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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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Vacant Land

Lt31 Primrose Cir, Oconomowoc, Wisconsin 53066

4Picture(s)
0Sqft
Prime lot in the Arrowhead Districtlocated on a cul-de-sac over looking Okauchee Lake backing to a wooded area and green space. Side sloping lot with a walk out basement exposure. Bay View Estates subdivision is a development of 53 home sites and includes a 7 acre centrally located gathering / play area. Conveniently located minutes from shopping close to Hartland, Delafield and Oconomowoc.
$79,900

Single-Family

255 Lakeridge Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
29Picture(s)
2,924Sqft
Beautifully updated home in Oconomowoc's Lakeridge! 2-story foyer greets you flanked by dining room and den. Hardwood flooring on main level. Large great room with fireplace. Kitchen has breakfast bar, center island, SS appliances included, and nice size dining area with patio doors to deck. Half bath on main.
$389,900

Condominiums

1003 Ann Marie Way, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
22Picture(s)
1,861Sqft
Exceptional property w/numerous upgrades in this side x side building w/golf course view in desirable Glen of Oconomowoc. Southern and Western exposure for all day sunQualify & craftsmanship throughout this spacious unit. Vaulted ceilings in every room! Gorgeous HWD floors throughout main living area.
$474,900

Vacant Land

Lt102 Harvard St, Oconomowoc, Wisconsin 53066

7Picture(s)
0Sqft
Walk to Fowler Lake Park and downtown Oconomowoc Small lot for a just enough home. A little more grass than if you owned a condo but nobody telling you what to do. No sidewalks. This lot is 50 feet wide and 100 feet deep.It backs to the Greenland School green space. Southern exposure to the rear. 7 foot side setbacks and 20 foot front and rear setbacks.
$44,900

Vacant Land

Lt103 Harvard St, Oconomowoc, Wisconsin 53066

7Picture(s)
0Sqft
Walk to Fowler Lake Park and downtown Oconomowoc Small lot for a just enough home. A little more grass than if you owned a condo but nobody telling you what to do. No sidewalks. This lot is 50 feet wide and 100 feet deep.It backs to the Greenland School green space. Southern exposure to the rear. 7 foot side setbacks and 20 foot front and rear setbacks.
$44,900

Single-Family

W380N6779 Lake Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
38Picture(s)
2,283Sqft
Rare opportunity to own this wonderful 4/5 BR, 2 full BA home on 7. 3 acres. Spacious Liv Rm w/tall ceilings & HWF's. Full BA on 1st floor has large claw foot soaking tub. KIT overlooks Fam Rm w/FP. Dutch door opens to 3-season rm. 3-Season Rm has views of extremely private back yard where nature abounds.Soaring pines & other wooded areas make this a private retreat.
$399,900

Two-Family

35 Park St, Oconomowoc, Wisconsin 53066

1Bedroom(s)
1Bathroom(s)
Electric door openerParking(s)
21Picture(s)
0Sqft
Rare investment opportunity awaits you in this bungalow style duplex, located within walking distance to Oconomowoc City Beach, Park Street Beach, city parks & all of downtown's amenities. Your tenants will love all the conveniences this property has to offer w/ private entrances.
$199,900

Single-Family

35 Park St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
21Picture(s)
1,273Sqft
Welcome home to your charming new bungalow on Park Street. You will love the location of this home! Take a short stroll to explore Oconomowoc City Beach, Park St. Beach, City parks, as well as downtown Oconomowoc shopping, restaurants and more! Sit back and relax as you enjoy your morning coffee on your three seasons porch.
$199,900

Single-Family

1823 Springhouse Ct, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
38Picture(s)
2,459Sqft
Eastlake Village at Pabst Farms is the setting for this split bedroom ranch style home. Custom built for the current owner. Open concept floor plan and gorgeous hardwood flooring. Kitchen boasts maple cabinetry, solid surface counters with snack bar and overlooks the great room with gas fireplace and southern exposure windows. Formal dining room could be a perfect den/office option.
$449,900

Vacant Land

Lt2 Buchanan Rd, Oconomowoc Lake, Wisconsin 53066

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0Sqft
First time ever offered! Over 358 ft of pristine swimming frontage on a fantastic wooded 5-acre estate sized lot. Recently split off from one of the major older estates on Oconomowoc Lake. Drive down a long wooded private road to view this gorgeous, heavily wooded lot. This property offers outstanding views, exceptional frontage, & a prime location on one of Wisconsin's premier lakes.
$2,750,000

Single-Family

N342W4861 Lindy Ln, Oconomowoc, Wisconsin 53058

2Bedroom(s)
1Bathroom(s)
18Picture(s)
924Sqft
Bright and sunny 2 bedroom 1 bath ranch with gleaming hardwood floors. Cook up a storm in the chefs kitchen with high end appliances, soak up the sun from the walls of windows with a lake view! Large level backyard with deck to enjoy the lake breeze. Stroll down to the shared access area with pier, firepit, picnic table and swimming/fishing pier.
$224,000

Single-Family

377 Lake Bluff Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
27Picture(s)
3,050Sqft
OCONOMOWOC. Within easy walking distance to downtown Oconomowoc this 3000 square foot custom built ranch is guaranteed to stand up to the most discriminating buyer.
$549,000

Condominiums

110 Marcella St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
32Picture(s)
1,824Sqft
Why rent when you can own this affordable open concept side x side ranch condominium. Main level offers spacious ML master w/WIC, open concept bright Living Room open to Kitchen. Full Bath. Lower level features large Family Room, full Bath and 2nd Bedroom with Thermal Dry Carpeted floor system. Newer windows w/lifetime warranty. Roof 9 years old. Self-managed so no condo fees. Pets permitted.
$150,000

Condominiums

112 Marcella St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
27Picture(s)
1,824Sqft
Oconomowoc Affordable ranch side x side Condominium. Why rent when you can own this 2/3 bedroom, 2 bath open concept ranch condo. This is a self managed condo, so no condo fees. 2 Bedrooms and 1 bath on ML spacious living room with large picture windows, open to kitchen. Lower provides you with a 22x17 family room. Shared 2.5 car garage, Asphalt driveway. Dead end street.
$150,000

Single-Family

35520 Pabst Rd, Oconomowoc Lake, Wisconsin 53066

4Bedroom(s)
5/1Bathroom(s)
33Picture(s)
6,441Sqft
Very privately situated on a beautiful 5 acre wooded knoll on one of the major private estates on the lake, with 600 feet of frontage! This newer ranch home with an exposed lower level offers the finest quality and workmanship available. Spectacular kitchen with great views overlooking the lake and open to the family room and lanai.
$4,895,000

Condominiums

200 Wisconsin Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
21Picture(s)
2,883Sqft
Customize your own condominium (for accepted offered received prior to 3/31/2020). Lakefront living at its finest with no maintenance! Gorgeous northwesterly view overlooking Lac La Belle from your balcony with glass railings. High-end finishes and all Wolf/SubZero appliances in a custom kitchen by DreamKitchens.
$1,225,000

Single-Family

1548 Oconomowoc Ave, Watertown, Wisconsin 53094

3Bedroom(s)
2Bathroom(s)
37Picture(s)
1,536Sqft
A HOME YOU MUST SEE IN PERSON!! 3 BED, 2 FULL BATH, 3 CAR GARAGE....Fantastic woodwork, vaulted ceilings, balcony off master bed overlooking beautiful sun room, spiral staircase, skylight, wood & gas burning stove, cedar kitchen, private TALL fenced yard.....
$192,500

Single-Family

1093 Spruce, 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.
$474,900

Vacant Land

W341N7150 Northern Lights Dr, Oconomowoc, Wisconsin 53066

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This 3.162 acre level lot is the perfect compliment to your dream home! Situated in the North Pole Estates, this parcel has plenty of mature trees around the border for a feeling of privacy, yet easy access for your commute! Bring your architectural ideas without having to compromise due to lot or subdivision restrictions. Arrowhead School District is a plus.
$239,900

Single-Family

1524 Westfield Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
35Picture(s)
2,200Sqft
Call this 4 Bedroom, 2.5 Bath Colonial ''Home'' today! Located on a quiet cul-de-sac in a convenient location w/easy access to freeways, downtown Oconomowoc, lakes and more! This house has it all. the space, the yard, the upgrades - just waiting for your personal touches. Main level houses the Family Room w/Fireplace, Living RM, Dining RM, Kitchen w/Stainless Appliances, 1/2 Bath & Laundry.
$329,900

Single-Family

1288 Ridgeside Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3Bathroom(s)
26Picture(s)
2,775Sqft
Exceptional 4BR/3BA ranch home in Oconomowoc's Longmeadow! Enjoy this desirable subdivision that has a community swimming pool. Spacious interior offers 2775 sq ft of living space and many upgrades throughout. Split bedroom design has vaulted main living area. Great room features gas fireplace. Kitchen has granite countertops, SS appliances included, and nice size dining area.
$479,900

Single-Family

N65W34255 Timberline Rd, Oconomowoc, Wisconsin 53066

5Bedroom(s)
3Bathroom(s)
36Picture(s)
4,000Sqft
Immediate Occupancy! The original owner now transferred offers this spacious open concept Stone Bank Exposed ranch with sunny southern exposure is in sought after Bay View Estates and the Arrowhead School District & overlooking the adjoining subdivision outlot & pond. The split bedroom design has the MBR fully insulated for privacy.
$479,900

Vacant Land

926 Roosevelt Ave, Oconomowoc, Wisconsin 53066

8Picture(s)
0Sqft
Here is your chance to fix up a three bedroom, one bath home in a fabulous location and build a new one on the lot abutting it. So many options such as a rental or occupy and invest! Located only a few blocks from Fowler Park, these properties are hidden gems. The house needs your attention with paint, carpet and appliances. The lot is a fully improved city lot awaiting construction.
$175,000

Single-Family

926 Roosevelt Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
32Picture(s)
1,000Sqft
Here is your chance to fix up a three bedroom, one bath home in a fabulous location and build a new one on the lot abutting it. So many options such as a rental or occupy and invest! Located only a few blocks from Fowler Park, these properties are hidden gems. The house needs your attention with paint, carpet and appliances. The lot is a fully improved city lot awaiting construction.
$175,000

Single-Family

35320 Pabst Ct, Oconomowoc Lake, Wisconsin 53066

4Bedroom(s)
4/1Bathroom(s)
52Picture(s)
6,871Sqft
One of a kind stunning retreat is set on over 5 acres giving you the private resort feeling you have been looking for! Custom designed interior spaces have rustic & modern touches throughout! Crown moldings, Built-ins, rustic beams & soaring ceilings! Incredible private master suite boasts a gas FP, french doors leading to covered Lanai overlooking pool & amazing ensuite! Remodeled a
$1,275,000

Vacant Land

Lt0 Valley Rd, Oconomowoc, Wisconsin 53066

6Picture(s)
0Sqft
Located on the southeast corner of Valley Rd. and Golden Lake Rd (B and BB) in the city of Oconomowoc, this 70 acre parcel is conveniently located close to Hwy. 67 and I-94. It is one of Oconomowoc's developable areas for residential use per the City Planner. A portion of the land includes a hill which offers pretty views of the area.
$1,300,000

Single-Family

1536 Miller Ct, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
6Picture(s)
2,410Sqft
3 bedrooms/2 bath/dining room/split bedroom ranch. Basement has one egress slider window and rough-in for full bath. Master bedroom has tray ceiling/2 WIC's. Master bath has ceramic tiled walk-in shower/2 shower heads/granite vanity tops/double sinks. 9' main floor ceilings/pitched ceilings in foyer, living room, kitchen, dinette. Knockdown drywall with rounded corners.
$494,990

Single-Family

N65W35199 Road J, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
31Picture(s)
978Sqft
Amazing property with over a half an acre and 42' of frontage on Okauchee Lake!!! Beautiful views of Okauchee Lake on a bay on the North West area of the lake.
$499,900

Single-Family

1694 Mamerow Ln W, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
11Picture(s)
1,893Sqft
NEW CONSTRUCTION by Stepping Stone Homes, the ELLINGTON model features all of today's smart home technology! This beautiful 3 bedroom/2 bath open concept ranch offers a gorgeous Kitchen w/quartz countertops, soft close cabinets, under cabinet lighting and high end appliances and overlooks a large Great Room w/electric fireplace.
$439,900

Single-Family

1601 Mamerow Ln W, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
18Picture(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.
$489,900
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