Back to Communities

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:

Sort Option
  • Listing ID
  • Square Footage
  • Price
  • Pictures
  • Add date
  • Featured
Grid
List

Single-Family

825 High St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,735Sqft
NEW CONSTRUCTION READY AUGUST 2024 This open concept 1,735 sq ft home features 3 spacious bedrooms & 2.5 baths is ideal for modern living and entertaining. You'll love the Amish built custom cabinets in the kitchen with new SS appliances & walk-in pantry which seamlessly flows into the dining area & living room, complete with a cozy fireplace making it the heart of the home.
$524,900

Single-Family

1384 Goldenrod Way, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
41Picture(s)
2,660Sqft
Stop Scrolling! This 2022 luxury ELITE series home offers $80K worth of upgrades already done for you. You won't find another home like it in the area. On the main floor you'll love the stunning kitchen w/ huge island, upgraded appliances, Kohler faucet & modern backsplash. Laundry room offers custom built-ins. Bonus flex room has crown molding & French doors.
$625,000

Condominiums

N53W35216 Lighthouse Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
Private garageParking(s)
44Picture(s)
2,300Sqft
This Splendid Bay Pointe condo has it all.3 bedrooms & 3 baths with a walk out lower level to patio and pond area, even a walking trail around pond, and yes, you can even fish with friends (catch & release). Amazing open floor plan. Granite kitchen with raised breakfast bar, stainless appliances, walk in pantry. Hardwoods on first floor. Covered deck open to Great Room.
$539,000

Single-Family

1601 W Mamerow Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
62Picture(s)
2,651Sqft
Don't miss out on this stunning newer build in Oconomowoc! The main level features a sprawling open-concept design encompassing a spacious living room, dining area, and gourmet kitchen completewith a sizable pantry, island, and backyard views. Additionally, you'll find an office, expansive mudroom area, and a convenient half bath.
$599,900

Single-Family

1414 Bluestem Trl, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/2Bathroom(s)
33Picture(s)
2,835Sqft
Stop the Car ! This beautiful Custom built PRAIRIE CREEK RIDGE SUBDIVISION home offers $60K worth of upgrades already done for you. 4 br,2 full ba,2 half ba open floor plan Can be yours. Gleaming wood floors flow throughout, Main floor features Flex/ Office Rm, Formal Dining Rm, Open Kitchen with staggered cappuccino maple custom cabinetry and granite center island.
$614,850

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

1Bedroom(s)
1/1Bathroom(s)
Private garageParking(s)
60Picture(s)
1,023Sqft
Introducing Fowler Lake Village and this downtown Oconomowoc premier condo home where modern design meets lakeside living at its finest. Nestled in the heart of the city, this contemporary building offers a host of desirable amenities aimed at enhancing your lifestyle including rooftop deck, luxury workout room, large dog-friendly patio, and oversized common areas.
$529,000

Single-Family

625 South St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
34Picture(s)
2,568Sqft
Stunning LARGE home in a GREAT location exudes old-world charm, lovingly maintained, featuring beautiful woodwork and built-in cabinets. Upstairs den can be a 5th bedroom. This spacious, unique residence is perfect for a large family and ideal for entertaining both indoors and outdoors. Relax on the upstairs deck, front porch or gazebo.
$449,999

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
37Picture(s)
2,176Sqft
Welcome to Luxury in sought after Oconomowoc! Enjoy stunning views from this 4th floor corner unit featuring southern and western exposure overlooking the city, Fowler Lake and Lac La Belle. Convenience is key in this building with restaurants, recreation room, gym, dog run and a knock your socks off roof top patio! The original owner offers this unique lifestyle with many upgrades.
$1,549,000

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

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
73Picture(s)
2,219Sqft
Walk in the clouds and enjoy breathtaking views of the sunsets, lakes and buzzing life right in the heart of downtown Oconomowoc. This three bedroom, two bath 2,219 sf stunning penthouse in the sky is your next dream home.
$1,999,500

Single-Family

W346N5263 Elm Ave, Oconomowoc, Wisconsin 53069

4Bedroom(s)
3Bathroom(s)
42Picture(s)
2,891Sqft
You have always dreamed of having that perfect lake home. Sunny sun, glistening water & a beautifully crafted dream home w/guest cottage. Believe it or not, it is here for you today! This home has been created to extend the ideal in residential living. Outfitted in classic lake elegance.
$1,495,000

Single-Family

755 Armour Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
27Picture(s)
1,652Sqft
WOW! Meticulously updated bi-level home with a fenced yard, near downtown Oconomowoc.
$425,000

Single-Family

W340N4739 Jaeckles Blvd, Oconomowoc, Wisconsin 53058

2Bedroom(s)
1/1Bathroom(s)
38Picture(s)
1,356Sqft
Clean, neat, and tidy with Okauchee Lake access, this turn-key ranch is an affordable way to get into Lake Country living or make a fun getaway spot. Completely freshnened with new paint and flooring throughout, this home offers a spacious living room, kitchen with ample cabinetry, a caverous sunroom, two bedrooms, and a half bath in the utility room to compliment the full bath.
$299,900

Single-Family

415 Oakwood Ave, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
33Picture(s)
1,348Sqft
Wonderfully updated and maintained centerpiece to the history of Oconomowoc! Right across from Fowler Park, walkable to downtown, find this Victorian beauty right on the parade path! 2 bedrooms upstairs with plenty of first floor living space & a full bath on each floor! New shed, new patio, and new back deck adorn a well manicured yard, abundant with flowers! Garage is spacious and doubles as
$364,000

Condominiums

1630 St Andrews Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3/1Bathroom(s)
Private garageParking(s)
25Picture(s)
3,604Sqft
Experienace the charm of this Tuscan inpire 3BR/3.5 bath home. Nestled next to Silver Lake, it features an open floor plan, gourmet kitchen, luxurious MBR and private courtyard. Elegant finishes throughout and spacious living areas make it perfect for entertaining. With over 650ft of shoreline this property is truly one of a kind.
$1,099,000

Single-Family

274 Thomas Trl, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3Bathroom(s)
38Picture(s)
2,441Sqft
Welcome to this stunning newer ranch-style home boasting exceptional curb appeal and situated on a picturesque lot. Enjoy the perfect blend of comfort and style with a partially fenced yard and a charming patio, ideal for outdoor gatherings. Step inside to discover a home that feels brand new, featuring an open concept design with vaulted ceilings in the spacious GR and KIT area.
$575,000

Condominiums

W398N6056 Autumn Woods Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
31Picture(s)
1,824Sqft
Lovingly cared for 2 BD/2 BA has the space to meet all your needs. This upper floor unit has so many lifestyle options. Need a home office? Check out the expansive den. How about a second living space for some quiet time or a place to watch your favorite TV show? The loft is ideal for that.
$329,000

Single-Family

820 Byron Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
61Picture(s)
3,902Sqft
Stunning 4 BR, 3.5 BA home is an entertainers paradise, with both indoor & outdoor amenities designed for relaxation and fun. Host BBQs by the in-ground pool, sip drinks at the outdoor bar, or unwind on the deck. Privacy & extra space of a oversized double corner lot with fenced yard. Updated eat-in KIT has newer appliances.
$775,000

Condominiums

1644 St Andrews Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
24Picture(s)
2,861Sqft
Lake life made easy! Enjoy all the benefits of a lake home without the work, including a pier, boat slip & PRIVATE beach for lakeside fun. Inside, the foyer will rise to greet you & impress w/ details like arched doorways & soaring ceilings. Kitchen is sure to delight w/ granite that flows up the backsplash & atop the breakfast bar.
$975,000

Condominiums

128 Wisconsin Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
2 or more spaces assignedParking(s)
45Picture(s)
2,688Sqft
This stunning home offers high end finishes and overlooks Lac La Belle! Enjoy your gourmet style kitchen which includes double ovens, gas cooktop, large island for entertaining, wine cooler, and more. Two private balconies offer opportunity for grilling, entertaining and relaxing.
$1,870,000

Condominiums

N52W35297 Lighthouse Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
36Picture(s)
1,588Sqft
FANTASTIC SIDE-BY-SIDE RANCH CONDO w/ common area pond, walking trails & mature backyard for privacy! This Open Concept 2 bedrooms, 2 full bath, 2.5 car attached garage is bursting with loads of windows.
$535,000

Single-Family

629 Lake Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
51Picture(s)
3,030Sqft
Welcome to your dream lake home. This exquisite 4 bed, 2.5 bath, 3000 sq ft Cape Cod is perfectly situated on the scenic Isthumus of Lac LaBelle & Fowler Lake. Boasting 92 feet of pristine lake frontage, this home offers breathtaking views and unparalleled access to serene waters.
$1,349,900
134 Results returned.Per Page