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:
Condominiums
W398N6066 Autumn Woods Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
14Picture(s)
1,506Sqft
This desirable 2-bedroom, 2-bath end unit in the beautiful Autumn Woods community is ready for you! Located in a wooded area, this condo offers added privacy and peaceful surroundings- a perfect retreat to call home. With over 1,500 sq ft of living space, you'll love the open layout and versatile upper loft, ideal for a bedroom, playroom, office, or whatever suits your lifestyle.
$299,000
Single-Family
1470 Allen Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
31Picture(s)
2,210Sqft
Amazing home and setting on a gorgeous 1 acre lot in the City of Oconomowoc! This remarkable property features a one-of-a-kind ranch home set on a wooded lot with huge outbuilding. Interior includes a finished lower level. Main level has custom kitchen with butcher block breakfast bar and appliances included. Wood-burner stove in living room.
$539,900
Single-Family
650 Harvard St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
37Picture(s)
1,092Sqft
Charming 3BR/2BA ranch in Oconomowoc's sought-after Presidents Neighborhood on Harvard--walk to downtown restaurants & shops, Fowler Lake, and the LaBelle beach! Sunny living room opens to an eat-in kitchen (all appliances included). Beautiful hardwood floors on the main level (except kitchen). Versatile partially finished lower level adds bonus space for rec/office/gym with great storage.
$349,900
Condominiums
688 Summer Creek Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
Private GarageParking(s)
33Picture(s)
1,793Sqft
A condo that lives like a single family home. No monthly dues. Original owner loves the neighborhood! You are greeted by a dramatic two story great room with lots of natural light. An open main level floor plan. A nice working kitchen with granite tops, a raised snack bar and nice HWF's.
$374,900
Single-Family
1275 Wild Rye Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,411Sqft
Thoughtfully designed 2-story home in Prairie Creek Ridge! The Acacia, on lot 389, includes upgraded features throughout. Kitchen features soft close cabinets, quartz countertops, tiled backsplash, spacious walk-in pantry & exterior vented range hood. Extended dinette provides plenty of space to enjoy a meal with loved ones & the cozy great room is complete with an electric fireplace.
$624,900
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.
$179,000
Single-Family
1380 Scotsland Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
12Picture(s)
2,059Sqft
Beautiful Split Ranch located on lot 12 in Olde Highlander! Community will feature a range of amenities including a walking path, swimming pool, clubhouse & more! Kitchen features stained soft close cabinets, quartz countertops, ext vented range hood & spacious walk-in pantry. Great room off kitchen has box tray ceiling & gas fireplace w/ stone detail.
$694,900
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
1150 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,584Sqft
Move-in Ready 116 ARW Harlow Farmhouse. Available 12/1/2025. 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.
$534,900
Single-Family
1259 Wild Rye Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
8Picture(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
1101 Niagara Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
39Picture(s)
3,020Sqft
Beautiful Ranch home built in 2002, offering the perfect blend of space, comfort, & functionality. This property provides a semi-private setting w/ plenty of room to enjoy both indoors and out. A bright & inviting floor plan featuring 3 BR's & 3 BA's - ideal for both family living & entertaining guests.
$500,000
Single-Family
631 Summer Creek Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
43Picture(s)
2,264Sqft
Beautifully maintained 4 Bed, 3 bath ranch featuring an inviting in-ground pool, perfect for summer entertaining! Main level offers a bright, open layout with cozy gas fireplace and spacious kitchen. Lower level boasts a huge family room, 4th bedroom with egress window, and a full bath - ideal for guests or private retreat. Enjoy indoor/outdoor living with plenty of room to relax or host.
$549,900
Single-Family
1270 W Mamerow Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,238Sqft
Welcome home to The GENEVA by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 Beds, 2.5 Baths and a 3 Car garage. This lot is a flat exposure. The kitchen comes w/ quartz countertops, island and LG appliances. LVP flooring in kitchen, dinette, and great room.
$589,900
Single-Family
1328 Periwinkle Pass, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
8Picture(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 2 Story ; Stunning 4515 SQ FT of Living Space ; 3.5 Car Garage ; .48 Acres ; 5 Bedrooms ; 3.
$768,000
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)
31Picture(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.
$659,900
Two-Family
W380N6368 Florence Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
Driveway entranceParking(s)
63Picture(s)
3,116Sqft
Spacious 2-family townhouse-style home, perfect for multi-generational living, investment, or potential condo conversion. Each residence lives like a single-family home, featuring a main-level primary bedroom with ensuite bath & dual closets, a gas fireplace with soaring vaulted ceilings in the living room & a full kitchen with dining area.
$649,000
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
449 Lake Bluff Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/2Bathroom(s)
70Picture(s)
3,664Sqft
Beautifully updated 4-bedroom, 2 full and 2 half bath two-story home in a desirable Oconomowoc neighborhood! Built in 2014, this spacious residence features many modernupdates throughout, offering both comfort and style.
$727,900
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
1435 Eldorado Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/2Bathroom(s)
57Picture(s)
2,306Sqft
Spacious 4-bed, 2 full bath, 2 half bath home in a desirable Oconomowoc neighborhood. With 2,306 sq ft plus a large partially finished basement, there's room for living, entertaining, and recreation. Main level highlights include a formal living and dining room, eat-in kitchen, family room, and convenient main floor laundry. Relax in the screened three-season room overlooking the private yard.
$515,000
Single-Family
434 Lyman St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
23Picture(s)
1,606Sqft
Welcome to the Union Subdivision, a desirable neighborhood in Oconomowoc near restaurants, parks, and within walking distance to Lac La Belle and Fowler Lake. This move-in ready home offers extensive updates. In 2023: new siding, roof, garage door, gutters. In 2024: a remodeled kitchen, new first-floor flooring, all-new appliances, and both bathrooms refreshed within the last year.
$349,900
Single-Family
W358N5963 Misty Ct, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
36Picture(s)
1,848Sqft
Exceptional colonial home set at the end of a cul-de-sac in Oconomowoc's Misty Meadows! Enjoy this great setting featuring large back yard with private wooded backdrop. Misty Meadows offers 20+ acres of common area including park, ponds, and walking/biking trail. Interior has family room with brick fireplace. Front living room has adjoining dining room and plenty of natural light.
$449,900
Single-Family
826 Oakwood Ave, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1/1Bathroom(s)
29Picture(s)
1,560Sqft
Oconomowoc living at its best - ck out this charming 2 BD, 1.5 BA Lannon stone ranch just minutes from Fowler Park & downtown! Updates include the kitchen, main bath, flooring & finished basement! As you enter the home, you're greeted by the spacious living room.
$339,900
Condominiums
245 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
39Picture(s)
1,484Sqft
Come fall in love with the convenience of condo living and experience all that Silver Ridge 55+ condos have to offer! Equipped with an elevator and spacious hallways, moving in will be a breeze! When you enter the unit, you're greeted with a coat closet with french doors, the sun-filled living room/dining area and your full kitchen.
$299,900
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
46Picture(s)
1,370Sqft
Welcome to Fowler Lake Village, where luxury condo living is done right! This 2 bedroom, 2 bathroom unit on the 3rd floor features an open concept layout, with large windows that fill the space with natural light. You will love your oversized balcony, large walk-in closet, and the convenience of in unit laundry.
$699,900
Single-Family
1479 Crestwood Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
51Picture(s)
2,235Sqft
Meticulously maintained & beautifully decorated, this charming home is nestled within walking distance to Nature Hill, schools & all the fun Oconomowoc has to offer! Enjoy your morning coffee on the cozy front porch.
$495,000
