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
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)
46Picture(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.
$4,499,000
Single-Family
1403 Bluebird Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
32Picture(s)
2,581Sqft
Outstanding 2-story home in the Wood Creek neighborhood of Oconomowoc! This 4 BR, 2.5 BA home boasts all-new Smart LP siding, roof, gutters & windows in 2023 - offering a move-in-ready experience. The open-concept main floor features a Great Room with a stunning stone-trimmed gas fireplace and a gourmet kitchen equipped with a breakfast bar, abundant cabinetry & appliances included.
$559,000
Condominiums
1061 Regent Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
1 space assignedParking(s)
23Picture(s)
1,012Sqft
Welcome to this lovely, newly refreshed two-bedroom unit in a peaceful Oconomowoc condo complex. Move-in-ready with two bedrooms & two full bathrooms. The spacious master bedroom has a private balcony and private entrance to the master bathroom. The second bedroom features tall ceilings boasting natural light. Plenty of closet space as well as attic storage with skylight.
$245,000
Single-Family
1299 Violet St, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
5Picture(s)
2,748Sqft
HOUSE IS IN ROUGH CARPENTRY. APPROX. COMPLETION AUG'25.4 bedrooms/2.5 bath/flex room/spacious 2-story. Basement has an egress slider window & drain/vent rough-in for future full bath. Corner ceramic tiled walk-in shower/2 shower heads/split sinks/granite or equivalent vanity tops. Jack and Jill family bath with double sinks. Spacious WIC master suite. Knockdown drywall w/rounded corners.
$619,990
Single-Family
1234 Green Tree Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
53Picture(s)
2,748Sqft
4 bedrooms/3 baths/Flex Room/ Partial Exposure/2-story. Basement drain/vent rough-in for future full bath & windows in exposure. Ceramic tiled walk-in shower/2 shower heads/split sinks/granite or equivalent vanity tops in master bath. Double sinks in Jack & Jill bathroom. Large WIC master bedroom. 9' 1st floor ceilings/tray ceiling master bedroom.
$594,990
Single-Family
926 Elderberry Rd, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
5Picture(s)
1,720Sqft
Move-in Ready 54 ARWT Julian Cottage I Unit B, 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
Vacant Land
W358N6309 Ennis Rd, Oconomowoc, Wisconsin 53066
5Picture(s)
0Sqft
The Snyder farm is a 77 lot premier residential community located in the heart of Lake country just minutes way from all the modern amenities and downtown Oconomowoc. Approximately 3/4 acre lots nestled into gently rolling farmland the Snyder Farm is an enclosed subdivision with no through streets for additional privacy.
$172,000
Vacant Land
W358N6291 Ennis Rd, Oconomowoc, Wisconsin 53066
5Picture(s)
0Sqft
The Snyder farm is a 77 lot premier residential community located in the heart of Lake country just minutes way from all the modern amenities and downtown Oconomowoc. Approximately 3/4 acre lots nestled into gently rolling farmland the Snyder Farm is an enclosed subdivision with no through streets for additional privacy.
$172,000
Vacant Land
W358N6271 Ennis Rd, Oconomowoc, Wisconsin 53066
5Picture(s)
0Sqft
The Snyder farm is a 77 lot premier residential community located in the heart of Lake country just minutes way from all the modern amenities and downtown Oconomowoc. Approximately 3/4 acre lots nestled into gently rolling farmland the Snyder Farm is an enclosed subdivision with no through streets for additional privacy.
$172,000
Vacant Land
W359N6209 Margaret Ct, Oconomowoc, Wisconsin 53066
5Picture(s)
0Sqft
The Snyder farm is a 77 lot premier residential community located in the heart of Lake country just minutes way from all the modern amenities and downtown Oconomowoc. Approximately 3/4 acre lots nestled into gently rolling farmland the Snyder Farm is an enclosed subdivision with no through streets for additional privacy.
$180,200
Condominiums
846 Stirling Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
31Picture(s)
1,631Sqft
Luxury Ranch Condominium with 2 Bedroom plus Flex Room, featuring open design concept with 9' Ceilings throughout. Beautiful Gourmet Kitchen for entertaining with a large center island, beautiful soft close cabinetry and quartz countertops. Spacious Great Room features a stunning stone to ceiling fireplace and box tray ceiling! Flex Room with a door offers a flexible space to fit your lifestyle.
$539,900
Condominiums
844 Stirling Dr, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
2Picture(s)
1,631Sqft
Luxury Ranch Condominium with 2 Bedroom plus Flex Room, featuring open design concept with 9' Ceilings throughout. Beautiful Kitchen for entertaining with a large center island, beautiful soft close cabinetry and quartz countertops. Spacious Great Room features a stunning stone to ceiling fireplace and box tray ceiling! Flex Room with a door offers a flexible space to fit your lifestyle.
$524,900
Single-Family
1581 Creekview Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
8Picture(s)
2,484Sqft
HOUSE IS FRAMED. APPROXIMATE COMPLETION JULY. 4 bedroom/2.5 bath/Partial Exposure/elite series spacious 2-story. Basement has 1 slider window in exposure & drain/vent rough-in for future full bath. Ceramic tiled shower/double sinks/granite or equivalent vanity tops in master bath. Double sinks family bath. Large WIC master suite. Tray ceiling master suite.
$619,990
Single-Family
831 Shady Ln, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2Bathroom(s)
42Picture(s)
2,580Sqft
Please do not contact Seller! Must see this updated ranch in prime Oconomowoc location! Extensive updates in the last 2 years include roof, LP siding, soffit and facia, guest bathroom, windows, patio, and flooring. The spacious great room features cathedral ceilings w/ a gas fireplace. Master suite with jetted tub and walk in closet.
$499,900
Condominiums
N53W35199 Lighthouse Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
3Bathroom(s)
Private garageParking(s)
42Picture(s)
2,700Sqft
Explore the walking paths around the 2 PONDS that this IMMACULATE RANCH CONDO OFFERS! A private backyard w/patio and many local convienences/w Okauchee lake and diners steps away! Open the private entryway into this sunlit spotless condo! The welcoming foyer leads to the great room w/an enchanting tiled FP as the focus and relax with the carpeting addition! The kitchen offers exquisite granite c
$519,000
Single-Family
1499 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.
$417,900
Single-Family
1252 Violet St, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
4Picture(s)
1,772Sqft
New Construction - Ready in March. Introducing our Canton Model in the beautiful Prairie Creek Ridge Subdivision. This open-concept, split ranch design features a spacious kitchen with a large island and quartz countertops, perfect for entertaining. Enjoy the cozy ambiance of the electric fireplace with a stone surround and mantle.
$539,900
Single-Family
1326 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
14Picture(s)
1,722Sqft
NEW Construction- Ready February 2025! Located in the desirable new development, Olde Highlander - this beautiful Caspian model has all the amenities you are looking for! The Kitchen includes quartz countertops, a workspace Island with overhang for seating, and is open to the Great Room which has LVP flooring and a corner gas fireplace with stone to 9' ceiling detail.
$524,900
Single-Family
1400 Scotsland Ln, Oconomowoc, Wisconsin 53066
3Bedroom(s)
2Bathroom(s)
9Picture(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
1441 Olde Highlander Dr, Oconomowoc, Wisconsin 53066
4Bedroom(s)
2/1Bathroom(s)
22Picture(s)
2,289Sqft
NEW CONSTRUCTION - Move in ready February 2025! 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 Ready February 2025! 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
Condominiums
1061 Regent Rd, Oconomowoc, Wisconsin 53066
2Bedroom(s)
2Bathroom(s)
SurfaceParking(s)
27Picture(s)
1,270Sqft
Set back off the main road you won't believe you're in Oconomowoc anymore. Quiet wooded prairie type setting. Yet close to plenty of shopping and dining options. Close to I94 and HWY 16 for the commuter. With 2 levels of living space and vaulted ceilings though out, this unit feels spacious and airy. HEATED underground garage spot and surface parking. Plenty of visitor parking.
$249,900
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
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
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 BD/3.5 BA, w/In-Law Suite, ''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
