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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:

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Condominiums

857 Stirling Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
27Picture(s)
1,631Sqft
NEW CONSTRUCTION - Ready April 2026. Welcome to this luxury ranch-style condominium offering 2 bedrooms plus a versatile flex room, thoughtfully designed with an open-concept layout and 9' ceilings throughout. The stunning kitchen is ideal for entertaining, featuring a large center island, soft-close cabinetry, and quartz countertops.
$534,900

Condominiums

859 Stirling Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
29Picture(s)
1,631Sqft
NEW CONSTRUCTION READY April 2026 - Luxury Ranch Condominium with 2 Bedroom plus Flex Room, featuring open design concept with 9' Ceilings throughout. Beautiful Gourmet Kitchen for entertaining with a large center island, beautiful soft close cabinetry, quartz countertops and appliances.
$549,900

Single-Family

N53W34956 Road B -, Oconomowoc, Wisconsin 53069

3Bedroom(s)
1Bathroom(s)
42Picture(s)
1,170Sqft
The main and lower level of this home have multiple sliding doors for quick access to a large wrap around deck. An extra large living room faces the lake and with the addition of headers the owner has made it possible to make the main floor open concept. The upper level is comprised of 3 bedrooms and a full bath.
$1,199,000

Single-Family

1333 Periwinkle Pass, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3/1Bathroom(s)
10Picture(s)
2,477Sqft
Welcome home to THE ELSA plan by Stepping Stone Homes, an award-winning builder. Open floorplan features 3 Beds, 3.5 Baths and 3 car Gar. This lot has LOOKOUT exposure. The KIT has quartz counters, soft close cabs and LG appliances. LVP flooring in kitchen, dinette and great room. We equip our homes with Smart Technology such as a Ring doorbell and touchless faucet.
$732,635

Single-Family

1214 W Arrowood Cir, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,400Sqft
Move-In Ready 108 ARW Margot Craftsman - Available Now!All 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.
$699,900

Single-Family

1757 Hammock Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
6Picture(s)
2,257Sqft
CERAMIC TILE FLOORING BEING INSTALLED. APPROXIMATE COMPLETION SEPTEMBER 2026.3 bedrooms/2 full baths/elite series ranch. Basement has 1 egress slider window and drain/vent rough-in for future full bath. Walk-in ceramic tiled shower/2 shower heads/granite or equivalent vanity tops/double sinks in master bath. Double sinks family bath. Large WIC master bedroom.
$639,990

Single-Family

1161 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,519Sqft
Move-In Ready 117 ARW Beryl California Bungalow - Available Now!All 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.
$509,900

Single-Family

1343 Periwinkle Pass, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
6Picture(s)
2,289Sqft
INSTALLING CERAMIC FLOORS- APPROX. COMPLETION SEPTEMBER 2026. 4 bedrooms/2.5 baths/elite series split ranch. 9' foundation wall/1 egress slider window/drain-vent rough in for future full bath in basement. Ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops. Double sinks in family bath.
$646,990

Single-Family

1672 Switchgrass St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
18Picture(s)
2,264Sqft
Craftsman inspired 2-story home in Prairie Creek Ridge. The Mulberry features upgrades throughout. Kitchen has soft close cabinets, quartz countertops, ext vented range hood, island w/ overhang & walk-in pantry. Spacious great room includes an electric fireplace with stone detail. Flex room w/ French doors off foyer makes a great office or playroom.
$659,900

Single-Family

1745 Hammock Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,748Sqft
HOUSE IS FRAMED - APPROX FINISH AUGUST '26.4 bedrooms/2.5 baths/flex room/elite 2-story design. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Ceramic tiled shower w/2 shower heads/double sinks/granite or equivalent vanity tops in master. Double sinks family bath. WIC's all bedrooms. 9' first floor ceilings/tray ceiling master bedroom.
$689,990

Single-Family

1120 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,720Sqft
Move-in Ready 91 ARW Julian Cottage II Unit A, Ground Level Foundation. TWIN HOME! 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 separate rate.
$509,900

Single-Family

N73W36308 Shore Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
23Picture(s)
536Sqft
Rare opportunity to own lake frontage property w/gorgeous sunset views & mature trees on almost 3 acres! Enjoy peaceful Ashippun Lake, approx 114 ft frontage as per GIS map. Bids available for demolish & removal of abandoned cottage & 2 car GA.
$499,900

Vacant Land

N73W36308 Shore Dr, Oconomowoc, Wisconsin 53066

23Picture(s)
0Sqft
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.
$499,900

Single-Family

1011 Elderberry Rd, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
5Picture(s)
1,304Sqft
Move-in Ready 78 ARW Wyatt Cottage B Unit B, Twin Home! AVAILABLE NOW! 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.
$444,900

Vacant Land

Lt41 Road B -, Oconomowoc, Wisconsin 53069

8Picture(s)
0Sqft
Buildable lot available on Okauchee lake!! This is the only lot for sale with sewer hook up on Okauchee. The property has 50 ft of frontage! 50' x118'on Waukesha county GIS. The lightly wooded and tiered lot would support a two story home with walkout. Imagine relaxing on your deck and looking over the serene area of Okauchee. The expansive lake frontage is level and has two piers.
$749,000

Single-Family

997 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
27Picture(s)
1,592Sqft
Move-in Ready 75 ARW Olivia Cottage II Unit A, TWIN HOME! 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 a separate rate.
$484,900

Vacant Land

Lt27 Lakeland Rd, Oconomowoc, Wisconsin 53066

12Picture(s)
0Sqft
Build your dream home in the heart of Lake Country on this rare 0.3636-acre lot! Less than half a mile from four lakes--Okauchee, Oconomowoc, Upper Oconomowoc & Florence--with public boat launches nearby within easy walking distance. Walk to downtown Okauchee and enjoy local favorites like Whisky Waters, Kiki's Cantina, Glenda's Cafe & more.
$169,000

Single-Family

1007 Elderberry Rd, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
30Picture(s)
1,317Sqft
Move-in Ready 77 ARW Wyatt Cottage Unit B - TWIN HOME. 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

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

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)
29Picture(s)
1,592Sqft
Move-in Ready 90 ARW Olivia Cottage II Unit B, Ground Level Foundation TWIN HOME! 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

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.
$165,000

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.
$199,900

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)
16Picture(s)
2,469Sqft
MOVE IN READY NEW CONSTRUCTION!-3 Bedrooms, 3 Full baths. Gorgeous Finished Lower Level with full size windows with AMAZING Rec Room and 3rd Bedroom/3rd Bath. Several new homesites available. Beautiful Lake Country Location. New Condos move in ready NOW, 2025 completions, 2026 completions. Make your PLANS! Listing priced as 3/3; photos of previously finished Weston Ridge property.
$619,990

Condominiums

1620 Belmont Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
27Picture(s)
1,929Sqft
Popular CASTILLIAN floor plan - New Construction - Ready for OCCUPANCY ~ Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, real wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full basements w/egress window, under-floor rough plumbing for future full bath & wet bar, concrete patio.
$684,900

Single-Family

1388 W Mamerow Ln, Oconomowoc, Wisconsin 53066

5Bedroom(s)
3/1Bathroom(s)
31Picture(s)
4,300Sqft
4,300 sq ft home offering luxury & functionality. Main level has open-concept living room, dining area & kitchen with large island, granite & stainless. Main-level bedroom can serve as office. Upstairs is primary suite with tiled walk-in shower & dual WICs, 3 additional large BRs, full bath & convenient laundry.
$790,000

Condominiums

1626 Belmont Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
5Picture(s)
1,571Sqft
New Construction - Occupancy February 2026 - Breton floor plan~ Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, real wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full basements w/egress window, under-floor rough plumbing for future full bath & wet bar, concrete patio.
$614,900

Single-Family

N49W35398 Wisconsin Ave, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4/1Bathroom(s)
96Picture(s)
8,158Sqft
Experience lakefront living in this furnished luxury retreat! Nestled on a pristine shoreline, this expansive lake home offers breathtaking water views from nearly every room. Step inside to discover exquisite woodwork throughout, from custom millwork to rich refinished hardwood floors that anchor every space with quality.
$4,895,000
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