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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:

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Single-Family

285 Lapham St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/2Bathroom(s)
33Picture(s)
2,768Sqft
Open concept ranch home in a desirable Oconomowoc neighborhood! This 3 bedroom split style ranch is immaculate! Main floor offers a convenient open concept floor plan with vaulted great room, primary en-suite with a private bath with newly tiled shower and 2 closets. Option for den or formal dining room.
$489,900

Single-Family

N53W34369 Road Q -, Oconomowoc, Wisconsin 53069

3Bedroom(s)
3/1Bathroom(s)
31Picture(s)
3,031Sqft
This exceptional lake home sits on a beautiful wooded setting with gentle slope down to 245 feet of frontage on Okauchee! Located on quiet Tierney Bay & a quick boat ride to all the action of the main lake. Custom built home has many quality features including maple cabinetry, hardwood floors, granite & quartz counters, 2 fireplaces & so much more.
$1,499,900

Single-Family

723 Concord Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
33Picture(s)
3,725Sqft
Nestled on 1.19 acres near Downtown Oconomowoc, this property blends city convenience with serene privacy and no HOA restrictions. Offering ample space both indoors and outdoors for comfortable living and entertaining. Step into the lower level, where an industrial-inspired vibe sets the tone with a painted concrete floor and an open black ceiling.
$650,000

Two-Family

220 Elm St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
Driveway entranceParking(s)
31Picture(s)
1,700Sqft
Rare opportunity to own a duplex in the desirable Oconomowoc area - steps away from all that downtown has to offer. This is the perfect place for owner occupant or a seasoned investor. Both units are currently vacant and the upper unit recently renovated.
$365,000

Single-Family

1523 Butternut Rdg, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
13Picture(s)
2,238Sqft
Welcome home to The GENEVA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 bedrooms, 2.5 baths and 2 car garage. Kitchen comes w/quartz countertops, maple stained cabinets and SS appliance package. LVP flooring in kitchen, dinette, and great room. We equip our homes with Smart Technology.
$537,900

Single-Family

1340 Orchard Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
46Picture(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 gas fireplace & granite stone flanked surround.
$539,900

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.
$398,000

Single-Family

653 Sherman Ave, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2Bathroom(s)
23Picture(s)
1,440Sqft
Beautifully updated charming 4 bedroom 2 bath home in quaint Fowler Lake neighborhood just a short walk to Fowler Lake and Lac La Belle. Where to begin....every room on the main and upper floors have been remodeled in 2020 to include New master bedroom, walk in closet and master bath added.
$409,900

Two-Family

W358N5893 Surrey Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
Driveway entranceParking(s)
22Picture(s)
2,830Sqft
Here is the perfect Owner Occupancy Situation or a Great Investment Opportunity with a Duplex that feels like a Single Family Home. Side by Side Townhouse Style Duplex is the way to Go!! Both Units have 3 Spacious Bedrooms and 1.5 Baths with an Attached Garage. This is what Everyone Wants. Both Units are currently occupied with 5893 Being available June 1st 2024. This Property is on .
$419,000

Single-Family

W340N8809 Townline Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
42Picture(s)
1,104Sqft
Welcome to your cozy country getaway! Set on an acre, this charming 3BR/1.5BA ranch home offers MANY updates including new windows, new central air, new flooring and remodeled kitchen to name just a few. The finished lower level provides additional living space, as well as lots of storage and even a workshop.
$374,900

Single-Family

1509 Whalen Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
42Picture(s)
2,181Sqft
Like-new, but with driveway and landscaping already done! A sun-filled 2 story foyer greets you upon entering this beautiful 4 bedroom home! Kitchen has quartz countertops, stainless appliances, center island, pantry and sleek tile backsplash. Living Room offers a stylish stone fireplace and LVP flooring. Large flex room perfect for play area or home office.
$609,900

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2/1Bathroom(s)
Private garageParking(s)
23Picture(s)
3,200Sqft
Indulge in stunning vistas from this opulent penthouse, gazing over Fowler Lake, downtown Oconomowoc, and Lac La Belle! Relish a vast 1,700 sq. ft. private terrace. This bespoke abode boasts premium finishes and smart home technologies, with direct elevator access, a game room, office, loft, stained glass, and cedar walk-in closets.
$3,200,000

Two-Family

665 Armour Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
Driveway entranceParking(s)
52Picture(s)
2,408Sqft
UNIQUE DUPLEX OPPORTUNITY IN OCONOMOWOC! Main floor 1BR unit is very well-kept & exudes a warmth from both the gas fireplace as well as its charming brick & natural wood accents. Spacious bathroom features tiled flooring & shower/tub combination.
$389,000

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, picturesque windows & 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.
$659,900

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

Single-Family

751 High St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
26Picture(s)
1,321Sqft
Welcome to this charming, well-maintained ranch-style home boasting 3 bedrooms and 1.5 bath. Coming to the market for the 1st time in 55 years, step inside to discover the meticulous beauty of this home. The property features a new roof, siding, and gutters, ensuring peace of mind for years to come. Enjoy the convenience of a 2.75-car detached garage with a workshop area.
$349,900

Condominiums

N49W36111 Nottingham Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
38Picture(s)
1,200Sqft
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.
$309,900

Single-Family

1612 Switchgrass St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
5Picture(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

Single-Family

W349N5389 Road B -, Oconomowoc, Wisconsin 53069

3Bedroom(s)
3Bathroom(s)
28Picture(s)
1,998Sqft
Perfect location! Be on Okauchee Lake before summer begins! Picturesque views of the water and sunsets. Experience the 4th of July fireworks from your year-round pier. Easy walk to town from this incredible location. Swim in the peaceful no-wake zone frontage. Enjoy an abundance of lake views from all levels and natural light.
$1,250,000

Single-Family

814 Burr Oak Ct, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,880Sqft
Move-In Ready 26 ARW Sawyer Cottage. AVAILABLE 8/7/24! 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, 70% better than a typical used home.
$554,900

Single-Family

1538 Creekview Ct, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
8Picture(s)
2,336Sqft
HOUSE IS FRAMED. APPROXIMATE COMPLETION FEBRUARY 2025.3 bedrooms/2.5 baths/Flex room/Split ranch. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Corner ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops/double sinks in master bath. Double sinks family bath. Hugh WIC master suite.
$649,990

Single-Family

1239 Ridgeside Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
46Picture(s)
3,400Sqft
Live in luxury without breaking the bank! Available for the 1st time, this immaculate 3bd with den, 3ba home is situated in desired Longmeadow neighborhood. Brazilian cherry floors throughout are just divine. LR features vaulted ceiling & gas fireplace perfect for chilly, rainy evenings. Prep area & cabinets aren't an issue in the kitchen, especially w/ the pantry pullout drawers.
$619,900

Single-Family

N59W34909 Lake Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
41Picture(s)
2,690Sqft
Welcome home to this charming split bedroom ranch located in the desirable Westshore subdivision. This inviting home offers a perfect blend of modern comfort and classic appeal. The open layoutseamlessly connects the great room to the dining area and kitchen, creating a warm and inviting atmosphere.
$659,900

Single-Family

W346N5312 Elm Ave, Oconomowoc, Wisconsin 53069

3Bedroom(s)
1/1Bathroom(s)
38Picture(s)
1,404Sqft
This charming and beautifully updated Okauchee Village home has limited access to the Lake and is walking distance from many nearby venues. The kitchen features concrete countertops and adjoins the living/dining rooms with an electric fireplace. Upstairs there is the main bedroom with walk-in-closet, utility room, 2nd and 3rd bedrooms and a full bath.
$339,500

Single-Family

1681 Hammock Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,404Sqft
This home is under construction. The Arielle is an inviting home that offers essential living spaces. The kitchen, has quartz counters, large pantry cabinets, & prep island w/ casual seating. The gathering room offers a cozy GFP. Finishing the 1st floor is a home office, powder room & large mudroom w/ a built-in bench & storage.
$627,900

Single-Family

1611 Creekview Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,403Sqft
This home is under construction. The Camille is a story & a half home which offers modern necessities. The first-floor primary bedroom features an oversized WIC along w/ a private bathroom w/ dual quartz vanity & a 5-ft. ceramic shower.
$624,900

Single-Family

1540 Creekview Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,350Sqft
This home is currently under construction. The Hailey 2350 offers a kitchen w/ plenty of cabinetry, quartz counters, WIP, kitchen appliances & prep island, a morning room for casual meals, a gathering room w/ gas fireplace, a formal dining room for large gatherings, a home office & a mudroom featuring a large closet & bench for everyday items.
$617,900

Single-Family

1691 Hammock Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,805Sqft
This home is under construction. The Lauren 1805 is a cleverly designed home that places the generously sized primary bedroom & shared living spaces - including the gathering room w/ GFP, kitchen, & dining area - at the back of the home for privacy.
$576,900

Single-Family

1621 Creekview Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,805Sqft
This home is under construction. The Lauren 1805 is a cleverly designed home that places the generously sized primary bedroom & shared living spaces - including the gathering room w/ GFP, kitchen, & dining area - at the back of the home for privacy.
$563,900
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