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
1400 Scotsland Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
12Picture(s)
1,926Sqft
The Lavender-located in Oconomowoc's newest community Olde Highlander! Community will include range of amenities such as Pool, Clubhouse, Walking Path, Sports Court, etc. This charming Split Ranch features upgrades throughout. Kitchen features Stained Cabs, Quartz Countertops, Range Hood, & Walk-In Pantry. Kitchen is open to Gr Rm which is complete w/ Gas Fireplace & Cathedral Ceiling.
$609,900
Single-Family
N72W39748 Lang Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
1Bathroom(s)
22Picture(s)
672Sqft
This charming 2-bedroom ranch home offers the perfect blend of nature and modern updates, set on a wooded half-acre lot. The recently remodeled kitchen and bathroom feature beautiful finishes, enhancing the home's inviting ambiance. Step outside onto the deck and take in the stunning fall foliage that surrounds you, providing a private retreat with tree-lined views. A full basement and detached 1.
$280,000
Single-Family
1620 Creekview Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
34Picture(s)
2,081Sqft
New Construction - ready to move right in!! Upgraded split design ranch features vaulted main living with corner gas fireplace, 9 ft. ceilings, owner supplied upgraded stainless steel appliances & high-end light fixtures, convenient drywall lockers, and walk-in pantry. The master suite has a large walk-in closet, private bath with tile shower and dual sinks.
$649,900
Single-Family
1441 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
22Picture(s)
2,289Sqft
NEW CONSTRUCTION - Move in ready January 2024! Our Sheridan model is a 4 Bed, 2.5 BA 2-Story with a private 1st floor Laundry Room and Flex Room. The Rear Foyer offers Lockers, a Drop Zone and access to the Powder Room.
$549,900
Single-Family
1485 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2/1Bathroom(s)
3Picture(s)
1,490Sqft
NEW CONSTRUCTION! Don't miss out on our newest floorplan, The Quentin! 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 walk-in pantry. The second level offers two suites both with a WIC and attached bathroom.
$389,900
Vacant Land
W340N7661 Townline Rd, Oconomowoc, Wisconsin 53066
14Picture(s)
0Sqft
New price w/ INCREDIBLE Location! Lake Country Land buy! 22.4 Acre parcel investment. This property's 130x230 pole barn built as indoor riding arena w/ observation deck. Inside two spacious bathrooms, fully plumbed on conventional septic. Two 250 AMP panels in building. Electrical hook ups for 10 horse travel trailers.
$799,500
Single-Family
1055 Hancock Dr, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2/1Bathroom(s)
30Picture(s)
2,044Sqft
Don't miss this rare opportunity! The sellers have just purchased this beautiful home under 2 months ago, but due to unforeseen circumstances, they must part with it. This well-loved property features 5 spacious bedrooms and 2.5 baths, making it perfect for families or those needing extra space.
$475,000
Vacant Land
Lt1 Crescent Dr, Oconomowoc Lake, Wisconsin 53066
15Picture(s)
0Sqft
Rarely available vacant land with access to Oconomowoc Lake. The property consists of a 1.5 acre main building site along with an auxiliary parcel boasting 55 feet of deeded frontage on a navigable channel. The channel is 3-5 feet deep, allowing access to Oconomowoc Lake by pontoon boats and other small watercraft.
$650,000
Single-Family
35320 Pabst Ct, Oconomowoc Lake, Wisconsin 53066
4Bedroom(s)
4/1Bathroom(s)
94Picture(s)
6,871Sqft
Enter the secluded winding drive, to discover a unique resort set w/in a serene landscape. The custom-designed residence merges classic architectural elements w/quality rustic details. The home reflects meticulous care, updates, & warmth from the impressive hand-hewn beams, soaring ceilings, custom millwork, 5 fireplaces, slate & hwfs.
$1,495,000
Single-Family
739 Lake Bluff Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
32Picture(s)
1,660Sqft
Welcome to this charming 3 bedroom, 2 bath ranch perfectly situated in an ideal Oconomowoc neighborhood within walking distance to schools and all downtown has to offer. From the moment you step inside you will feel right at home. The open concept layout perfectly blends the kitchen and living areas, providing plenty of space to cook & entertain.
$425,000
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
704 Washington St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
49Picture(s)
2,310Sqft
This charming 3-bedroom Cape Cod in ''President's Row'' in Oconomowoc will not disappoint! Just steps from 2 parks and the popular ''Walk around Fowler'', this home has easy access to all the festivals and amenities that downtown Oconomowoc has to offer.
$425,000
Single-Family
1176 Sandpiper Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2/1Bathroom(s)
45Picture(s)
2,698Sqft
Bright & sunny layout; large windows throughout. Dramatic great room with vaulted ceiling and 2- way gas fireplace leading to the kitchen and dining areas. The kitchen features a center work island with breakfast counter, ceramic tile flooring, custom cabinetry, granite counters, and newer appliances.
$515,000
Condominiums
1061 Regent Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
27Picture(s)
1,270Sqft
Terrific 2 story condo in a super Oconomowoc location. With vaulted ceilings though out both levels, this unit feels spacious and airy. Main level includes Great Room, Dining Room, Galley KIT with granite , laundry, and 2 full baths one of which attached the primary bedroom. Open staircase leads you to the guest BR , large storage room and loft area over looking Great Room..
$259,000
Single-Family
1445 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
3Picture(s)
2,189Sqft
NEW CONSTRUCTION- Move In Ready - January 2025!! - This beautiful Hudson model has all the amenities you are looking for! The Kitchen includes upgraded quartz countertops, cabinets with soft close, a workspace island with overhang for additional seating, and is open to the Great Room which has a gas fireplace with beautiful stone to 9' ceiling detail and LVP flooring.
$534,900
Single-Family
W358N6724 Stonewood Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3/1Bathroom(s)
60Picture(s)
3,682Sqft
Welcome to your dream home! This stunning walkout split-level ranch, set on nearly an acre, features 3 bedrooms plus a den/4th bedroom in the lower level, along with a main floor home office. The kitchen is a chef's delight, boasting high-end appliances and an open design with soaring 12-foot ceilings.
$814,900
Condominiums
320 Pleasant St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
2 or more spaces assignedParking(s)
35Picture(s)
1,615Sqft
Experience effortless lake living in this 3rd-floor condo overlooking beautiful Fowler Lake! This condo offers the perfect balance of downtown convenience and tranquil lakeside living. Enjoy stunning elevated lake views from multiple rooms, creating the feel of a lakeside treehouse. The large balcony, accessible from two rooms, provides a peaceful spot to relax all day long.
$457,000
Condominiums
842 Stirling Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
28Picture(s)
1,808Sqft
NEW CONSTRUCTION!! Look no further for Luxury Ranch Condominium living with 2 Bedrooms plus an open Sunroom, featuring open design concept with 9' Ceilings throughout. Beautiful large Gourmet Kitchen for entertaining with large island, cabinetry with soft close hardware and quartz countertops.
$549,900
Condominiums
902 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
39Picture(s)
1,525Sqft
Condo living at its best! This impeccably kept 3 bedroom, 2 full bath corner unit is walking distance from shopping, dining, trails and minutes from golf course, downtown and lakes in the lake country area!!! 2 underground parking spots in heated garage and surface parking as well! You do not want to miss your opportunity on this one, schedule your showing now! Welcome home! Buyer to verify room m
$297,399
Condominiums
W397N5881 Autumn Woods Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
32Picture(s)
1,212Sqft
This desirable first-floor condo in the vibrant Autumn Woods 55+ Community is a must-see! Located just minutes from downtown Oconomowoc, it boasts an open-concept floor plan with 2 bedrooms and 2 baths. Enjoy the convenience of a private 2-car garage, a stylish kitchen featuring a stainless farmhouse sink and appliances, and a cozy gas fireplace.
$290,000
Single-Family
1355 Gridley Ct, Oconomowoc, Wisconsin 53066
5Bedroom(s)
3/1Bathroom(s)
50Picture(s)
4,074Sqft
5 bedrooms, 3.5 bath, ''Modern Farmhouse'' design, ML open concept layout w/kitchen, dining area, living rm, 4 season sunroom w/gas fireplace, front room/formal dining rm, private office, laundry and mudroom w/pet suite! Professionally finished lower-level APARTMENT consists of full kitchen, family room, bedroom, bath, and 2 flex rooms. Updates and amenities to the exterior/ interior.
$840,000
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
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.
$646,900
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.
$647,900
Single-Family
1611 Creekview Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
39Picture(s)
2,403Sqft
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
1217 Green Tree Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
3Picture(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.
$627,900
Single-Family
N56W35574 Lisbon Rd, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
60Picture(s)
2,051Sqft
Welcome to this beautifully updated open-concept home in Oconomowoc, featuring 4 spacious beds & 2.5 baths. Cozy up in the front room with a gas fireplace, perfect for fall and winter evenings. The family room seamlessly connects to the kitchen and a versatile three-season room, ideal for a hot tub or workout space. Upstairs, discover 3 beds, including a primary suite.
$464,000
Single-Family
1225 Green Tree Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
3Picture(s)
1,805Sqft
This home is framed & under construction. 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.
$592,900
Single-Family
N68W34478 County Road K -, Oconomowoc, Wisconsin 53066
5Bedroom(s)
2Bathroom(s)
36Picture(s)
2,772Sqft
Welcome to this versatile home in the Stone Bank School District! Featuring a full mother-in-law suite on the lower level, this property is ideal for multi-generational living. With convenient access to Cty K, it offers both accessibility and charm. The main level includes 3 bedrooms, while the lower level features 2 additional bedrooms, each level with its own kitchen, living area, and bathroom.
$449,900
Single-Family
N57W38248 Lakeland Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
3/1Bathroom(s)
41Picture(s)
3,870Sqft
At the end of Lakeland Drive, on the highly coveted east shore of Lac La Belle, you'll find a mid-century modern home cherished by the same family for over 60 years. This property exudes timeless charm with serene spaces for relaxation and ample room for gatherings, along with 100 feet of pristine lake frontage showcasing stunning western views.
$2,150,000
