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
1286 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,583Sqft
Move-in Ready 99 ARW Harlequin Craftsman. Available 12/17/25! All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well.
$519,900
Single-Family
417 Franklin St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
51Picture(s)
1,534Sqft
Oconomowoc: Step into timeless charm with this delightful 3 Bedroom, 1.5 Bath home that blends character with comfort. Warm and welcoming living spaces with natural light pouring through large windows. Cozy kitchen with updated new stainless-steel appliances and plenty of cabinet space. A reopurposed pantry enhances the space off the kitchen.
$409,000
Condominiums
W354N5315 Coastal Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private GarageParking(s)
46Picture(s)
3,600Sqft
Grand and gracious would not overstate the ambience of this detached, ranch-style home. Views of Bay Pointe pond welcome you to condo living. Natural light enters every room. Overhanging roof shelters your steps to the Great Room. Cathedral ceiling and corner fireplace inspire warm arrangements for gathering. French doors open to east facing den, capturing the water view.
$689,000
Single-Family
1200 Juniper Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
26Picture(s)
2,137Sqft
Spacious 4BR home with walkout lower level in Oconomowoc's Pine Ridge Estates! Partial stone exterior and covered front entrance greet you. Extensive luxury vinyl plank flooring on main level. Great room offers corner gas fireplace. Open kitchen has island breakfast bar, walk-in pantry, and appliances included. Large mud room off 3.5-car garage.
$675,000
Condominiums
1755 Derby Ln, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
41Picture(s)
2,110Sqft
This spotless 2100 SF ranch condo is Kingsway's largest model, the Estonian! Enter the foyer and delight in the maple flooring and beautiful open staircase leading to the lower level with egress window and rough plumbing for a full bath. the family chef will LOVE the gourmet kitchen with large center island, quartz countertops, pantry, Sub-Zero refrigerator, Wolf stove and custom backsplash.
$674,900
Single-Family
1709 Hammock Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,142Sqft
The Walnut-split ranch located on lot 373 in Prairie Creek Ridge! Kitchen features stained cabinets, quartz countertops, tile backsplash, ext vented range hood & walk-in pantry. Cathedral ceiling spans across living space & great room includes a gas fireplace with stone detail.
$639,900
Single-Family
W383N8797 Blue River Pass, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3Bathroom(s)
53Picture(s)
3,016Sqft
Discover this spacious 5 bed, 3 bath ranch, set on a beautiful acre, minutes from downtown. With a 3-car garage and an exposed LL, this property combines comfort and function. The main floor welcomes you with warm hardwood floors, open living spaces, and natural light. A large deck extends your living area outdoors, perfect for gatherings overlooking the back yard.
$729,000
Single-Family
64 Chestnut St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1/1Bathroom(s)
16Picture(s)
1,900Sqft
This newly updated home beautifully blends modern amenities with timeless character. Step inside to find an open, inviting floor plan filled with natural light, featuring fresh, contemporary finishes throughout. The spacious living area flows seamlessly into a stylish, updated kitchen complete with granite countertops & SS appliances.
$349,900
Single-Family
1692 Switchgrass St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
11Picture(s)
2,410Sqft
The Acacia is a beautifully designed 2-story with w/ an eye catching exterior & modern upgrades throughout! Located on lot 397 in Prairie Creek Ridge. Kitchen includes stained cabinets, quartz countertops, exterior vented range hood & a generously sized walk-in pantry. Extended dinette offers plenty of space for comfortable dining & entertaining.
$649,900
Single-Family
646 Summit Ave, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
33Picture(s)
1,648Sqft
Step inside and imagine the possibilities! This 3 bedroom 1.5 bath ranch is host to a warm and bright open floor plan, hardwood floors and a natural fireplace you will want to cozy up to. The walk-out lower level offers you the perfect opportunity to create a home office, gym, or additional living space and effortlessly delivers convenient access to the garage, patio and a fence-in backyard.
$398,000
Single-Family
997 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,592Sqft
Move-in Ready 75 ARW Olivia Cottage II Unit A, TWIN HOME! AVAILABLE 1.16.26 Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes w/ private yards. Monthly association fee $245 covers lawn mowing, fertilization, & snow removal; plus a la carte seasonal services are available for a separate rate.
$484,900
Single-Family
1254 W Arrowood Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
6Picture(s)
2,455Sqft
Move-in Ready 103 ARW Atwood California Bungalow. Available 1/20/26! All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well.
$664,900
Single-Family
719 Main St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
30Picture(s)
1,056Sqft
Unbeatable location in the heart of Oconomowoc! Situated right across from Roosevelt Park and just a short walk to downtown, this home puts you in the center of it all--shopping, dining, and year-round activities are just steps away. The spacious yard offers plenty of room for outdoor living, entertaining, and relaxation, making it perfect for both everyday life and special gatherings.
$269,999
Condominiums
296 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
36Picture(s)
1,200Sqft
Welcome to this beautifully maintained 3 bed, 2 bath ranch side-by-side condo offering comfort, convenience, and scenic views. Enjoy an open concept living space with a cozy 3 sided fireplace and large windows that fill the home with natural light. The kitchen offers ample storage and flows into the dining area, perfect for entertaining. The primary suite includes a private bath.
$349,000
Condominiums
N51W34681 Wisconsin Ave, Oconomowoc, Wisconsin 53069
2Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
26Picture(s)
1,642Sqft
One of the best and largest units at Mission Lakes condominiums in Okauchee Village!This corner unit-top level condo provides sweeping views of clean spring fed Florence lake from every room. Open kitchen /dining /great room with vaulted ceilings, gas FP, and balcony deck. Quality finishes include custom Maple cabinetry and millwork, granite countertops, wood and ceramic floors.
$494,900
Single-Family
1367 Scotsland Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
10Picture(s)
2,780Sqft
The Juneberry-Modern Sprawling 2-Story located on lot 85 in Olde Highlander! Community will feature a range of amenities including a walking path, swimming pool, clubhouse & more! Kitchen features stained soft close cabinets, tile backsplash, ext vented range hood & island w/ seating space. Great Room includes a cozy electric fireplace w/ stone detail.
$689,900
Single-Family
1714 Hammock Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
19Picture(s)
2,481Sqft
Concrete Driveway & Seeded Yard Included! The Monterey-located in Prairie Creek Ridge! This unique 2-story plan features 4 bedrooms & a flex room, plus upgrades throughout. Kitchen has soft close cabinets, granite countertops, tile backsplash, exterior vented range hood, and walk-in pantry. Great Room off kitchen boasts cathedral ceiling & has electric fireplace with stone detail.
$659,900
Condominiums
201 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Opener IncludedParking(s)
35Picture(s)
1,580Sqft
Not very often do you come across a 1st floor condo unit in the highly sought-after 55+ development of Silver Ridge! This beautiful corner unit offers 3 spacious bedrooms & 2 bathrooms. Featuring a cozy gas fireplace in the living area & an open-concept galley kitchen w/breakfast bar & Corian countertops. Solid six-panel doors & walk-in closets add ample storage.
$319,900
Single-Family
1331 Wood Creek Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
46Picture(s)
2,054Sqft
From the welcoming entrance to the relaxing sun room and secluded feeling deck, this beautifully maintained home has it all. The open floor plan flows seamlessly, while the sunroom offers a private hideaway adjacent to the open living and dining rooms. A gas fireplace warms the heart of this home, as does the spacious kitchen with separate eating, island, and breakfast bar areas.
$575,000
Condominiums
843 Stirling Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
29Picture(s)
1,631Sqft
NEW CONSTRUCTION READY NOW - Luxury Ranch Condominium with 2 Bedroom plus Flex Room, featuring open design concept with 9' Ceilings throughout. Beautiful Gourmet Kitchen for entertaining with a large center island, beautiful soft close cabinetry, quartz countertops and appliances.
$539,900
Single-Family
888 High St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
52Picture(s)
2,127Sqft
A rare gem on.74 acres & a no thru street; an easy walk to the vibrant shopping/dining/lake of downtown Ocon. & the high school. Its vaulted living room & kitchen area provide an open & airy feel & great flow for entertaining. Envision quiet mornings/relaxing evenings on your deck. The living room fireplace beckons you for cozy nights with family & friends.
$474,900
Single-Family
337 River Bluff Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
58Picture(s)
3,058Sqft
Timeless elegance meets modern comfort in this stunning classic colonial set on over an acre, overlooking the treetops of Oconomowoc! A thoughtful layout showcases hardwood floors & oversized windows that capture breathtaking views. The main floor offers generous living spaces & convenient laundry.
$750,000
Single-Family
1410 Blazing Star Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
60Picture(s)
3,453Sqft
Welcome to effortless living in Prairie Creek Ridge-where shopping, dining, schools & more are less than a mile away! If you've been looking for an open-concept ranch home with a 3 car garage, you've now found it! Enjoy your morning coffee in spacious great room by the cozy fireplace or on the generously sized back patio.
$643,500
Single-Family
1506 River Highlands Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
32Picture(s)
2,393Sqft
Don't miss out on this one! This inviting ranch home blends modern updates with cozy charm. The spacious primary bedroom suite features brand new LVP flooring, while the updated kitchen boasts quartz countertops, and stylish finishes perfect for everyday living and entertaining. Enjoy holiday meals in the dining room with the gas fireplace or unwind in the living room by the natural fireplace.
$499,900
Single-Family
224 Worthington St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
41Picture(s)
1,954Sqft
Gorgeous complete renovation with just the right amount of old world charm. Wonderful covered front porch. New white kitchen with granite, tile backsplash, walk in pantry and SS appliances. Formal dining with BICC;s. Refinished hardwood floors on the main level. Huge living room and family room with electric fireplace and leaded glass accent window.
$449,900
Single-Family
940 Old Tower Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/2Bathroom(s)
92Picture(s)
2,564Sqft
Stately Colonial with Room to Live, Relax & Entertain! This beautifully updated 4BDR/4BA two-story just minutes from downtown. Step inside to find a sun-filled living room with a cozy woodburning fireplace, a chef-ready kitchen with stainless steel appliances, and a formal dining room.
$568,900
Condominiums
906 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
UndergroundParking(s)
22Picture(s)
1,475Sqft
Beautifully updated main-floor 2BR, 2BA condo in desirable Oconomowoc! Features all new flooring, stylish lighting, new bathroom fixtures, and updated appliances- move-in ready. Open layout with spacious living/dining areas and a large primary suite with private bath. Includes 2 heated underground parking spaces and a secured storage unit.
$295,000
Single-Family
W359N5707 Surrey Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
35Picture(s)
1,640Sqft
Spacious ranch home nestled on a generous .734-acre lot in a peaceful, well-established neighborhood. Located within the highly regarded Oconomowoc School District, this property offers a perfect blend of comfort, space, and potential.Enjoy the tranquility of the park-like yard, ideal for relaxing, entertaining, or gardening.
$470,000
Two-Family
217 Cross St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
Paved drivewayParking(s)
20Picture(s)
1,642Sqft
Great opportunity to own this single-family/duplex in a great location near downtown Oconomowoc! This home was most recently used as a two-family home but offers the flexibility to work as a single or two family property. Newer exterior with replaced roof, siding, gutters, and added insulation. Large sun porch along the front of home.
$299,900
Single-Family
217 Cross St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
20Picture(s)
1,642Sqft
Great opportunity to own this single-family/duplex in a great location near downtown Oconomowoc! This home was most recently used as a two-family home but offers the flexibility to work as a single or two family property. Newer exterior with replaced roof, siding, gutters, and added insulation. Large sun porch along the front of home.
$299,900
