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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

1477 Olde Highlander Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
3Picture(s)
1,675Sqft
NEW CONSTRUCTION! Introducing our newest floorplan, The Mitchell! This rear load townhome offers a first-floor open floorplan with a large Great Room - perfect for entertaining family and friends, a beautiful Kitchen with a large center island and corner pantry. The second level offers the Primary Suite with a WIC and attached bath with a double bowl vanity.
$439,421

Single-Family

227 Shore Cir, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
48Picture(s)
2,483Sqft
Step inside this stunning Colonial where sunlight fills every room highlighting crisp white trim and a bright, open layout designed for living and entertaining. Enjoy morning coffee on the expansive deck with private conservancy views, host movie nights and games in the finished basement and take advantage of the extra large garage for projects and storage.
$599,000

Single-Family

1084 Spruce Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
28Picture(s)
2,165Sqft
Don't miss this 4 bedroom, 2.5 bath home in the desirable Pine Ridge neighborhood. This well-maintained two-story home features great curb appeal with stone accents and a covered porch. The 3-car garage leaves ample room for outdoor storage and parking. Inside enjoy an open and functional layout with bright living spaces, generous bedroom and modern finishes throughout.
$619,900

Single-Family

1333 Periwinkle Pass, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3/1Bathroom(s)
10Picture(s)
2,477Sqft
Welcome home to THE ELSA plan by Stepping Stone Homes, an award-winning builder. Open floorplan features 3 Beds, 3.5 Baths and 3 car Gar. This lot has LOOKOUT exposure. The KIT has quartz counters, soft close cabs and LG appliances. LVP flooring in kitchen, dinette and great room. We equip our homes with Smart Technology such as a Ring doorbell and touchless faucet.
$732,635

Single-Family

1174 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,583Sqft
Move-In Ready 113 ARW Harlequin Craftsman- Available 2/25/26! 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. As your local home builder, you can expect the best local brands and trades for your home as well.
$519,900

Single-Family

1214 W Arrowood Cir, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,400Sqft
Move-In Ready 108 ARW Margot Craftsman - Available 3/23/26! 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. As your local home builder, you can expect the best local brands and trades for your home as well.
$699,900

Single-Family

1158 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,619Sqft
Move-In Ready 115 ARW Astoria Farmhouse - Available 3/9/26! 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. As your local home builder, you can expect the best local brands and trades for your home as well.
$524,900

Single-Family

727 Browning Cir, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3Bathroom(s)
53Picture(s)
3,200Sqft
Step into this well-kept classic in the Heart of Oconomowoc, offering 4 bedrooms, 3 full baths, and a layout full of potential. The home features its original character throughout-perfect for buyers looking to add their personal touch or bring their vision to life. Large living room, vaulted ceilings, lots of southern exposure windows, fireplace and gas stove to stay warm and cozy in winter.
$555,000

Single-Family

1749 Hammock Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
25Picture(s)
2,432Sqft
Start 2026 in this brand new charming 2-story home in Prairie Creek Ridge! The Evergreen features upgrades throughout. The welcoming front foyer leads to a flex room w/ French doors, making a great office or playroom. Kitchen has a spacious island w/ overhang, soft close cabinets, oversized pantry, ext vented range hood & kitchen sink below a window overlooking the backyard.
$629,900

Single-Family

1757 Hammock Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
4Picture(s)
2,257Sqft
HOUSE IS FRAMED. APPROXIMATE COMPLETION SEPTEMBER 2026.3 bedrooms/2 full baths/elite series ranch. Basement has 1 egress slider window and drain/vent rough-in for future full bath. Walk-in ceramic tiled shower/2 shower heads/granite or equivalent vanity tops/double sinks in master bath. Double sinks family bath. Large WIC master bedroom.
$639,990

Single-Family

1161 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
5Picture(s)
1,519Sqft
Move-In Ready 117 ARW Beryl California Bungalow - Available 3/17/26! 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. As your local home builder, you can expect the best local brands and trades for your home as well.
$509,900

Single-Family

1710 Whalen Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,767Sqft
New Construction - Ready in February! Step into luxury living with this stunning Prentice model home in the Prairie Creek Ridge subdivision of Oconomowoc. Featuring quartz countertops, stylish LVT flooring in the bathrooms, and a cozy gas fireplace, this home blends modern elegance with everyday comfort.
$549,900

Condominiums

245 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
35Picture(s)
1,484Sqft
Come fall in love with the convenience of condo living and experience all that Silver Ridge 55+ condos have to offer! Just a stones throw away from Silver Lake!! Equipped with an elevator and spacious hallways, moving in will be a breeze! When you enter the unit, you're greeted with a coat closet with french doors, the sun-filled living/dining area and your full kitchen.
$289,900

Single-Family

1343 Periwinkle Pass, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,289Sqft
HOUSE IS FRAMED - APPROX. COMPLETION SEPTEMBER 2026. 4 bedrooms/2.5 baths/elite series split ranch. 9' foundation wall/1 egress slider window/drain-vent rough in for future full bath in basement. Ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops. Double sinks in family bath.
$646,990

Single-Family

1672 Switchgrass St, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
6Picture(s)
2,264Sqft
Craftsman inspired 2-story home in Prairie Creek Ridge. The Mulberry features upgrades throughout. Kitchen has soft close cabinets, quartz countertops, ext vented range hood, island w/ overhang & walk-in pantry. Spacious great room includes an electric fireplace with stone detail. Flex room w/ French doors off foyer makes a great office or playroom.
$659,900

Single-Family

N55W37033 Harvard St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
51Picture(s)
1,919Sqft
Opportunity knocks! This 3 bed, 2 bath Cape Cod-style home sits on nearly one-third of an acre and offers a solid foundation for your updates. The main-floor bedroom includes an attached bath w/a zero-threshold tile shower. Upstairs, you'll find two spacious bedrooms w/hardwood floors plus a bonus room opportunity- ideal for creating a home office, hobby room, or extra storage.
$349,900

Single-Family

1230 Oriole Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
24Picture(s)
1,668Sqft
This spacious ranch home features a welcoming great room with a stone gas fireplace and an open-concept kitchen complete with hardwood floors, a dining area, breakfast bar, and included appliances. A formal dining room is conveniently located off the entry foyer. Down the hall are three well-sized bedrooms, including a primary suite with a large walk-in closet and private bath.
$520,000

Single-Family

1745 Hammock Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
4Picture(s)
2,748Sqft
HOUSE IS FRAMED - APPROX FINISH AUGUST '26.4 bedrooms/2.5 baths/flex room/elite 2-story design. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Ceramic tiled shower w/2 shower heads/double sinks/granite or equivalent vanity tops in master. Double sinks family bath. WIC's all bedrooms. 9' first floor ceilings/tray ceiling master bedroom.
$689,990

Single-Family

1717 Hammock Ln, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,580Sqft
Charming English inspired 2-story home in Prairie Creek Ridge! The Juneberry features upgraded features throughout. Kitchen features soft close cabinets, quartz countertops, island w/ overhang & exterior vented range hood. Dinette separates kitchen & great room, GR is complete with a cozy gas fireplace with stone detail.
$639,900

Single-Family

1120 Elderberry Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,720Sqft
Move-in Ready 91 ARW Julian Cottage II Unit A, Ground Level Foundation. TWIN HOME! AVAILABLE 12.19.25! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes w/ private yards. Monthly association fee of $245 covers lawn mowing/fertilization/snow removal; plus a la carte seasonal services are available for separate rate.
$509,900

Single-Family

1278 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,482Sqft
Move-In Ready 100 ARW Elaine Prairie - Available 2/23/26! 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.
$529,900

Single-Family

1388 Periwinkle Pass, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
37Picture(s)
1,772Sqft
New Construction - Ready in Now! Discover the Canton model in Oconomowoc's desirable Prairie Creek Ridge subdivision--a thoughtfully designed split ranch that blends modern style with everyday comfort. With 1,772 sq. ft., this home offers 3 bedrooms and 2 baths, plus a spacious 3-car garage on a .26-acre lot.
$564,900

Condominiums

510 Frederick Ct, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2/1Bathroom(s)
Private GarageParking(s)
20Picture(s)
1,780Sqft
Fantastic Opportunity in the Heart of Oconomowoc! Don't miss your chance to own this townhouse-style condo just minutes from downtown Oconomowoc's shopping, restaurants, and festivals! A vaulted entryway welcomes you into the spacious great room featuring a cozy gas fireplace.
$319,000

Single-Family

N73W36308 Shore Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
23Picture(s)
536Sqft
Rare opportunity to own lake frontage property w/gorgeous sunset views & mature trees on almost 3 acres! Enjoy peaceful Ashippun Lake, approx 114 ft frontage as per GIS map. Bids available for demolish & removal of abandoned cottage & 2 car GA.
$499,900

Vacant Land

N73W36308 Shore Dr, Oconomowoc, Wisconsin 53066

23Picture(s)
0Sqft
Rare opportunity to own lake frontage property w/gorgeous sunset views & mature trees on almost 3 acres! Enjoy peaceful Ashippun Lake & 114 ft of frontage as per GIS map. Bids available for demolish/removal of existing abandoned cottage & 2 car GA.
$499,900

Condominiums

845 Stirling Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
27Picture(s)
1,808Sqft
NEW CONSTRUCTION - ready March 2026! Look no further for Luxury Ranch Condominium living with 2 Bedrooms plus a Sunroom, featuring open design concept with 9' Ceilings throughout. Beautiful Gourmet kitchen for entertaining with large island, soft close cabinetry and quartz countertops.
$539,900

Single-Family

208 Maple Ter, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
57Picture(s)
2,872Sqft
Enjoy affordable Lake Living on Lac La Belle with this charming 1950's Lannon Stone Cape Cod in the desirable Maple Terrace neighborhood, within walking distance to downtown Oconomowoc's shops and restaurants. Includes deeded access to a private lakeside park with pier and boat slip rights.
$850,000

Condominiums

847 Stirling Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private GarageParking(s)
28Picture(s)
1,808Sqft
NEW CONSTRUCTION - ready March 2026! Look no further for Luxury Ranch Condominium living with 2 Bedrooms plus a Sunroom, featuring open design concept with 9' Ceilings throughout. Beautiful kitchen for entertaining with large island, soft close cabinetry and quartz countertops.
$549,900

Single-Family

1187 W Arrowood Cir, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,861Sqft
Move-In Ready 120 ARW Sawyer Cottage B - Available 2/5/26! 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.
$559,900

Single-Family

W398N8740 Amber Ln, Oconomowoc, Wisconsin 53036

3Bedroom(s)
2/1Bathroom(s)
66Picture(s)
1,569Sqft
Welcome to this peaceful 4-acre retreat on the Ashippun River! This 3BR/2.1BA split-level home showcases stunning California drift stone accents and warm knotty pine throughout. Enjoy peaceful river views and wildlife from your private wooded paradise. Impressive 24x24 outbuilding (approx. 600 sq ft) offers endless possibilities-workshop, studio, or even income potential.
$499,900
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