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
N52W35577 Lake Dr, Oconomowoc, Wisconsin 53066
6Bedroom(s)
4/2Bathroom(s)
46Picture(s)
5,016Sqft
Remarkable 5000+ sq ft ranch home with 120 ft of gorgeous lake frontage on the Upper Oconomowoc section of Okauchee Lake! This amazing property offers a large lot with level swim frontage, 3 permanent piers, sand beach area, and boathouse with rooftop deck. Home is a stunning masterpiece that includes a beautifully finished walkout lower level. 5-6 BR's, 4 full baths, and 2 half baths.
$2,699,999
Condominiums
N49W36150 Nottingham Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
50Picture(s)
1,750Sqft
Rare opportunity to own this well-maintained 3BR, 2BA condo in Oconomowoc! Townhome style, multi-level design offers a spacious great room with a cozy wood-burning stove, an updated kitchen with breakfast bar, built-in buffet, dining area, and stainless steel appliances. A three-season sunroom and private patio overlook an expansive green space.
$300,000
Single-Family
1721 Hammock Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,312Sqft
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. Great Rm is off kitchen & features an electric fireplace with stone detail. Flex room off the front foyer has French doors, making it a great office or playroom.
$629,900
Condominiums
1622 Saint Andrews Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
4/1Bathroom(s)
SurfaceParking(s)
54Picture(s)
4,191Sqft
Experience luxury lake living in this custom-built condo featuring high end finishes throughout. Stunning kitchen boasts sleek granite countertops, deluxe cabinetry and massive central island, perfect for food prep or casual dining. Soaring ceilings and cherry HWF throughout the main living space. Three spacious bedroom ensuites provides the opportunity for multiple primary suites.
$1,200,000
Single-Family
1611 Creekview Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
39Picture(s)
2,403Sqft
Move-in-ready! 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. Also located on the 1st floor is an open-concept living area that includes a roomy gathering room w/ GFP, dining area, & an impressively large kitchen.
$667,900
Single-Family
1241 Green Tree Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,404Sqft
This home is under construction. The Arielle 2404 is a plan that offers all the essential living spaces starting w/ the kitchen, which features a walk-in-pantry, quartz counters, appliances & prep island w/ extra seating. The gathering room offers a cozy gas fireplace. Finishing the first floor is a flex space/home office, powder room & large mudroom w/ a built-in bench & storage.
$691,900
Single-Family
1225 Green Tree Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,805Sqft
This home is move-in-ready. The Lauren 1805 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. A large island that doubles as a snack bar, spacious walk-in-pantry, quartz counters & ample storage cabinets in the kitchen provide the perfect space for meal prep.
$592,900
Single-Family
1233 Green Tree Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,431Sqft
This home is under construction. 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.
$690,900
Single-Family
1753 Hammock Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
2,059Sqft
The Marigold-located in the heart of Oconomowoc! This prairie inspired ranch style home features upgrades throughout. Kitchen has soft close cabinets, quartz countertops, spacious walk-in pantry & exterior vented range hood. Cathedral ceilings spans across kitchen & great room & an electric fireplace w/ stone detail in GR completes the space.
$644,900
Single-Family
828 Silver Lake St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
39Picture(s)
1,132Sqft
Discover this charming 2 bedroom, 1 bath home in the heart of downtown Oconomowoc. Offering the perfect blend of comfort and convenience, this home has been impeccably maintained & is ready for it's new owner. This charmer has lots to offer; hardwood floors in the dining room, ample cabinet space in the kitchen, new roof & siding, plus a 3+ car detached car garage that is a rare find.
$325,000
Single-Family
1832 Glenn Spring Ct, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
42Picture(s)
3,500Sqft
Beautifully updated home on a cul-de-sac lot in Pabst Farms! Spacious interior includes 4 BRs, 3.5 baths, and a finished lower level. Large great room with fireplace. Open kitchen has breakfast bar, new quartz countertops, and bayed dining area with back yard views. Main floor den-office. Large mud-laundry room has lockers and washer-dryer included.
$734,900
Single-Family
223 Shore Cir, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
35Picture(s)
3,269Sqft
Exceptional home and setting on a gorgeous lot with beautiful wooded backdrop! This home features many updates, 4-5 BR's, and a finished exposed lower level. Large vaulted great room has gas fireplace. Kitchen offers adjoining dining room, breakfast bar, and SS appliances included. French doors lead to main floor den. Mud-laundry room with washer and dryer included.
$574,900
Single-Family
N53W37153 Madison St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
1Bathroom(s)
36Picture(s)
1,400Sqft
Welcome home to this stunning 3 bed 1 bath home in Oconomowoc. The interior features beautiful hardwood floors throughout, contributing to its classic charm. The charming kitchen is open to the living space with beautiful granite countertops and tons of cabinet space. The beautifully remodeled full bathroom features a new shower, vanity and lighting.
$349,900
Condominiums
861 Stirling Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
28Picture(s)
1,808Sqft
NEW CONSTRUCTION - ready June 2025! 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.
$539,900
Single-Family
1366 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,608Sqft
Move-in Ready 74 ARW Weston Traditional. Available 5.2.25! 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.
$524,900
Single-Family
1363 W Arrowood Cir, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
6Picture(s)
1,503Sqft
Move-in Ready 44 ARW Beryl Shingle. Available 5.21.25! 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.
$509,900
Condominiums
112 Marcella St, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
17Picture(s)
1,824Sqft
This charming 2 bedroom, 2 full bath condo has what you are looking for. Large sun drenched living room leads to an open concept kitchen. Two spacious bedrooms lead to a full bath. The finished basement has ample room for all your entertainment needs which includes a large updated full bath and laundry room and large room for crafting, office space or additional storage.
$245,900
Single-Family
764 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
41Picture(s)
3,240Sqft
Sometimes a home comes along that just ticks all the boxes, from style and functionality to ease of use. Oconomowoc Parkway exudes character and you will love the generous spaces and the 4-5 bedrooms. The quintessential floor plan shows like a home featured in a design magazine. Each room exudes warmth, comfort and charm.
$724,900
Single-Family
35198 Castle Rock Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
58Picture(s)
3,070Sqft
Rare opportunity and a second chance to call this home! Back on market only due to buyer financing! Modern meets elegance in this sprawling ranch located in the Estates of the desirable Lake Country Villages! Open concept split ranch featuring current/ on trend colors, updated lighting and class. LR features cathedral ceiling & gas FP.
$809,900
Single-Family
1242 Green Tree Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,926Sqft
The Lavender-a lovely split ranch featuring 3 beds/2 plus plus a sunroom! Located in the heart of Oconomowoc in the Prairie Creek Ridge community. Kitchen features soft close cabinets, quartz countertops, walk-in pantry & exterior vented range hood. Cathedral ceiling spans across kitchen & great room, and gas fireplace completes the space.
$609,900
Single-Family
1540 Bluestem Trl, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,804Sqft
New construction - Ready in May. The Lakewood model in the Prairie Creek subdivision of Oconomowoc is a remarkable open-concept home that beautifully balances comfort and style. Featuring cathedral ceilings and a spacious kitchen island, it's perfect for entertaining. Each bedroom comes with a walk-in closet, providing ample storage.
$549,900
Single-Family
245 Hillside Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
32Picture(s)
3,231Sqft
Priced Below Assessed Value - A Spacious and Inviting Cape Cod Home that offers a perfect blend of comfort and functionality. Step inside to find an inviting layout with a large formal dining room and a spacious living room. The open-concept family room, complete with a cozy fireplace, seamlessly connects to the eat-in kitchen featuring beautiful granite countertops.
$529,900
Condominiums
215 Pleasant St, Oconomowoc, Wisconsin 53066
1Bedroom(s)
1/1Bathroom(s)
1 space assignedParking(s)
67Picture(s)
1,061Sqft
Live that walkable downtown Oconomowoc lifestyle in this stunning third-floor condo! Sunny, south-facing unit allows for great views of city parades right from your private balcony. Upgraded GE Cafe appliances, quartz countertops, motorized window shades, updated light fixtures, pantry closet & Murphy bed for guests all serve to elevate your lifestyle.
$550,000
Single-Family
987 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,592Sqft
Move-in Ready 61 ARW Olivia Cottage I Unit B, 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
1308 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. Open floor plan features 3 bedrooms, 2.5 baths, office & 2 car garage. This home has a partial exposure lower level. 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.
$594,900
Single-Family
1443 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
14Picture(s)
1,763Sqft
NEW CONSTRUCTION Olde Highlander Community - Ready May 2025! Our Wingra model is a 3 Bed, 2 BA, 3 Car Garage, split ranch with an open concept layout.
$549,900
Single-Family
1376 Scotsland Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,456Sqft
The Mulberry-located in Oconomowoc's newest community Olde Highlander! Community will include range of amenities such as Pool, Clubhouse, Walking Path, Sports Court, etc. This 2-story home features 4 bedrooms & upgrades throughout. Kitchen has soft close cabinets, quartz countertops, exterior vented range hood & walk-in pantry. Great room off kitchen has electric fireplace w/ stone detail.
$669,900
Single-Family
1345 Rosewood Ct, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
45Picture(s)
3,470Sqft
Situated on a quiet cul-de-sac, this 5 bedroom, 3.5 bath home with 3 car garage has a bank of two-story windows giving ample natural Eastern exposure light to the open concept Living room & kitchen. Eat-in kitchen has large island, pantry, backsplash and patio doors to backyard. Main floor en-suit with tiled WIS, laundry room and mudroom complete 1st floor.
$699,900
Condominiums
W389N7112 Pennsylvania St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private garageParking(s)
31Picture(s)
2,800Sqft
Don't be fooled by the peaceful country feeling, this condo is just a few miles from downtown Oconomowoc! Stunning luxury custom unit boasts an open floor plan with upscale, quality features that include solid woodwork, Caesarstone & granite countertops, black stainless appliances, solid hardwood flooring, ceramic tiling, 2 fireplaces, & a 1st-floor laundry.
$794,000
Single-Family
1387 W Mamerow Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
26Picture(s)
1,827Sqft
Gorgeous craftsman-style single family home, built in 2008, 3BR 2.25 bath, 1,827 sq ft, open concept, LR w/ gas FP, Dine-in Kitchen w/ stainless steel appliances, Formal DR, Main floor MBR w/ensuite & spa tub & lg walk-in closet, 3.5 car insulated garage, HWF and carpeting, corner lot on pond with views, HVAC, Basement potential to finish for rec room and plumed for full bath.
$529,900
