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493 Sutherland Cir, Oconomowoc
$515,000
4 Beds ⋅ 3 Baths
Move right in and enjoy easy condo living in this beautifully updated and exceptionally cared-for first-floor ranch-style condo in the heart of Oconomowoc! Major updates are already complete, including a new roof, furnace/AC and interior paint, within the last few years, offering peace of mind for years to come. The bright, open-concept main level features a spacious kitchen with beautiful hardwood cabinetry, solid-surface countertops, and convenient access to the private porch. Three bedrooms and a full bath complete the main level, while the finished lower level provides an incredible extension of the living space with an additional bedroom, full bath, and plenty of room for family, guests, or entertaining. Tucked away on a quiet circle yet within walking distance of charming downtown.

493 Sutherland Cir, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

333 N Lake Rd Unit 201, Oconomowoc
$345,000
2 Beds ⋅ 2 Baths
Enjoy the ease of lake life from this inviting 2nd floor condo on beautiful Fowler Lake. The expansive west-facing balcony is your perch above the neighborhood, offering golden sunsets and peek-a-book views of Lac La Belle, changing seasons and the simple pleasure of watching life unfold below. Just outside your door, a swimming pier and kayak launch invite you to enjoy the lake in every season - from summer swims and paddles to winter ice fishing and snowshoeing. The famous Fowler Lake Loop is also right outside your door, offering daily walks and waterfront views, while downtown Oconomowoc's dining, shopping and year-round events are just a few blocks away. Here, lake life and a walkable lifestyle come together naturally.

333 N Lake Rd Unit 201, Oconomowoc

Listing courtesy of Andrus Realty, LLC.

1155 Arrowood Cir E, Oconomowoc
$549,900
3 Beds ⋅ 2 Baths
Move-In Ready 134 ARW Harlequin Farmhouse - Available 12/28/26! All of our homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, much better than a typical used home. As your local home builder, you can expect the best local brands and trades for your home as well. We have partnered with Lindsay Windows, Kohler, Floor360 and Auburn Ridge just to name a few.

1155 Arrowood Cir E, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

1100 Elderberry Rd, Oconomowoc
$519,900
3 Beds ⋅ 2 Baths
Move-in Ready 93 ARWT Olivia Cottage II Unit B, TWIN HOME! 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. All of our homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, much better than a typical used home. As your local home builder, you can expect the best local brands and trades for your home as well. We have partnered with Lindsay Windows, Kohler, Floor360 and Auburn Ridge just to name a few.

1100 Elderberry Rd, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

143 E Luther Ave, Oconomowoc
$290,000
3 Beds ⋅ 1 Baths
Fantastic opportunity in the heart of Oconomowoc! This charming 3 bed home offers incredible potential in a highly desirable location. With a generous sized kitchen and living room warmed by a natural fireplace, the functional layout provides a great foundation to make this home your own. Whether you're a first-time buyer, investor, or looking for a home with room to add your personal touches, this property is worth a look. Enjoy the convenience of being close to downtown Oconomowoc, shopping, dining, parks, schools, and all the amenities this vibrant community has to offer. Don't miss this opportunity to bring your vision to life!

143 E Luther Ave, Oconomowoc

Listing courtesy of First Weber Inc - Delafield.

530 S Main St Unit 530A, Oconomowoc
$435,000
Charming duplex perfectly located in the center of all things Oconomowoc! Wonderful yard offers plenty of green grass and shade trees, along with ample off street parking. Exterior has been updated: Roof, gutters, siding and paint in 2022! All of the windows are modern too. The main floor unit has a timeless, covered front porch that invites you into a good sized living area. You can move right in or rent it out immediately, because this place is turn key ready! Eat in kitchen is clean and bright with modern cabinets. Bathroom has been redone with modern finishes and it shows! Upper unit has a separate entrance, in-unit laundry & flows well as the living room is open to kitchen with a pronounced modern feel. 3rd floor loft area has heat & AC and could be used for storage! Basement=Storage!

530 S Main St Unit 530A, Oconomowoc

Listing courtesy of Realty Executives Integrity~Brookfield.

855 Stirling Dr Unit Bldg 21, 41, Oconomowoc
$559,900
2 Beds ⋅ 2 Baths
NEW CONSTRUCTION Caroline plan - Ready January 2027. Welcome to this luxury ranch-style condominium offering 2 bedrooms plus a versatile flex room, thoughtfully designed with an open-concept layout and 9' ceilings throughout. The stunning Gourmet kitchen with built in appliances is ideal for entertaining, featuring a large center island, soft-close cabinetry, and quartz countertops. The spacious great room showcases a dramatic floor-to-ceiling stone fireplace and a box tray ceiling, creating a warm yet upscale atmosphere.

855 Stirling Dr Unit Bldg 21, 41, Oconomowoc

Listing courtesy of Harbor Homes Inc.

853 Stirling Dr Unit Bldg 21, 42, Oconomowoc
$549,900
2 Beds ⋅ 2 Baths
NEW CONSTRUCTION Caroline plan - Ready January 2027. Welcome to this luxury ranch-style condominium offering 2 bedrooms plus a versatile flex room, thoughtfully designed with an open-concept layout and 9' ceilings throughout. The stunning kitchen is ideal for entertaining, featuring a large center island, soft-close cabinetry, and quartz countertops. The spacious great room showcases a dramatic floor-to-ceiling stone fireplace and a box tray ceiling, creating a warm yet upscale atmosphere. Retreat to the private primary suite, highlighted by a box tray ceiling and a spa-inspired ensuite with a ceramic tiled shower and bench, double-bowl vanity, and a generous walk-in closet.

853 Stirling Dr Unit Bldg 21, 42, Oconomowoc

Listing courtesy of Harbor Homes Inc.

235 W South St, Oconomowoc
$424,900
5 Beds ⋅ 3 Baths
WOW! This home has all the space you will need with so many updates they can not be listed! Walk Score is really high, located close to everything! places to eat, shopping, the beach, downtown, parks and more! Schools are near by as well. This home has updated bathrooms (3 full) updated kitchen with new countertops, all appliances included too! Everyone will have their own space in this updated home! Grab this steal under $500k in sought after Oconomowoc! Take a stroll to coffee and breakfast at the downtown area! Enjoy days at the beach at Lake Fowler. Lots of parks, green space and things to enjoy. Or just enjoy this nicely updated home, New asphalt driveway, plenty of off street parking, nice sized yard and deck to enjoy. 1 block from Fowler Lake/Lac Labelle and City Beach!

235 W South St, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC.

29 S Locust St, Oconomowoc
$259,900
4 Beds ⋅ 2 Baths
Discover the opportunity to make this charming home your own! Ideally located just two blocks from the public beach on the beautiful shores of Lac La Belle, this property offers the perfect setting to enjoy lake life and all the area has to offer. Conveniently located near downtown, you'll have easy access to the band shell, shopping, dining, and local entertainment. Bring your vision and transform this home into a space that reflects your style and lifestyle. Whether you're looking for a year-round residence, weekend getaway, or investment opportunity, this property offers an excellent location and plenty of potential.

29 S Locust St, Oconomowoc

Listing courtesy of Fathom Realty, LLC.

668 Tulip Ct, Oconomowoc
$449,900
3 Beds ⋅ 2 Baths
Discover the perfect blend of comfort, style, and location in this beautifully maintained ranch home tucked away at the end of a cul-de-sac in Oconomowoc! Step inside and be welcomed by a sun-filled living room, while the family room addition offers soaring vaulted ceilings, skylights, and a striking stone gas fireplace. The kitchen flows seamlessly into the adjoining dining room, and three bedrooms feature hardwood floors. The partially finished lower level provides extra space for entertaining, hobbies, or relaxation. Outside, enjoy a private patio, fenced area, and peaceful backyard setting. A 2.5-car garage, newer windows, and new roof in 2022 add value and peace of mind. Exceptional location, charming neighborhood, and move-in-ready appeal make this a home that you don't want to miss!

668 Tulip Ct, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

983 Chesterton Ct, Oconomowoc
$550,000
4 Beds ⋅ 2 Baths
Welcome to this classic 4-bedroom, 2.5-bath Colonial in a desirable Oconomowoc neighborhood. Fresh interior paint throughout and brand-new upstairs carpeting create a bright, move-in-ready feel. Gather in the inviting rec room with a natural fireplace, or enjoy warm-weather living on the fabulous screened porch overlooking the back yard. Use your imagination in the heated backyard bonus building- perfect for a home office, hobby studio, game-day retreat or cozy gathering space. Comfortable, versatile and ideally located near shopping, dining, and all that Oconomowoc has to offer, this home is ready for its next chapter! Estate sale 9/20-9/21.

983 Chesterton Ct, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

334 W 2nd St, Oconomowoc
$269,900
2 Beds ⋅ 1 Baths
Welcome to this charming Cape Cod just blocks from Downtown Oconomowoc! This beautiful 2-bedroom, 1-bath home offers timeless character, comfortable living spaces, and an unbeatable location. Enjoy easy access to downtown restaurants, shops, entertainment, parks, and all that Oconomowoc has to offer. Whether you're looking for a place to call home or a smart investment opportunity, this property offers excellent flexibility and potential. A wonderful opportunity to own in a highly desirable Oconomowoc location! Updates include Kitchen Faucet (2026), Front/Back door and strom door (2025), Siding (2024), Roof (2022), Bathroom (2019), Carpet and closet doors in both bedrooms (2019), Wine Bar (2018), AC unit (2017).

334 W 2nd St, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country.

1236 Wild Rye Ln, Oconomowoc
$584,900
3 Beds ⋅ 2 Baths
New Construction - Ready in November! Discover the perfect blend of comfort and modern style in the Benton model at Prairie Creek Ridge in Oconomowoc. This thoughtfully designed ranch-style home features high ceilings, an electric fireplace, and durable LVP flooring throughout the main living areas with LVT in the bathrooms. The kitchen shines with elegant quartz countertops, offering a beautiful space for cooking and entertaining. With 3 bedrooms, 2 baths, and 1,756 sq. ft. of open, functional living space, this home is crafted for everyday ease. Situated on Lot 425, a .30-acre homesite, and complete with a 3-car garage, the Benton model brings style, efficiency, and convenience together in one exceptional package.

1236 Wild Rye Ln, Oconomowoc

Listing courtesy of Loos Custom Homes,LLC.

320 E Pleasant St Unit 106, Oconomowoc
$380,000
2 Beds ⋅ 2 Baths
Enjoy lake living in this 2-bedroom, 2-bathroom first-floor corner unit featuring peaceful green-space views and a sizable patio. 2 patio door access to private patio. Underground parking is a sought after condo convenience. Located just one block from downtown Oconomowoc's shopping, dining, and year-round activities. Your new home places you steps away from beautiful Fowler Lake. Launch a kayak, enjoy easy boating access, or relax beside the gorgeous in-ground pool surrounded by beautifully maintained gathering areas overlooking the lake. Pier slips may also be available for the ultimate lakeside lifestyle.

320 E Pleasant St Unit 106, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC.

W343N6300 S Bayview Rd, Oconomowoc
$574,900
4 Beds ⋅ 1 Baths
Sitting on a gorgeous 1+ acre lot, this 4 bedroom ranch home unfolds like a private estate! The spacious interior includes vaulted ceilings and a skylit great room that is sure to please. The kitchen offers plenty of cabinetry and a sunlit dining area opening to a back patio built for unforgettable nights. Hallway leads to 4 bedrooms and a full bath. Primary bedroom includes two closets, one being a walk-in. An open staircase leads to the finished lower level including a rec room, exercise room, and two dens--your own underground getaway! Dual garages featuring a 2.5-car attached and 2.5-car detached are perfect for hobbies and abundant storage. Relax on the front or back patio, or around the firepit area. Set within the coveted Arrowhead-Stone Bank School District!

W343N6300 S Bayview Rd, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

1097 Elderberry Rd, Oconomowoc
$459,900
2 Beds ⋅ 2 Baths
Move-in Ready 87 ARW Wyatt Cottage Unit B, TWIN HOME! AVAILABLE 9/29/26! 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. All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, much better than a typical used home. As your local home builder, you can expect the best local brands and trades for your home as well. We have partnered with Lindsay Windows, Kohler, Floor360 and Auburn Ridge just to name a few.

1097 Elderberry Rd, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

1417 Mamerow Ln W, Oconomowoc
$585,000
3 Beds ⋅ 2 Baths
Welcome home to this 3-bdrm ranch in desirable Oconomowoc! Featuring a smart split-bedroom design combined with open concept living areas. Enter from the covered front patio through a large foyer & into the inviting living room (with gas fireplace), kitchen with breakfast bar seating, and a dining area with patio access. The spacious primary suite has two closets, a private bath with double sinks & huge walk-in shower. Two additional bdrms, 2nd full bath, plus the convenience of first-floor laundry in the rear foyer. The unfinished basement offers unlimited potential for additional living space and is plumbed for a future full bath. 2.5-car attached garage, low-maintenance exterior, included appliances, and fantastic outdoor space with a deck and patio overlooking the quiet backyard.

1417 Mamerow Ln W, Oconomowoc

Listing courtesy of RE/MAX Preferred-Delafield.

642 Summit Ave, Oconomowoc
$299,000
3 Beds ⋅ 1 Baths
Welcome to the heart of Lake Country! Fully remodeled in 2019, located within walking distance to downtown Oconomowoc, lakes, shops, restaurants, parks, imagination station, the splash pad and Oconomowoc High School. This cozy original farm home was remodeled down to the studs making it easy to move right in. The open main level, first floor laundry, master walk-in closet and newly added half bath give it a modern feel. Perfect for a starter home, someone downsizing or a rental property. All furnishings included! Being sold ''As-Is''. The home has operated as a successful Airbnb since 2019 with returning guests in a perfect location. Move right in or start your own turnkey business with the name, future bookings and all furnishings for $360,000.

642 Summit Ave, Oconomowoc

Listing courtesy of Byowner.com.

1544 Riverdale Dr, Oconomowoc
$445,000
3 Beds ⋅ 2 Baths
Welcome to the neighborhood. Here is a chance to own a very well maintained 3 bedroom 2.5 bath home. Newer siding, roof, windows, doors and paint. Other upgrades since 2017 include: finished basement with bathroom and laundry room, shed with power and concrete and newer garage door. It boasts a big lot that is level and easy to maintain. A huge patio in the back with lots of privacy. This home is truly move in ready.

1544 Riverdale Dr, Oconomowoc

Listing courtesy of Best Realty of Edgerton.

1205 Blue Dahlia Rd, Oconomowoc
$539,900
5 Beds ⋅ 2 Baths
Set in one of Oconomowoc's most sought after neighborhoods, this 5 bedroom, 2.5 bath home delivers space, character, and a relaxing backyard retreat! Mature landscaping frames the partial brick exterior, while a private composite deck with a tranquil water feature creates an unforgettable outdoor escape in back. Inside, hardwood floors anchor a large living room and formal dining room, leading to a kitchen with tile flooring, walk in pantry, and built in dining table. The main floor primary suite addition impresses with a vaulted ceiling, fireplace, built ins, walk in closet, and spa like bath. Four generous upper level bedrooms and a partially finished lower level with workshop complete a home that blends comfort, charm, and lasting quality! New roof in 2022. Conveniently located!

1205 Blue Dahlia Rd, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

W358N5884 Surrey Dr, Oconomowoc
$539,900
4 Beds ⋅ 2 Baths
Welcome home to this beautifully updated 4BR, 2.5BA home nestled in a mature, welcoming neighborhood. Thoughtful updates throughout include a stunning gourmet kitchen with all-new appliances, refreshed baths, newer carpeting, trim, vinyl windows, and an energy-efficient tankless water heater. Step outside to the new oversized deck, perfect for summer gatherings, grilling, or relaxing while overlooking the beautiful backyard and adjoining neighborhood green space. Offering the ideal blend of move-in-ready comfort, outdoor living, and convenience, all just a short drive from downtown Oconomowoc's dining, shopping, entertainment, and vibrant community events.

W358N5884 Surrey Dr, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC.

1758 Bess Ct, Oconomowoc
$599,900
3 Beds ⋅ 3 Baths
Sophisticated Lake Country living awaits in this beautifully curated 3BDRM/3BATH ranch-style condo in PABST FARMS. Thoughtfully designed with an elevated aesthetic, the bright, open-concept interior features soaring ceilings, abundant natural light, custom woodwork, designer lighting, and refined finishes throughout. The kitchen showcases quartz countertops, a beautiful complementary backsplash, custom wall accents, and brand-new appliances. Step outside to the oversized private patio overlooking mature landscaping and peaceful green space--an exceptional setting for entertaining or enjoying beautiful sunset views. Ideally located in the heart of Lake Country, this exceptional residence offers comfort, privacy, style, and effortless maintenance-free living.

1758 Bess Ct, Oconomowoc

Listing courtesy of Patrick Bolger Realty Group.

229 S Concord Rd, Oconomowoc
$354,900
3 Beds ⋅ 1 Baths
Charming 3-bedroom, 1-bath bungalow in a fantastic location just walking distance to downtown Oconomowoc! This well-maintained home features beautiful hardwood floors throughout the main level, a tastefully updated bathroom, and a refreshed kitchen with newer countertops and sink. Recent updates include newer roof, siding, gutters, furnace, and plumbing for added peace of mind. Fresh paint throughout provides a bright, move-in-ready feel. Step outside to enjoy the fenced-in backyard, perfect for pets, play, or entertaining. A wonderful opportunity to own an updated home close to shops, restaurants, parks, and all that downtown Oconomowoc has to offer!

229 S Concord Rd, Oconomowoc

Listing courtesy of Froemming Realty LLC.

317 E Pleasant St, Oconomowoc
$360,000
3 Beds ⋅ 1 Baths
If walkability and being part of the Downtown Oconomowoc community are important to you, this is the house for you! Perfectly perched on Pleasant Street, this charming farmhouse-style home offers character, function and a fantastic location. A dedicated first-floor office keeps you connected to the home while providing a defined workspace. Storage is everywhere, including a walk-in closet, full basement, mudroom with built-ins and a detached garage with additional workshop/storage space at the rear. Step out the back door to a deck and wide-open backyard with plenty of room to relax, garden or entertain. A wonderful opportunity to enjoy the Downtown Oconomowoc lifestyle!

317 E Pleasant St, Oconomowoc

Listing courtesy of Stapleton Realty.

1326 Orchard Ter, Oconomowoc
$460,000
2 Beds ⋅ 1 Baths
Discover ease of living in this well maintained ranch home on a wooded cul-de-sac. The overhanging roof shelters and extends your welcome! Note hardwood floors throughout and the space saving closets/storage. Step out to the sun-side patio from the modern kitchen featuring black hard surface counter tops with center island, newer appliances and maple cabinetry. Newer roof, gutters and a bonus garage. Please notice completely finished lower level with areas staged for extended hospitality. River Highlands welcomes you!

1326 Orchard Ter, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

686 S Concord Rd, Oconomowoc
$474,900
4 Beds ⋅ 1 Baths
This spacious and inviting home is filled with natural light and thoughtful spaces designed for both everyday living and relaxation. The living and family rooms feature large windows, creating a bright and welcoming atmosphere. Kitchen offers a convenient breakfast bar and opens to family rm, complete with a natural fireplace to enjoy cozy nights. Spacious three-season rm overlooking large yard makes for a wonderful spot to relax, enjoy the great outdoors and admire the beauty of the apple orchard, sunset, and wildlife. Other features include stainless-steel appl, new floors on main level, new roof, leaf guard, gutters and siding in 2022.With its comfortable living spaces and beautiful outdoor surroundings, this home offers a blend of warmth, charm and space for you to enjoy for years.

686 S Concord Rd, Oconomowoc

Listing courtesy of Expert Realty.

1061 Regent Rd Unit 612, Oconomowoc
$229,000
2 Beds ⋅ 1 Baths
Welcome to Lake Country Village! This freshly updated 2BR, 1.5BA condo offers new carpeting, fresh paint, underground parking plus additional surface parking, and an exceptionally convenient location. Rentals are allowed, making this an attractive opportunity for investors, with strong rental potential in the area. Enjoy everyday convenience with Chipotle, Panera and numerous restaurants, shopping, services and daily necessities just minutes away, many within walking distance. Exciting new residential development is also underway directly behind the community, adding to the continued growth of the surrounding area. Whether you're looking for a comfortable place to call home or a smart investment property, this move-in-ready condo offers affordability, convenience and potential!

1061 Regent Rd Unit 612, Oconomowoc

Listing courtesy of Milwaukee Flat Fee Homes.

727 E Madison St, Oconomowoc
$585,000
6 Beds ⋅ 2 Baths
Back and Better than Ever! This custom contemporary home is nestled in one of Oconomowoc's highly desirable Fowler Lake area neighborhoods, offering an expansive 3,700+ square feet of living space, It features large bedrooms, Huge closets, two large bathrooms, double sink and dual shower heads in upper bath, and is flooded with natural light, soaring ceilings & architectural details that you don't see often! Private primary bedroom on its own level or guest quarters. Upper lofted rec rm and so much more. Enjoy a Private yard with patio, 10/10 walkability score to all that Downtown and Fowler Park/ lake loop have to offer. If you are looking for wow, come now!

727 E Madison St, Oconomowoc

Listing courtesy of Froemming Realty LLC.

1334 Aberdeen Pl Unit Lt148, Oconomowoc
$599,900
4 Beds ⋅ 2 Baths
New Construction - ready October 2026 - The Harrington model features 4 BR's 2.5 BA's and a 1st floor Flex Room. The Great Room includes a corner gas fireplace with 9ft stone detail to ceiling. The Primary Suite features a Box Tray Ceiling, large Walk-In Closet, a Luxury Primary Bath with Tile Floors & Tile Bench in Shower and Double Bowl Vanity. Other Highlights include a Rear Foyer with a Drop Zone and Lockers, 2nd floor Laundry Room, 2.5 Car Garage and SO MUCH MORE!!

1334 Aberdeen Pl Unit Lt148, Oconomowoc

Listing courtesy of Harbor Homes Inc.

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.