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

Condominiums

333 Lake Rd, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
25Picture(s)
1,300Sqft
Exceptional 2BR/2BA condo on Fowler Lake near downtown Oconomowoc! This corner 4th floor unit offers balcony views of both Fowler Lake and Lac La Belle. Enjoy the large great room with dining area and plenty of windows and natural light. Huge covered balcony. Beautifully remodeled kitchen with appliances included. Large master suite features walk-in closet and private bath.
$399,900

Single-Family

1232 Dorchester Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
36Picture(s)
1,933Sqft
Welcome to your new home in beautiful Oconomowoc! This inviting 3-bedroom, 1.5-bath ranch-style house offers a perfect blend of comfort & convenience. The main level features a spacious, light-filled living room area, dining space, kitchen & family room off the kitchen, hardwood floors throughout.
$394,900

Condominiums

1622 Saint Andrews Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
4/1Bathroom(s)
SurfaceParking(s)
50Picture(s)
4,191Sqft
Experience luxury living in this custom-built condo featuring high end finishes throughout. Stunning kitchen boasts sleek granite countertops, deluxe cabinetry and massive central island, perfect for food prep or casual dining. Soaring 14' ceilings and cherry HWF throughout the main living space. Three spacious bedroom ensuites provides the opportunity for multiple primary suites.
$1,200,000

Single-Family

N55W34691 Lake Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
24Picture(s)
1,100Sqft
Bright and updated home with west facing frontage. Primary bedroom is on the main floor along with the living room, updated kitchen, 2nd bedroom, and updated bath with laundry. Large loft bedroom in the upper would fit multiple beds. The house is nicely updated. Or Build your dream home! Very large lot with sunsets and ease of access.
$798,000

Single-Family

W376N7955 McMahon Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
40Picture(s)
3,430Sqft
Stunning Open-Concept Split-Level RanchThis beautiful open-concept split-level ranch offers modern living with spacious flow. The finished basement features partial exposure, 9' ceilings, and is plumbed for a custom bar. Situated on a serene 2-acre lot, you'll love the outdoor firepit and peaceful views of the conservancy.
$849,500

Vacant Land

578 Concord Rd, Oconomowoc, Wisconsin 53066

16Picture(s)
0Sqft
Have you been looking for a meandering scenic Oconomowoc River front lot that is ready for your home plans to be built upon? Well look no further, this rare waterfront lot has everything you may be looking for with all the amenities of a beautiful city location. Kayaking right out your front door, blocks to schools & shopping.
$269,900

Vacant Land

578 Concord Rd, Oconomowoc, Wisconsin 53066

16Picture(s)
0Sqft
Have you been looking for a meandering scenic Oconomowoc River front lot that is ready for your home plans to be built upon? Well look no further, this rare waterfront lot has everything you may be looking for with all the amenities of a beautiful city location. Kayaking right out your front door, blocks to schools & shopping.
$249,900

Single-Family

1447 Olde Highlander Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,927Sqft
NEW CONSTRUCTION- Move in Ready December 2024! - This beautiful Charleston model has all the amenities you are looking for! The main living area is an open area concept connecting the Kitchen, Dinette and Great Room.
$544,900

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
39Picture(s)
2,698Sqft
Incredible 4th floor corner unit with gorgeous view of Fowler Lake and downtown Oconomowoc. Quick walk from restaurants, great boutiques and coffee shops. Direct elevator access to your home and a private 3 car garage. Beautiful hard wood floors with inlayed medallion to tray ceilings with accent lighting.
$2,350,000

Single-Family

1334 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,482Sqft
Move-in Ready 70 ARW Elaine Cottage. AVAILABLE 12/16/24! Built by Wisconsin's leading homebuilder, you can expect nationally recognized, award-winning, quality craftsmanship in this Veridian home. All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, much better than a typical used home.
$499,900

Single-Family

927 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,516Sqft
Move-in Ready 65 ARW Olivia Cottage II Unit B, TWIN HOME! AVAILABLE 12.3.24! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes with private yards. Monthly association fee of $245 covers lawn mowing, fertilization and snow removal; plus a la carte seasonal services are available for a separate rate.
$469,900

Single-Family

931 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,516Sqft
Move-in Ready 64 ARW Olivia Cottage II Unit A, TWIN HOME! AVAILABLE 12.3.24! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes with private yards. Monthly association fee of $245 covers lawn mowing, fertilization and snow removal; plus a la carte seasonal services are available for a separate rate.
$459,900

Single-Family

1414 Bluestem Trl, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/2Bathroom(s)
37Picture(s)
2,835Sqft
This Beautiful Custom Built PRAIRIE CREEK RIDGE SUBDIVISION home offers $60K worth of upgrades already done for you. 4 br,2 full bath, 2 half bath, Open floor plan Can be yours. Gleaming wood laminated floors flow throughout, Main floor features Flex/ Office Rm, Formal Dining Rm, Open Kitchen with staggered maple custom cabinetry and granite center island snack bar.
$585,000

Single-Family

W346N5364 Elm Ave, Oconomowoc, Wisconsin 53069

2Bedroom(s)
1/1Bathroom(s)
14Picture(s)
1,443Sqft
Come see this Okauchee Lake cottage built in the 1950's with 86' of wonderful frontage at the very end of Elm Ave (no traffic!)! Renovate this charming vintage home or use this fantastic parcel to build the new lake house of your dreams! With 2 bedrooms, 1.5 bathrooms, a living room and a retro kitchen - this cottage could certainly be brought up to modern day standards.
$949,900

Single-Family

N55W34913 Lake Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3/1Bathroom(s)
58Picture(s)
3,811Sqft
The Okauchee Lake home you've been waiting for! This single family condo will check all of your boxes. So many extras! Permanent private pier, 2 car attached PLUS an extra 2 car detached garage for your boat and lake toy storage, gated fruit and veggie garden, firepit, outdoor pizza oven, plenty of parking...
$2,495,000

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
56Picture(s)
2,176Sqft
A condo community like no other! This stunning third floor condo showcases incredible views of Fowler Lake and downtown Oconomowoc! As you walk through the condo, every room is bright and inviting. One of the few units that has a balcony in the front and back of the unit offering views of Fowler Lake and downtown Oconomowoc.
$1,349,000

Single-Family

1563 Switchgrass St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
20Picture(s)
2,386Sqft
Welcome to this stunning home on a spacious lot with a thoughtful layout! It features an oversized, insulated, drywalled garage with 8' doors, measuring 26' deep and 34' wide. Inside, a mudroom offers a handy drop zone with lockers and a bench. The basement is primed for future finishing with plumbing, an egress window, and a radon system.
$629,900

Condominiums

1784 Regal Ct, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
Private garageParking(s)
44Picture(s)
3,234Sqft
Location is key for this beautiful Village Crossing Condo in Pabst Farms. Set on a quiet cul de sac, appreciate the privacy most other condos do not.
$749,900

Condominiums

492 Sutherland Cir, Oconomowoc, Wisconsin 53066

2Bedroom(s)
3Bathroom(s)
Private garageParking(s)
40Picture(s)
2,157Sqft
Welcome to this open concept, split 2 bedrooms (privacy), ranch condo with a finished lower level, in the prime Oconomowoc location! Step inside & be greeted by natural light creating an inviting & warm atmosphere. A den / multi purpose room offers versatility. Living room w/ gas fireplace & plenty of space for your big TV.
$469,900

Single-Family

1742 Springhaven Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
52Picture(s)
3,960Sqft
This former Kaerek Homes' parade model in the heart of Oconomowoc's Pabst Farms presents a timeless floor plan with design features all will admire. Find eye-catching trey ceilings, lit alcoves, fresh paint and rich cherry flooring across the open concept main. Wet bar w/beverage cooler & GFP in the LR.
$749,900

Condominiums

926 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
39Picture(s)
1,602Sqft
Discover this beautifully updated 3-bedroom, 2-bath condo, featuring modern amenities and stylish finishes. Located on the second floor, this unit boasts walk-in closets in both the primary and third bedrooms. Enjoy the comfort of newer systems, including the furnace, AC, water heater, and appliances. The entire condo is adorned with sleek LVP flooring.
$299,900

Single-Family

1449 Olde Highlander Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
33Picture(s)
2,137Sqft
NEW CONSTRUCTION - Ready in December 2024! The Bridgeport model features 4 BR's 2.5 BA's and a 1st floor Flex Room. The Kitchen offers plenty of storage space complete with a large kitchen island, quartz countertops and a walk-in pantry. The Great Room includes a corner gas fireplace with beautiful stone to 9ft ceiling detail.
$539,900

Single-Family

W343N6209 Bayview Rd, Oconomowoc, Wisconsin 53066

6Bedroom(s)
2/1Bathroom(s)
55Picture(s)
3,000Sqft
OKAUCHEE LAKE. This is a once in a lifetime opportunity to own a generational property. Set on 2.3 acres with a grand 500 feet of prime level lake walk-out frontage this nicely wooded peninsula lot offers both privacy & tremendous views of the main lake along w/ the best frontage on the lake.A coveted southern exposure means views include both sunrise & sunset & receives sun all day.
$8,000,000

Condominiums

N53W35277 Lighthouse Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
27Picture(s)
1,588Sqft
Gently lived in two bedroom ranch condo in Oconomowoc's Bay Pointe! The spacious kitchen features a large island and brand new appliances! The dining area is great for gathering w/room for a large table! Open concept great room offers a gas fireplace and leads to the beautiful sunroom overlooking the private covered porch! The comfortable primary suite easily accommodates a king bed, offers a larg
$465,000

Condominiums

1779 Derby Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
3Bathroom(s)
Private garageParking(s)
55Picture(s)
3,500Sqft
Welcome to your new home in Pabst Farm's Village Crossing. Every aspect of this 2 bed, 3 bath, 3500 sq ft condo has been thoughtfully designed and masterfully curated. From the moment you enter, you'll be captivated by the high-end finishes, sleek hardwood floors, and a gourmet kitchen with top-tier appliances. Natural light fills every room, creating a bright and inviting atmosphere.
$749,900

Single-Family

936 Tanglewood Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
39Picture(s)
2,692Sqft
Exceptional property and wonderful floor plan awaits the buyer of this charming home. Welcoming foyer with hardwood floors & open staircase. Sun drenched kitchen with beautiful cabinets, granite counters, island and pantry. Well designed family room offers cozy fireplace, pretty views & is open to the large dinette & kitchen. Spacious living and dining rooms.
$469,900

Condominiums

N51W34861 Wisconsin Ave, Oconomowoc, Wisconsin 53069

2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
38Picture(s)
1,353Sqft
Experience Resort Lake Living at Beautiful Mission Lake Condos Overlooking Florence Lake! Enjoy the pier, a boat house with sun deck, pontoon, fishing boat, and paddle boats for lots of outdoor fun! Attached clubhouse includes a full kitchen, bar, exercise loft, two fireplaces, and patio for relaxing, entertaining, or special events.
$349,500

Single-Family

220 Summit Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
29Picture(s)
1,038Sqft
Nicely updated 3BR farmhouse in an outstanding location near downtown Oconomowoc! Enjoy a large private fenced-in back yard. Exterior updates includes a new front porch, roof, and gutters. Main level offers refinished hardwood floors. Large open kitchen area has appliances included. Living room with plenty of windows and natural light. One bedroom with large walk-in closet on main level.
$317,700

Condominiums

333 Lake Rd, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
27Picture(s)
1,600Sqft
Live on the Isthmus, one of Oconomowoc's premier addresses! Enjoy lake living with walk-ability to downtown. Life is better at the top, and you will love this penthouse style, 2 bedroom, 2 bath condo. Stunning views, gracious room sizes and a spacious lakeside balcony create a carefree lifestyle.
$499,000

Single-Family

555 River Bluff Cir, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4Bathroom(s)
49Picture(s)
4,380Sqft
Outstanding 4BD/4BA home in the desirable River Bluff Subdivision, close to downtown & all it has to offer! Definitely a must see & ready for new owners to move right in & enjoy! This beautiful home has a newly remodeled kitchen, w/new floor to ceiling cabinetry, quartz counters & large eat up island - Perfect for entertaining! You'll love relaxing in the gorgeous backyard oasis co
$809,900
128 Results returned.Per Page