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
1007 Elderberry Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
6Picture(s)
1,317Sqft
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.
$444,900
Single-Family
1213 W Arrowood Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
6Picture(s)
2,056Sqft
Move-in Ready 124 ARW Everest Four Square. Available 12/29/25. All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well.
$589,900
Single-Family
1238 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,503Sqft
Move-in Ready 105 ARW Beryl Shingle. Available 12/23/25! All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well.
$509,900
Single-Family
1259 Wild Rye Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
14Picture(s)
2,247Sqft
Spacious split ranch in Prairie Creek Ridge! The Kendall features upgraded features throughout. Front foyer leads to open concept living space, with flex room on the right. Kitchen features soft close cabinets, quartz countertops, tile backsplash, walk-in pantry & exterior vented range hood.
$644,900
Single-Family
1328 Periwinkle Pass, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
13Picture(s)
2,502Sqft
Welcome home to THE JULIA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 bedrooms, 3.5 baths & 3 car garage. The lot has partial exposure. Kitchen comes w/quartz countertops. doors & LG appliance package. LVP flooring in kitchen, dinette & great room. We equip our homes with Smart Technology such as a Ring Doorbell & touchless faucets.
$699,900
Single-Family
W351N5747 Westshore Rd, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
24Picture(s)
4,313Sqft
Fantastic Lake Country Home, Stunning 4,515 SQ FT of Living Space, 3.5 Car Garage, Sits upon .48 Acres. 5+ Bedrooms w/ 4 Baths. Large Finished Basement w/ Theatre Room- Kitchen - Full Bath - Bedroom and Office. Incredible Kitchen boasting top of the Line Cabinetry with Cooks Island. Large Family Room w/ Fireplace.
$749,000
Condominiums
503 Lake Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3/1Bathroom(s)
Private GarageParking(s)
9Picture(s)
3,920Sqft
Discover timeless elegance at this exclusive Lavinia by the Lakes penthouse 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.
$3,917,000
Single-Family
1690 Whalen Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
30Picture(s)
2,499Sqft
Welcome home to The PRESCOTT by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 Beds, 2.5 Baths and a 3 Car garage. The kitchen comes w/quartz countertops, maple-stained cabinets, and LG appliance package. LVP flooring in kitchen, dinette, and great room.
$649,900
Condominiums
1320 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
18Picture(s)
1,760Sqft
Experience easy, elegant living in this stunning new construction ranch condo ready for immediate move-in! Featuring 3 bedrooms, 2 baths, & a spacious open layout, this home impresses w/it's quality & unique architectural details. The chef's kitchen offers quartz counters, SS appliances & a large island.
$599,000
Single-Family
402 3rd St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
26Picture(s)
1,400Sqft
Enjoy the best of Oconomowoc living in this fully updated home, ideally situated on a corner lot just steps from Park Lawn Elementary and ashort stroll to City Beach and eclectic downtown Oconomowoc. Located in a welcoming, walkable neighborhood, this move-in-ready gem featuresupdates including roof, windows, siding, exterior doors, gutters with guards, and a painted garage exterior.
$385,000
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)
10Picture(s)
2,770Sqft
Discover timeless elegance at this exclusive Lavinia by the Lakes custom 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
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.
$379,900
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.
$459,900
Single-Family
35300 Pabst Rd, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
27Picture(s)
5,973Sqft
Experience luxury and privacy on 14 secluded acres in the Village of Oconomowoc Lake. This exceptional estate offers wooded, huntable land and open spaces perfect for recreation or a future sport court. Enjoy a wraparound deck, multiple outdoor entertaining areas, and a finished outbuilding ideal as a studio, workshop, or guest retreat, with options for additional structures.
$1,999,999
Vacant Land
N56W36834 Lisbon Rd, Oconomowoc, Wisconsin 53066
5Picture(s)
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
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
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
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
618 Anne St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
34Picture(s)
1,536Sqft
You Must See this Completely Renovated Open Floor Plan Victorian Home with 3 Bedrooms and 2 Full Baths in the Heart of Oconomowoc. This Beautiful Home is less than 1 block away from Fowler Lake and the Lakes Walking Path.
$319,000
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
Single-Family
1733 Hammock Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,350Sqft
This home is under construction. The Hailey 2350 offers a kitchen w/ plenty of cabinetry, quartz counters, WIP, kitchen appliances & prep island, a morning room for casual meals, a gathering room w/ gas fireplace, a formal dining room for large gatherings, a home office & a mudroom featuring a large closet & bench for everyday items.
$657,900
Single-Family
W352N6080 Bauers Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
44Picture(s)
1,986Sqft
Experience the perfect blend of modern construction and lakefront tranquility in Stumpy Bay on Okauchee Lake! This thoughtfully designed home features expansive lake views across the lake, a main-level primary suite, and a covered deck perfect for relaxing or entertaining. The rare flat lot leads directly to 54 feet of private frontage, beautifully complemented by lush perennials and a peach tree.
$1,798,000
Single-Family
1279 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,628Sqft
Move-in Ready 132 ARW Astoria Cottage II. Available by 10/29/25! All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well.
$524,900
Single-Family
N84W36411 Riverwood Ln, Oconomowoc, Wisconsin 53066
5Bedroom(s)
5/3Bathroom(s)
73Picture(s)
8,500Sqft
This French Manor estate, on 35 acres, epitomizes luxury & tranquility. A private oasis awaits, complete with serene pond & charming bridge leading to a secluded island with picturesque gazebo. Meticulously crafted residence harmonizes architectural elegance with natural beauty. A sanctuary unlike any other.
$2,349,999
Condominiums
1596 Weston Ridge Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private GarageParking(s)
26Picture(s)
2,469Sqft
HOME UNDER CONSTRUCTION AND READY FOR CUSTOMIZATION. 2-3 Bedrooms, 2-3 Full baths. Gorgeous Finished Lower Level with full size windows with AMAZING Rec Room and 3rd Bedroom/3rd Bath depending on buyer needs. Several new homesites available. Beautiful Lake Country Location. New Condos move in ready NOW, 2025 completions, 2026 completions.
$619,990
