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
618 2nd St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
17Picture(s)
832Sqft
Charming bi-level home in Oconomowoc with thoughtful updates and smart use of space! Enter from the wood deck into an open-concept living room and kitchen featuring laminate floors, shaker cabinets, included appliances, and a removable island with breakfast bar.
$289,900
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
36Picture(s)
1,500Sqft
Summer is just around the corner, and this 4th floor 2 bdrm 2 bath condo has your dreams of lake living calling. An open concept living area with an expansive balcony is host to beautiful lake views, warm southern exposure and plenty of natural light. Bedrooms are separated by main living area providing privacy with guests or remote work.
$435,000
Single-Family
W354N6260 Williams Ct, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
7Picture(s)
2,413Sqft
Home & Lot Package. Build The Mia, a beautifully crafted 2,413 sq. ft. ranch style home offering 3 bedrooms and 2.5 baths. Designed for modern living, it features an open-concept layout, a gourmet kitchen with a spacious island, and a bright great room with soaring ceilings. Enjoy outdoor living on the covered patio. The serene primary suite includes a spa-like bath and walk-in closet.
$874,900
Condominiums
W397N5921 Autumn Woods Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
24Picture(s)
1,212Sqft
Awesome Main Level Condo offers a generous amount of living space, is updated throughout including New LVP Flooring & complete paint scheme. The unit fills with sunlight from its south-facing living center. Popular Autumn Woods open concept design is available for any age Buyer, is available for immediate occupancy & allows pets.
$329,900
Single-Family
881 Summer Creek Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
36Picture(s)
1,765Sqft
AMAZING VIEWS OF OCONOMOWOC RIVER! Beautifully maintained, open concept 3BR, 2BA ranch in Hickory Creek on .455 acre along the tranquil Ocon River. Great room w/ beautiful GFP. Airy KIT incl island & pantry w/ newer counters, lighting, oven & refrigerator, open to sunny DR w/ patio doors to deck, spacious MBR suite w/ whirlpool tub, WICs in all BRs. Main flr cath ceilings. HWFs.
$475,000
Single-Family
812 Dante Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
39Picture(s)
1,632Sqft
Welcome to this beautifully updated 3-bedroom ranch, ideally located in a desirable neighborhood just a short walk from a city park and the high school. Dutifully maintained and move-in ready, this home features numerous updates including luxury vinyl flooring (2017), a refreshed kitchen with added cabinetry, new sink, and appliances (2019), a new roof (2022), and fully remodeled bathrooms (2025).
$419,900
Condominiums
267 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
36Picture(s)
1,674Sqft
If you're looking to simplify without sacrificing space, this rarely available 3-bedroom, 2-bath end unit condo offers the perfect blend of comfort, function, & low-maintenance living. Ideal for downsizers, this thoughtfully designed condo features newer carpeting, a cozy gas fireplace, & plentiful closets and storage throughout.
$325,000
Single-Family
1361 Mockingbird Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
26Picture(s)
1,822Sqft
Welcome home to this spacious 3 BD, 2 BA ranch home in Wood Creek! Boasts 10ft ceilings in the open concept KIT/DR & LR. KIT also incl. breakf bar, large planning desk & walk-in pantry, open to sunny dining room w/ extra tall patio drs that walk out to the 12x24 maintenance-free deck (that's reinforced for your future hot-tub!). HWF in entry, hallway, KIT/DR. GFP w/ lovely stone surround.
$475,000
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
1Bedroom(s)
1/1Bathroom(s)
Opener includedParking(s)
44Picture(s)
1,182Sqft
This beautifully designed, 1Bdm End Unit Condo offers stunning views of the lakes from its rooftop with a bright southeast exposure. Located in the heart of walkable Oconomowoc, it boasts a range of amenities. 6th-floor rooftop deck overlooks two lakes and the city, providing a perfect spot for outdoor entertaining.
$569,000
Single-Family
1221 E Mamerow Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3/1Bathroom(s)
75Picture(s)
2,466Sqft
Step into this quality-built, spacious ranch home that perfectly blends modern comfort w/timeless design. Located in the heart of Lake Country, this beautifully maintained home features an open-concept layout ideal for both everyday living & entertaining. The expansive great room flows seamlessly into the kitchen & dining areas, all bathed in natural light.
$699,900
Single-Family
1342 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,575Sqft
Move-in Ready 71 ARW Harlequin Modern. Available 8/28/25! 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.
$519,900
Condominiums
320 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
1 space assignedParking(s)
31Picture(s)
1,222Sqft
Beautiful Fowler Lake 2BR 2BA southern exposure end unit with views of green space! Dramatic decorating and well maintained, this one will instantly capture your heart. Large balcony off living room and primary BR. Open dining room and ample kitchen. 1 car underground heated garage parking space, elevator & a storage locker included. 2022 roof.
$359,900
Single-Family
718 Marigold St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2Bathroom(s)
27Picture(s)
2,469Sqft
Inviting ranch on Marigold Street in the beloved Flower Patch neighborhood. Lovingly maintained by one family for over 55 years. The private backyard is ready for summer with an inground pool, lush perennials, and mature landscaping.Inside, you'll find spacious living areas and a lower level built for entertaining--complete with a wet bar, Franklin stove, and room for a pool table.
$489,000
Condominiums
N52W35336 Lighthouse Ln, Oconomowoc, Wisconsin 53066
2Bedroom(s)
3Bathroom(s)
Private garageParking(s)
38Picture(s)
2,243Sqft
Amazing updated ranch condo with walk out LL in desirable Bay Pointe! Enjoy spectacular priceless pond views from the new composite deck (2024), the sunroom, both BR's, and the walk-out LL! The welcoming entryway leads to the refreshed eat-in KIT with quartz counter-tops & backsplash. The open airy concept LR/DR combination boasts a GFP, 10' ceilings, newer flooring, with soothing nat.
$559,900
Single-Family
957 Elderberry Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
6Picture(s)
1,317Sqft
Move-in Ready 63 ARW Wyatt Cottage Unit B - TWIN HOME. Available NOW! 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
647 Lake Bluff Dr, Oconomowoc, Wisconsin 53066
6Bedroom(s)
4Bathroom(s)
49Picture(s)
5,810Sqft
Gorgeous home and setting on a park-like lot in a convenient Oconomowoc neighborhood! This remarkable home offers 5-6 BR's, 2 covered porch entrances, amazing kitchen-sun room, and a huge finished lower level. Gas fireplace in great room. Kitchen features breakfast bar and granite countertops. Adjoining dining-sun room with large windows.
$749,900
Single-Family
1561 Creekview Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
2Picture(s)
2,004Sqft
HOUSE IS IN ROUGH CARPENTRY. APPROX. FINISH FEBRUARY '25.3 bedroom/2 full bath/partial exposure/ranch design. Windows in exposure & drain/vent rough-in for future full bath. Double sinks in family & master baths/granite or equivalent vanity tops. Large WIC master suite. 9' main floor ceilings: pitched in foyer, living room, kitchen, dinette/tray ceiling in master bedroom.
$609,990
Single-Family
1142 Shoal Ridge Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
50Picture(s)
1,678Sqft
Welcome home to this 3 bed, 1.5 bath 2-story home in the Hawthorne Ridge Trails subdivision of Oconomowoc! Step into a bright 2-story entryway and cozy living room with a gas fireplace. The open layout flows into the dining area and spacious kitchen, featuring new countertops, sink, and tiled backsplash.
$469,900
Single-Family
W343N7303 North Pole Ln, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
76Picture(s)
4,500Sqft
Experience Tranquil Living in this Custom Built Stone Bank Homestead. Nestled amidst the serene landscapes of the Lake Country, this expansive 4 or 5-bedroom, 2.5-bathroom estate spans over 4,500 sq ft on a lush 2.3 -acre lot. The home seamlessly blends natural beauty.
$799,900
Single-Family
N66W34839 Baltic Pass, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
9Picture(s)
2,800Sqft
Step into a new era of quality home building with this incredible new construction home from Elegant Builders LLC in the new Meadowlands subdivision nestled in the northwest corner of Okauchee Lake. Sitting on an acre lot backed up to Conservancy Land (no building), this 2800 sqft, 4 bedroom, 2.5 bath open concept ranch with tons of natural light is waiting for you.
$1,199,900
Single-Family
1746 Whalen Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,805Sqft
The Lauren 1805 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.
$643,900
Single-Family
1271 Evergreen Trl, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/2Bathroom(s)
39Picture(s)
3,576Sqft
Tim O'brien home with stylish updates throughout-better than new construction! Enjoy a private fenced backyard with custom patio, pergola, and fireplace. Inside features include updated lighting, flooring and a dog washing station. The Finished basement is perfect for entertaining with a wet bar and ample space. Tucked away on a cul-de-sac, this home offers both comfort and convenience.
$699,000
Single-Family
1280 Orchard Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
58Picture(s)
3,200Sqft
Move right into this great open concept split ranch. You will enjoy sitting by the gas fireplace in the open great room adjacent to the kitchen which is perfect for entertaining. Or relax on the large deck overlooking the private back yard. The primary suit has a private bathroom and walk-in closet. Two additional bedrooms and main floor laundry round out the main level.
$554,900
Single-Family
603 Highland Ave, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
25Picture(s)
1,037Sqft
Nicely updated ranch home in a convenient Oconomowoc neighborhood! Plenty of newer updates throughout. Gorgeous updated kitchen with black SS appliances, and beautiful cabinets and countertops-backsplash. Large front living room offers plenty of natural light. Nice size bedrooms. Ceramic tile in main floor bath. Bonus breezeway makes a great office or sun room.
$334,900
Condominiums
521 Frederick Ct, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
42Picture(s)
1,912Sqft
Nestled in the quiet cul de sac of Sheldon Knoll condo development is the well-maintained 2 Bedroom & 2.5 bath unit within walking distance to downtown shopping & restaurants. This condo has plenty to offer including: private entrance w/2 car attached garage & plenty of storage.
$374,900
Single-Family
1536 Creekview Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
4/1Bathroom(s)
3Picture(s)
2,660Sqft
HOUSE IS IN ROUGH CARPENTRY. APPROX. FINISH FEBRUARY '25.4 bedrooms/2.5 bath/flex room/spacious 2-story. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Master bath w/double sinks/granite or equivalent vanity tops/ceramic tiled shower. Double sinks family bath. WIC's all bedrooms. Knockdown drywall w/rounded corners.
$619,990
Single-Family
1591 Creekview Ln, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,874Sqft
HOUSE IS IN RGH CARPENTRY. APPROXIMATE FINISH FEB.'25.5 bedrooms/2.5 baths/flex room/spacious 2-story. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops/double sinks in master bath. Double sinks family bath. 2 WIC's master suite. 9' first floor ceilings/pitched ceiling master bedroom.
$629,990
Single-Family
214 Jefferson St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
9Picture(s)
897Sqft
Calling all investors or buyers looking to design their home from top to bottom....Bring your vision, and give this property life again. Whether you plan on living there or using it as an investment, you get the final say in what this becomes. Currently set up as a quaint 2 bed, 1 bath in a great neighborhood, close to everything you could want.
$120,000
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
52Picture(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.
$399,900
Single-Family
N53W34938 Road B -, Oconomowoc, Wisconsin 53069
2Bedroom(s)
1Bathroom(s)
42Picture(s)
876Sqft
Set on 50+ feet of swimmable frontage in Bay 5, this gem is perfectly situated within walking distance or a short boat ride to all the fun Okauchee Lake has to offer! Stylishly updated top to bottom. The main floor offers a new kitchen featuring all modern conveniences, great room with amazing lake views, bedroom and full spa like bath complete with heated floors and steam shower.
$900,000
