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
1241 Green Tree Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
33Picture(s)
2,404Sqft
Move-in-ready. 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.
$691,900
Single-Family
N66W38493 Woodlake Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
5Bathroom(s)
60Picture(s)
5,218Sqft
Mediterranean-inspired one-of-a-kind Woodlake ranch home on nearly an acre surrounded by open space & pond. South facing home with fully exposed LL giving every room sunlight and views. Designed with a cozy feel throughout, the split ranch has multiple spaces for entertainment.
$1,050,000
Condominiums
1802 Lindens Ct, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
SurfaceParking(s)
29Picture(s)
2,810Sqft
Welcome to Village Crossing at Pabst Farms! Hard to find 3BR plus den condo with sleek modern feel in PRIME location. Luxury finishes throughout including hardwood floors, 10 ft ceilings & arched doorways. Functional and beautiful floor plan features LR with floor-to-ceiling gas FP with new stacked stone surround & main floor den/office.
$649,900
Vacant Land
Lt86 Scotsland Ln, Oconomowoc, Wisconsin 53066
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0Sqft
Lot 86-Located in The Estates at Olde Highlander. Olde Highlander offers a variety of amenities for homeowners to enjoy, including a Pool, Clubhouse, Walking Path, Playground & Outdoor Activity Area. Lot 86 has partial/lookout exposure. Only available as a home & lot package with Tim O'Brien Homes.
$162,900
Vacant Land
Lt87 Scotsland Ln, Oconomowoc, Wisconsin 53066
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0Sqft
Lot 87-Located in The Estates at Olde Highlander. Olde Highlander offers a variety of amenities for homeowners to enjoy, including a Pool, Clubhouse, Walking Path, Playground & Outdoor Activity Area. Lot 87 has partial/lookout exposure. Only available as a home & lot package with Tim O'Brien Homes.
$162,900
Vacant Land
Lt89 Scotsland Ln, Oconomowoc, Wisconsin 53066
1Picture(s)
0Sqft
Lot 89-Located in The Estates at Olde Highlander. Olde Highlander offers a variety of amenities for homeowners to enjoy, including a Pool, Clubhouse, Walking Path, Playground & Outdoor Activity Area. Lot 89 has full/walkout exposure. Only available as a home & lot package with Tim O'Brien Homes.
$169,900
Vacant Land
Lt88 Scotsland Ln, Oconomowoc, Wisconsin 53066
1Picture(s)
0Sqft
Lot 88-Located in The Estates at Olde Highlander. Olde Highlander offers a variety of amenities for homeowners to enjoy, including a Pool, Clubhouse, Walking Path, Playground & Outdoor Activity Area. Lot 88 has partial/lookout exposure. Only available as a home & lot package with Tim O'Brien Homes.
$165,900
Single-Family
1388 W Mamerow Ln, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
31Picture(s)
4,300Sqft
4,300 sq ft home offering luxury & functionality. Main level has open-concept living room, dining area & kitchen with large island, granite & stainless. Main-level bedroom can serve as office. Upstairs is primary suite with tiled walk-in shower & dual WICs, 3 additional large BRs, full bath & convenient laundry.
$790,000
Condominiums
1626 Belmont Ln, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
5Picture(s)
1,571Sqft
Breton model - New Construction - Occupancy March 2026 ~ Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, real wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full basements w/egress window, under-floor rough plumbing for future full bath & wet bar, concrete patio.
$614,900
Condominiums
1624 Belmont Ln, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
5Picture(s)
1,571Sqft
Breton ~ Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, real wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full basements w/egress window, under-floor rough plumbing for future full bath & wet bar, concrete patio.
$604,900
Condominiums
N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
33Picture(s)
1,238Sqft
Beautifully maintained 2BR/2BA condo in Mission Lakes! Enjoy this outstanding location along Florence Lake in downtown Okauchee. Complex has lakeside patio, boathouse, & association owned pontoon & fishing boats. Unit offers an open concept floor plan. Great room features gas fireplace with patio doors to patio with direct outside access for easy in and out.
$361,900
Single-Family
N49W35398 Wisconsin Ave, Oconomowoc, Wisconsin 53066
4Bedroom(s)
4/1Bathroom(s)
96Picture(s)
8,158Sqft
Experience lakefront living in this furnished luxury retreat! Nestled on a pristine shoreline, this expansive lake home offers breathtaking water views from nearly every room. Step inside to discover exquisite woodwork throughout, from custom millwork to rich refinished hardwood floors that anchor every space with quality.
$4,895,000
Vacant Land
Lot 41 Road B -, Oconomowoc, Wisconsin 53069
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0Sqft
Confirmed at the Village of Lac Labelle board hearing, Lot 41 has a sewer rec assigned and is buildable!Rare buildable lot availability on Okauchee lake! The property has 50 ft of frontage! 50' x118'on Waukesha county GIS. Lightly wooded and tiered lot is perfect for multiple levels of windows and sliding doors. Down by the water the lake frontage is level and has two piers.
$759,000
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
4513 Hewitts Point Rd, Oconomowoc Lake, Wisconsin 53066
7Bedroom(s)
8/2Bathroom(s)
38Picture(s)
20,890Sqft
This standout Oconomowoc Lake landmark property is available for the first time ever! A magnificent and substantial 20,000+ square foot stone home, it features 7 bedrooms, 12 bathrooms, 8 fireplaces, an elevator, garage parking for 10 cars, an indoor pool, theatre, gym and a guest suite/apt in its own wing.
$14,995,000
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
40Picture(s)
1,500Sqft
This 4th flr 2 bdrm 2 bath condo with southern exposure has your dreams of lake living calling. An open concept living area with an expansive balcony is host to beautiful lake views, plenty of natural light and front row seats to the annual 4th of July fireworks. Bedrooms are separated by main living area giving you privacy with guests or working remote.
$399,000
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 for fireworks displays this season! 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.
$539,900
Single-Family
1342 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
29Picture(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
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
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.
$699,000
Single-Family
1536 Creekview Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
4/1Bathroom(s)
4Picture(s)
2,660Sqft
HOUSE IS IN ROUGH TRADES. APPROXIMATE FINISH FEBRUARY '264 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)
7Picture(s)
2,874Sqft
HOUSE IS BEING DRYWALLED. APPROXIMATE FINISH FEB.'26.5 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
Vacant Land
W354N6260 Williams Ct, Oconomowoc, Wisconsin 53066
2Picture(s)
0Sqft
Let your imagination take flight at Snyder Farms, a premier residential community featuring spacious, improved single-family home sites. Nestled in the gently rolling hills of Lake Country, this exceptional development offers a perfect balance of natural beauty and modern convenience. The Snyder Farm subdivision in the Town of Oconomowoc provides everything you need to create your dream home.
$179,900
Vacant Land
N62W35431 William Ct, Oconomowoc, Wisconsin 53066
2Picture(s)
0Sqft
Let your imagination take flight at Snyder Farms, a premier residential community featuring spacious, improved single-family home sites. Nestled in the gently rolling hills of Lake Country, this exceptional development offers a perfect balance of natural beauty and modern convenience. The Snyder Farm subdivision in the Town of Oconomowoc provides everything you need to create your dream home.
$179,900
Vacant Land
Lt1A Lalumiere Rd, Oconomowoc Lake, Wisconsin 53066
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LOT 1A South is approx. 1.52 acres on a secondary channel with outbuilding allowed. It includes Lot 1B (.11 acre) & 55 ft. of frontage on primary channel (newly dredged) allowing for pier & boats access to Oconomowoc Lake. Lots are permanently attached and never sold separately. No structure allowed on Lot 1B. House plan and site design are included.
$479,900
Single-Family
1299 W Arrowood Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
38Picture(s)
2,033Sqft
Move-in Ready 51 ARW Hoffman Cottage. Available 7/22/25! 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.
$634,900
Single-Family
1724 Whalen Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,337Sqft
HOUSE IS BEING FRAMED-APPROXIMATE COMPLETION FEBRUARY 2026.4 bedrooms/2.5 baths/flex room/spacious 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/double sinks/granite or equivalent vanity tops in master bath. 2 WIC's master suite. Knockdown drywall w/rounded corners.
$604,990
Single-Family
1539 Creekview Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,866Sqft
HOUSE IS IN ROUGH TRADES - APPROX. FINISH MARCH '26.4 bedrooms/2.5 baths/flex room/elite series spacious 2-story. Basement has 1 slider egress window & drain/vent rough-in for future full bath. Master bath has corner ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops. Family bath w/double sinks. 2 WIC's master suite.
$689,990
Single-Family
1700 Whalen Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
34Picture(s)
2,002Sqft
Welcome home to The ELIZA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 3 bedrooms, 2 baths, office & 3 car garage. This lot is a flat exposure. The kitchen comes w/quartz countertops, soft close doors and LG appliance package. LVP flooring in kitchen, dinette and great room.
$664,900
G
530 Franklin St, Oconomowoc, Wisconsin 53066
30Picture(s)
13,721Sqft
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.
$720,000
