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W389N7644 Pennsylvania St, Oconomowoc
$450,000
3 Beds ⋅ 2 Baths
This 3 BR, 2 BA home is situated on over an acre of peaceful land in the town of Oconomowoc. Step inside to discover a completely updated interior that radiates the allure of a brand-new residence. The renovated kitchen is a chef's dream, featuring a substantial center island, elegant Corian countertops, and sleek slate appliances. The main level is adorned with new luxury vinyl plank flooring, offering a seamless flow that ties the space together. Every detail has been thoughtfully considered, from the updated bathrooms to the modern doors and light fixtures, ensuring that this home is as inviting as it is stylish. A decorative fireplace graces the lower-level family room, offering the potential to be transformed into an inviting gas FP. Exterior has new vinyl siding, gutters, and deck.

W389N7644 Pennsylvania St, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC. Selling Office: Lake Country Flat Fee.

1350 Arrowood Cir W, Oconomowoc
$564,900
3 Beds ⋅ 2 Baths
Newer 3 bedroom, 2 bath ranch in Arrowood, this home delivers modern style, smart design, and sunset views! An open concept layout with LVP flooring flows from the large great room to a quartz topped kitchen featuring stainless appliances, breakfast bar island, and a dining area with patio doors to private deck. The split bedroom design offers a comfortable primary suite with walk in closet organizer and a spa like bath with dual sink vanity and oversized shower. Two additional bedrooms and a full bath sit on the opposite wing. Open staircase leads to a bright lower level with full size windows and barn doors to large workshop area. With upgraded landscaping, a level yard backing to trees and fields, and Energy Expert Certification, this home stands out!

1350 Arrowood Cir W, Oconomowoc

Listing courtesy of Lake Country Flat Fee. Selling Office: Realty Executives - Integrity.

970 Oconomowoc Pkwy, Oconomowoc
$428,000
2 Beds ⋅ 2 Baths
UPDATES UPDATES! From floor to ceiling, updates are everywhere in this 2 Bedroom, 2.5 Bathroom Parkway Green Condo w/Fresh Paint, New Carpet, Refinished HWF's, Updated Electrical & Light Fixtures, & New Kitchen. This two story side by side offers an open layout that flows into beautifully remodeled Kitchen featuring Quartz counters, tile backsplash, SS appliances, painted cabinets, & hardware. Kitchen opens to dining area & living space w/GFP, private covered 3 season patio & views of pond. Main floor primary bedroom provides WIC & ensuite bath & jetted tub. Plenty of storage throughout including spacious basement w/Rec Room, full-size windows, stubbed full bath & storage area. Handicap Accessible. Per Seller: Furnace & AC-4 yrs, Water Heater-3 yrs. Centrally located shopping & amenities!

970 Oconomowoc Pkwy, Oconomowoc

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

136 S Maple St, Oconomowoc
$400,000
3 Beds ⋅ 2 Baths
Discover this move-in ready 3 bedroom, 2 bath home on a quiet no-through street in the heart of Oconomowoc. Ideally located within walking distance to vibrant downtown, City Beach, the farmers market, elementary school, restaurants, and year round community events. The fully fenced double wide lot offers exceptional outdoor space with firepit and the potential to build an additional garage or outbuilding. Inside, enjoy an updated kitchen with refreshed countertops and newer appliances. 1.5 attached garage with smart enabled door perfect for WI winters. Major improvements include a new roof, gutters, and gutter guards in 2022. New air conditioner and smart thermostat installed in 2024. Don't miss this opportunity to own a well-maintained home in one of Oconomowoc's most desirable locations!

136 S Maple St, Oconomowoc

Listing courtesy of Avanti Realty LLC. Selling Office: The Real Estate Company Lake & Country.

1016 Ann Marie Way, Oconomowoc
$668,000
3 Beds ⋅ 3 Baths
Welcome to refined living on Ann Marie Way in The Glen of Oconomowoc, where elevated design meets everyday comfort. The main level features vaulted ceilings, an open-concept layout, and walls of windows that fill the space with natural light. The chef-inspired kitchen offers generous workspace and flows seamlessly for entertaining. The primary suite provides a private, spa-like retreat with dual vanities. The finished lower level adds a spacious family room, guest space, and ample storage. Enjoy low-maintenance living with access to a clubhouse, fitness center, and outdoor pool, just minutes from shopping, dining, and all that Oconomowoc has to offer. Ideal closing Date ASAP

1016 Ann Marie Way, Oconomowoc

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

520 W Wisconsin Ave, Oconomowoc
$630,000
3 Beds ⋅ 2 Baths
Timeless elegance meets modern convenience in this beautifully updated Victorian in the coveted Merchants Plat neighborhood. This exceptional home showcases exquisite original woodwork & pocket doors along with thoughtful modern updates throughout. The stunning kitchen features custom cabinetry & hardware with butcher block countertops. Upstairs are 3 spacious bedrooms, a convenient laundry in the walk-in closet & 2 full baths. The spa-like bath is complete with a classic clawfoot tub and a luxurious walk-in shower with multiple shower heads. A walk-up storybook attic on the 3rd floor is ready for your touch. Relax in the sunny sunroom or on the deck overlooking the expansive backyard. Newer windows & roof provide added peace of mind. Just steps from City Beach, downtown shopping & more.

520 W Wisconsin Ave, Oconomowoc

Listing courtesy of Lake Country Flat Fee. Selling Office: Keller Williams-MNS Wauwatosa.

1736 Switchgrass St, Oconomowoc
$668,200
4 Beds ⋅ 2 Baths
Driveway included in purchase price. Energy efficient two-story home with space in the right place! The Evergreen is located on lot 403 in Prairie Creek Ridge. Kitchen features soft close cabinets, spacious island, walk-in pantry & exterior vented range hood. Dinette separates the kitchen & great room. Great room includes electric fireplace with shiplap. Flex room w/ French doors makes a great office or playroom. WIC in rear foyer provides extra storage space. 2nd floor features primary suite, 3 secondary bedrooms, hall bathroom & laundry room. Primary includes a box tray ceiling, 2 WICs, a tiled shower & two sinks. Lower level has egress window, full bath rough-in, ERV system & space for future finishing. Home is currently under construction, estimated completion September.

1736 Switchgrass St, Oconomowoc

Listing courtesy of Tim O'Brien Homes LLC. Selling Office: NON MLS.

416 E Jefferson St, Oconomowoc
$467,000
3 Beds ⋅ 2 Baths
Location is everything, and this property places you right in the heart of it all: Enjoy a quick walk to downtown Oconomowoc's vibrant shops, dining, and cafes. Minutes from Fowler Lake and Lac La Belle for summer strolls and community events. Step into your private outdoor paradise, meticulously designed for hosting and relaxation with a gourmet outdoor kitchen, firepit lounge, and storage shed. Inside, enjoy absolute peace of mind with recent, high-value upgrades. Brand-new carpet (2026), and LVP, kitchen counters and backsplash (2020), on garage and house brand-new LP smart siding and durable new roof (2022), and two outdoor EV charging stations to name just a few updates. (see upgrade document for full list) Schedule your showing today!

416 E Jefferson St, Oconomowoc

Listing courtesy of Keller Williams-MNS Wauwatosa. Selling Office: NON MLS.

222 E Pleasant St, Oconomowoc
$2,750,000
5 Beds ⋅ 4 Baths
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 St, Oconomowoc

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

936 S Silver Lake St, Oconomowoc
$405,000
3 Beds ⋅ 1 Baths
Welcome home to this charming 3-bedroom, 1.5-bath Colonial nestled on a fenced corner lot in desirable Oconomowoc! A welcoming 3-season porch leads into a warm and inviting interior featuring hardwood floors, crown molding, and beautifully updated kitchen and baths. The spacious eat-in kitchen flows into the formal dining room and bright living room, while a versatile main-floor bedroom makes a perfect home office or guest room. Upstairs offers two generous bedrooms with walk-in closets, a bonus room, and an updated full bath. Relax or entertain on the large rear deck overlooking the private backyard. The heated garage features an expansive workspace, and the unfinished basement provides abundant storage. This move-in-ready home blends timeless character with modern updates-don't miss out!

936 S Silver Lake St, Oconomowoc

Listing courtesy of Keller Williams Realty-Milwaukee Southwest. Selling Office: NON MLS.

48 S Worthington St, Oconomowoc
$450,000
3 Beds ⋅ 2 Baths
NEW. FRESH. BEAUTIFUL. Imagine leaving your front door and walking to the beach, your favorite coffee shop, dinner downtown, the farmers market, or an evening concert at the bandshell. That's everyday life in this completely renovated Oconomowoc home just one block from City Beach and Lac La Belle. Offering 3 bedrooms and 1,650 sq. ft. of comfortable space, the home features a main-floor primary suite w/ a custom walk-in closet and designer tile shower. Two bedrooms upstairs connected by a Jack-and-Jill bath. Nearly every inch inside & out is NEW (see documents for complete improvements). Main Fl. Laundry, large Pantry, plus off-street parking for 4 vehicles, room for your boat or RV--a rare find downtown! Lake living has never been this easy. Looks & feels like a New Construction home!

48 S Worthington St, Oconomowoc

Listing courtesy of RE/MAX Preferred-Delafield. Selling Office: Shorewest Realtors, Inc..

1390 Foxwood Pass, Oconomowoc
$679,900
4 Beds ⋅ 3 Baths
A bright and inviting newer-construction gem in Prairie Creek Ridge, this home blends modern comfort with effortless style! Step through a spacious foyer into an open, sun-filled living area anchored by a sleek electric fireplace. The kitchen shines with quartz counters, stainless appliances, an island made for gathering, and a dining space that flows to a backyard deck perfect for summer evenings. Upstairs, four generous bedrooms include a serene primary suite with a huge walk-in closet and spa-like bath. The finished lower level adds full-size windows, a second fireplace, fitness space, full bath, and bonus room. In-ground sprinkler system and many Smart Home features. A 3-car garage and an exceptional neighborhood complete the package! Ready to move right in!

1390 Foxwood Pass, Oconomowoc

Listing courtesy of Lake Country Flat Fee. Selling Office: Compass RE WI-Lake Country.

W342N4861 W Lindy Ln, Oconomowoc
$325,000
2 Beds ⋅ 1 Baths
Welcome to this cozy cottage with water access on Okauchee Lake! This charming, recently remodeled 2-bedroom, 1-bath home is full of character and ready for you to enjoy every season. Tucked away on a quiet no-thru street, it's the perfect place to unwind after a busy day. Take advantage of shared swim access to Okauchee Lake, then come home to relax in the spacious fenced yard--ideal for summer cookouts, bonfires, pets, or yard games. Leave the car behind and enjoy an easy walk to nearby parks, downtown Okauchee, local restaurants, and all the fun the lake community has to offer. Whether you're searching for a weekend retreat, stairless ranch, a year-round home, or an investment rental property. This sweet cottage is ready to welcome you home.

W342N4861 W Lindy Ln, Oconomowoc

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

N61W35366 Mariner Ct, Oconomowoc
$1,250,000
3 Beds ⋅ 3 Baths
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 Ct, Oconomowoc

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

924 Wallace Loop Unit 29, Bldg 15, Oconomowoc
$562,037
2 Beds ⋅ 2 Baths
NEW CONSTRUCTION - ready Sept 2026! 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. Enjoy a spacious great room that features a stunning stone to ceiling fireplace and box tray ceiling! The Sunroom opens up to the Dinette and lets in so much natural light. The private primary suite includes a box tray ceiling, with a luxury bathroom with ceramic tile shower and bench, a double bowl vanity, and a large walk in closet. Make The Reserve at Olde Highlander your future home!

924 Wallace Loop Unit 29, Bldg 15, Oconomowoc

Listing courtesy of Harbor Homes Inc. Selling Office: Realty Executives Integrity~Brookfield.

415 N Oakwood Ave, Oconomowoc
$464,000
2 Beds ⋅ 2 Baths
Located in the heart of Oconomowoc, directly across from Fowler Park, this beautifully updated Victorian blends timeless character with the comforts of modern living. Original millwork showcases the home's old-world craftsmanship, while thoughtful updates make it truly move-in ready. The fenced backyard and mature landscaping provide exceptional curb appeal along with a private outdoor retreat.A finished oversized 2+ car garage, complete with its own heating and AC, offers incredible flexibility as a home office, fitness studio, workshop, or additional entertaining space.Recent updates include new luxury carpeting, an updated bathroom, and numerous other improvements throughout the home. If you're looking for classic Victorian charm without sacrificing today's conveniences don't delay.

415 N Oakwood Ave, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country. Selling Office: Shorewest Realtors, Inc..

524 E Jefferson St, Oconomowoc
$457,300
2 Beds ⋅ 1 Baths
Rarely does a property offer such exquisite craftsmanship & artistic detail while providing seemingly endless potential. Owned for decades by Master Woodworker & Fine Art Photographer Tony Casper, this amazing 2 bedroom, 1.5 bath colonial is a testament to his limitless talent & ability to create beauty, even in the most unassuming places. Whether walking up the charming front entry past his beloved Ginko, enjoying time in the custom crafted gazebo or relaxing fireside in the beechwood family/gallery room (with heated floor) built to display artifacts from world travels, Casper's creative touch is evident throughout. Make the lower studio your own space & don't miss the 15x12 office/work room off the garage!

524 E Jefferson St, Oconomowoc

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

677 Tulip Ct, Oconomowoc
$500,000
3 Beds ⋅ 2 Baths
Tucked into a quiet, tranquil cul-de-sac, just a short walk to downtown shops, lakes, restaurants, parks, trails & all Oconomowoc has to offer, this beautiful mid-century ranch provides everything astute buyers expect in a quality home. With several living spaces throughout, the ''kitchen open to family room with natural fireplace'' is possibly the most sought-after floorplan designs for contemporary living and entertaining. Impressive updates such as newer cooks kitchen, and baths, as well as recent carpet in the living room and brand new carpet downstairs! Special features include: home warranty, heated garage, patio doors to private (lockable) fenced back yard and side garden shed with extra parking! See documents section for property details/updates.

677 Tulip Ct, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: Keller Williams-MNS Wauwatosa.

607 Poppy St, Oconomowoc
$425,000
4 Beds ⋅ 2 Baths
Welcome to this well-maintained 4-bedroom, 2-bath home in a desirable location near beautiful Fowler Lake, parks, walking trails, and local amenities in the desired Oconomowoc School District. The spacious floor plan offers comfortable living with plenty of room for family, guests, or a home office. Step outside to enjoy the large backyard, perfect for entertaining, gardening, or relaxing. Whether you're looking for convenience, outdoor recreation, or a great place to call home, this property has it all. Don't miss this fantastic opportunity! Updates include: Hardwood flooring under carpet on main level. Roof 2022, Windows 2016, Garage Door 2026. Furnace and AC about 10 years.

607 Poppy St, Oconomowoc

Listing courtesy of Lake Country Flat Fee. Selling Office: Shorewest Realtors, Inc..

N76W36096 Saddlebrook Ln, Oconomowoc
$2,580,000
5 Beds ⋅ 4 Baths
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 Ln, Oconomowoc

Listing courtesy of Coldwell Banker Elite. Selling Office: Arkenstone Real Estate Experts.

1522 Champion Ct, Oconomowoc
$605,000
2 Beds ⋅ 2 Baths
This stunning 2-bed, 2.5-bath Kingsway ranch condo at Village Crossing at Pabst Farms is move-in ready with every detail thoughtfully executed. The gourmet kitchen features a quartz island, stainless appliances, walk-in pantry, and custom backsplash, flowing into the great room with 10-ft coffered ceilings and a stone-surround gas fireplace. The owner's suite offers a spa-like walk-in shower, quartz baths, and custom closet systems throughout. Hardwood floors round out the finishes. Enjoy a landscaped patio -- no build wait required. Enjoy a finished lower level with a half bath and ample storage. Walking distance to shops, restaurants, offices, and the YMCA -- Lake Country living at its finest.

1522 Champion Ct, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: Kings Way Realty, LLC.

1682 Switchgrass St, Oconomowoc
$738,330
5 Beds ⋅ 2 Baths
5 bedrooms/2.5 baths/Flex room/elite series 2-story. Basement has 1 egress slider window & drain/vent rough-in for future full bath. Corner ceramic tiled walk-in shower/2 shower heads/granite or equivalent vanity tops/double sinks in master bath. Family bath double sinks. 2 WIC's master suite. 9' first floor ceilings/pitched ceiling master bedroom. Kitchen cabinets w/hardware are staggered w/cabinet crown moulding/granite or equivalent countertops/backsplash/island/pantry closet. Mudroom w/drywall lockers, sink, & closet. 3-car garage w/service door & large storage area (12'1'' x 23'4''). Buyer added kitchen/laundry appliances, electrical pkg., shower bench, fireplace stone & upgraded cabinets, carpet pad, plumbing fixtures, shower wall tile, fireplace stone & chimney style range hood.

1682 Switchgrass St, Oconomowoc

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

491 Thurow Dr, Oconomowoc
$635,000
4 Beds ⋅ 3 Baths
Beautifully designed ranch, in the highly sought-after Thurow's Golden View near parks, walking trails & downtown festivities. Offering modern open concept design complete with vaulted ceiling, gas fireplace & split-bedroom layout Kitchen boasts granite countertops, W/I pantry & island snack bar that flows into the living/dining space perfect for entertaining. Retreat to the master suite, w/ elegant tray ceiling, W/I/C & bath w/large shower & dbl sinks. The wow factor continues in the beautifully finished LL featuring a spacious family rm. dedicated wine bar, separate wet bar, exercise rm w/ rubber mat flooring, & 4th BR/office w/full-size window. You'll love the fenced-in yard and a partially covered patio ideal for relaxing or hosting summer barbecues. 3 car heated garage added bonus.

491 Thurow Dr, Oconomowoc

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

320 E Pleasant St Unit 105, Oconomowoc
$575,000
2 Beds ⋅ 2 Baths
Lakefront Living on Beautiful Fowler Lake! Enjoy breathtaking lake views from this beautiful end unit main-floor condo featuring 2BRs, 2BAs, 2 GA spaces, heated outdoor pool, community pier, & the opportunity to apply for your own private boat pier. Open-concept design offers a beautiful KIT with quartz counters & Samsung black SS appliances, updated BAs, newer flooring in main living areas, and stunning Fowler Lake views from both BRs and the living area. Relax on your lakeside patio just steps from the pool, and enjoy stunning sunsets over the water. This secure building has an elevator and includes a private storage locker just 20 ft from your front door & easy access to the underground heated GA! Exceptional restaurants, boutiques, parks, year-round events all within walking distance.

320 E Pleasant St Unit 105, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: Realty Executives - Integrity.

Source of listing data: Metro MLS. Copyright 2026 Multiple Listing Service, Inc. - All Rights Reserved. Information is supplied by seller and other third parties and has not been verified. 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.

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