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
956 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,516Sqft
Move-in Ready 56 ARW Olivia Cottage II Unit A, TWIN HOME! AVAILABLE 6.30.25! 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.
$489,900
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
1 space assignedParking(s)
34Picture(s)
1,514Sqft
Welcome to Mission Lakes! This bright two-bedroom, two-bath corner unit offers an open layout filled with natural light. Spacious living and dining areas connect to a private balcony, perfect for relaxing or entertaining. The primary suite features a walk-in closet and en suite bath, while the second bedroom and full bath provide flexibility for a guest room, home office, or hobby space.
$350,000
Condominiums
1620 St Andrews Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
Private garageParking(s)
60Picture(s)
3,900Sqft
OCONOMOWOC-SILVER LAKE. If you appreciate the look and feel of old world Italy you will absolutely adore this exquisite condo. One of only 2 units custom built by the original developer this amazing home has the look and feel of an authentic Italian Villa combined w/ superior quality, luxurious appointments & modern conveniences.
$1,200,000
Single-Family
1299 Yosemite Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
52Picture(s)
2,729Sqft
Immaculate 4BD 3.5BA home in sought after Lakewood Estates! Fall in love w/the open concept layout & stunning hand scraped birch HWFs throughout main floor. Lrg kitchen w/beautiful island, gas range & tons of storage! Spacious family room w/cozy nat. stone gas FP & abundant natural light w/windows on every wall.
$699,000
Single-Family
431 Thurow Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
49Picture(s)
1,926Sqft
Step into comfort and space with this inviting 3-bedroom, 2-bath ranch featuring vaulted ceilings and generous-sized rooms throughout. The open layout offers an airy feel, while the large windows bring in tons of natural light.Enjoy the peaceful wooded views from your back deck--perfect for relaxing or entertaining. Need storage? The spacious basement provides ample room for all your extras.
$564,900
Single-Family
N59W35530 Sulky Ct, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
37Picture(s)
3,083Sqft
Come home to this award winning architect/owner built gem in the middle of lake country. First time offered after being built by current owner. Minutes from Ocauchee Lake. The Town of Oconomowoc has been recently named the first safest city in Wisconsin. Over 3,000 sq.ft. of finished living space in addition to a long 3 season veranda, and a sunroom off of the main floor Family Rm.
$499,000
Single-Family
N56W35287 Appletree Ct, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
55Picture(s)
2,992Sqft
Set on a quiet cul de sac, this 3BR, 2.5BA ranch on a 3/4 acre lot is a perfect blend of updates, space & location! Some recent updates incl: Weathertight windows, furnace, A/C, HWH, iron filter, softener, roof and concrete driveway/garage floor/walkway. Updated kitchen w/quartz counters, SS appliances & soft-close cabinets is open to the morning room complete w/NFP.
$499,900
Single-Family
954 Duchess Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
42Picture(s)
2,589Sqft
Welcome home to this exceptional 3-bedroom, 2.5-bath home on a quiet corner lot, backing to a serene conservancy and adjacent to a park. Enjoy outdoor living and entertaining with an inground pool, patio, gazebo and peaceful surroundings. The bright first floor features a beautiful kitchen, living room with a natural fireplace, dining room, and family room with ample natural light.
$525,000
Single-Family
71 Happy Hollow Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
44Picture(s)
3,088Sqft
Exceptional 4 bedroom, 3 bath ranch home with modern updates! Impressive, sun-drenched great room that opens up to the chef's kitchen boasting sleek granite countertops, stainless steel appliances and access to the spacious deck. The primary suite is a true retreat, complete with a spa-like bathroom featuring exquisite tile details and walk-in shower.
$539,900
Single-Family
1301 Blue Dahlia Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
41Picture(s)
2,208Sqft
Enjoy this spacious and inviting 4 bedroom, 3 bath Split Level home that offers a perfect blend of comfort and functionality. On the main floor you'll find an eat in kitchen, dining area and living room. Upstairs you'll find 3 bedrooms and 2 baths.
$495,000
Single-Family
605 Westover St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
32Picture(s)
1,440Sqft
Enjoy timeless character with countless updates in this 3 BR 1 1/2 bath Oconomowoc classic located a stone's throw from the vibrant downtown Oconomowoc scene. Beautiful Westover Park with tennis court and playground just across the street. 1st floor layout has private Den, spacious dining room living room with tall windows providing loads of natural light.
$414,900
Condominiums
1588 Weston Ridge Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
SurfaceParking(s)
28Picture(s)
2,571Sqft
This exquisite ranch condo offers over 2,500 sq. ft. of elegant living space, including a finished lower level with full-size windows. The great room, with a cozy gas fireplace, flows into a stunning kitchen with quartz countertops and premium appliances. Entertain in the spacious dining room with cove ceilings, just steps from the oversized island.
$634,900
Single-Family
W342N5150 Road P -, Oconomowoc, Wisconsin 53069
6Bedroom(s)
4/1Bathroom(s)
52Picture(s)
6,977Sqft
The definition of lakeside luxury on over 1.5 acres at this stunning custom-built Okauchee Lake property featuring 139 feet of prime frontage. Ready for year-round fun, this remarkable residence includes 3 piers and a rare boathouse. With nearly 7,000 sq. ft. of thoughtfully designed spaces this home offers endless opportunities for relaxation and entertainment.
$5,750,000
Single-Family
3810 Southwood Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
4Bathroom(s)
60Picture(s)
3,654Sqft
Enjoy benefits of Lake Country living in this entertaining showstopper featuring an outdoor oasis w/lookout deck & NEW railing, 2 outdoor kitchen areas, in-ground pool w/''swim up bar'', hot tub, large stone & bonfire area.
$749,900
Single-Family
1290 Winterberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
25Picture(s)
2,300Sqft
Exceptional Ranch Home in Long Meadow Neighborhood. This meticulously maintained home in Lake Country offers elegance and comfort with soaring 10'+ ceilings, Brazilian cherry hardwood floors, and an updated gourmet kitchen with a spaciousisland -- ideal for entertaining. Recent upgrades include a new roof, fresh paint, and Andersen windows.
$685,000
Single-Family
W351N5850 Westshore Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
36Picture(s)
1,936Sqft
This charming 3-bed, 2-bath ranch home offers an inviting open-concept layout with vaulted ceilings, creating a spacious, and airy feel throughout. The split-bedroom design ensures privacy, with the master suite thoughtfully separated from the other two bedrooms. The kitchen boasts sleek stainless steel appliances, perfect for home cooking and entertaining.
$624,900
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
24Picture(s)
1,292Sqft
Immerse yourself in effortless luxury within this like new condo, ideally situated in the heart of a lively lake community. Revel in the stunning lake panoramas from your private balcony and the expansive rooftop terrace. Inside, discover a meticulously crafted residence featuring a warm, three-sided fireplace, a built-in workspace, and exquisite finishes throughout.
$725,000
Condominiums
1380 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
33Picture(s)
1,942Sqft
*IMMEDIATE Occupancy* the EMORY unit. Includes deck and partial exposure with lookout windows for future finished basement.The development consists entirely of side-by-side and double-duplex ranch condominiums that range in square footage from 1,571 to 1,942+ with sunroom add-on options. Spacious open concept floor plans feature generous entertaining spaces.
$679,900
Condominiums
1382 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
2Picture(s)
1,878Sqft
*IMMEDIATE OCCUPANCY* The DALEA unit. Includes deck and partial exposure with lookout windows for future finished basement.The development consists entirely of side-by-side and double-duplex ranch condominiums that range in square footage from 1,571 to 1,942+ with sunroom add-on options. Spacious open concept floor plans feature generous entertaining spaces.
$669,900
Single-Family
809 Oakwood Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
22Picture(s)
1,566Sqft
Charming and updated Cape Cod home near Fowler Park in Oconomowoc! This well-maintained 3 bedroom, 1.5 bathroom home is filled with character and modern updates. The primary bedroom, formerly a den, offers versatility to fit your needs. Upstairs, both bedrooms feature removable bookshelves that can easily convert to match the other closets. Enjoy peace of mind with an HSA home warranty included.
$340,000
Multi-Family Investment
530 Franklin St, Oconomowoc, Wisconsin 53066
Outdoor spaceParking(s)
30Picture(s)
0Sqft
Amazing opportunity in the heart of Oconomowoc. This unique multi-purpose property offers three residential units and over 7000 sq ft of commercial space. All residential units (one 2 BR/1.5 BA, one 2 BR/1 BA and one 1 BR/1 BA) have been updated throughout including new windows. Commercial space is currently split between 3 tenants and offers 3 half baths. All tenants are month to month.
$750,000
Two-Family
128 Jefferson St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
Parking spaceParking(s)
24Picture(s)
1,133Sqft
Two houses, one lot! Great owner occupied property with an income potential, or investment property. Conveniently located within walking distance to downtown Oconomowoc and City Beach. One block from from Roosevelt Park, Imagination Station, LC Rotary Splash Pad and LC Trail. Main house offers 3 bedrooms (one does not have a closet) hardwood flooring & dining area with loads of built-ins.
$265,000
Single-Family
128 Jefferson St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2Bathroom(s)
24Picture(s)
1,150Sqft
Two houses, one lot! Great owner occupied property with an income potential, or investment property. Conveniently located within walking distance to downtown Oconomowoc and City Beach. One block from from Roosevelt Park, Imagination Station, LC Rotary Splash Pad and LC Trail. Main house offers 3 bedrooms (one does not have a closet) hardwood flooring & dining area with loads of built-ins.
$265,000
Single-Family
W359N6972 Brown St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1/1Bathroom(s)
59Picture(s)
2,396Sqft
This spectacular lake country home sits on almost 3/4 of an acre for plenty of privacy with the added convenience of no HOA telling you what to do. This 4 bedroom home was transformed into a large 2 bedroom home with a spacious full bathroom upstairs and office/den on the main floor including beautiful 6 panel doors throughout.
$425,000
Single-Family
36082 Beach Rd, Oconomowoc Lake, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
31Picture(s)
3,736Sqft
Set on 2.7 acres along the shores of prestigious Oconomowoc Lake, this exceptional brick home offers a rare opportunity to own a private lakeside retreat. With 99' of pristine water frontage, breathtaking views, & serene setting. Step inside to find an inviting floor plan featuring HWFs throughout the main & upper levels.
$2,995,000
Single-Family
1311 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,880Sqft
Move-in Ready 50 ARW Sawyer Cottage. Available 6.24.25! 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.
$559,900
Condominiums
110 Marcella St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
39Picture(s)
1,612Sqft
Great open concept 2 bedroom, 2 full bath condo is perfect for you. Nice sized living room that is open to kitchen and dining area. Good size Master bedroom with walk in closet, next to a full bath. Finished lower level with a great room. Full bathroom and laundry area and another room as well at the end of hall. Shared garage with private backyard.
$254,900
Condominiums
239 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
48Picture(s)
1,315Sqft
This well-maintained condo offers comfortable living with 2 bedrooms and 2 bathrooms, perfect for relaxed, low-maintenance living. Located in a 55+ community, enjoy peace of mind with a secure lobby and convenient access to heated parking, including 2 parking spots. A must-see for anyone looking for a cozy, well-cared-for condo to call home in a great location.
$299,900
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
1 space assignedParking(s)
28Picture(s)
1,500Sqft
Enjoy the ease of low-maintenance condo living on the water in this Draper Hall unit--perfect for a secondary home or a right-sized retreat. Start your day with coffee overlooking Fowler Lake, then take a short stroll to downtown for shopping, dining, and entertainment. With split bedrooms, guests have their own space.
$440,000
Single-Family
W351N5789 Westshore Rd, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
43Picture(s)
3,023Sqft
Discover this spectacular home in the sought-after Westshore subdivision of Oconomowoc. A charming covered front porch welcomes you, leading to a dramatic entryway and a skylit living room. The chef's kitchen is a culinary dream, featuring a massive center island, granite countertops, and high-end finishes.
$724,900
