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$3,917,000
3 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
Discover timeless elegance at this exclusive Lavinia by the Lakes penthouse condo on Oconomowoc's historic isthmus, crafted for those who cherish sophistication and serene lakeside living. Nestled between Fowler Lake and Lac La Belle, enjoy panoramic stunning sunrise and sunset views. Revel in your custom interior with a library, dual fireplaces, hydronic floor heating, pantry, seven outdoor porches, boat dock, elevator, and a secure heated garage. Personalize your retreat with curated finishes and cutting-edge technology for an additional $683,000. Experience single-family privacy without the maintenance, just steps from a charming, walkable downtown. Completion in early 2026. Secure your lakeside legacy. Contact for a private tour.

503 N Lake Road Road Unit 5, Oconomowoc

Listing courtesy of Tenderland Real Estate LLC. Selling Office: .

$3,225,000
4 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
Experience the ultimate Lake Country lifestyle with 140 ft. of level frontage on Upper Oconomowoc Lake, direct boat access to Okauchee Lake's popular dining and entertainment, plus kayak or paddleboard access down the scenic Oconomowoc River to Oconomowoc Lake, Fowler Lake, and vibrant downtown Oconomowoc. This custom contemporary ranch with a full walkout features soaring ceilings, walls of floor-to-ceiling windows, spectacular lake views, and upscale finishes. Enjoy a chef's kitchen with oversized island and double ovens, luxurious primary suite, 2 additional bedrooms, circular dining room, main-floor laundry, and 4-car garage. The walkout level offers a rec room, wet bar, pub lounge, two-way fireplace, 4th bedroom, and patio leading to your private waterfront retreat.

W356N5136 Lakeshore Drive Drive, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: .

$2,750,000
5 Beds ⋅ 4 Baths ⋅ CLOSED Status
Sophisticated luxury meets casual elegance in this newly constructed custom lakefront home on historic Fowler Lake. With 5 BRs & 4 BAs, it offers the rare opportunity to enjoy lake living in the heart of downtown Oconomowoc. Spend summer days boating, swimming, or fishing. Enjoy weekly waterski shows & watch 4th of July fireworks from your own back yard. Restaurants, shops, and year-round festivals are just steps away. Thoughtful design shines throughout, from the bluestone walkway & covered lakeside entertaining area with in-floor radiant heat, to the chef's KIT & open DR & GR framed by expansive lake-view windows. LL adds a rec room, full BA, 5th BR with egress, & auxiliary kitchenette. Curated finishes throughout deliver relaxed sophistication rarely found in new construction.

222 E Pleasant Street Street, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: .

$2,580,000
5 Beds ⋅ 4.5 Baths ⋅ CLOSED Status
Lovingly maintained executive estate in the prestigious Saddlebrook Farms. Offering abundant space for both living & hobbies. Discover elegant finishes: dining room highlighted by a striking coffered ceiling, great room with soaring 18-foot ceilings, a cozy fireplace, & direct access to the outdoor deck/patio. Maple floors lead to a large, bright kitchen featuring quartz countertops. Relax in the window-lined sunroom or retreat to the primary suite, where a private balcony overlooks the sunroom & offers picturesque sunset views. Equestrians, auto enthusiasts, & hobbyists will be captivated by the exterior amenities. The property features a newer barn complete with 11 horse stalls, indoor arena & 2 separate apartments.Total of 7 additional stalls in other barns. Truly a remarkable property

N76W36096 Saddlebrook Lane Lane, Oconomowoc

Listing courtesy of Coldwell Banker Elite. Selling Office: .

$2,350,000
3 Beds ⋅ 2.5 Baths ⋅ CLOSED Status
Enjoy the conveniences of downtown Oconomowoc and the pleasures of lake living without the maintenance of a house! This immaculate luxury 3-bedroom, 2.5-bath condo offers timeless style with an open-concept floor plan, high ceilings, 2 fireplaces, natural light, and two covered porches. The kitchen features Quartz countertops, Wolf & Subzero appliances and opens to the dining and living areas, where stunning views of Lac La Belle create the perfect backdrop for everyday living and entertaining. Residents of The Parc enjoy exceptional amenities, including two pontoon boats, a lakeside patio with grill and fire pit and private indoor parking. With downtown Oconomowoc out your door, you'll enjoy restaurants, shopping, coffee shops, the Farmers Market, and year-round community events.

200 W Wisconsin Avenue Avenue Unit 202, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country. Selling Office: .

$1,900,000
5 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
Model Home - LAST WEEKEND!!! This home is currently under contract. Simply Luxury Homes will continue to use the property as a model home and it will remain available for scheduled showings throughout the month of June to showcase available floor plans and new construction opportunities. Please contact Tina Stapelfeldt for further informationExperience refined living New Construction in this stunning 4,476 sq ft modern-transitional w/ 5BR, 3.5BA & upscale finishes. Open floor plan w/ great rm + 100''electric FP. Kitchen w/ Thermador appl pkg, bev cooler, rift-sawn oak cabs, 8' sliders & Marvin windows.Primary suite w/ porch access, heated flrs, wet rm (dual/rain/handheld)airtub, floating vanity & large WIC. Main lvl: 8' doors, engineered wood flrs,

N67W34857 Ireland Drive Drive, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: .

$1,900,000
3 Beds ⋅ 2.5 Baths ⋅ CLOSED Status
Nestled in a serene, peaceful bay on Okauchee Lake, this renovated home offers 124.4' of prime hard-bottom frontage, perfect for larger boats, fishing & swimming. Recent renovation includes updated roof & Marvin windows w/ 2 quad sliding patio doors overlooking the lake. Low-maintenance LPSmart siding & composite deck w/ glass railings & stunning lake views. Refreshed seawall 2021; 5000 gal holding tank 2020. Kitchen w/ quartz counters that seats 8. Master bedroom suite w/ vaulted ceiling & lake views. Great room has vaulted ceiling & hardwood floors on the main. Mechanicals recently updated w/ zoned HVAC. Newer asphalt driveway. Easy walk to the lake on this gently-sloped frontage. Walk-out lower level w/ bonus & rec room+1/2 bath, great for guests! Oversized garage is 25 deepx28 wide.

W345N5746 Road G, Oconomowoc

Listing courtesy of Realty Executives - Integrity. Selling Office: .

$1,450,000
4 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
*Under Construction* The Willow by Kings Way Homes blends timeless architecture with modern luxury. A stone facade, steep gables, and covered entry create exceptional curb appeal. Inside, a dramatic see-through fireplace connects the great room and covered deck, while the chef's kitchen features a large island, quality cabinetry, and an adjoining dining area with a built-in buffet. Designed for gathering and everyday living, the home offers refined craftsmanship throughout. In addition, the main level includes 3 bedrooms plus a private office. The finished lower level features a 4th bedroom, rec room, and a dedicated wellness retreat with a sauna, and space for a cold plunge, creating the perfect balance of comfort, function, and relaxation.

N63W35883 Frederick Drive Drive, Oconomowoc

Listing courtesy of Kings Way Realty, LLC. Selling Office: .

$1,250,000
3 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
Experience the best of Okauchee Lake living without the waterfront taxes. Set on a beautifully landscaped .8-acre lot adjoining the 12-acre Lakeview Acres park, this property offers sweeping lake views and includes a deeded boat slip along with access to the private HOA boat launch, beach & pavilion. The beautifully updated kitchen with oversized island opens to inviting gathering spaces, while the dramatic great room features soaring ceilings, a floor-to-ceiling stone fireplace, and access to the expansive deck. The walkout lower level features an 33x18 indoor pool, sauna, rec room, and patio access. A refreshed primary bath, heated garage with epoxy-coated floors, and an exceptional setting complete this rare offering just steps from the water.

N61W35366 Mariner Court Court, Oconomowoc

Listing courtesy of Century 21 Affiliated - Delafield. Selling Office: .

$1,250,000
4 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
Discover an extraordinary private retreat tucked away on 3+ secluded acres. Surrounded by nature and breathtaking sunsets, this custom-built estate offers the perfect blend of luxury, comfort, and tranquility with no neighbors in sight. Overflowing with natural light, the living spaces include a gourmet kitchen overlooking the serene grounds, a private main-level owner's suite with vaulted ceiling, heated spa bath, walk-in closet, and patio access, plus a stunning office with floor-to-ceiling windows. Designed for entertaining, the walkout lower level features a theater, second kitchen, bedroom, and bonus room. Enjoy two patios, a fire pit, raised gardens, dog wash, garage stairs, and an unmatched sense of privacy just minutes from Lake Country's finest dining, shopping, and golf.

N69W34498 Oconomowoc Road Road, Oconomowoc

Listing courtesy of Realty Executives Integrity Brookfield. Selling Office: .

$1,180,000
7 Beds ⋅ 4.5 Baths ⋅ CLOSED Status
Experience refined waterfront living in this luxurious home set along the shores of a beautiful spring-fed pond. Designed for everyday comfort and upscale entertaining, this expansive residence showcases soaring ceilings, oversized windows, and picturesque water views. Upper level offers three generously sized bedrooms, plus additional gathering spaces including a versatile loft and an impressive game room or possible in-law suite complete with hardwood floors, vaulted ceilings, wet bar, and private bath. A dedicated home office, and convenient main-level master add to the home's functionality and appeal. Updates: New Roof, Composite Deck, Fin. 1800+ sq ft Basement, Gas Firepit and Built in Grill, Int. Painting, Ext. Painting, Garage Doors, Tile Flooring, Updated Master Bath, and more!

N57W34997 Pondview Lane Lane, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC. Selling Office: .

$1,150,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status
Lovely 4-bedroom Okauchee Lake home offering the perfect blend of charm and lifestyle on sought-after Ice House Bay. Enjoy 50 feet of swimmable frontage and stunning water views from multiple vantage points, including a private deck off the upper-level primary suite, ideal for morning coffee. The open kitchen flows seamlessly into the living space, highlighted by a cozy gas fireplace. Two full baths provide comfort for guests and family alike. Outside, a beautifully designed two-tier patio with fire pit invites lakeside entertaining and relaxation. Just a short walk to downtown Okauchee's popular restaurants and close to Lions Park, this is lake living at its best.

W342N4870 W Lindy Lane Lane, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: .

$1,145,000
2 Beds ⋅ 1 Baths ⋅ CLOSED Status
Rare opportunity on sought-after Okauchee Lake with an impressive 150ft of frontage with 3 piers and beautiful lake views from nearly every room. This 2 bedroom, 1 bath home offers the chance to enjoy the lake lifestyle today while bringing your own vision and updates to the property over time. Enjoy a spacious kitchen, 2 generous bedrooms and a living room with bar and patio doors to huge deck for entertaining. The large yard offers ample space for entertaining, and the frontage is great for swimming. The garage offers added storage for lake essentials and toys. Located within walking distance to popular restaurants, bars, and nightlife, this property combines a prime location, expansive frontage, and endless potential on one of Lake Country's most desirable lakes.

N50W35096 Wisconsin Avenue Avenue, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: .

$1,000,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status
Discover your ultimate lake country retreat in Oconomowoc, perfectly situated on 1.44 acres of peaceful, scenic land just minutes from Lac La Belle and all the charm Lake Country has to offer. This meticulously maintained 4-bedroom, 3-bath home provides abundant space for everyone to spread out, including a main-floor office, convenient laundry, large living room, inviting family room, and a massive bonus room ideal for a private suite, hobby space, or flexible living area. Three fireplaces add warmth and character throughout, while the heated 3-car garage offers year-round convenience. With a new roof in 2023, several updates, and stunning natural surroundings, this home is move-in ready. Close to shopping, dining, parks, and lakes, homes like this are rare. Schedule your showing today!

N59W38235 Mainland Drive Drive, Oconomowoc

Listing courtesy of Coldwell Banker Realty. Selling Office: .

$971,000
2 Beds ⋅ 2 Baths ⋅ CLOSED Status
Indulge in stunning vistas from this mint penthouse, with views of Fowler Lake, downtown Oconomowoc & Lac La Belle! Enjoy a private terrace for entertaining. This bespoke abode boasts premium finishes--black walnut kitchen cabinetry, custom-finish granite counters, Bosch kitchen appliances, a 2-sided fireplace, 18' ceilings with clerestory windows, hickory floors & convenient elevator access. Building perks include a 6th-floor deck, sun deck, club room, fitness center, dog run, plus ground-floor amenities like a coffee shop, bakery, spa, salon, cocktail lounge & upscale restaurant. Crafted with concrete for sound insulation, it offers secure heated parking & extra storage. Nestled in a quaint, walkable downtown--near lakes, boardwalk, trails, parks & shops. The epitome of luxury living!

215 E Pleasant Street Street Unit 507, Oconomowoc

Listing courtesy of Tenderland Real Estate LLC. Selling Office: .

$955,000
4 Beds ⋅ 2.5 Baths ⋅ CLOSED Status
Exceptional craftsmanship & modern design in this stunning new construction home by Elegant Builders LLC, Every detail reflects artistry, precision & timeless quality. Desirable Meadowlands subdivision in NW corner of Okauchee Lake. Impressive open-concept ranch on 1 acre lot backs to a conservancy. 4 BRs & 2.5 BAs, including a split floor plan, full primary suite, & 2 more BRs w/shared full BA on main level. 4th BR & bonus room offer versatility above the expansive 3.5 car GA- perfect for an office, game room, or guest suite. Inviting GR flows into a designer KIT featuring quartz counters & a full GE Cafe appliance package. Enjoy cozy evenings on the porch complete w/built-in NFP. Additional highlights: 1st floor laundry & 2000 sq ft unfinished basement offering endless opportunities.

N66W34839 Baltic Pass Pass, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: .

$925,000
5 Beds ⋅ 3.5 Baths ⋅ CLOSED Status
Tucked away on a quiet cul-de-sac, this custom-built residence offers an exceptional blend of elegance, privacy, & timeless design. From your arrival, the dramatic roofline & stately presence create a lasting first impression, setting the tone for the quality & craftsmanship found throughout the home. Inside, soaring ceilings & thoughtfully designed living spaces enhance the sense of openness & grandeur. The home features 5 spacious bedrooms, each offering comfort & versatility, along w/ huge walk-in closets providing abundant storage. Meticulously maintained & in pristine condition, every detail reflects pride of ownership & enduring quality. The setting is equally impressive--situated on a private property where wildlife is often seen & breathtaking sunsets can be enjoyed! A must see!

743 Royal Troon Court Court, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: .

$917,500
4 Beds ⋅ 3 Baths ⋅ CLOSED Status
Fully updated house with a specific, assigned boat slip on Okauchee Lake. Tucked away on a quiet cul-de-sac in Lakeview Acres, this beautifully maintained home offers the perfect blend of privacy, neighborhood charm and Okauchee Lake lifestyle. Set on a spacious lot in an established neighborhood, the property features generous bedroom spaces, mature trees, and access to the subdivision's private 12-acre park, sandy beach, pavilion, volleyball court, boat launch and gated parking lot. Enjoy peaceful surroundings while remaining minutes from downtown Oconomowoc, top-rated schools, shopping, dining, and commuter access. A rare opportunity to enjoy lake community living without waterfront taxes.

W356N6054 Anchor Court Court, Oconomowoc

Listing courtesy of Lake Vida LLC. Selling Office: .

$850,590
4 Beds ⋅ 2.5 Baths ⋅ CLOSED Status
4 bedrooms/2.5 bath/elite series split ranch. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Ceramic tiled walk-in shower w/2 shower heads/double sinks in master bath. WIC's all bedrooms. 9' main floor ceilings/pitched ceiling in living room & foyer/tray ceiling master bedroom. Box-tray ceiling in kitchen & dinette. Kitchen cabinets are staggered w/cabinet crown moulding/cabinet hardware/granite or equivalent countertops/backsplash/island w/sink/spacious pantry closet. Laundry & mudrm w/drywall lockers, closet, cabinets & sink. 3-car garage with large storage area (14'7'' x 16'9''). Buyer added water softener, concrete driveway, walkway, patio, sodded lawn, dryer outlet & upgraded kitchen cabinets, backsplash, hardware, fireplace stone & plumbing fixtures.

1754 Switchgrass Street Street, Oconomowoc

Listing courtesy of Kaerek Homes, Inc.. Selling Office: .

$850,000
2 Beds ⋅ 2 Baths ⋅ CLOSED Status
Rare, nearly one of a kind stand alone condo unit in the sought-after Pine Terrace Condos along the shores of Fowler Lake. The stunning elegance of this hidden gem offers a gentile charm and easy to use floor plan. Surrounded by pines each window has a view of nature. Divine guest room and easy access to the well-crafted hall bath is sure to please. Have it all in your very own condo with no shared walls! Added to the unique character of this unit is the private patio with bricked walls and a lovely wrought iron gate. allowing for plenty of room for guests. A generous dining area, formal living area and comfortable family room complete the space. Generous main level laundry has a beautiful wooded view out the window. Slips are available on a first come first serve basis on Fowler Lake.

506 Pine Terrace Terrace, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: .

$850,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status
Discover your dream home in Oconomowoc, just steps from Okauchee Lake! Stunning 3-bedroom, 3-bathroom Ranch offers over 3,300 sq ft of beautifully updated living space. Built by Rob Miller Builders, the open-concept design features a completely remodeled kitchen w/ quartz countertops, custom island, Viking gas range, beverage center, walk-in pantry & new hardwood floors. Inviting living room showcases custom fireplace cabinetry, while the primary suite boasts a remodeled luxury bath with tiled walk-in shower, upgraded vanity, and custom walk-in closet. A professionally finished lower level adds a spacious rec room, game area & full bath. Enjoy a newer roof, garage doors, painted exterior, pergola, paver patio w/ fire pit, oversized heated garage & subdivision common space behind the home!

W347N5943 Lake Drive Drive, Oconomowoc

Listing courtesy of The Wisconsin Real Estate Group. Selling Office: .

Copyright 2026 WIREX Multiple Listing Service. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.

Copyright 2026 WIREX Multiple Listing Service. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.