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
104 Pine Ter, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
55Picture(s)
2,320Sqft
Beautiful Pine Terrace condo has Fowler Lake access and all the fun activities. Walking loop takes you downtown to all the Oconomowoc venues. Spacious 3 bedrooms, 2.5 baths, stunning hardwood floors, cathedral ceiling, granite counters, gas fireplace, wet bar, doors off kitchen to the private deck.
$495,000
Single-Family
W354N5013 Road T -, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
34Picture(s)
970Sqft
Long time owner offering this very well maintained home in Okauchee. Many updates over the years including, windows, siding, gutters, a new roof (2024). Spacious interior includes 2 nice size bedrooms, formal dining and large living room, sunroom used as an office. Full Basement with high ceilings. Situated on a park like yard is easy walk to downtown Okauchee bars and eatery's.
$379,900
Single-Family
W350N6763 Baltic Pass, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
67Picture(s)
2,322Sqft
Welcome to your dream 3 Bedrooms with walk in closets, 2.5 Bathroom home with attached 3 car garage in the charming Town of Oconomowoc! Nestled on 1+ acre lot, offers the perfect blend of comfort, privacy, and luxury. The backyard features an inviting in-ground pool surrounded by a spacious patio, ideal for entertaining; a touch of elegance to your outdoor oasis.
$650,000
Single-Family
1299 Yosemite Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
17Picture(s)
2,729Sqft
Spacious 4bdrm 3.5 BA home in the sought after Lakewood Estates!Exterior features Professional Landscaping, an Irrigation system for watering and a Stamped Patio with Firepit for your relaxation.
$649,000
Single-Family
239 Hillside Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
19Picture(s)
1,976Sqft
Beautiful home and setting in Oconomowoc's Riverwood Trails! Enjoy plenty of new features including the roof, siding, soffits, gutters, windows, water heater, interior paint, and more! Main level offers large living room with plenty of natural light. Adjoining dining room. Kitchen with updated cabinets/hardware, countertops, and sink/faucet. 2 bedrooms and a full bath on the main level.
$379,900
Single-Family
N52W35319 Lake Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1/1Bathroom(s)
19Picture(s)
1,512Sqft
If lake living is calling your name, than this property answers the call. This site, with southern exposure, offers over 50 feet of frontage on Okauchee Lake, with an additional guest house (3 BR/1 BA) offering direct lake views and more living space. The piers allow for parking of water toys or swimming.
$1,050,000
Single-Family
W352N6484 Road J -, Oconomowoc, Wisconsin 53066
4Bedroom(s)
1Bathroom(s)
35Picture(s)
1,752Sqft
Quintessential lake cottage ready to enjoy just in time for summer! Features include boathouse, 2.5 car detached garage, quaint wood paneled great room with vaulted ceiling and 3 season room to take in all of the lake views! Newly updated bath and durable LVP flooring throughout the main floor.
$925,000
Single-Family
1421 Waters Edge Dr, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
46Picture(s)
3,689Sqft
A relocation out of WI brings this gorgeous 5 bdrm/3.5 bath Colonial in popular Hickorywood Farms to the market. Wonderfully taken care of by both its previous owners, you'll be drawn in by the welcoming foyer spaces that lead to the living room with gas fireplace, a bright, spacious kitchen & tranquil morning room w/vaulted ceiling. Large patio w/desirable flat lot perfect for entertaining.
$650,000
Single-Family
1284 Violet St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,939Sqft
New Construction - Ready for your family in September, the covered porch entryway opens to the spacious Kitchen with cathedral/ vaulted ceilings in this popular Vienna ranch! Loaded with desirable features, such as kitchen with center island and large pantry, two-tone cabinets and Quartz countertop, a master suite with 2 WIC's, upgraded plumbing and lighting fixtures, and an abundance of windows f
$549,900
Single-Family
1492 Turnberry Cir, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
55Picture(s)
2,918Sqft
Introducing this beautifully updated Briarwood colonial, offering 4 bedrooms and 2.5 baths. Revel in the modern elegance of the updated kitchen and baths, while the hardwood floors in the entryway, kitchen, and dining areas exude timeless charm. Brand new carpeting adorns the rest of the main floor and upper level, enhancing comfort and style.
$549,000
Single-Family
W356N5212 Lakeshore Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
4Bathroom(s)
20Picture(s)
5,145Sqft
Gorgeous and expansive Upper Oconomowoc Lake (Okauchee) executive lake home. The update list is endless , so come see for yourself.
$1,629,990
Single-Family
1281 Orchard Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
2,030Sqft
**PROPERTY BEING SOLD AS-IS** This diamond in the rough needs some good TLC to shine again! Though it'll take a bit to get to it's formal glory, this is a wonderful opportunity to gain some sweat equity and to get into Oconomowoc affordably! This 3-bedroom, 2-bath split ranch home w/2.
$379,900
Single-Family
W354N6191 Marina Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
28Picture(s)
2,004Sqft
Rare offering in Lakeview Acres - home with a private boat slip on Okauchee Lake!!! This 3BR home offers a spacious interior and a gorgeous lot with huge private back yard. Location is close to the private neighborhood park with sandy beach, piers, and your private boat slip on the lake.
$579,900
Single-Family
39 Mcdowell Ct, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
32Picture(s)
1,792Sqft
Welcome home to this 3 bedroom 3 FULL bathroom charming home on a private drive. Hardwood floors, newer windows and doors, generous room sizes, main floor laundry and huge lot with vegetable/flower gardens, and a chicken coop for farm fresh eggs! Relax on the front porch or the deck and enjoy what feels like country living, or walk to downtown and enjoy the city.
$384,900
Single-Family
1453 W Mamerow Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3Bathroom(s)
48Picture(s)
3,531Sqft
The ideal floor plan with volume ceilings and a split bedroom design is sure to please. A large master suite with full bath and walk-in closet is definitely a plus for this home. The family room, just off the kitchen, is appointed with a fireplace and ample room for entertaining or enjoying your favorite show.
$579,000
Condominiums
1768 Bess Ct, Oconomowoc, Wisconsin 53066
2Bedroom(s)
3Bathroom(s)
Private garageParking(s)
37Picture(s)
2,146Sqft
The lot makes this!! Extra large southern exposure patio w/9 mature arborvitae's for privacy!! Extra parking space @lenghty driveway. Beautiful Plantings along sidewalk to front porch. Many mature trees, lots of green space!!!! Bright & cheery with east & south sun into home. Upscale neutral up/down blinds.
$569,900
Single-Family
W342N5150 Road P -, Oconomowoc, Wisconsin 53069
6Bedroom(s)
4/1Bathroom(s)
47Picture(s)
6,977Sqft
The definition of lakeside luxury on over 1.5 acres at this stunning custom-built Okauchee Lake property featuring 139 feet of prime frontage. Ready for year-round fun, this remarkable residence includes 3 piers and a rare boathouse. With nearly 7,000 sq. ft. of thoughtfully designed spaces this home offers endless opportunities for relaxation and entertainment.
$5,750,000
Single-Family
264 Lakeridge Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
38Picture(s)
2,800Sqft
Location is absolutely ideal for this custom designed Westridge Builders ranch home. A stones throw from Silver Lake, Paganica Golf Course and Lake Country Recreation Trail, and schools (Summit, Silver Lake and OHS). Built in 2002 it has been delightfully updated and immaculately maintained. Tasteful foyer with gleaming wood floors, a standout archway and pillars.
$584,900
Single-Family
830 Oakwood Ave, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1/1Bathroom(s)
42Picture(s)
1,616Sqft
Discover your ideal retreat in Oconomowoc! This charming brick ranch home is just blocks from Fowler Park, downtown amenities, and schools. Cozy up in the great room by the fireplace with new flooring. The galley kitchen offers both style and function. Two spacious bedrooms feature hardwood floors and custom closets. Enjoy an updated bathroom.
$370,000
Single-Family
1603 Switchgrass St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
5Picture(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.
$629,900
Single-Family
1302 W Mamerow Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
20Picture(s)
2,239Sqft
Welcome home to The RILEY by Stepping Stone Homes, an award-winning home builder. Open floor plan features 3 Beds, 2.5 Baths and a 2 Car garage. This lot is a LOOK OUT 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
1283 W Mamerow Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
6Picture(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.
$579,900
Single-Family
1340 Orchard Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
48Picture(s)
1,668Sqft
Your Lake Country opportunity awaits, this beautiful split bedroom ranch is located minuets from downtown Oconomowoc. As you enter you're greeted by a beautiful tiled foyer entry with views of gleaming hardwoods & the pine vaulted ceiling in the living/great room, complete w/gas fireplace & granite stone flanked surround.
$534,900
Condominiums
333 Lake Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
1 space assignedParking(s)
30Picture(s)
1,400Sqft
Picturesque Fowler Lake condo near downtown Oconomowoc! Expansive living room with sliding windows to balcony & glimpse of Lac La Belle. 2 spacious bedrooms & 2 full bathrooms. Well-loved, maintained, & ready for your vision to make it your own. Plentiful closets plus storage unit on ground level. Secure lobby & elevator for convenience & peace of mind.
$358,900
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
26Picture(s)
3,200Sqft
Indulge in stunning vistas from this opulent penthouse, with views over Fowler Lake, downtown Oconomowoc, and Lac La Belle! Enjoy a vast 1,700 sq. ft. private terrace. This bespoke abode boasts premium finishes, smart home tech, direct elevator access, a game room, office, loft, stained glass, cedar walk-in closets.
$3,200,000
Single-Family
1244 Violet St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,506Sqft
This home is currently under construction. The Charlotte offers a gathering room featuring a 2-story ceiling & gas fireplace, the 1st-floor primary floorplan is a home to impress. You'll enjoy the kitchen w/ its abundance of storage that includes a WIP, & oversized island w/ snack bar. For more formal gatherings, a dining room is conveniently located off the kitchen.
$703,900
Single-Family
1311 Whalen Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,431Sqft
This home is framed. The Skylar 2431 is a 2-story home that offers plenty of living space w/ the kitchen featuring quartz counters, morning room & gathering room w/ GFP positioned in an open-concept format. The home has a mudroom that features plenty of storage including a closet & convenient bench for everyday items. The formal dining room makes for a welcoming entertainment area.
$632,900
Single-Family
228 Concord Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
36Picture(s)
1,632Sqft
Centrally located between Downtown & Roosevelt Park, enjoy the pleasures of this quintessential old-style victorian 3 Bed 1 Bath home within walking distance shopping, restaurants, & City Beach. As you enter the large living/dining spaces, hardwood flooring, detailed casings/baseboards, & 10' ceilings flow through each area. Main level bedroom used as office/den.
$299,900
Condominiums
N49W36111 Nottingham Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
38Picture(s)
1,650Sqft
Spacious open concept wonderfully updated 3 bedroom 2 full bath Oconomowoc condo. Open concept kitchen with breakfast bar looking in to dining area. Patio doors lead in to a screened in porch with tall ceilings perfect for outdoor entertaining. Huge great room with brick natural fireplace. Newer flooring, freshly painted, and several rooms with new carpet.
$299,900
Single-Family
1612 Switchgrass St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
13Picture(s)
2,479Sqft
The Monterey-located in the heart of Oconomowoc! This 4 bed 2-story features upgrades throughout. 2-story Front Foyer leads to main living space, & a Flex Room w/ French Doors to the right. Open Concept Living Space is perfect for gathering w/ family/friends. Kitchen features Soft Close Cabinets, Quartz Countertops, Exterior Vented Range Hood & Walk-In Pantry.
$589,900
