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:
Single-Family
833 Roosevelt Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
20Picture(s)
1,048Sqft
Available to you for the first time in nearly 40 years, this 3 BRM/1 full bath ranch style home has been properly maintained and updated including features such as refinished hardwood floors in the bedroom, updated electrical, new furnace and a newer concrete driveway. The convenience also makes this home desirable with all rooms being on the main floor and includes a easy walk-in shower.
$199,900
Single-Family
321 Concord Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
21Picture(s)
1,430Sqft
Here's your opportunity to live in the heart of Lake Country close to evolving Downtown Oconomowoc! This three bedroom Victorian home has a fully updated kitchen with a large center island and stainless steal appliances, two updated full baths, dining room and a extra room. Fenced in yard with a outdoor bonus room, fire pit and chicken coup.
$269,900
Single-Family
1424 Blazing Star Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
29Picture(s)
1,759Sqft
Two year NEW construction has all the benefits of a move-in ready established home with lush landscaping! Enjoy the open concept layout and spacious rooms that allow you to absorb beauty from every angle! Welcoming foyer leads to great room with gas fireplace and top/down Graber blinds, spacious dining area off kitchen with beautiful cabinetry, granite countertops.
$385,000
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
15Picture(s)
1,292Sqft
Move-in ready. View of lake from balcony. Beautifully designed, luxuriously finished, amenity rich new condo in the heart of walkable lake country.
$529,900
Single-Family
N66W35960 Farmstead Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
31Picture(s)
4,231Sqft
Step into this beautiful home by premier builder M.D. Custom Homes, known for impeccable quality and attention to detail. Accented with rustic & custom details the open concept design offers an effortless flow from the great room to the kitchen and dining area. Enjoy the floor to ceiling stone fireplace from either the great room or dining area.
$675,000
Single-Family
169 Maple St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
40Picture(s)
1,256Sqft
This charming 3 bed, 1 bath farmhouse in the City of Oconomowoc is sure to please. Breathtaking hardwood floors provide the warmth and character of a time gone by. A truly spacious kitchen means entertaining and cooking can be seamlessly integrated. Located just under a mile from downtown Oconomowoc means a night out for dinner or dessert is just a short summer stroll away.
$219,900
Single-Family
W356N6676 Stonewood Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
40Picture(s)
3,736Sqft
Stunning, custom split-bedroom ranch w/high end features. Spacious open concept for casual living. 1+ acre lot on quiet lake. Great for kayaking/fishing, private pier. Many windows for ample natural light & lake views. Hand scraped hickory hardwood floors. Custom design kitchen w/island, banquette, full extension drawers/shelves, built-in storage for easy cooking/clutter free counters, lrg.
$659,900
Single-Family
1483 Saint Andrews Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
36Picture(s)
3,482Sqft
No spring cleaning needed when you move into this well kept, clean, updated colonial! The great curb appeal will invite you into this 4 bedroom 2.5 bath home. The open floor plan offers a spacious kitchen with plenty of seating at the snack bar, a breakfast nook and living area. A family room with fireplace, formal dining room, half bath and laundry room complete the main floor.
$459,900
Single-Family
4560 Beach Rd, Oconomowoc Lake, Wisconsin 53066
1Bedroom(s)
3Bathroom(s)
26Picture(s)
3,467Sqft
Imagine owning a private island! The spectacular floor-to-ceiling windows of this home give the sensation of living directly on the water with southerly views of the lake. No expense was spared in designing this coastal masterpiece. The moment you cross the private stone bridge and view the lush landscaping and secluded inlet, you are somewhere that few will ever get to experience.
$2,890,000
Vacant Land
4753 Jaeckles Blvd, Oconomowoc, Wisconsin 53066
13Picture(s)
0Sqft
Build your dream home with access to Okauchee Lake! Enjoy swimming and kayaking all summer long. Minutes away from downtown Okauchee, Lions Park and Nashotah Park.
$55,000
Single-Family
1152 Saratoga Pkwy, Oconomowoc, Wisconsin 53066
4Bedroom(s)
1/1Bathroom(s)
44Picture(s)
1,860Sqft
This is it! Look no further! Beautifully updated 4 bedroom 1 and a half bath colonial in the desirable Heritage Heights Neighborhood. Featuring a handsome chef's pleasing kitchen with stainless steel appliances, this open concept layout is perfect for family meals or entertaining friends. Partially finished lower level with wet bar.
$299,900
Single-Family
1269 Juniper Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
13Picture(s)
1,663Sqft
Welcome to Stepping Stone Homes! The Avery is a beautiful open concept split bedroom ranch built for the way you live. Kitchen & Great room w/ vaulted ceiling. Large dining room with beautiful laminate HWF's. The Master suite provides a private retreat for the end of a long day. White painted woodwork, large quartz island, clean and crisp subway tile back splash, etc.
$364,900
Single-Family
2031 Oakwoods Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
16Picture(s)
3,515Sqft
Quality built Log style ranch home with fully finished lower level walk-out on private low maintenance 2.5 partially wooded acres. Open concept floor plan features volume ceilings with an impressive floor to ceiling fieldstone fireplace and custom solid hickory wood floors. Lower level features a rustic bar/entertainment area with a den/workout room along with a fourth bedroom and full bath.
$699,900
Single-Family
1299 Redwing Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
46Picture(s)
2,743Sqft
This home checks all the boxes! Entertaining is easy with open concept island kitchen with newer black & stainless steel appliances and beautiful granite counters that flow into the large family room with gas fireplace. Beautiful laminate wood plank flooring throughout the main level. Spacious bedrooms and freshly updated bathrooms include ceramic tile and updated vanities.
$380,000
Single-Family
N56W35275 Pondview Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
25Picture(s)
2,100Sqft
Hard to find completely updated 4 bedroom 2 1/2 bath colonial in the highly desirable Westshore subdivision. This beautiful, meticulously maintained home features a first floor master suite, first floor laundry, and a chefs kitchen with separate stainless steel refrigerator and freezer.
$382,900
Condominiums
948 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
1Picture(s)
1,475Sqft
High demand first floor unit in prime location!!! Meticulously maintained large 2BR, 2BA condo end unit with walk-in closets and loads of storage space. The kitchen and baths have tiled flooring and many updates. Living room, dining room has hardwood floors with a beautiful gas fireplace for those cozy evenings with tiled surrounded and decorative mantle.
$184,900
Single-Family
254 Blue Ridge Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
31Picture(s)
2,372Sqft
Freshly updated throughout with new paint, carpeting, flooring & more! Newer stainless appliances in the kitchen which is open to the family room with a gas fireplace. Patio doors lead to a large deck for summer fun. Main floor laundry room.
$324,900
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.....
$189,900
Single-Family
3214 Walleye Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
34Picture(s)
2,323Sqft
Stunning New Construction home in the heart of Lake Country. HighPoint Design Build Group is offering this split 3-bedroom ranch, 2.5-bathroom home with a 3 car garage. Beautiful open concept kitchen w/ 9' long island, walk-in pantry, equipped with Bosch appliances. Custom cabinetry throughout. Great room has a gas fireplace, distressed mantel, shiplap, and wood beams inside a 10' ceiling.
$649,000
Single-Family
1431 Mamerow Ln W, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
23Picture(s)
2,036Sqft
Nicely updated 4BR home on a large lot in Oconomowoc's Hickorywood Farms! This move-in ready home is full of great features throughout. Large great room has beautiful stone gas fireplace. Kitchen-dinette area features hardwood floors, breakfast bar, and SS appliances included. Huge main floor laundry room. Nice size bedrooms on the upper level.
$379,900
Vacant Land
Lt4 Northern Lights Dr, Oconomowoc, Wisconsin 53066
5Picture(s)
0Sqft
Exceptional opportunity to build your dream home on this 3.162 acre lot.This parcel is nestled in a gorgeous subdivision, offers privacy,seclusion and yet is conveniently located for an easy commute. Large level rear yard with mature trees. Start designing your luxury home todaywithout having to compromise due to restrictive lot or subdivisionrestrictions.
$229,900
Single-Family
W352N5980 Nelson Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
49Picture(s)
4,508Sqft
Magnificent quality built home with fabulous layout features towering cathedral ceiling Great Room with FP & huge wall of windows. Large kitchen boasts solid oak cabinets and floors with generous counter space and all new stainless appliances included. Spacious master suite also has cathedral ceilings and jetted tub. Fantastic finished basement includes wet bar, tile floors and family room.
$465,900
Single-Family
1749 Eastlake Dr, Oconomowoc, Wisconsin 53066
5Bedroom(s)
4/1Bathroom(s)
67Picture(s)
4,591Sqft
Why build when this stunning home is move in ready?WOW!! This home offers 5/6 bedrooms and 4.5 baths!! There is plenty of room for everyone with quality finishes! The beautiful kitchen boasts granite counters and GE Monogram Stainless appliances. Spacious dinette overlooks the sunroom with pond views. Versatile formal dining room.
$575,000
Condominiums
1061 Regent Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
1 space assignedParking(s)
20Picture(s)
1,012Sqft
NEW Carpet-NEW Paint-NEW Flooring throughout! Come and visit this rare opportunity to own your own condo in Lake Country. This unit comes with a washer and dryer combo, stove, refrigerator and dishwasher. Second level bedrooms offer soaring ceilings and view of open space from your private balcony.
$119,900
Single-Family
1209 Northview Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
41Picture(s)
2,541Sqft
Price Improvement! Welcome to this contemporary, 4 BR, 2.5 BA home located in the highly sought after Longmeadow Subdivision. Take notice of the beautiful, Brazilian cherry floors, vaulted ceilings, and arched entries throughout most of the 1st floor. 2 story great room boasts a floor-to-ceiling stone, gas fireplace and triple French doors which lead to the backyard patio and nature conservancy.
$449,000
Single-Family
N71W35498 Mapleton Lake Dr, Oconomowoc, Wisconsin 53066
5Bedroom(s)
4Bathroom(s)
87Picture(s)
1Sqft
*Please see drone video under videos. Click on pictures first then video. Beauty, tranquility, breathatking. This gorgeous 48 acres offers stunning views from the spacious 5 bedroom hilltop home, superbly positioned to take advanatage of the panoramic scenery.
$1,300,000
Single-Family
2 Earling Ct, Oconomowoc Lake, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
33Picture(s)
4,278Sqft
Wake up every morning to a beautiful view overlooking Oconomowoc Lake! Step inside to the two-story family/front room finished with magnificent floor to ceiling windows and a loft area. The wood floors flow through the family room, great room, kitchen, and dining room. Relax by the great room fireplace with large window taking advantage of the lake view & a walk out to the patio.
$1,275,000
Single-Family
26 Park St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
22Picture(s)
1,296Sqft
Charming two story home with seasonal porch located near the heart of downtown. 3 Bedrooms, 1 bath, kitchen, dining room and quaint space for office or craft room. This home offers plenty of storage and has a patio and spacious back yard for entertaining. Unique to this property is a car and a half garage with loft. This home presents itself to lifestyle living.
$175,000
Single-Family
415 Oakwood Ave, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
36Picture(s)
1,348Sqft
Remarkable turnkey Oconomowoc Victorian home in an excellent location across from Fowler Park! Enjoy the views, walk to park or downtown Oconomowoc, and right on the Fowler lake walk loop. Home features many updates and is full of Old World character and charm and newly painted exterior! Plenty of hardwood flooring. Front living room with large windows.
$265,900
Single-Family
440 Thurow Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
22Picture(s)
1,518Sqft
This fantastic split bedroom ranch is located in a lively neighborhood with walking trails & a park! Open concept with formal dining room that opens to the great room with vaulted ceiling & wired for surround sound. The eat-in kitchen with walk-in pantry is home to ALL NEW APPLIANCES in the popular ''slate'' color. Master suite features ample closets & private bath.
$299,900
