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:
Condominiums
1018 Ann Marie Way, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
67Picture(s)
3,061Sqft
Stunning condominium in mature development with incredible amenities! Great locations, just minutes to downtown Oconomowoc, restaurants, stores, coffee shops and more! The condo features quartz countertops, a sunroom, den, two sola-tubes (one with nightlight), ceramic tile, engineered hardwood flooring, large rec room, all in a quiet side street of Oconomowoc.
$699,900
Single-Family
1561 Woodside Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,673Sqft
New Construction - Ready in December! Introducing the Lakewood Model, your new construction dream home in our Morgan Station Subdivision in Oconomowoc. This open-concept gem features an abundance of natural light, courtesy of four large windows in the great room with a gorgeous fireplace and cathedral ceilings.
$489,900
Single-Family
1451 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
23Picture(s)
2,312Sqft
NEW Construction- Ready January 2025! The Catalina model features 4 BR's 2.5 BA's and a 1st floor Flex Room. The Kitchen offers plenty of space with quartz countertops, a pantry, Dinette bump out and soft close cabinetry. The Great Room includes a corner gas fireplace with 9ft stone detail to ceiling.
$539,900
Single-Family
N60W38457 Blackhawk Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
68Picture(s)
2,258Sqft
BRING YOUR BOAT! Deeded Lac LaBelle access for this spacious ranch on .5 acre double lot w/wooded backdrop & large circular drive. So many amenities: heated floors, updated kitchen with granite & wood counters, glass-front cabinetry, island, access to patio, planning center, large pantry, lazy Susan.
$849,900
Single-Family
N53W34956 Road B -, Oconomowoc, Wisconsin 53069
3Bedroom(s)
1Bathroom(s)
41Picture(s)
1,170Sqft
Frontage is everything! You have 125 +/- feet of level frontage with multiple piers. Lots of lake side room to relax and play. Build a boat house if you'd like. Multiple piers have been here for decades. Lots and lots of parking, A large garage with a spancrete floor giving you lots of room in the lower level.
$1,780,000
Single-Family
1562 Switchgrass St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
8Picture(s)
2,020Sqft
Beautiful ranch in the heart of Lake Country. The Holly features upgrades throughout the entire home. Covered Front Porch entry leads to front foyer with Flex Rm to the right, complete w/ French Doors. Open Concept Living Space is perfect for entertaining & gathering w/ family. Kitchen has Vaulted Ceiling, Soft Close Cabs, Quartz Countertops, Ext Vented Range Hood & Walk-In Pantry.
$559,900
Single-Family
1627 W Mamerow Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
10Picture(s)
2,191Sqft
Welcome home to The CHARLOTTE by Stepping Stone Homes, an award-winning home builder. Open floorplan features 3 Beds, 2 Baths, and a 3 Car garage. This lot is a lookout exposure. The kitchen comes w/quartz countertops, soft close doors and LG appliance package. LVP flooring in kitchen, dinette and great room. We equip our homes with Smart Technology such as a Ring Doorbell and touchless faucet.
$612,579
Single-Family
1275 W Mamerow Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
2,002Sqft
Welcome home to The ELIZA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 3 bedrooms, 2 baths, office & 2 car garage. This lot is a flat exposure. The kitchen comes w/quartz countertops, soft close doors and LG appliance package. LVP flooring in kitchen, dinette and great room.
$576,811
Condominiums
320 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
22Picture(s)
1,222Sqft
This top floor LAKESIDE Condo on beautiful Fowler Lake is ready for its new owner. The 2 bed/ 2 bath condo has been recently updated with high end finishes and beautiful solid wood details and doors. A large eat-in kitchen w/ a large counter for stools and spacious dining area makes for easy entertaining.
$410,000
Single-Family
245 Hillside Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
51Picture(s)
3,231Sqft
Priced Below Assessed Value. Spacious and Inviting is a great way to describe this beautiful cape cod, Enjoy coffee on the front porch Large formal dining room to the right and living room for entertaining to the right. Your open concept family room with fireplace looks into the large eat in kitchen with granite counter tops. Main floor bedroom is accessible and makes a great office too.
$549,999
Single-Family
1603 Switchgrass St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
21Picture(s)
2,253Sqft
Welcome home to The CLARA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 3 Beds, 2.5 Baths and 2 Car garage. This lot is a flat exposure. The kitchen comes w/quartz countertops, soft close doors and LG appliance package. LVP flooring in kitchen, dinette and great room. We equip our homes with Smart Technology such as a Ring Doorbell & touchless faucet.
$604,900
Single-Family
1527 Whalen Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
28Picture(s)
1,805Sqft
Introducing a beautifully designed 3-bedroom, 2-bath ranch home, ready to become your dream space! This thoughtfully crafted layout ensures both comfort and privacy. The master bedroom located at the back of the home, offers a tranquil retreat with an on-suite bathroom featuring a walk-in closet, granite countertops, a tile shower, and tile floors.
$625,000
Single-Family
1550 Creekview Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
22Picture(s)
2,502Sqft
Welcome home to The Julia by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 Beds, 3.5 Baths and a 3 Car garage. This lot is a flat exposure. The kitchen comes w/ quartz countertops, soft close doors and LG appliance package. LVP flooring in kitchen, dinette, and great room. We equip our homes with Smart Technology such as a Ring Doorbell and touchless faucet.
$624,900
Single-Family
417 Worthington St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
23Picture(s)
1,440Sqft
Here's a beautifully aged farmhouse on a large lot with many updates! Great location with City Beach at one end of the street and Roosevelt Park at the other, downtown a half-mile away and easy access to Hwy 16. Upstairs are three bedrooms and a full bath, downstairs is a galley kitchen, half bath, dining room, living room, and entry flex room that would make a great office. 2.
$345,900
Single-Family
980 Glencoe Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,025Sqft
NEW CONSTRUCTION - Move in Ready January 2025- Our Alexander model is a 2-story 3 bed, 2.5 bath townhome with an open concept first floor. The Kitchen includes quartz countertops, pantry, a large island and soft close cabinetry. The Great Room features a stunning stone to 9' ceiling gas fireplace. In addition, the first floor offers a Powder Room and Rear Foyer with WIC.
$439,900
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
40Picture(s)
1,300Sqft
Mid Century Modern condo in coveted Isthmus district of Oconomowoc. Enjoy sunrise to sunset views of Fowler Lake to La LaBelle from 4th floor balcony. Kayak from pier on Fowler lake to Oconomowoc River or portage at Rockwell Park to Lac LaBelle. Fireworks and parade can be seen from balcony. A short walk to downtown shop and restaurants. Plenty of storage space.
$399,900
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.
$695,000
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.
$819,500
Vacant Land
578 Concord Rd, Oconomowoc, Wisconsin 53066
19Picture(s)
0Sqft
Beautiful meandering scenic Oconomowoc River front lot that is ready for your home plans to be built upon. This rare riverside/waterfront lot has everything your looking for with all the amenities of a beautiful city location. Kayaking right out your front door, blocks to schools, shopping & restaurants. Only a recent land split makes this, and/or Lot 1 available to some lucky buyers.
$249,900
Vacant Land
578 Concord Rd, Oconomowoc, Wisconsin 53066
20Picture(s)
0Sqft
Beautiful meandering scenic Oconomowoc River front lot is ready for your home plans to be built upon. 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 & restaurants. Only a recent land split makes this, and Lot 2 available to some lucky buyers.
$219,900
Single-Family
1447 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
20Picture(s)
1,927Sqft
NEW CONSTRUCTION-Ready December 2024! - This Charleston has it all! The main area is an open concept. The Kitchen includes quartz countertops, a workspace island with overhang, and is open to the Great Room which has a gas fireplace with beautiful stone to 9' ceiling detail.
$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
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.
$734,900
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)
28Picture(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
$444,900
