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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

222 Pleasant, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
31Picture(s)
2,700Sqft
5-star lake lot, on gem of a lake, near quaint walkable downtown. Property features a gentle slope to the water, mature park-like trees, and panoramic views of the lake with a pier and small sand beach area. Fowler Lake is about 100 acres, 50 feet deep, great for fishing, and has very clear water.
$1,300,000

Single-Family

W347N6765 Shoreview Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
89Picture(s)
4,300Sqft
Ready to fall in love at first sight? When luxury & comfort collide, top notch quality of life happens. Each space in this amazing Ranch has been carefully designed. LVP covers every room of open concept main floor w/spacious GR w/stacked stone GFP.
$899,900

Condominiums

N52W35344 Lighthouse Ln, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
Private garageParking(s)
26Picture(s)
2,588Sqft
Enjoy waterfront views from most rooms in this beautifully appointed ranch condo in tranquil Bay Pointe close to Okauchee Village. The kitchen has maple cabinetry and granite countertops and opens to the great room with vaulted ceilings, a 2 sided gas fireplace, and adjoining 4 season sun room. Enjoy your private deck and sunsets over the large fishing pond.
$509,900

Condominiums

W389N7112 Pennsylvania St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
3Bathroom(s)
SurfaceParking(s)
27Picture(s)
3,000Sqft
Unique opportunity on 5 acres, only 6 units in this development-absolutely no detail has been spared! This stunning, open floor plan, 3 bdrm, 3 bath condo with a walk-out lower level features custom, solid wood trim & 9' ceilings throughout.
$749,999

Single-Family

334 Maple Ter, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4/2Bathroom(s)
34Picture(s)
4,322Sqft
Known as LaBelle Point, this gorgeous home is located on an amazing 1.4-acre lot within walking distance to downtown Oconomowoc. Truly a unique property with over 364 feet of pristine lake frontage- next to impossible to find! This prime location on a point offers magnificent lake views. The home is beautifully decorated, well maintained & current with today's styles.
$3,650,000

Single-Family

938 Royalty Ct, Oconomowoc, Wisconsin 53066

4Bedroom(s)
1/2Bathroom(s)
46Picture(s)
2,624Sqft
Ideally located 2-story Colonial on quiet cul-de-sac. Open concept KIT leads into LR with cozy fireplace. Den on main is ideal for home office, study, or playroom. Separate DR is perfect for gatherings. Sliding doors off KIT lead to a bright, airy, year round sunroom. You will want to spend all your time here! Walk outside to find a wraparound composite deck, brick paved patio, and garden shed.
$400,000

Single-Family

708 Oakwood Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
20Picture(s)
1,939Sqft
A charming ranch in the heart of Oconomowoc. Come and see this well-cared for house and all the character it entails. Large, open living room opens into the dining area and sits adjacent to the recently updated kitchen with granite countertops and built-in refrigerator. Walk down the hall to the 3 generous-sized bedrooms, and updated bathroom with carara marble, along with its newer floor and tub.
$319,500

Single-Family

733 Sherman Ave, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
43Picture(s)
1,500Sqft
This Mid-Century Ranch has been completely restored with care, while respecting its original charm. New eat-in kitchen includes new cabinets, quartzcounters & floors. Main level full bath with new modern fixtures, cabinet, tub and terrazzo flooring. This classic mid century home was built by father/son craftsmen. Family Room with corner windows & classic mid-century fireplace.
$350,000

Single-Family

N62W37740 Wadebridge Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1/1Bathroom(s)
33Picture(s)
1,594Sqft
Meticulously maintained ranch in a location that can't be beat! This 3 bed, 1.5 bath home is perched on a large lot across from Rosenow Creek. Beautiful, secluded lot includes mature trees and perennial garden beds. Amenities include an open concept kitchen, natural fireplace, updated bathrooms.
$325,000

Single-Family

34625 Springbank Rd, Oconomowoc Lake, Wisconsin 53066

6Bedroom(s)
5/1Bathroom(s)
46Picture(s)
7,730Sqft
Stunning Tuscan home reminiscent of a Villa overlooking Lake Como! Gorgeous southern views add to the ambiance of this architectural masterpiece, once the site of the Captain Parker Mansion. This fabulous estate incorporates beautiful architectural antiques throughout the home with the use of stone, marble and hand carved fireplaces, railings, & ceilings.
$4,850,000

Single-Family

438 Franklin St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
1Bathroom(s)
24Picture(s)
1,040Sqft
Affordable Ranch within close proximity to parks, trails, and downtown, you can enjoy all that Oconomowoc has to offer. Recent updates include flooring in the kitchen, granite countertops, and backsplash. Enjoy privacy and relaxation on the spacious deck in the fenced back yard.
$260,000

Single-Family

1557 Riverdale Dr, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2/1Bathroom(s)
25Picture(s)
2,022Sqft
Welcome Home to this beautiful 2-sotry colonial in River Highlands! 3 Large bedrooms upstairs with Full Bath. Master has large WIC. Eat in Kitchen with updated cabinets, ceramic tile flooring and sliding patio door leads to your private refinished large deck perfect for your BBQ party! Full size dining room for your family get togethers.
$375,000

Condominiums

992 Oconomowoc Pkwy, Oconomowoc, Wisconsin 53066

2Bedroom(s)
3/1Bathroom(s)
Private garageParking(s)
21Picture(s)
2,139Sqft
Beautiful 2 bedroom (with the possibility of making a 3 bedroom), 3 1/2 bath condo with 2 car attached garage, screened in porch off the main floor with a bonus balcony on the second floor. Main floor: has an open floor concept with vinyl and carpeted flooring that leads to the living/dinning room where you can cozy up to the gas fireplace.
$340,000

Single-Family

625 South St, Oconomowoc, Wisconsin 53066

5Bedroom(s)
2/1Bathroom(s)
40Picture(s)
2,568Sqft
Just in time for Summer! Come see this AMAZING 5 Bedroom, 2.5 bath home, Loaded with lots of old world charm. Even the pickiest of buyers will have a hard time not loving the charm of this home. This Home features lots of natural wood work throughout. On the main floor you have a large Living Room with natural hardwood floors. A Lovely Dining Room with Built In China Cabinets.
$386,400

Single-Family

1451 Rosewood Pass, Oconomowoc, Wisconsin 53066

4Bedroom(s)
2/1Bathroom(s)
1Picture(s)
2,473Sqft
NEW CONSTRUCTION, COMPLETION AUGUST 31ST! Spacious 2-story home features a Master suite with private bath and 2 walk-in closets, 3 more generous bedrooms , all with walk-in closets, main level consists of kitchen with an abundance of cabinets, solid surface counters, appliance suite, island and a walk-in pantry, great room with gas fireplace, LVP flooring, carpets in bedrooms and flex room! Lower
$569,900

Single-Family

1293 Blue Dahlia Rd, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
22Picture(s)
1,410Sqft
Step thru the front door into the living room featuring cathedral ceilings, natural fireplace and updated LVP flooring. The spacious eat in kitchen was redone with a country kitchen, tiled back splash, counters and loads of cabinets. Primary bedroom has a private full bath. 2 more bedrooms and a second full bath round out the home. First floor laundry.
$319,900

Condominiums

W398N5977 Autumn Woods Dr, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
41Picture(s)
1,824Sqft
This very spacious & sunny upper - end unit condo features a vaulted ceiling in the great room with loft /flex room above with large walk-in closet A sitting room offers extra space separate from the main living area. The kitchen has granite countertops, newer stainless appliances, maple cabinetry & floors, and adjoins the great room with a gas fireplace and patio doors to a private deck.
$269,900

Single-Family

W356N5212 Lakeshore Dr, Oconomowoc, Wisconsin 53066

4Bedroom(s)
4Bathroom(s)
71Picture(s)
5,145Sqft
Sandy Bottom Beach comes with this awesome Spacious Ranch style lake home. Gentle slope to the lake. Entertain friends and family with the indoor pool! Pool room with views of the lake! Huge master suite with jacuzzi tub and sunroom. Open concept layout. Large concrete patio and decks. Beautifully manicured park like lot. Paint and wood floors refinished.Tenant Occupied.
$1,499,999

Single-Family

1730 Cool Water Crescent, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3Bathroom(s)
58Picture(s)
3,850Sqft
Approach this luxurious executive ranch with awe. Enter through the stain glass front door to an open concept great room with a double side gas fireplace. The kitchen features hickory floors, cherry cabinets, a sitting room, and dinette. Great kitchen space with an island for visiting and meal prep. A butlers pantry takes you to a formal dining room.
$590,000

Single-Family

828 Dixie Pl, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
13Picture(s)
1,404Sqft
Great home and setting on a no-through street in a convenient Oconomowoc neighborhood! This property features many mature trees and a private back yard with beautiful wooded backdrop. Plenty of curb appeal with the stone front. Interior offers 3 BR's and one full bath on main level. Large front living room has hardwood floors and plenty of natural light. Hallway leads to bedrooms and bathroom.
$298,000

Single-Family

W342N4837 Oak Ln, Oconomowoc, Wisconsin 53058

3Bedroom(s)
2Bathroom(s)
19Picture(s)
2,563Sqft
Exceptional single family deeded condo in the Town of Oconomowoc! This spacious home offers 3BR/2BA and over 2500 sq ft of living space with the finished rec room on lower level. Enjoy a long list of recent years improvements plus a 2-car attached and 3+ car detached garage! Main level has large great room with gas fireplace. Kitchen with adjoining dining area and appliances included.
$439,900

Single-Family

N72W39748 Lang Rd, Oconomowoc, Wisconsin 53066

2Bedroom(s)
1Bathroom(s)
16Picture(s)
672Sqft
This has to be the cutest Cape Cod Style, 1 Story around located on a quiet road! Offering 2 Main Floor Bedrooms with beautiful hardwood floors, 1 Full Main Floor Bathroom with shower over tub. The Cozy Living Roon with maintable laminate floors. The farmhouse decorated Eat-In Kitchen boasts white timeless cabinets, and laminate counters.
$189,000

Single-Family

1872 River Lakes Rd S, Oconomowoc, Wisconsin 53066

4Bedroom(s)
3/1Bathroom(s)
48Picture(s)
3,758Sqft
Spectacular home set on a premier lot in Eastlake Village at Pabst Farms! Spacious kitchen features maple cabinetry, Zodiac counters and stainless appliances along with breakfast bar! Great room offers a gas fireplace and french style doors leading to den/living room. A formal dining room and generous laundry complete the main level.
$675,000

Condominiums

N55W35038 Coastal Ave, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
4Picture(s)
1,506Sqft
Under Construction off pond unit. The Adalyn is our new open-concept ranch side x side condo. Offering a no-step entry @ the garage & wider doorways for easy accessibility. The private front entry opens to the main living areas, which has gourmet kitchen w/ quartz counters, stainless appliances, island w/ seating WIP & dining area.
$549,900

Condominiums

N55W35032 Coastal Ave, Oconomowoc, Wisconsin 53066

2Bedroom(s)
2Bathroom(s)
Private garageParking(s)
4Picture(s)
1,506Sqft
Under Construction off pond unit. The Adalyn is our new open-concept ranch side x side condo. Offering a no-step entry @ the garage & wider doorways for easy accessibility. The private front entry opens to the main living areas, which has gourmet kitchen w/ quartz counters, stainless appliances, island w/ seating WIP & dining area.
$549,900

Single-Family

W342N4924 Lindy Ln, Oconomowoc, Wisconsin 53058

3Bedroom(s)
2Bathroom(s)
42Picture(s)
1,980Sqft
OKAUCHEE LAKE just in time for summer! 55 feet of prime frontage with a pier, wharf, and deck lakeside for entertaining and watching life float by in the sunshine.Open concept Living Rm and Kitchen with a wall of patio doors overlooking the lake with composite deck and view rail glass railing. 3 levels with walk out lower level rec room with a bar, full bathroom, and hot tub on patio.
$1,200,000

Condominiums

215 Pleasant St, Oconomowoc, Wisconsin 53066

3Bedroom(s)
2Bathroom(s)
Private garageParking(s)
57Picture(s)
2,219Sqft
Situated steps from the delicious restaurants and plentiful shopping of downtown Oconomowoc, experience the best of what Lake Country has to offer in luxury. This condo is the penthouse unit, which means it's a corner unit with a beautiful view of Fowler lake, a spacious loft, and an immense and airy vaulted ceiling exclusive to just this unit.
$1,800,000

Two-Family

207 Jefferson St, Oconomowoc, Wisconsin 53066

1Bedroom(s)
1/1Bathroom(s)
Electric door openerParking(s)
42Picture(s)
0Sqft
Here's your opportunity to purchase the 'Cutest Home' in Oconomowoc. Awarded ''Beautiful Yard of the month'' This two family home has updates galore! Upscale amenities that aesthetically flow with the early 1900's charm.Unit 1 has completed an updated kitchen with attractive beam ceiling, hard wood floors, and stainless steel appliances. Large Master bedroom suite with 1/2 bath.
$339,900

Single-Family

W350N5364 Road B, Oconomowoc, Wisconsin 53069

2Bedroom(s)
1Bathroom(s)
24Picture(s)
713Sqft
BUILD YOUR DREAM HOME! Stellar Okauchee Lake property w/approx 190' of frontage due to its unique peninsula which incl: 4 piers. This 0.268 acre lot feats a gradually sloping lot conducive to constructing a home w/an exposed LL. The existing home offers 2BRs & 1BA & a walkout LL.
$725,000

Single-Family

W350N5362 Road B, Oconomowoc, Wisconsin 53069

4Bedroom(s)
2Bathroom(s)
15Picture(s)
1,728Sqft
BUILD YOUR DREAM HOME! Stellar Okauchee Lake property w/approx 82' of frontage. This 0.340 acre lot feats a gradually sloping lot conducive to constructing a new home w/an exposed LL. There are existing homes ea offering 2BRs & 1BA & 1 w/a walkout LL. 1 unit is currently rented & both are in need of repairs/renovations & are being sold for the land value.
$725,000
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