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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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Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
37Picture(s)
1,685Sqft
This lightly lived in condo (since 2021) will be a place to create a new story. 760 square feet of terraced wrap-around views! The openness of the sitting area with its southern exposure will be a great gathering spot for everyday living or celebrations. Easy living at its best in charming downtown with many unique shops and restaurants.
$1,250,000

Single-Family

1652 Switchgrass St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
2Picture(s)
2,004Sqft
HOUSE IN ROUGH CARPENTRY-APPROX. FINISH OCT.' 25.3 bedroom/2 full bath/ranch design. Basement has 1 egress window & drain/vent rough-in for future full bath. Master bath shower w/ceramic tiled walls/double sinks/granite or equivalent vanity tops. Double sinks Family bath. Large WIC master suite.
$599,990

Single-Family

269 Thomas Trl, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
39Picture(s)
3,055Sqft
New year, new home, new you? This 4-year-old custom ranch is ready to check every box on your wish list!With a smart split floor plan and high-end finishes, the main floor offers an open layout, a cozy gas fireplace, and a spacious deck perfect for relaxing or hosting friends.
$544,900

Condominiums

W398N6077 Autumn Woods Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
40Picture(s)
1,824Sqft
Beautiful Condominium home located in private end building location. Spacious upper unit with large office/den complete with skylights. Kitchen includes breakfast bar counter. Open concept living room with corner gas fireplace leads to balcony to enjoy the peaceful surroundings. Inviting upper loft with plenty of room for enjoying movie night. In unit laundry.
$329,900

Single-Family

1242 Yosemite Rd, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
78Picture(s)
2,931Sqft
Move right into this stately home in Lakewood Estates! Two-story open staircase entry with HWFs leads into a private office. Updated eat-in kitchen with Granite counters, Terrazzo Tile backsplash, and Maple cabinets open to bright sunroom with vaulted ceiling and patio doors to deck and patio and private, and large yard backing up to treed backdrop. Corner FP in FR, formal DR and LR too.
$649,900

Vacant Land

1270 Corporate Center Dr, Oconomowoc, Wisconsin 53066

2Picture(s)
0Sqft
Excellent commercial/industrial/business opportunity in Oconomowoc! Good visibility with close proximity to I-94 and Hwy 67. Over 1.7 acres of vacant land in a prime location within the Oconomowoc Corporate Center near Pabst Farms.
$599,900

Single-Family

639 Roland St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
19Picture(s)
1,050Sqft
Great location near Fowler Park for this 3 bedroom 2 full bath home with a 2.5 car garage. Enjoy walking to downtown Oconomowoc and around Fowler Lake. New roofs on home and garage in 2023. Open floor plan. New dishwasher, sink, range & hood, washer in last two years. Lower level with newer full bathroom, rec room & den. Enjoy the large deck and fenced yard.
$359,000

Single-Family

1259 Violet St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,874Sqft
FOUNDATION COMPLETE. APPROX. FINISH NOV' 25.4 bedroom/2.5 bath/flex room/elite series 2-story. Basement has 1 egress window & drain/vent rough-in for future full bath. Ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops in master bath.Double sinks family bath. 2 WIC's master suite. 9' 1st floor ceilings/pitched in master bedroom.
$649,990

Single-Family

739 Silver Lake St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
31Picture(s)
1,248Sqft
With walking distance to downtown Oconomowoc, schools, Roosevelt Park & the Imagination Station this charming farm style Victorian home is your opportunity to complete your home ownership dreams! Including two three seasonporches and updates throughout this is a must see! The home has been lovingly updated throughout (see add. property info in documents).
$375,000

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Opener includedParking(s)
53Picture(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.
$1,249,000

Single-Family

1630 Creekview Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
3Picture(s)
2,004Sqft
HOUSE IS FRAMED. APPROXIMATE COMPETION IN OCT '25.3 bedrooms/2 full baths/ranch design. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Ceramic tiled master shower/double sinks master & family baths w/granite or equivalent vanity tops. Large WIC master suite.
$599,990

Condominiums

1400 Prairie Creek Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
34Picture(s)
1,760Sqft
MOVE IN READY! The Cypress floor plan offers a spacious open concept floor plan and architectural features like alcoves and ceiling designs elevate the overall feel of the space.
$599,900

Single-Family

1439 Olde Highlander Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
9Picture(s)
2,355Sqft
NEW CONSTRUCTION - Move in ready April 2025! Our Atwater model is a 4 Bed, 2.5 BA 2-Story with 2 story front foyer and Flex Room. The Rear Foyer offers Lockers, a Drop Zone and a large WIC.
$559,900

Single-Family

991 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,592Sqft
Move-in Ready 60 ARW Olivia Cottage I Unit A, GROUND LEVEL FOUNDATION -TWIN HOME!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.
$439,900

Single-Family

1350 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,572Sqft
Move-in Ready 72 ARW Harlow Craftsman. Available 2-24-25! Built by Wisconsin's leading home builder, 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, better than a typical used home.
$534,900

Single-Family

715 Washington St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/2Bathroom(s)
23Picture(s)
1,560Sqft
**RIVERFRONT RETREAT!** This beautifully updated 3-bedroom home blends modern comfort with timeless charm. Enjoy stunning Oconomowoc River views through large south-facing windows in the sunny open-concept living area. The gourmet kitchen features stainless steel appliances and a Kucht gas range.
$510,000

Single-Family

1283 Violet St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
7Picture(s)
1,788Sqft
Charming split ranch in Oconomowoc! The Lavender features 3 bedrooms, 2 bathrooms & upgraded features throughout. Kitchen features soft close cabinets, granite countertops, exterior vented range hood & walk-in pantry. Kitchen is open to the great room which has gas fireplace with stone detail & cathedral ceiling spans across kitchen & great room.
$584,900

Single-Family

930 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,720Sqft
Move-in Ready 55 ARW Julian Cottage I Unit A, TWIN HOME! AVAILABLE 1.28.25! 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.
$529,900

Single-Family

1450 Olde Highlander Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
6Picture(s)
2,548Sqft
The Monterey-located in Oconomowoc's newest community Olde Highlander! Community will include range of amenities such as Pool, Clubhouse, Walking Path, Sports Court, etc. This unique 2-story plan features upgrades throughout. 2-story foyer leads to flex room w/ French doors, which makes a great office or playroom.
$654,900

Single-Family

1320 Rosewood Ct, Oconomowoc, Wisconsin 53066

5Bedroom(s)
3Bathroom(s)
37Picture(s)
3,684Sqft
This stunning 5-bedroom, 3-bathroom home in the heart of Oconomowoc offers the perfect blend of comfort and modern design. Vaulted ceilings and skylights fill the living spaces with natural light, while the thoughtfully designed kitchen features granite countertops, a generous island, and ample cabinetry, seamlessly flowing into the open-concept living and dining areas.
$699,900

Single-Family

1226 Green Tree Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
11Picture(s)
2,328Sqft
The Mulberry-located in Prairie Creek Ridge. This charming 2-story plan features 4 bedrooms plus a flex room. Kitchen has stained soft close cabinets, quartz countertops, exterior vented range hood & walk-in pantry. Kitchen is open to great room, which features a gas fireplace with stone detail. Flex room at front of home has French doors, making a great office space or playroom.
$609,900

Single-Family

228 Shore Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
39Picture(s)
2,862Sqft
Beautiful 3-bed, 3-bath ranch in Oconomowoc! Low-maintenance exterior with new roof and siding. Open-concept main floor features a kitchen with stainless steel appliances, granite counters, and ceramic tile, flowing into a living room with hardwood floors, vaulted ceilings, and a gas fireplace.
$525,000

Condominiums

689 Hickory Creek Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3Bathroom(s)
Private garageParking(s)
40Picture(s)
2,020Sqft
Welcome to this spacious 4-bedroom, 3-bathroom condo, thoughtfully updated & ready for modern living. Recent updates include new roof, gutters, siding, and downspouts(2022), a brand-new water heater (2022), refrigerator & stove (2022), and new dishwasher (2024), ensuring ease & convenience.
$399,900

Condominiums

1628 Belmont Ln, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
15Picture(s)
1,570Sqft
Breton ~ MOVE IN READY! - Planned community in Village Crossing II Condominiums. Luxury finishes are standard. 10' high ceilings, real wood floors, granite kitchen countertops, Corian countertops in baths, kitchen appliances, full basements w/egress window, under-floor rough plumbing for future full bath & wet bar, concrete patio.
$604,900

Single-Family

1531 Woodside Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,951Sqft
New Construction - Ready in March! Nestled in the picturesque Oconomowoc, Morgan Station Subdivision, an exciting opportunity awaits in the form of a brand-new two-story home. This beautiful property combines modern design with thoughtful features that will make it the perfect place to call home.
$499,900

Condominiums

N54W35286 Coastal Ave, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
25Picture(s)
1,517Sqft
THE BEST OF BAY POINTE! Truly move-in ready with over $16k in updates during seller's ownership, this open concept ranch condo offers a split bedroom layout, 4 season room, private patio, & gorgeous finishes. Italian Carrara marble tile surrounds the gas fireplace in the living room w/maple HWFs in main living area.
$500,000

Single-Family

1480 Knoll Ter, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
31Picture(s)
2,080Sqft
This 3-bedroom, 2-bathroom bi-level home in Oconomowoc's River Highlands neighborhood is bursting with possibilities. Featuring hardwood floors, spacious bedrooms, and a large wraparound deck overlooking a beautiful backyard, this home has endless potential and is perfect for those ready to add their personal touch. The lower level offers a cozy family room with a fireplace and a second full bath.
$374,900

Single-Family

N60W38598 Blackhawk Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4Bathroom(s)
32Picture(s)
5,051Sqft
Discover lakefront living at its finest on prestigious Lac La Belle. This magnificent home offers sophisticated living space, harmoniously blending historic charm with modern elegance. The grand living room features a natural fireplace & intimate dining nook, while the spacious eat-in kitchen caters to both casual meals & formal entertaining.
$1,790,000

Condominiums

265 Thurow Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
45Picture(s)
1,260Sqft
Enjoy this sun splashed open concept 2nd floor condominium viewing an oak tree grove & walking distance to many conveniences. Just 4 years old, this corner unit with transom windows & southwest exposure has a very spacious owner's suite. Heated 1 car underground parking space and storage space., plus extra deep detached garage for car/workshop.
$349,500

Single-Family

W346N6701 Whittaker Rd, Oconomowoc, Wisconsin 53066

6Bedroom(s)
4/1Bathroom(s)
88Picture(s)
6,639Sqft
This exquisite executive estate on Okauchee Lake features 6 bedrooms, 4.5 baths, and a fully finished walk-out lower level complete with a billiard room, bar, natural fireplace, laundry, changing room, full kitchen, bedroom, and full bath.
$4,750,000
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