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
1754 Switchgrass St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
8Picture(s)
2,806Sqft
House in rough trades. Completion 2026.4 bedrooms/2.5 bath/elite series split ranch. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Ceramic tiled walk-in shower w/2 shower heads/double sinks in master bath. Double sinks family bath. WIC's all bedrooms. 9' main floor ceilings/pitched ceiling in living room & foyer/tray ceiling master bedroom.
$799,990
Single-Family
1121 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,592Sqft
Move-in Ready 90 ARW Olivia Cottage II Unit B, Ground Level Foundation TWIN HOME! AVAILABLE 12.9.25! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes w/ private yards. Monthly association fee of $245 covers lawn mowing, fertilization, & snow removal; plus a la carte seasonal services are available for a separate rate.
$464,900
Condominiums
503 Lake Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3/1Bathroom(s)
Private GarageParking(s)
9Picture(s)
2,770Sqft
Discover timeless elegance at this exclusive Lavinia by the Lakes bespoke condo on Oconomowoc's historic isthmus, crafted for those who cherish sophistication and serene lakeside living. Nestled between Fowler Lake and Lac La Belle, enjoy panoramic stunning sunrise and sunset views.
$2,991,000
Single-Family
1117 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,592Sqft
Move-in Ready 89 ARW Olivia Cottage II Unit A, Ground Level Foundation TWIN HOME! AVAILABLE 12.9.25! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes w/ private yards. Monthly associate fee of $245 covers lawn mowing/fertilization/snow removal; plus a la carte seasonal services are available for a separate rate.
$449,900
Single-Family
W354N5252 River Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
44Picture(s)
1,530Sqft
Charming Cape Cod home, steps away from Okauchee Lake & all the fun this area has to offer. Bright & inviting, this 2 bed, 2 bath home features large windows that flood the space with natural light. The freshly painted interior offers a main floor primary bedroom and laundry.
$449,000
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
41Picture(s)
1,495Sqft
Welcome to Mission Lakes Condominium where serene lakefront living blends seamlessly with sophisticated design. The beautifully updated 2-bed, 2-bath features open-concept living that maximizes comfort &style. Step into the spacious great room, where a sleek gas fireplace anchors the space & sets a cozy tone.
$434,900
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
61Picture(s)
1,300Sqft
Well maintained Fowler Lake 2BR, 2Ba Condo with many updates. Enjoy Lake living within walking distance to downtown. Lake views from every room and from your wrap around balcony. Nicely updated throughout. Newer kitchen with new cabinets, granite countertops and SS appliances. Updated baths with heated floors & newer vanities with granite tops. Spacious master suite with walk-in closet.
$388,900
Vacant Land
00 Riverwood Lane S10 T8N R17E Ln, Oconomowoc, Wisconsin 53066
5Picture(s)
0Sqft
Saddlebrook Farms listing of a rare 35 acre vacant-land property in the Lake Country area that is nestled among similar large single family tracts, all enclosed with wood fences. Located north of the city of Oconomowoc, the land is ready for developing into an attractive life-style living farm.
$825,000
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
31Picture(s)
1,458Sqft
Don't wait to see this premium 3rd flr condo with panoramic views of Florence Lake from every room and the balcony! Positioned in the bend of the building, it has a larger feel than standard units, offering a more open and airy layout. Some features include vaulted ceilings, gas FP, in-unit laundry, walk-in closets, bamboo flrs, high end carpet in both br's & beautiful window treatments.
$469,000
Single-Family
35300 Pabst Rd, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
23Picture(s)
5,973Sqft
Discover this exceptional custom estate on 14 private acres in the prestigious Village of Oconomowoc Lake. This luxury retreat offers a rare blend of sophistication and seclusion, featuring wooded, huntable land and stunning outdoor spaces. Enjoy a wrap-around deck, multiple entertaining areas, and a finished outbuilding perfect as a she shed or man cave.
$2,300,000
Vacant Land
N56W36834 Lisbon Rd, Oconomowoc, Wisconsin 53066
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0Sqft
Location Location Location! Close proximity to downtown Oconomowoc and down town Okauchee as well as easy highway access. Bring your own builder to this beautiful non-HOA level lot with mature trees. No neighbors to the south or the north. There is also a 77x84 deeded area on the neighbor to the north for a future septic mound.
$185,000
Single-Family
1529 Miller Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
51Picture(s)
3,155Sqft
No need to build when you can buy this Briarstone Signature Series ranch by Kaerek w/custom features & finishes in highly desirable neighborhood of Prairie Creek Ridge! Entertaining possibilities are endless from main level open concept layout to LL rec room spaces.
$689,900
Condominiums
1640 Toscano Ter, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
32Picture(s)
1,903Sqft
Stunning European-style condo with breathtaking lake views from every room! CUSTOM build by Kingsway- upgrades throughout! This elegant home features timeless architectural details, an open-concept layout, and built-in wine bar--perfect for entertaining. Enjoy a luxury kitchen with high-end finishes and abundant natural light throughout.
$889,000
Single-Family
1749 Hammock Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,432Sqft
Charming 2-story home located in Prairie Creek Ridge! The Evergreen features upgrades throughout. The welcoming front foyer leads to a flex room w/ French doors, making a great office or playroom. Kitchen has a spacious island w/ overhang, soft close cabinets, oversized pantry, ext vented range hood & kitchen sink below a window overlooking the backyard.
$629,900
Condominiums
320 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
UndergroundParking(s)
37Picture(s)
1,222Sqft
Experience the perfect blend of tranquility and convenience in this beautifully updated 2-bedroom, 2-bath corner unit on scenic Fowler Lake. Remodeled in 2019, this spacious condo features an open-concept layout, abundant natural light, and a private balcony ideal for morning coffee.
$389,000
Single-Family
N79W34221 Petersen Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
1/1Bathroom(s)
34Picture(s)
1,482Sqft
Sprawling ranch on nearly 2 acres in the Stone Bank/Arrowhead School District! Fully updated, low taxes (under $3k 2025 net tax), & no HOA! Features: 4 BED, 1.5 BA, 2.5+ Car GA. Set on a mature 1.87-acre lot w/ a stately brick exterior, colorful landscaping, towering trees, & a true park-like backdrop.
$480,000
Single-Family
208 Maple Ter, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
50Picture(s)
2,310Sqft
Discover this beautifully maintained 1950s Lannon stone Cape Cod, situated in the desirable Maple Terrace neighborhood, within walking distance of vibrant downtown Oconomowoc. Enjoy the rare privilege of deeded ownership in a private park on Lac La Belle, complete with pier and boat slip rights for lakefront access.
$850,000
Condominiums
291 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
25Picture(s)
1,750Sqft
Spectacular end unit with panoramic views! This highly desirable condo features three spacious bedrooms, two full bathrooms and a three season patio that has one of the best views in Oconomowoc! The living area is bright, highlighted by the north and east facing windows warmed by a cozy gas fireplace. The galley kitchen features solid surface countertops and includes all appliances.
$325,000
Single-Family
1017 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,720Sqft
Move-in Ready 79 ARW Julian Cottage II Unit A, TWIN HOME! AVAILABLE 11/25/25! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes w/ private yards. Monthly association fee $245 covers lawn mowing, fertilization, & snow removal; plus a la carte seasonal services are available for separate rate.
$539,900
Single-Family
1088 Evergreen Trl, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
41Picture(s)
1,893Sqft
The Ranch You've Been Waiting For!Welcome to this beautiful 3-bedroom, 2-bathroom split ranch built by Stepping Stone Homes. Situated on a serene outlot with a peaceful pond, this home offers both comfort and charm. Enjoy an open-concept layout featuring a vaulted great room, a versatile flex room, and stunning quartz countertops.
$569,900
Single-Family
W357N7134 Rainbow Ter, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
25Picture(s)
1,552Sqft
Come check out this beautiful 3BR family home on nearly 3/4 acre lot located in the highly rated oconomowoc schools district! New vinyl siding with maintenance free aluminum trim, updated full bath, LVP flooring and granite countertops in Kitchen. Large family room with natural brick fireplace perfect for entertaining.
$424,900
Single-Family
372 River Bluff Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3/1Bathroom(s)
78Picture(s)
3,345Sqft
Inviting ranch home in River Bluff - located just minutes from downtown Oconomowoc, yet wrapped in wooded seclusion. Airy & open floorplan flows from entry to great room, dining, family, & 3-season rms where walls of windows blur the line between indoors & out. A skylit kitchen offers generous cabinet space & room to gather.
$724,900
Single-Family
W342N5150 Road P -, Oconomowoc, Wisconsin 53069
6Bedroom(s)
4/1Bathroom(s)
53Picture(s)
7,268Sqft
Unparalleled lakeside luxury awaits with 139' of Okauchee Lake frontage, 3 piers, and a rare wet boathouse on 1.5+ acres. Inside, 7,000 + sq. ft. of custom design offers soaring ceilings, walls of windows, and a chef's kitchen perfect for entertaining. Retreat to a main-level primary suite with a sitting area, spa bath, and rooftop perch.
$5,250,000
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
N66W34306 Primrose Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
75Picture(s)
4,523Sqft
Welcome to Bay View Estates! This beautiful home is designed with families in mind. Step inside and enjoy soaring ceilings, welcoming arched entryways, a charming leaded glass front door, and a kitchen that's perfect for gathering with friends and family. A convenient main floor laundry and spacious 3.5-car garage add to everyday ease.
$799,900
Condominiums
N55W35025 Coastal Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
Private GarageParking(s)
32Picture(s)
2,195Sqft
Stunning 3-bedroom, 2.5-bath condo in desirable Lake Country offers style, comfort, and convenience. Featuring an open-concept design with engineered hardwood floors, quartz countertops, tray ceilings, and a cozy gas fireplace, this unit blends elegance with functionality. The kitchen flows seamlessly into the dining and living areas, perfect for entertaining.
$634,900
Condominiums
1047 Ann Marie Way, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
SurfaceParking(s)
52Picture(s)
2,647Sqft
Exceptionally designed open-plan Oconomowoc ranch condo w/wooded conservancy views from the private deck-large enough to relax & dine al fresco. Sunlight pours through skylights illuminating the vaulted great room w/gas fireplace, seamlessly connected to the dining room & a culinary-inspired kitchen featuring high-end appliances, stylish tile, pantry & large custom island.
$719,500
Single-Family
452 River Bluff Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
61Picture(s)
4,363Sqft
A rare opportunity to own this stunning 3/4-acre wooded lot in the sought-after River Bluff subdivision,just 5 minutes from downtown Oconomowoc,City Beach & Bender Beach. Welcome guests into the grand two-story foyer, leading to the Great Room w/a cozy natural fireplace & open to kitchen. Flex room, first-floor laundry & powder room offer effortless convenience & functionality.
$699,900
Vacant Land
Pcl4 Poppy St, Oconomowoc, Wisconsin 53066
6Picture(s)
0Sqft
Welcome to the last remaining lot in the coveted Flowers Street area of Oconomowoc! This spacious, flat, and open 0.35-acre parcel sits quietly at the end of a dead-end street, offering rare privacy with no through traffic. Enjoy the convenience of city utilities--sewer and water already in the street--so there's no need to deal with septic or well systems.
$224,900
Vacant Land
578 Concord Rd, Oconomowoc, Wisconsin 53066
10Picture(s)
0Sqft
Beautiful meandering scenic Oconomowoc River lot is ready for your home plans to be built upon. This rare waterfront lot has everything you may be looking for with all the amenities of a beautiful city location & kayaking right out your front door.
$149,900
