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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

514 Lyman St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
32Picture(s)
1,366Sqft
Great location, walking distance to downtown, Large city lot. Possible road access from Union St per city of Oconomowoc. Seller has done numerous updates to this home, windows, roof, furnace A/C, siding to name a few.
$274,500

Single-Family

4560 Hewitts Point Rd, Oconomowoc Lake, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
36Picture(s)
3,722Sqft
Welcome to ''Hewitts Point'' & The Village of Oconomowoc Lake, an upscale community. This astonishing home is a magical mix of design and site. Situated on a private 1.6 acre lot w/circle driveway & surrounded by multi-million dollar homes.
$795,000

Single-Family

320 Wentworth Street, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
32Picture(s)
1,368Sqft
this is the first sale of this 65 year old ranch home. 3 bedrooms large living and family room, dining area and large kitchen. Full basement 2 car detached garage, spacious lot close to schools and walking distance to downtown. This sale is to settle an Estate.
$252,500

Single-Family

673 Summit Ave, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
17Picture(s)
1,224Sqft
WOW come check out this freshly updated super clean home close to all the conveniences of shopping, schools, recreation and transportation. Updated kitchen includes stainless steel appliances and new flooring. Updated bathroom with subway tiles in the shower. New carpeting and light fixtures throughout.
$219,900

Single-Family

1299 Juniper Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
30Picture(s)
1,863Sqft
Well maintain Tim O'Brien build home with many nice features and upgrades. Open concept living with the kitchens 6' Island, granite, maple cabinets, walk in pantry, open to dinette and great room with box tray ceiling, direct vent gas fireplace with cultured stone. Master bedroom suite is spacious, walk in closet, bath with tile floors, tile shower with bench, and double vanity.
$469,900

Single-Family

N50W36115 Golf View Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
29Picture(s)
2,292Sqft
Remarkable home and setting on a gorgeous 3+ acre lot on a no-thru street in a convenient Town of Oconomowoc location! Enjoy a huge fenced-in back yard and additional outbuilding. Home offers lots of curb appeal with the partial stone exterior and plenty of great interior features throughout. Kitchen has white cabinets, large dining area, and SS appliances included.
$444,900

Single-Family

1020 Lexington Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
1/1Bathroom(s)
23Picture(s)
1,760Sqft
Perfectly set on a large corner lot in Heritage Heights subdivision, this home has everything you've been looking for, & so much to offer! Close to schools, downtown, lakes & 1-94 & Hwy 16. In the kitchen you will find brand new Quartz counter tops, brand new stainless steel appliances, & new flooring.
$320,000

Single-Family

W344N6664 Jorgenson Way, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
34Picture(s)
3,854Sqft
Great home and setting in the Town of Oconomowoc, Arrowhead School District! Spacious interior offers plenty of great features throughout, including a huge finished lower level. Family room has gas fireplace. Kitchen with hardwood floors and SS appliances included. Living-dining room area. Main floor office. Wide staircase to 4 upper level bedrooms.
$545,000

Single-Family

533 Lyman St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
35Picture(s)
1,144Sqft
Enclosed front porch greets you and leads into this charming 3 bed, 1 bath house. First floor has open concept. Family room leads into a nice sized dining room, both with wood floors. Upstairs has master bedroom with walk in closet, 2 more bedrooms, and a tiled full bath. Enjoy cookouts from your brick patio. Very desirable location within walking distance to downtown Oconomowoc and high school.
$225,000

Single-Family

N84W36421 Riverwood Ln, Oconomowoc, Wisconsin 53066

5Bedroom(s)
4/1Bathroom(s)
40Picture(s)
7,729Sqft
This is truly one-of-a-kind! 7729 sf of finished living space on 35 acres in the Saddlebrook Farms II sub'n. This is a very functional, beautiful, comfortable home w/ perfect detailing in every room. Has been maintained in like-new condition, combining fresh, sunny spaces with old-world charm.
$2,249,900

Condominiums

N54W35287 Coastal Ave, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
29Picture(s)
1,517Sqft
Just outside of downtown Okauchee lies this beautiful condominium development, Bay Pointe. Five years new, this exceptionally-maintained unit offers all the finishing touches of a quality home. Perennial landscape and asphalt drive. Att. 2-car garage. Inside, enjoy upgraded SS appliances, granite kit. counter, Kohler bath fixtures, Hunter Douglas blinds, all window treatments.
$459,000

Single-Family

1217 Ridgeside Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
35Picture(s)
3,888Sqft
Desirable split ranch located in the heart of Lake Country can now be yours! Positioned privately within the Longmeadow Subdivision, enjoy a secluded backyard and a resident-only in-ground pool and clubhouse. Beautifully updated with new shutters, new light fixtures on the main level and some interior wall and trim paint throughout the home.
$525,000

Single-Family

1131 Whittier Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
35Picture(s)
2,144Sqft
Enjoy pleasures of shopping, restaurants, & City Beach in this centrally located colonial between I94 & the heart of downtown Oconomowoc. The well-maintained 3BED/2.5BA sits on 1/3 acre lot. Light shines into large LR w/NFP that opens to DR w/sliding patio doors out to private deck. Nearly entire interior has been repainted.
$374,900

Single-Family

86 Chestnut St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
31Picture(s)
1,407Sqft
Location, location, location! Live minutes from the heart of Downtown Oconomowoc and immerse yourself in the community by walking to the beach, eating at local restaurants, or playing a round at the Oconomowoc Golf Club! Or, spend time at home in your corner-lot, Victorian 2BR. Drink your morning coffee in the 3-Season front porch or on the swing underneath the covered deck.
$200,000

Single-Family

678 Heather Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
37Picture(s)
2,256Sqft
The original owners have meticulously cared for every corner of this home. All brick ranch on over half acre corner lot. Four Bedrooms, 2 full baths. Spacious living room with bay window and gorgeous natural fireplace is open to the dining room with loads of space for entertaining. Master suite with huge walk-in closet and private bath.
$400,000

Single-Family

W342N4906 Lindy Ln, Oconomowoc, Wisconsin 53058

3Bedroom(s)
2Bathroom(s)
32Picture(s)
2,263Sqft
Completely renovated inside and out. New ''Forever'' pier, Firepit patio, Gazebo, 6 person hot tub, cedar shake siding, all new Pella windows and doors, all new mechanicals and appliances, 2 fireplaces inside, all hardwood floors on main floor, new cabinets in garage with epoxy floor. 5 bars/restaurants to boat to for dinner or drinks. Short 5-10 minute walk to Lions park or Nashotah's dog park.
$900,000

Single-Family

561 River Bluff Cir, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
56Picture(s)
3,710Sqft
The wait is over! Pack your bags & move right in to this beautifully updated River Bluff colonial. The traditional, yet open floorplan offers countless living possibilities. Hardwood floors flow throughout the entire main level.
$535,000

Single-Family

1346 Goldenrod Way, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
22Picture(s)
2,129Sqft
New Construction 3 bedroom Ranch with a large office. Located in Prairie Creek Ridge Subdivision. Black Stainless Steel kitchen appliances included with open concept living/dining room. Granite/Quartz countertops in bathrooms and kitchen. Main floor laundry room and attached oversized three car garage. Basement has partial exposure with two egress windows.
$534,900

Single-Family

472 Wisconsin Ave, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
55Picture(s)
2,720Sqft
Pictures and Videos coming Soon!!! Pictures are supposed to be up today. Videos and Matterport will be available on Monday.Stunning, historic home in one of the most popular neighborhoods in Ocon. This house has all the charm and unduplicatable craftsmanship of the past with all the modern updates and conveniences you could ask for.
$464,900

Single-Family

N63W37817 Vista Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
18Picture(s)
2,085Sqft
This 3 BR, 2 BA home features a NFP, HWf's in two bedrooms, eat-in-kitchen, formal dining room, sunroom, office with private entrance and a lower-level walk-out workshop. Master bedroom has a large picture window overlooking the sprawling backyard, a full master bath and WIC. The deck is perfect for relaxing, entertaining, or taking in wildlife. This home is nestled on 1.
$345,000

Two-Family

702 Silver Lake St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
Driveway entranceParking(s)
15Picture(s)
0Sqft
Here's the opportunity you've been waiting for! Beautiful Oconomowoc duplex in fantastic location. Take advantage of all the city has to offer while having a tenant help with the mortgage! Close walk to downtown, public beach, shopping and dining. Easy to convert back to single family if you're looking for an affordable 4 bed home.
$269,900

Single-Family

723 Silver Lake St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
18Picture(s)
1,195Sqft
Oh, the cuteness factor is in overdrive in this charming 3 bedroom, 1 bath Cape just a short stroll from downtown Oconomowoc. Hardwood floors on the main level and an updated kitchen make this location and home a dream come true. You will love the arched openings and WOW factor space that this home has to offer. Upstairs are two adorable bedrooms each with a small closet.
$219,900

Single-Family

W359N5244 Crestview Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
38Picture(s)
2,300Sqft
Beautifully updated ranch resting on a private, nearly 3/4 acre lot with mature trees. Spacious Kitchen has tile floors, new stainless steel appliances and is open the Family Room and Formal Dining Room!. The inviting natural fireplace has stone surround flanked with built in bookcases and patio door opening to the large deck.
$339,900

Condominiums

1766 Derby Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
1,570Sqft
UNDER CONSTRUCTION! A 1570 SF side-by-side ranch condo, with all the amenities you can expect from a Kings Way build. Granite counter tops in the kitchen, hardwood floors, full basement with egress window and rough in plumbing for future finished basement. 2 bed 2 full bath.
$474,900

Single-Family

1471 Whalen Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
1Picture(s)
1,914Sqft
Welcome to Prairie Creek Ridge! This 3-bedroom, 2.5 bath ranch home offers an open-concept kitchen, dinette, and great room that is perfect for entertaining and daily living. The kitchen has a center island, quartz countertops, maple cabinetry, luxury LVP flooring, and a walk-in pantry. This well-designed floor plan includes separate mudroom and laundry rooms next to the kitchen.
$474,900

Single-Family

1225 Mockingbird Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
29Picture(s)
3,068Sqft
Welcome home! As you walk into the foyer the dining room and living room greet you with warmth. Family room and kitchen flow, making great space for entertaining. Upstairs loft is a great space for you to create a haven of your own. This Colonial offers 3 bedrooms, 2.
$439,900

Single-Family

653 Washington St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
58Picture(s)
2,144Sqft
Former Carnation Guest House* in perfect location! The second-floor five-year-old addition added the space you need with just a short walk from Fowler Lake Park! Enter to Living room with NFP and HWFs under carpet*. Attached sunroom with French Doors (currently off). Formal DR is adjacent to kitchen and large back porch is perfect for back foyer and laundry.
$369,900

Single-Family

W351N5705 Westshore Rd, Oconomowoc, Wisconsin 53066

5Bedroom(s)
2/2Bathroom(s)
41Picture(s)
2,964Sqft
OMG! Pull the car over ! You will love this like new 5br,2/2 bath open concept 2 story Beauty . Detailed white cabinetry and granite counters, granite center island snack bar, gleaming wood floors,gas fireplace with dual flanked patio doors . Den/office with French Doors, Open great room, dinette. main laundry with Locker cabinetry,Large primary suite and WHAT! Large primary walk in closet.
$539,900

Vacant Land

N65W35199 Road J, Oconomowoc, Wisconsin 53066

18Picture(s)
0Sqft
Executive homesite with 42 feet of frontage on Okauchee Lake! This property offers .58 acres and plenty of room to build your dream home. Due to the generous size of the lot, seller states that you would also be allowed to build an additional detached garage, just perfect for all of your storage needs.
$647,900

Single-Family

1513 Whalen Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
1Picture(s)
2,295Sqft
Welcome to Prairie Creek Ridge! A sun-filled 2 story foyer greets you upon entering this 4 bedroom, 2.5 bath home with a modern farmhouse vibe! Spacious kitchen, dinette, and great room offer plenty of room for entertaining and daily living. Great room focal point is the beautiful stone fireplace.
$489,900
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