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
966 Valentine Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
Private GarageParking(s)
40Picture(s)
1,830Sqft
Lakehouse vibes! Beautiful updated townhouse style condo with high end finishes throughout! Welcome home to your slice of heaven in the heart of Oconomowoc.
$384,900
Condominiums
1750 Bess Ct, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private GarageParking(s)
47Picture(s)
2,300Sqft
OCONOMOWOC.. Built in 2015 by Kingsway Builders, this stunning condo blends timeless elegance w/ modern comfort. Soaring 10-foot beamed ceilings & rich hardwood floors create a warm, inviting atmosphere throughout the main living spaces. The chef's kitchen is a true centerpiece, featuring premium Viking appliances, custom mahogany cabinetry, & ample space for entertaining.
$635,000
Single-Family
1361 Scotsland Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,479Sqft
The Monterey-spacious craftsman inspired 2-story on lot 86 in Olde Highlander! Community will feature a range of amenities including a walking path, swimming pool, clubhouse & more! 2-story front foyer leads to open concept living space. Kitchen has soft close cabinets, quartz countertops, exterior vented range hood & walk-in pantry.
$699,900
Condominiums
1508 Weston Ridge Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private GarageParking(s)
4Picture(s)
2,450Sqft
There's still a ''big sky'' location left in Lake Country! Premium corner build w/a bit of extra privacy & beautiful view of untouched wooded landscape. Home has an architecturally unique floorplan designed for daily functionality while maintaining the WOW factor you'll be proud to share w/guests.
$658,900
Single-Family
517 Union St, Oconomowoc, Wisconsin 53027
3Bedroom(s)
1Bathroom(s)
19Picture(s)
1,800Sqft
Lets get you moving in this Charming 3 BR, 1 BA home located within walking distance of downtown Oconomowoc is awaiting. Updates include: New roof & Siding in 2023. LVP flooring (3/2026) and Stair ballisters in upper level of home. New Water Heater (14 days ago) & New Furnace (2024). Beautful Fully Updated bath in 2023 with ceramic tub surround,,Wood kitchen cabinetry and ceramic flooring.
$374,900
Single-Family
1713 Switchgrass St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
2Picture(s)
2,452Sqft
HOUSE IN ROUGH CARPENTRY.3 bedrooms/2.5 bath/Elite series ranch. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Master bath has ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops/double sinks. Large WIC master suite. Family bath has double sinks. 9' 1st floor ceilings: pitched ceiling in living room. Tray ceiling in master bedroom.
$759,990
Single-Family
1723 Switchgrass St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
2Picture(s)
2,257Sqft
HOUSE IN ROUGH CARPENTRY.3 bedrooms/2 full baths/elite series ranch. Basement has 1 egress slider window and drain/vent rough-in for future full bath. Master bath has ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops/double sinks. Large WIC master suite. Family bath has double sinks. 9' 1st floor ceilings; pitched ceiling in foyer, living room, kitchen, dinette.
$659,990
Single-Family
1302 Lynn Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
3Picture(s)
2,004Sqft
3 bedrooms/2 full baths/elite series ranch. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Master bath has ceramic tiled shower/granite or equivalent vanity tops/double sinks. Family bath has double sinks. Large WIC master suite. 9' main floor ceilings: pitched in foyer, living room, kitchen, dinette. Tray ceiling master bedroom.
$629,990
Single-Family
1301 Lynn Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,748Sqft
HOUSE IS IN ROUGH CARPENTRY. APPROXIMATE COMPLETION - JANUARY 2027.4 bedrooms/2.5 baths/Flex room or 5th bedroom/elite series 2-story. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Walk-in-shower/2 shower heads/double sinks/granite or equivalent vanity tops in master bath. Double sinks family baths. WIC's upper bedrooms.
$699,990
Single-Family
1348 Aberdeen Pl, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
14Picture(s)
1,808Sqft
NEW CONSTRUCTION Olde Highlander Community - Ready August 2026! Our Windsor model is a 3 Bed, 2 BA, 3 Car Garage, split ranch with an open concept layout.
$589,900
Single-Family
1198 W Arrowood Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,446Sqft
Move-In Ready 110 ARW Atwood Craftsman - Available 7/7/26!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.
$684,900
Single-Family
322 Park St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
20Picture(s)
1,036Sqft
Well-appointed ranch conveniently located a stone's throw from the vibrant downtown Oconomowoc scene. The sun-filled kitchen offers ample cabinetry and workspace and opens to the spacious living room. Updated bathroom and nicely sized bedrooms provide functional, easy living. Unfinished lower level offers potential for additional living or workspace, with an existing toilet in place.
$324,900
Single-Family
1288 Northview Dr, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
57Picture(s)
3,400Sqft
Welcome to Longmeadow of Oconomowoc. This spacious 5-bed, 3.5-bath offers exceptional versatility and room to live, work, and entertain. The finished lookout LL lives like a private suite, complete with a bedroom, full bath, kitchen, living area, and laundry--ideal for guests or multi-generational living. A Second laundry on the main level adds convenience.
$719,900
Condominiums
W397N5883 Autumn Woods Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
28Picture(s)
1,842Sqft
Stylish 2 bed, 2 bath condo with soaring ceilings and a stunning floor-to-ceiling gas fireplace anchoring the living space. The main level offers a versatile office or formal dining room and features large closets throughout. Enjoy an open-concept layout with natural hardwood floors in the kitchen and newer neutral carpeting throughout.
$339,000
Single-Family
14 White Tail Ln, Oconomowoc Lake, Wisconsin 53066
5Bedroom(s)
5/3Bathroom(s)
87Picture(s)
8,925Sqft
A rare opportunity to own one of Lake Country's most extraordinary private residences. Custom built by Regency Builders and set on 4.58 acres, this one-of-a-kind estate blends craftsmanship, privacy, and resort-style living. Featuring 5 bedrooms, 5 full baths, 3 half baths, a 4-car garage, private elevator, and exceptional storage, every detail was designed for elevated daily living.
$4,995,000
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
1Bedroom(s)
1/1Bathroom(s)
1 space assignedParking(s)
62Picture(s)
1,062Sqft
Welcome to the finest in lake country living! You will love the many amazing features and amenities available here! Enjoy the amazing rooftop deck with breathtaking views ofFowler lake and Lac La Belle as well as the city skyline! Chill and hang out in the grilling area or star gaze around the firepit and sitting area. Got a dog? This condo has a privatedog run and wash area.
$549,900
Single-Family
N59W39568 Laketon Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
38Picture(s)
1,827Sqft
Tucked on a picturesque .65-acre lot just 2 blocks from Lac La Belle and minutes to downtown Oconomowoc, this well-maintained home offers privacy, character, and an unbeatable location. Enjoy cozy evenings by the Lannon stone natural fireplace in the spacious family room or summer days in the private backyard or at the lake.
$525,000
Single-Family
1189 Mockingbird Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
31Picture(s)
2,839Sqft
Welcome home to this inviting 3-bedroom, 2.5-bath ranch located in desirable Oconomowoc, just steps from a nearby park. This well-maintained property features a cozy gas fireplace, a flexible office/den that could be easily converted to a 4th bedroom, and a finished lower level perfect for extra living or entertaining space.
$559,900
Single-Family
W348N5818 Snapdragon Ct, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
36Picture(s)
3,460Sqft
Discover this beautifully designed home in Oconomowoc's sought-after Westshore subdivision, ideally located just minutes from downtown, shopping, and area lakes. The open-concept main level features soaring 10+ ft ceilings, hardwood floors, and elegant archways for character.
$724,900
Condominiums
1538 Weston Ridge Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private GarageParking(s)
21Picture(s)
2,470Sqft
Modern living at its finest in these 3bed, 3bath townhome-style ranch condos. COMPLETION est for 7/26. Several available that could include STEPLESS ENTRY. Open & thoughtful floorplans flow seamlessly, meeting the needs of every day living while maintaining that WOW factor you can feel proud to share w/guests.
$639,900
Single-Family
N87W36989 Mapleton Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
59Picture(s)
2,229Sqft
Discover the perfect blend of comfort, style, and space in Oconomowoc! This beautifully renovated 3BR/2BA home sits on 3.3+ scenic acres on the outskirts within the Oconomowoc School District. The bright, updated interior offers inviting living spaces filled with natural light, modern finishes, and convenient main floor laundry.
$564,900
Single-Family
1001 Spring Waters Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
46Picture(s)
1,683Sqft
BEAUTIFULLY MAINTAINED ONE OWNER OPEN CONCEPT RANCH HOME. Great Rm w/ Cathedral Ceiling, Gas Fireplace & Wall of Windows w/ Charming Window Seat.
$565,000
Single-Family
N60W38457 Blackhawk Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
42Picture(s)
2,302Sqft
Beautifully updated home offering access to Oconomowoc's sought-after Lac La Belle through a shared neighborhood pier. Set on a rare double lot in a charming lakeside neighborhood, this property offers space, character, and an ideal location just minutes from downtown Oconomowoc's shops, dining, and lakefront amenities.
$799,000
Single-Family
N66W34839 Baltic Pass, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
41Picture(s)
2,800Sqft
Exceptional craftsmanship & modern design in this stunning new construction home by Elegant Builders LLC, Every detail reflects artistry, precision & timeless quality. Desirable Meadowlands subdivision in NW corner of Okauchee Lake. Impressive open-concept ranch on 1 acre lot backs to a conservancy. 4 BRs & 2.
$1,050,000
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
43Picture(s)
1,353Sqft
Experience Resort-Style Lake Living at Stunning Mission Lake Condos with Views of Florence Lake! Enjoy access to the pier, a boathouse with sundeck, pontoon, fishing boat, and paddle boats for endless outdoor enjoyment. The attached clubhouse features a full kitchen, bar, fitness loft, two fireplaces, and a patio perfect for relaxing, entertaining, or hosting events.
$359,900
Single-Family
W354N5854 Lisbon Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
54Picture(s)
2,753Sqft
Welcome to Misty Meadows in the Village of Lac La Belle! This beautifully maintained 3BR, 2BA ranch blends warmth, character, and space in a sought-after setting. Enjoy 1,728 sq ft on the main level plus 1,028 sq ft of finished lower-level living--ideal for entertaining, relaxing, or flex space.
$599,000
Vacant Land
1365 Morgan Rd, Oconomowoc, Wisconsin 53066
10Picture(s)
0Sqft
Build your dream home on a 2+ acre lot with mature trees and rural feel, but close proximity to thriving downtown Oconomowoc and easy access to I-94. With well & septic already on-site, this site is ready for you to bring your own builder.
$299,900
Condominiums
512 Frederick Ct, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2/2Bathroom(s)
Private GarageParking(s)
35Picture(s)
1,582Sqft
Sharing a fantastic new listing for a 2 bedroom, 2 full, 2 half bath condo that truly has it all. This property features a full walkout basement, a two-car garage, and professional landscaping with a private entry and a beautiful wooded backyard.Inside, the home offers a spacious living room centered around a gas fireplace with plenty of natural lighting.
$399,900
Single-Family
1080 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,720Sqft
Move-in Ready 95 ARW Julian Cottage I Unit A, TWIN HOME! AVAILABLE 4/15/26! 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.
$554,900
Single-Family
726 Wisconsin Ave, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
57Picture(s)
2,437Sqft
Exceptional opportunity to enjoy Lac La Belle lake life with a boat slip, private neighborhood park access, and a fully updated ranch just a short walk from vibrant downtown Oconomowoc.
$699,900
