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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:

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Single-Family

1449 Olde Highlander Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
33Picture(s)
2,137Sqft
NEW CONSTRUCTION - Ready in December 2024! The Bridgeport model features 4 BR's 2.5 BA's and a 1st floor Flex Room. The Kitchen offers plenty of storage space complete with a large kitchen island, quartz countertops and a walk-in pantry. The Great Room includes a corner gas fireplace with beautiful stone to 9ft ceiling detail.
$539,900

Single-Family

W343N6209 Bayview Rd, Oconomowoc, Wisconsin 53066

6Bedroom(s)
2/1Bathroom(s)
55Picture(s)
3,000Sqft
OKAUCHEE LAKE. This is a once in a lifetime opportunity to own a generational property. Set on 2.3 acres with a grand 500 feet of prime level lake walk-out frontage this nicely wooded peninsula lot offers both privacy & tremendous views of the main lake along w/ the best frontage on the lake.A coveted southern exposure means views include both sunrise & sunset & receives sun all day.
$8,000,000

Condominiums

N53W35277 Lighthouse Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
28Picture(s)
1,588Sqft
Gently lived in two bedroom ranch condo in Oconomowoc's Bay Pointe! The spacious kitchen features a large island and brand new appliances! The dining area is great for gathering w/room for a large table! Open concept great room offers a gas fireplace and leads to the beautiful sunroom overlooking the private covered porch! The comfortable primary suite easily accommodates a king bed, offers a larg
$444,900

Condominiums

N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069

2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
38Picture(s)
1,353Sqft
Experience Resort Lake Living at Beautiful Mission Lake Condos Overlooking Florence Lake! Enjoy the pier, a boat house with sun deck, pontoon, fishing boat, and paddle boats for lots of outdoor fun! Attached clubhouse includes a full kitchen, bar, exercise loft, two fireplaces, and patio for relaxing, entertaining, or special events.
$349,500

Single-Family

823 High St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,420Sqft
NEW CONSTRUCTION READY FOR OCCUPANCY!Welcome to this beautiful new construction ranch home, boasting 1,420 sq. ft. of thoughtfully designed living space. This inviting residence features 3 spacious bedrooms, 2 modern bathrooms, & open-concept layout perfect for contemporary living. Upgraded features such as Custom-built Amish cabinets, upgraded tops & tiled baths.
$499,900

Single-Family

37715 Wildwood Ln, Oconomowoc, Wisconsin 53066

5Bedroom(s)
4Bathroom(s)
81Picture(s)
6,479Sqft
A home of this quality doesn't come along very often. Built by a high end custom builder for his own residence this gorgeous ranch home combines a gorgeous setting with unparalleled luxury and craftsmanship At 6500 sq ft this stunning home is set on a private 1.27 acre lot surrounded by conservancy land. The back yard is all epitome of peace and quiet.
$1,250,000

Single-Family

1582 Switchgrass St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
61Picture(s)
2,430Sqft
Motivated seller! $15k total price reduction. Move-in ready Open Concept home with 1 Yr Home Warranty from Lake Country homes. The GR features soaring ceilings w/cozy gas FP that opens to the kitchen & dinette. Kitchen quartz counters w/tile backsplash and a large quartz island for your culinary skills. Dinette patio door leads to the patio & backyard.
$569,900

Single-Family

1208 Northview Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3Bathroom(s)
37Picture(s)
4,029Sqft
Stunning ranch home in pool community -- Longmeadow subdivision! With its spacious layout, abundance of natural light, & exquisite finishes, it's a perfect place to call home. Whether sitting by a fire in the great room, lounging on the peaceful back patio or having parties in your finished lower level, this house has it all! Oversized 4 car garage will provide plenty of storage or car space.
$814,900

Single-Family

1235 Violet St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
6Picture(s)
2,735Sqft
HOUSE IS IN ROUGH TRADES. APPROX. FINISH JUNE 2025.4 bedrooms/2.5 baths/flex room/Elite series 2-story. Basement has 1 egress slider window and drain/vent rough-in for future full bath. Ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops in master bath. Double sinks in family Jack & Jill bath. Two WIC's master suite.
$639,990

Single-Family

1570 Creekview Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
7Picture(s)
2,251Sqft
HOUSE IS IN ROUGH TRADES. APPROXIMATE COMPLETION JUNE 2025.3 bedrooms/2 full baths/ flex room/split ranch. 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. Large WIC master suite. Double sinks family bath.
$589,990

Single-Family

1541 Creekview Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,764Sqft
HOUSE IS BEING FRAMED. APPROX. COMPLETION JUNE 2025.4 bedrooms/2.5 baths/flex room/elite series 2-story. Basement has 1 egress slider window and drain/vent rough-in for future full bath. Master bath has corner ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops. Double sinks master & family baths. 2 WIC's master suite.
$629,990

Single-Family

1261 Shoal Ridge Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
1Picture(s)
2,328Sqft
Investors your search is over! Minutes from downtown Oconomowoc. Endless possibilities with this Large open concept Colonial located in the Hickory Green Subdivision. Book your showing today! Home is being as is sold by a personal representative of an estate. No additional photos to follow and no yard sign at listing.
$289,900

Single-Family

N84W36411 Riverwood Ln, Oconomowoc, Wisconsin 53066

5Bedroom(s)
5/3Bathroom(s)
90Picture(s)
8,500Sqft
This French Manor estate, on 35 acres, epitomizes luxury & tranquility. A private oasis awaits, complete with serene pond & charming bridge leading to a secluded island with picturesque gazebo. Meticulously crafted residence harmonizes architectural elegance with natural beauty. A sanctuary unlike any other.
$2,499,999

Condominiums

1626 St Andrews Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
30Picture(s)
2,046Sqft
UNDER CONSTRUCTION Dolcetto - Only 2 units available. Located a stones throw from Silver Lake in the City of Oconomowoc, this development features European-style architecture inspired by a romantic sea-side village in Porticello, Italy.
$749,900

Single-Family

N53W35963 Lake Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
29Picture(s)
2,144Sqft
Remarkable 4BR colonial home on a gorgeous 1+ acre lot in the Town of Oconomowoc! Enjoy this great setting featuring many mature trees and private back yard. Spacious interior offers hardwood flooring throughout. Large front living room with adjoining dining room. Family room has brick natural fireplace. Kitchen features island, granite countertops, bay window, and appliances included.
$449,000

Condominiums

1380 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
32Picture(s)
1,942Sqft
*UNDER CONSTRUCTION * EMORY unit. Includes balcony and partial exposure with lookout windows for future finished basement.The development consists entirely of side-by-side and double-duplex ranch condominiums that range in square footage from 1,571 to 1,942+ with sunroom add-on options. Spacious open concept floor plans feature generous entertaining spaces.
$664,900

Condominiums

1382 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
1Picture(s)
1,878Sqft
*UNDER CONSTRUCTION* DALEA unit. Includes balcony and partial exposure with lookout windows for future finished basement.The development consists entirely of side-by-side and double-duplex ranch condominiums that range in square footage from 1,571 to 1,942+ with sunroom add-on options. Spacious open concept floor plans feature generous entertaining spaces.
$654,900

Condominiums

1320 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
34Picture(s)
1,760Sqft
Cypress~ Move-In-Ready The development consists entirely of side-by-side and double-duplex ranch condominiums that range in square footage from 1,571 to 1,942+ with sunroom add-on options. Spacious open concept floor plans feature generous entertaining spaces and architectural features like alcoves and ceiling designs elevate the overall feel of the space.
$599,900

Condominiums

1376 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
1Picture(s)
1,760Sqft
Cypress unit Future Clubhouse and Swimming Pool!* Photo from previously finished unit** Taxes have not been assessed
$589,500

Condominiums

1378 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
1Picture(s)
2,531Sqft
Cypress unit with finished lower levelFuture Clubhouse and Swimming Pool!* Photo from previously finished unit** Taxes have not been assessed
$667,320

Condominiums

1384 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
1Picture(s)
2,699Sqft
Cypress unit with optional sunroom and 3 car garage. Future Clubhouse and Swimming Pool!* Taxes are not assessed** To Be Built** Pictures from a previously finished unit.
$743,373

Condominiums

1390 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
1Picture(s)
2,046Sqft
Dalea unit with added sunroom and 3 car garage.Future Clubhouse and Swimming Pool!*Taxes are not assessed.** Pictures are of a previously finished unit.
$643,400

Condominiums

1615 Belmont Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
5Picture(s)
1,570Sqft
Breton ~AUGUST 2024 OCCUPANCY - Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, 3/4'' wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full 9' basements w/egress window, rough plumbing for future full bath & wet bar, concrete patio.
$589,900

Condominiums

1603 Belmont Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
8Picture(s)
1,942Sqft
Estonian ~ OCCUPANCY IN LATE AUGUST - Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, 3/4'' wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full 9' basement w/egress window, rough plumbing for future full bath & wet bar, concrete patio.
$644,900

Single-Family

W342N5150 Road P -, Oconomowoc, Wisconsin 53069

6Bedroom(s)
4/1Bathroom(s)
47Picture(s)
6,977Sqft
The definition of lakeside luxury on over 1.5 acres at this stunning custom-built Okauchee Lake property featuring 139 feet of prime frontage. Ready for year-round fun, this remarkable residence includes 3 piers and a rare boathouse. With nearly 7,000 sq. ft. of thoughtfully designed spaces this home offers endless opportunities for relaxation and entertainment.
$5,750,000

Single-Family

1538 Creekview Ct, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
7Picture(s)
2,336Sqft
HOUSE IS IN FINISHED CARPENTRY. APPROXIMATE COMPLETION FEBRUARY 2025.3 bedrooms/2.5 baths/Flex room/Split ranch. 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. Double sinks family bath. Huge WIC master suite.
$674,990

Single-Family

1691 Hammock Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,805Sqft
This home is under construction. 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.
$619,900

Single-Family

1613 Switchgrass St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
49Picture(s)
2,484Sqft
HOUSE IS IN FINISH TRADES. APPROXIMATE COMPLETION NOVEMBER 2024.4 bedroom/2.5 bath/2-story. Basement has an egress slider window & drain/vent rough-in for future full bath. Master bath shower w/ceramic tiled walls & shower pan. Double sinks master & family baths. Granite or equivalent vanity tops. Huge WIC master bedroom. Knockdown drywall w/rounded corners.
$574,990

Single-Family

1362 Windwood Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
42Picture(s)
2,172Sqft
Move-in Ready 3 ARW Hudson Farmhouse! Buyers may be eligible for GREAT RATE! A 4.99 intro interest rate first year with 5.99 interest rate on following 29 years. Details noted on veridianhomes.com or call a New Home Specialist for details. Built by Wisconsin's leading homebuilder, you can expect nationally recognized, award-winning, quality craftsmanship in this Veridian home.
$634,900

Single-Family

1358 Windwood Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
38Picture(s)
2,392Sqft
Move-in Ready 4 ARW Margot Farmhouse. Buyers may be eligible for GREAT RATE! A 4.99 intro interest rate first year with 5.99 interest rate on following 29 years. Details noted on veridianhomes.com or call a New Home Specialist for details. Built by Wisconsin's leading homebuilder, you can expect nationally recognized, award-winning, quality craftsmanship in this Veridian home.
$664,900
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