground parking spaces and private storage.
$435,000
Single-Family
1751 Switchgrass St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,788Sqft
Cozy split ranch located in Oconomowoc's Prairie Creek Ridge! Vaulted ceiling spans across Kitchen & Great Room. Kitchen features soft close cabinets, exterior vented range hood & walk-in pantry. Great room is complete with electric fireplace w/ shiplap. Primary suite is tucked in the back of the home & includes a box tray ceiling, 2 WICs, tiled shower & double sinks in vanity.
$619,900
Single-Family
959 Lagom Way, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
15Picture(s)
1,980Sqft
NEW CONSTRUCTION Buildable Floor Plan - Our Alexander model is a 2-story 3 bed, 2.5 bath townhome with an open concept first floor. The Kitchen includes a walk in pantry, a large island and soft close cabinetry. The Great Room features plenty of natural light and 9' ceilings. In addition, the first floor offers a Powder Room and Rear Foyer with WIC.
$474,900
Condominiums
1763 Derby Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private GarageParking(s)
46Picture(s)
2,179Sqft
Why wait for new construction when you can move right into this exceptional Kingsway condo, truly better than new and perfectly located in desirable Pabst Farms. The gourmet kitchen features quartz countertops, a spacious pantry, and an open flow to the dining and living area with soaring 10' coffered ceilings, a cozy gas fireplace, and expanded patio doors to a private concrete patio.
$628,000
Single-Family
W379N5787 Meadowview Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
21Picture(s)
1,065Sqft
Excellent ranch home in a great neighborhood and location just north of downtown Oconomowoc! Enjoy this great setting featuring a large lot with mature trees and fenced-in back yard. Interior includes an open concept main living area. Gorgeous new kitchen has new cabinets, quartz countertops, SS appliances included, and pantry. Open dining room. Stone natural fireplace in living room.
$349,900
Condominiums
W398N5975 Autumn Woods Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
41Picture(s)
1,824Sqft
Say goodbye to shoveling and mowing! This spacious upper-level 3-bedroom condo is ideally located just minutes from Downtown Oconomowoc and close to the Lac La Belle public launch. The versatile den offers the perfect space for a home office, fitness area, or flex room, with ample storage throughout.
$329,900
Single-Family
805 Oakwood Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
52Picture(s)
1,927Sqft
Live just steps from Fowler Lake and walk to downtown Oconomowoc's charming shops, restaurants, coffee spots, and lakefront parks. This fully updated ranch offers 3 oversized bedrooms and 2 full baths, elevated with designer lighting, stunning blonde oak LVP flooring, and plush new carpet. Sunlight fills the spacious living room, anchored by a beautiful fireplace for cozy nights at home.
$599,900
Single-Family
1367 Scotsland Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
18Picture(s)
2,780Sqft
The Juneberry-Modern Sprawling 2-Story located on lot 85 in Olde Highlander! Community will feature a range of amenities including a walking path, swimming pool, clubhouse & more! Kitchen features stained soft close cabinets, tile backsplash, ext vented range hood & island w/ seating space. Great Room includes a cozy electric fireplace w/ stone detail.
$689,900
Single-Family
N55W34691 Lake Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
24Picture(s)
1,096Sqft
Quaint cottage with southern exposure on a bluff above serenity bay. Nice shallow path to your frontage. You'll enjoy calm waters for paddle boarding or pontoon rides. Golden mast, Hideaway, and Han's island all have casual dining and drinks to enjoy. You can take the short journey by water to the big lake or lower/little Okauchee and upper Oconomowoc lake.
$679,000
Single-Family
1750 Switchgrass St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
6Picture(s)
2,502Sqft
Welcome home to The JULIA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 Beds, 3.5 Baths and a 3 Car garage. Lot is flat. The kitchen comes w/ quartz countertops, soft close cabinetry and LG appliance package. LVP flooring in kitchen, dinette, and great room. We equip our homes with Smart Technology such as a Ring Doorbell and touchless faucet.
$729,900
Single-Family
1252 Wild Rye Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,851Sqft
The Lauren 1851 that places the generously sized primary bedroom & shared living spaces - including the gathering room w/ GFP, kitchen, & dining area - at the back of the home for privacy. A large island that doubles as a snack bar, spacious walk-in-pantry, quartz counters & ample storage cabinets in the kitchen provide the perfect space for meal prep.
$644,900
Single-Family
1268 Wild Rye Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,404Sqft
This home is under construction. The Arielle 2404 is a plan that offers all the essential living spaces starting w/ the kitchen, which features a walk-in-pantry, quartz counters, appliances & prep island w/ extra seating. The gathering room offers a cozy gas fireplace. Finishing the first floor is a flex space/home office, powder room & large mudroom w/ a built-in bench & storage.
$675,900
Single-Family
1260 Wild Rye Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,809Sqft
This home is under construction. This Rylee is a split-bedroom ranch home currently under construction. The oversized gathering room w/ GFP offers the opportunity to create multiple seating layouts. The kitchen has quartz counters, tile backsplash, a walk-in pantry, & a prep island w/ seating.
$634,900
Single-Family
1702 Switchgrass St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,428Sqft
This home is under construction. The Francesca 2428 is an ideal home that needs both communal & private spaces. The 1st-floor is home to the gathering room, formal dining room, & dinette. The kitchen features quartz counters, a prep island w/ seating, walk-in pantry, s.s. appliances, & tile backsplash. The main floor also features a private home office.
$724,900
Single-Family
1721 Arthurs Pass, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
42Picture(s)
2,031Sqft
This beautiful two year new home in Morgan Station is the one you've been waiting for & move in ready! Better than new construction, with a open floor plan makes entertaining a breeze. Spacious eat-in KT w/quartz center island, large pantry & elegant tile backsplash. Two story GR is washed in natural light, overlooks the backyard & patio.
$574,900
Single-Family
222 Pleasant St, Oconomowoc, Wisconsin 53066
5Bedroom(s)
4Bathroom(s)
50Picture(s)
3,400Sqft
Sophisticated luxury meets casual elegance in this newly constructed custom lakefront home on historic Fowler Lake. With 5 BRs & 4 BAs, it offers the rare opportunity to enjoy lake living in the heart of downtown Oconomowoc. Spend summer days boating, swimming, or fishing. Enjoy weekly waterski shows & watch 4th of July fireworks from your own back yard.
$3,499,900
Single-Family
542 Oakwood Ave, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
24Picture(s)
985Sqft
This charming 1920's bungalow is ideally located right next to Fowler Park, offering immediate access to green space, recreation, and impressive views of Fowler Lake. Enjoy easy sidewalk access all the way around the almost-2-mile lake loop, which can include stops on the boardwalk or downtown shopping and dining.
$326,500
Single-Family
N56W36792 Cherokee Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
45Picture(s)
1,570Sqft
Stunning, updated ranch home in the Town of Oconomowoc, set on a beautiful, established wooded .7-acre lot just minutes from downtown amenities, shopping, and restaurants.
$520,000
Single-Family
227 Shore Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
54Picture(s)
2,483Sqft
Meticulously maintained, this beautiful Colonial offers 4 bedrooms & 3.5 baths in an unbeatable location! Backing up to peaceful a conservancy, this home provides privacy & scenic views while being just minutes from amenities & walking trails. The thoughtfully designed floor plan features spacious room sizes, ideal for everyday living.
$599,000
Vacant Land
1330 Prairie Creek Blvd, Oconomowoc, Wisconsin 53066
8Picture(s)
0Sqft
Build your dream home in established Prairie Creek Ridge neighborhood! This prime lot offers spectacular sunset views overlooking the conservancy, a lovely arborvitae hedge, plum trees and potential for a partially exposed lower level. Enjoy easy access in and out of the neighborhood - no winding roads. Just blocks from Meadow View Elementary, Oconomowoc Park and close to shopping and dining.
$159,900
Single-Family
N58W39641 Sunnyfield Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
60Picture(s)
1,752Sqft
Enjoy peaceful, easy living in this beautifully updated ranch on a private .703-acre lot in Sunnyfield Acres, with easy access to Lac La Belle for kayaking and quiet lake time. Major updates include a new roof and gutters (2025), professional landscaping (2025), newer windows (2017), siding (2017), and a low-maintenance privacy fenced yard (2022).
$450,000
