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
1682 Switchgrass St, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
3Picture(s)
3,013Sqft
HOUSE IS FRAMED - APPROXIMATE COMPLETION SEPTEMBER 2026.5 bedrooms/2.5 baths/Flex room/elite series 2-story. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Corner ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops/double sinks in master bath. Family bath double sinks. 2 WIC's master suite.
$729,990
Single-Family
1752 Switchgrass St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
3Picture(s)
3,013Sqft
4 bedrooms/3 full baths/flex room or 5th bedroom/elite features/2-story. Basement has 1 egress window & drain/vent rough-in for future full bath. Corner ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops in master bath. Double sinks family bath. WIC's all bedrooms. 9' first floor ceilings/tray ceiling master bedroom.
$734,990
Single-Family
1267 Wild Rye Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
5Picture(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.
$624,900
Single-Family
1283 Wild Rye Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,809Sqft
This Rylee is a split-bedroom ranch home currently under construction. The oversized gathering room w/ GFP offers the opportunity to create multiple seating layouts. The kitchen has quartz counters, tile backsplash, a walk-in pantry, & a prep island w/ seating.
$630,900
Single-Family
1733 Hammock Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,350Sqft
This home is under construction. The Hailey 2350 offers a kitchen w/ plenty of cabinetry, quartz counters, WIP, kitchen appliances & prep island, a morning room for casual meals, a gathering room w/ gas fireplace, a formal dining room for large gatherings, a home office & a mudroom featuring a large closet & bench for everyday items.
$657,900
Single-Family
1737 Hammock Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,404Sqft
This home is under construction. The Arielle 2404 is a plan that offers all the essential living spaces starting w/ the kitchen, which features a walk-in-pantry, quartz counters, appliances & prep island w/ extra seating. The gathering room offers a cozy gas fireplace. Finishing the first floor is a flex space/home office, powder room & large mudroom w/ a built-in bench & storage.
$672,900
Single-Family
1750 Whalen Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,428Sqft
This home is under construction. The Francesca 2428 is an ideal home that needs both communal & private spaces. The 1st-floor is home to the gathering room, formal dining room, & dinette. The kitchen features quartz counters, a prep island w/ seating, walk-in pantry, s.s. appliances, & tile backsplash. The main floor also features a private home office.
$721,900
Single-Family
1746 Whalen Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,805Sqft
Move-in-ready, the Lauren 1805 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.
$664,900
Single-Family
1372 MacGregor Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
27Picture(s)
2,355Sqft
MOVE IN READY! Rare opportunity in one of Oconomowoc's most desirable neighborhoods! This 4-bedroom, 2.5-bath home offers 2,355 SF above grade, plus a main-level flex room, and a 3-car finished garage. Enjoy quartz countertops throughout, LVP flooring in the kitchen/dinette/walkway, and a luxe primary suite with tiled floors and shower. Added peace of mind with a radon mitigation system.
$615,000
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
61Picture(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.
$379,900
Single-Family
1269 W Arrowood Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,086Sqft
Move-In Ready 131 ARW Everest Craftsman! 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.
$589,900
Single-Family
1227 Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,647Sqft
Move-In Ready 126 ARW Emerald Cottage - Available 4/22/26! 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.
$524,900
Condominiums
1388 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
32Picture(s)
1,942Sqft
IMMEDIATE OCCUPANCY. Experience refined, low-maintenance living in this beautifully designed new-construction 2-bedroom, 2-bath condo. The elegant eat-in kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and a stylish snack counter open to the sun-filled great room. A cozy gas fireplace and private deck create an inviting space for relaxing or entertaining.
$679,900
Condominiums
1380 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
29Picture(s)
1,942Sqft
IMMEDIATE OCCUPANCY. Experience refined, low-maintenance living in this beautifully designed new-construction 2-bedroom, 2-bath condo. The elegant eat-in kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and a stylish snack counter open to the sun-filled great room. A cozy gas fireplace and private deck create an inviting space for relaxing or entertaining.
$694,900
Condominiums
1382 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
32Picture(s)
1,878Sqft
IMMEDIATE OCCUPANCY. Discover effortless elegance in this newly constructed 2-bedroom, 2-bath condo designed for upscale, low-maintenance living. The gourmet eat-in kitchen impresses with quartz countertops, stainless steel appliances, generous cabinetry, and a sleek snack bar overlooking the light-filled great room.
$684,900
Condominiums
1320 Prairie Creek Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
18Picture(s)
1,760Sqft
Discover effortless living in this stunning new construction ranch condo! Designed with an open-concept layout and unique architectural details, this 3-bed, 2-bath home is ready for immediate move-in. The gourmet kitchen serves as the home's centerpiece, featuring quartz ctps, ss appliances and expansive island.
$599,000
Single-Family
W355N5745 Lisbon Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
38Picture(s)
1,792Sqft
Remarkable home in the popular Misty Meadows neighborhood has a spacious yard that adjoins 22 acres of expansive green space dotted with towering trees. Enjoy the views and the summer fireworks show from the deck or the adorable screened in gazebo. The lovely interior features hardwood floors, new matte black door hardware, new ceiling lights and fans, and tons of windows.
$489,000
Single-Family
1498 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2/1Bathroom(s)
30Picture(s)
1,490Sqft
NEW CONSTRUCTION Buildable Floor plan - The Quentin! Discover The Quentin, a thoughtfully laid out 2 bedroom, 2.5 bath townhome featuring an open-concept first floor ideal for modern living and entertaining. The spacious Great Room flows seamlessly into a beautifully appointed Kitchen complete with a large center island and a corner walk-in pantry.
$400,000
Single-Family
909 York Imperial Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
37Picture(s)
2,158Sqft
Welcome to your new home located in the beautiful Orchards neighborhood in the heart of Oconomowoc. This stunning 3 Bed, 2 bath cozy family floor plan is sure to be the perfect place to make the happiest memories. Plenty of updates, private yard, 2 car garage and more. You must see to appreciate. The location is prime, close to everything that creates joy in life. Schedule your showing today.
$495,000
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
35Picture(s)
1,495Sqft
Welcome to Mission Lakes Condominium where serene lakefront living blends seamlessly with sophisticated design. This beautifully updated 2-bed, 2-bath features open concept living that maximizes comfort & style. Step into the spacious great room, where a sleek gas fireplace anchors the space & sets a cozy tone.
$434,900
Condominiums
320 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
25Picture(s)
1,193Sqft
This gorgeous, fully renovated condo offers an open kitchen & living space, and large balcony with views of the lake perfect for entertaining and relaxing Every detail was considered in the update: concrete island countertop, quartz on the perimeter, pantry with pullouts, wine storage, beverage fridge & glass storage, top of the line appliances, bench seating with ample storage, pull-out s
$599,000
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
Condominiums
201 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
46Picture(s)
1,580Sqft
Not very often do you come across a freshly painted 1st floor condo unit in the highly sought-after 55+ development of Silver Ridge! This beautiful corner unit offers 3 spacious bedrooms & 2 bathrooms. Featuring a cozy gas fireplace in the living area & an open-concept gallery kitchen w/breakfast bar & Corian countertops. Solid six-panel doors & walk-in closets add ample storage.
$319,900
Single-Family
1533 Fay Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
30Picture(s)
2,004Sqft
Remarkable newer luxury ranch home in Oconomowoc's Prairie Creek Ridge! Enjoy this beautifully designed home with many upgrades and outstanding features. Open concept vaulted main living area offers LVP flooring and gas fireplace in great room. Kitchen has large island breakfast bar with quartz countertops, walk-in pantry, SS appliances, and Zephyr range hood.
$699,900
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
1286 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
13Picture(s)
2,355Sqft
BUILDABLE FLOOR PLAN - Contact Harbor Homes now to build our Atwater model in phase III of Olde Highlander (home/lot package through Harbor). Choose from our standard or Gourmet Kitchen that opens up to a spacious great room with optional fireplace - open the space up even more by adding a sunroom.
$595,000
Single-Family
813 High St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
25Picture(s)
2,108Sqft
Beautifully modernized home completely finished with high quality materials. Large lot on quiet cul-de-sac. Tasteful kitchen with oversized Nantucket bluff cabinets and pantry. Bathrooms include custom vanities, quartz countertops, tile shower/surround, and stylish tile floors. New flooring throughout including durable LVP and carpet in bedrooms, staircase, and 4-season room.
$575,000
Single-Family
1257 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,572Sqft
Move-In Ready 130 ARW Harlow Classical - Available 4/2/26! 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.
$539,900
Condominiums
1045 Ann Marie Way, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
36Picture(s)
1,400Sqft
Welcome to The Glen of Oconomowoc-where condo living is done right. This exceptionally well-built, European-inspired side-by-side ranch condo offers a bright, open-concept layout with a desirable split-bedroom design. The kitchen features an eat-in area and breakfast bar and flows seamlessly into the great room with a cozy gas fireplace.
$515,000
