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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

371 Yosemite Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
29Picture(s)
1,886Sqft
This very sharp, split ranch design offers a condo-like experience yet with all the benefits of a single-family home. The open concept is ideal, showcasing the generous kitchen, rich use of real hardwood floors, island, volume ceilings and additional light from the skylights. A handsome fireplace is the focal point of the easy-to-view area from the food prep in the kitchen.
$339,900

Single-Family

825 Roosevelt Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
21Picture(s)
1,100Sqft
Beautifully maintained 3 Bedroom, 1 Bath ranch in the heart of Oconomowoc. Light and bright kitchen and bathroom are sure to impress along with beautiful hardwood floors that run throughout the main floor living area. The manicured yard is the icing on the cake with a partially fenced back yard and beautiful new patio ready to entertain and enjoy the Wisconsin seasons.
$234,900

Single-Family

524 Main St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
40Picture(s)
1,016Sqft
Downtown is within half a mile & Roosevelt Park within half a block! This home will charm the buyer looking for one-level living in a fantastic location. The three-season sunroom opens to a large living room with gleaming hardwood floors. Beyond that is the dining room or family with the same lovely floors.
$184,900

Single-Family

N62W38169 Westwinds Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
44Picture(s)
3,614Sqft
Enjoy Lac La Belle access and 2.45 Acres with this beautiful 4 Bedroom 3.5 Bathroom home on 2.45 Acres! The home has brand new carpet and other updates inside. There is an indoor hot tub, a finished basement rec room, balcony, deck, extra garage with tons of storage, and more! Located in a quiet culdesac in a desirable private location.
$669,900

Single-Family

214 Maple Ter, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
25Picture(s)
1,850Sqft
LAC LA BELLE. Frank Lloyd Wright style home. Built by a student of Wright's this mid century contemporary clearly stands the test of time with it's open concept floor-plan.
$450,000

Single-Family

N88W34800 Mapleton Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
25Picture(s)
2,800Sqft
Escape the crowded city life for the big skies, blue lakes and fresh country air of the Oconomowoc area.
$530,000

Single-Family

1101 Christopher Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
65Picture(s)
2,193Sqft
This home has so much to offer, from location to space, to updates, to schools. Living Room with fireplace and vaulted ceilings. Kitchen with granite counters and ss appliances. Multiple living spaces, 4 spacious bedrooms, 2 full bathrooms. Balcony off the master bedroom looks into the beautifully landscaped backyard. Front and back patios offer great outdoor space.
$290,000

Single-Family

653 Sherman Ave, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
11Picture(s)
1,440Sqft
Beautifully updated charming 4 bedroom 2 bath home in quaint Fowler Lake neighborhood just a short walk to Fowler Lake and Lac La Belle. Where to begin....every room on the main and upper floors have been remodeled. New master bedroom, walk in closet and master bath added.
$309,900

Single-Family

1310 Foxwood Pass, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
32Picture(s)
3,734Sqft
Brand new split 3 bedroom ranch home loaded with extras. Family room with cathedral ceilings, remote controlled gas fireplace, and open concept design. Master bedroom with tray ceiling, large walk in closet with master bath having a tiled shower and floor with a huge linen closet and granite counter with dual sinks.
$499,900

Single-Family

42 Eastmans Alley, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
46Picture(s)
1,580Sqft
Quiet dead end street within walking distance to beach, library, parks and downtown. Enjoy coffee in the morning on your three seasons porch. Updated bathrooms, new windows, new water softener being installed, new central air. Lovely fenced in backyard.One year home warranty included.
$235,000

Single-Family

111 Elm St, Oconomowoc, Wisconsin 53066

1Bedroom(s)
1Bathroom(s)
31Picture(s)
736Sqft
Welcome to Downtown Oconomowoc! This ranch home is located 1 block from Wisconsin Avenue, within walking distance to popular restaurants, parks, shopping, beach & lakes! Brand NEW concrete & approach in deep 18 x 30 garage! Fresh paint interior & exterior of the home. New window wells, tall privacy fence around the back yard. New carpet & flooring throughout. Tile shower.
$159,900

Single-Family

1203 Saratoga Pkwy, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
35Picture(s)
1,404Sqft
OCONOMOWOC RANCH ~ RECENTLY REMODELED OPEN CONCEPT LIVING CENTER ~ PRIVATE BACK YARD! Open floor plan features a large living room adjoining a beautifully remodeled kitchen with abundant cabinets, hardwood floors, and a large open dining area. 3 bedrooms with hardwood floors. Separate family room leads to an adjoining enclosed screened porch.
$279,000

Condominiums

1045 Ann Marie Way, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
22Picture(s)
1,400Sqft
The Glen of Oconomowoc Condominiums are exceptionally well built European style homes. This split 2 bedroom, 2 bath ranch condo is full of sunlight and charm. Open concept layout features a breakfast bar, eat in kitchen and a gas fireplace in the great room. Entertain and grill out on your patio and private yard.
$397,500

Single-Family

1601 Mamerow Ln W, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
29Picture(s)
2,651Sqft
NEW CONSTRUCTION by Stepping Stone Homes, the ISABELLA model features all of today's smart home technology! This beautiful 4 bedroom/2.5 bath open concept 2 story offers a gorgeous Kitchen w/quartz countertops, soft close cabinets, under cabinet lighting and high end appliances. Large Great Room w/electric fireplace.
$484,900

Single-Family

647 Anderson St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
6Picture(s)
946Sqft
Settle in to ''Lake Life'' in the heart of vibrant downtown Oconomowoc! Imagine boating, fishing, and kayaking right out your back door. This home has a brand new floor plan, and has been completely renovated, from the studs out, with professional craftsmanship and high-end finishings. The new floor plan has it all for modern living.
$335,000

Single-Family

W347N5133 Road Q, Oconomowoc, Wisconsin 53069

2Bedroom(s)
1Bathroom(s)
24Picture(s)
650Sqft
A quaint and cozy gem nestled in the heart of Lake Country. Bordering downtown Okauchee with convenient access to Highway 16. This updated home offers 2 bedrooms, living area. The eat in kitchen has been updated with laminate floors and includes the appliances. 1.5 car detached garage. Tree-lined yard. A short walk to deeded Okauchee Lake access.
$179,900

Single-Family

N57W34997 Pondview Ln, Oconomowoc, Wisconsin 53066

5Bedroom(s)
3/1Bathroom(s)
58Picture(s)
4,117Sqft
Nestled on the edge of a glistening spring-fed pond is this luxurious home offering the very best in waterfront living. Entertain in style in this sprawling, open-plan home that has been expertly crafted to ensure a life of leisure. Enter the family room where a soaring stone fireplace creates a cozy ambience & the sky-high ceiling & oversized windows ensure a bright & welcoming space.
$630,000

Single-Family

1398 Lakeridge Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
34Picture(s)
2,800Sqft
Fantastic two-story loaded with quality living space! Kitchen and great room are open to each other and provide loads of light throughout. Kitchen has beautiful cabinetry, granite countertops, stainless steel appliances that are included, beautiful glass tile backsplash and a very large snack bar. This layout is ideal for entertaining. There are three spacious bedrooms on the second floor.
$424,900

Single-Family

N55W35791 Lisbon Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3/1Bathroom(s)
42Picture(s)
2,887Sqft
3 BR, 3.5 BA ranch offers room for everyone! Front LR w/cherry HWFs, vaulted ceiling & lge picture window. FR w/stone NFP & twin BIBC is open to updated kitchen featuring Cherry cabs, granite counters, CT flr & new SS appliances (except DW). MBR suite offers priv BA w/dual sink vanity, SS & soaking tub. Delightful screened porch off MBR perfect for morning coffee.
$335,000

Single-Family

1290 Victoria Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
34Picture(s)
1,913Sqft
Experience everything Oconomowoc has to offer in this move in ready, bright and open 3 bed, 2.5 bath split ranch. Boasts enough space for now but potential for added space in the exposed lower level already plumbed for a full bath later. Enjoy quiet evenings on the maintenance free deck and space to play in the large flat backyard.
$389,900

Single-Family

516 Cassie Lynn Ln, Oconomowoc, Wisconsin 53066

5Bedroom(s)
3/1Bathroom(s)
45Picture(s)
4,935Sqft
Are you looking for a new home with plenty of space? This is the one. A full 5 bedroom home with lots of room to spread out! All 5 bedrooms are on the upper level. Wonderful main floor living room, dining room, family room and den/office. Large deck off the wonderful 4-season room. Head downstairs to the theatre room/rec room areas.
$499,999

Condominiums

217 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
26Picture(s)
1,674Sqft
Top floor end unit with 3 season porch overlooking the pond & conservancy. This 3rd floor 1674 SF open concept condo has a vaulted ceiling & gas fireplace, The great room & dining area are open to the kitchen which has a breakfast bar & lots of cabinets & counter space. Spacious master bedroom has a walk-in closet & bath with shower stall & jetted tub.
$237,500

Single-Family

W341N6778 Lancelot Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
18Picture(s)
1,494Sqft
Attention Investors and Rehabbers!! This home is set on a wonderful 1.5 acre lot in Stone Bank, and is ready for some renovation ideas and TLC. Home is being sold AS-IS. Cash offers or conventional financing only. New roof installed in June, 2020.
$189,900

Single-Family

318 Forest St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1/1Bathroom(s)
16Picture(s)
1,008Sqft
Enjoy this move-in ready home with 2 bedrooms on the 1st floor and flex room on the second floor for a possible 3rd bedroom. Many updates include newer roof, electrical panel, kitchen cabinets, and gas furnace in 2016.
$239,900

Single-Family

1501 Waters Edge Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
37Picture(s)
3,100Sqft
COME SEE THIS WELL MAINTANED RANCH HOME SETTLED IN THE HICKORYWOOD FARMS SUBDIVISION! Come fall in love with this open-concept home! The kitchen provides a walk-in pantry and informal seating at the kitchen peninsula. The dining area flows nicely from the kitchen and into the main living area.
$389,900

Single-Family

1306 Grandview Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
18Picture(s)
1,871Sqft
Fantastic Brick 3 Bedroom 2 Bath Ranch on over 1/2 acre in River Highlands! Welcome to Oconomowoc! This original owner dwelling offers a low maintenance brick exterior, and the convenience of easy commuting to Milwaukee or Madison.
$289,000

Single-Family

W340N6202 Breezy Point Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4Bathroom(s)
64Picture(s)
5,177Sqft
Beautifully remodeled ranch home with walk-out lower level! Free standing single family condo with 137 feet of prime frontage. Enter the 2-story foyer and take in the spectacular panoramic lake views! Custom tile, soaring ceilings with unique design, gleaming HWFs and more! Great room is amazing with huge windows.
$1,899,000

Condominiums

W340N6202 Breezy Point Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4Bathroom(s)
Private garageParking(s)
62Picture(s)
5,177Sqft
Beautifully remodeled ranch home with walk-out lower level! Free standing single family condo with 137 feet of prime frontage. Enter the 2-story foyer and take in the spectacular panoramic lake views! Custom tile, soaring ceilings with unique design, gleaming HWFs and more! Great room is amazing with huge windows.
$1,899,000

Single-Family

W356N6693 Stonewood Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
25Picture(s)
3,246Sqft
Remarkable 3-4 BR ranch home with exposed lower level and finished bonus room in Oconomowoc's Woodside Farms! This spacious home offers plenty of upgrades throughout. Open concept kitchen-great room with vaulted ceiling and hardwood flooring. Great room with brick gas fireplace. Kitchen offers large breakfast bar island and granite countertops. Bayed dining area with back yard views.
$569,900

Single-Family

1682 Arthurs Pass, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
26Picture(s)
2,178Sqft
This luxurious Colonial home is beautifully set on a quiet street. Walk into a bright, inviting 2 story foyer that leads into the homey living room with hardwood floors and stone fireplace.
$364,900
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