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69 S Chestnut St, Oconomowoc
$376,000
3 Beds ⋅ 1 Baths
This meticulously maintained home has been lovingly cared for over 35 years and is available to be yours! Newer windows, roof, and well maintained mechanicals make this home perfect for easy living. 69 S Chestnut features 3 bedrooms including a spacious primary bedroom and a beautifully remodeled bathroom (2025). The dining room features brick accents that enhance the character of this charming home. A sun filled, enclosed front porch is the perfect place to enjoy a cup of coffee and take in the beautifully manicured landscape. The spacious double lot has plenty of room for all your outdoor activities from gardening, to hosting parties. All of this is just steps away from downtown Oconomowoc, City Beach, and Lac La Belle. Don't miss this opportunity to see this amazing home today!

69 S Chestnut St, Oconomowoc

Listing courtesy of Keller Williams Ozaukee. Selling Office: Central WI Real Estate.

N51W34861 Wisconsin Ave Unit 3112, Oconomowoc
$375,000
2 Beds ⋅ 2 Baths
Meticulously maintained 2BR/2.5BA condo in desirable Mission Lakes, steps from private Florence Lake and downtown Okauchee! Beautiful upgraded exotic Merbau engineered hardwood floors add warmth and elegance throughout the main living areas. The great room features a gas fireplace and patio doors leading to a private balcony with western exposure. The kitchen offers granite countertops, a breakfast bar, an adjoining dining area, and stainless steel appliances. The spacious primary suite features a large walk-in closet and private bath. A second bedroom, full bath, and in-unit laundry with washer and dryer. Deeded parking spot and storage unit complete the home. The complex offers a lakeside patio, boathouse, and association-owned pontoon. Please note: Mission Lakes is a 55+ community.

N51W34861 Wisconsin Ave Unit 3112, Oconomowoc

Listing courtesy of Avanti Realty LLC. Selling Office: Avanti Realty LLC.

517 E Union St, Oconomowoc
$372,000
3 Beds ⋅ 1 Baths
Lets get you moving in this Charming 3 BR, 1 BA home located within walking distance of downtown Oconomowoc is awaiting. Updates include: New roof & Siding in 2023. LVP flooring (3/2026) and Stair ballisters in upper level of home. New Water Heater (14 days ago) & New Furnace (2024). Beautful Fully Updated bath in 2023 with ceramic tub surround,,Wood kitchen cabinetry and ceramic flooring. Attic space that is currently used as a walk in closet that has much more potential with an imagination and talent to refinish. Fenced in backyard. Detached garage with a replaced overhead door. Location of this home is ideal....Close to hospitals, medical faciliites, shopping, schools, restaurants, parks, lakes, freeways and MORE!

517 E Union St, Oconomowoc

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

512 Frederick Ct, Oconomowoc
$371,000
2 Beds ⋅ 3 Baths
Sharing a fantastic new listing for a 2 bedroom, 2 full, 2 half bath condo that truly has it all. This property features a full walkout basement, a two-car garage, and professional landscaping with a private entry and a beautiful wooded backyard. Inside, the home offers a spacious living room centered around a gas fireplace with plenty of natural lighting. The kitchen is well-appointed with a dinette. The master suite is particularly impressive, offering both a private bath and a walk-in closet. Additionally, the layout includes a large family room, loft, skylight and a coffee bar! Loads of storage space. The location is ideal, situated close to local bike paths, downtown, the beach, and the lakes. Finished LL. This is truly a must-see property for anyone looking for comfort and style.

512 Frederick Ct, Oconomowoc

Listing courtesy of Leitner Properties. Selling Office: Coldwell Banker Elite.

W348N5133 Elm Ave, Oconomowoc
$362,500
2 Beds ⋅ 1 Baths
Pics coming soon! The location is a great vibe! This home is within a 2 minute walk to the lake, Golden Mast featuring public boat launches, and the town circle that includes restaurants and shopping. The 2 car garage was built less than 2 years ago! House has newer siding and windows, a brand new kitchen featuring custom cabinets and stainless steel appliances boasting a ton of natural light with extra large windows overlooking the backyard. First floor includes a completely remodeled bathroom, new vinyl plank flooring in the main and, open feeling, living/dining/kitchen space, and a main floor bedroom. Master includes the entire second floor, so much room and privacy! Basement has 2 bonus rooms perfect for an office or play room, 1/2 bath and plenty of storage.

W348N5133 Elm Ave, Oconomowoc

Listing courtesy of EXP Realty, LLC~MKE. Selling Office: Keller Williams Realty-Lake Country.

888 Wildwood Pl, Oconomowoc
$355,500
3 Beds ⋅ 1 Baths
Unique 3-4 bedroom property on over half an acre lot, located in a fantastic neighborhood, close to everything Oconomowoc offers! The newer addition offers so many possibilities with a family room overlooking your backyard, and a bedroom with large closet. Turn it into a master suite if you desire! The patio door off the family room also allows for separate entry to this wing. Main area of the home includes the kitchen with extra cabinet space, a main living area with large windows facing your park like back yard, 2 bedrooms, a lofted family room, extra large full bath with double sinks, and a half guest bath. No basement steps to worry about! You are going to love this lot, and the shed that comes with it! Bring your finishing touches and make it sparkle!

888 Wildwood Pl, Oconomowoc

Listing courtesy of EXP Realty, LLC~MKE. Selling Office: Compass RE WI-Northshore.

N51W34861 Wisconsin Ave Unit 3113, Oconomowoc
$344,500
2 Beds ⋅ 2 Baths
Beautifully maintained 2BR/2BA condo in Mission Lakes! Enjoy this outstanding location along Florence Lake in downtown Okauchee. Complex has lakeside patio, boathouse, and association owned pontoon and fishing boats. Unit offers an open concept floor plan. Great room features gas fireplace with patio doors to private balcony with western exposure. Kitchen with granite countertops, breakfast bar, and SS appliances included. Adjoining dining area. Nice size bedrooms. Primary suite has large walk-in closet and private bath. 2nd bedroom, full bath, and in-unit laundry with washer and dryer included completes the floor plan. Underground parking with 2 assigned spaces and storage locker. Amazing clubhouse! Very conveniently located! Note this complex is a 55+ community.

N51W34861 Wisconsin Ave Unit 3113, Oconomowoc

Listing courtesy of Lake Country Flat Fee. Selling Office: First Weber Inc - Delafield.

N51W34861 Wisconsin Ave Unit 1113, Oconomowoc
$340,000
2 Beds ⋅ 2 Baths
Experience Resort-Style Lake Living at Stunning Mission Lake Condos with Access to Florence Lake! Enjoy access to the pier, a boathouse with sundeck, pontoon, fishing boat, and paddle boats for endless outdoor enjoyment. The attached clubhouse features a full kitchen, bar, fitness loft, two fireplaces, and a patio perfect for relaxing, entertaining, or hosting events. This spacious first-floor unit offers an open concept split-bedroom design with quality finishes including maple cabinetry and trim, granite countertops, gas fireplace, 2 bedrooms, 2 full baths, private balcony, and in-unit laundry. The unit also includes 2 underground parking spaces and a storage locker. The Association can approve buyers under 55 years of age, age verification form and BOD approval is needed.

N51W34861 Wisconsin Ave Unit 1113, Oconomowoc

Listing courtesy of Homestead Realty, Inc. Selling Office: Homestead Realty, Inc.

W397N5883 Autumn Woods Dr, Oconomowoc
$339,000
2 Beds ⋅ 2 Baths
Stylish 2 bed, 2 bath condo with soaring ceilings and a stunning floor-to-ceiling gas fireplace anchoring the living space. The main level offers a versatile office or formal dining room and features large closets throughout. Enjoy an open-concept layout with natural hardwood floors in the kitchen and newer neutral carpeting throughout. The spacious loft serves as a 3rd bedroom, relaxation space or exercise area, complete with a huge walk-in closet. The primary suite features a beautifully updated modern shower and ceramic tile in both baths. Relax on your private balcony overlooking a peaceful, natural setting, and take advantage of the clubhouse for recreation or social events.

W397N5883 Autumn Woods Dr, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC. Selling Office: Keller Williams-MNS Wauwatosa.

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.

614 S Silver Lake St, Oconomowoc
$325,000
3 Beds ⋅ 1 Baths
Charming 3-bedroom, 1-bath, 2-story home full of timeless character and conveniently located close to local amenities. Situated directly across from the park, this inviting home features beautiful natural woodwork, hardwood floors, spacious bedrooms, and a welcoming front porch with a low-maintenance composite deck--perfect for relaxing and enjoying the neighborhood setting. The formal dining room showcases a classic built-in china cabinet, adding warmth and functionality for entertaining or everyday living. A walk-up attic provides excellent storage or future expansion potential. Outside, enjoy a nice-sized backyard with room to relax, garden, or play. Conveniently located near shopping, dining, schools, and downtown Oconomowoc, this home offers classic appeal in a desirable location.

614 S Silver Lake St, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: Berkshire Hathaway HomeServices Metro Realty.

920 Oconomowoc Pkwy, Oconomowoc
$320,000
3 Beds ⋅ 2 Baths
Welcome home to this beautifully maintained 3BR, 2BA condo offering the perfect blend of comfort, convenience, and privacy! The open-concept layout features a spacious great room with a cozy gas fireplace and patio doors leading to your private deck overlooking a peaceful backyard setting. The kitchen and dining areas flow seamlessly together, making everyday living and entertaining easy. Relax in the primary suite with a private bath, while two additional bedrooms offer space for guests, an office, or hobbies. Enjoy the convenience of in-unit laundry, two underground heated parking spaces, and a private storage locker. Carefree condo living with the space and amenities you've been looking for!

920 Oconomowoc Pkwy, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: Century 21 Benefit Realty-LC.

273 Oconomowoc Pkwy, Oconomowoc
$315,000
2 Beds ⋅ 2 Baths
LIVE YOUR BEST LIFE in this beautifully updated 2BR/2BA condo at Oconomoc's Silver Ridge! Unbeatable prime location near downtown, the interstate, and the Lake Country Trail. This sought-after third-floor unit features cathedral ceilings, great views, & easy elevator access. Updates include newer carpet, stylish kitchen backsplash, stainless appliances, and marble tile bath surround. Both bedrooms have walk-in closets and private bath access. Relax in the bright three-season room with floor-to-ceiling windows. Additional highlights include a den/office, in-unit laundry, secure entry, community room and 2 heated underground garage spaces. Although it's a 55-plus community, up to 4 units can be owned by people under 55, and that threshold has not been met! Water/sewer included in dues!

273 Oconomowoc Pkwy, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: Coldwell Banker Realty.

W398N5953 Autumn Woods Dr, Oconomowoc
$310,000
2 Beds ⋅ 2 Baths
Welcome home to this beautiful 2-bedroom, 2-bathroom ground floor condo in desirable Oconomowoc. The open-concept floor plan offers a spacious and inviting living area, perfect for everyday living and entertaining. Large windows fill the home with natural light, creating a bright and airy atmosphere throughout. The primary suite features a private bath and generous closet space, while the second bedroom and full bath provide flexibility for guests or a home office. Relax on the covered patio or enjoy the community clubhouse. A two-car garage offers plenty of space for vehicles or added storage. With low property taxes and a great location near shopping, dining, parks, and recreation, this home offers comfort, value, and convenience in a low maintenance condo lifestyle.

W398N5953 Autumn Woods Dr, Oconomowoc

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

W398N5983 Autumn Woods Dr, Oconomowoc
$300,000
2 Beds ⋅ 2 Baths
Exceptional first floor condo in Oconomowoc's Autumn Woods! Enjoy this premium complex that offers a beautiful setting amongst mature trees. This unit sits in a great location within the complex bordering private tree line. Private outside entrance and attached garage. Well-maintained interior features an open concept design. Large great room includes stone gas fireplace. Kitchen has breakfast bar, SS appliances included, attached dining area, and storage pantry. In-unit laundry with washer and dryer included. Two nice size bedrooms with abundant closet space. Primary suite includes private bath. Main bath off hallway. Relax on the private covered patio overlooking nature and wooded backdrop. Complex also has a neighborhood clubhouse. Low town/village taxes. Very conveniently located!

W398N5983 Autumn Woods Dr, Oconomowoc

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

207 Oconomowoc Pkwy, Oconomowoc
$300,000
2 Beds ⋅ 2 Baths
Welcome to easy main-level living at 207 Oconomowoc Pkwy! This beautifully appointed 2-bedroom, 2-bathroom condo + den offers the perfect blend of comfort and convenience. Step inside to a bright, open layout designed for effortless everyday living. The spacious primary suite provides a private retreat, while the second bedroom and den offer flexible space for guests or hobbies. The standout feature? A versatile three-season room perfect for morning coffee, evening relaxation, or enjoying the outdoors in just about any weather. Located in sought-after Oconomowoc, just steps from trails, dining, shopping, and the charm of Lake Country, plus a community room. Don't miss this gem! This is a 55+ community; the occupancy quota has currently been met--please inquire for details

207 Oconomowoc Pkwy, Oconomowoc

Listing courtesy of Compass RE WI-Lake Country. Selling Office: Keller Williams-MNS Wauwatosa.

334 W 2nd St, Oconomowoc
$297,000
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. Selling Office: Keller Williams Realty-Lake Country.

972 Valentine Rd, Oconomowoc
$293,000
3 Beds ⋅ 1 Baths
Welcome to easy living in this charming 3 bedroom traditional townhouse style condo, nestled in one of Oconomowoc's most unique communities. Featuring resort style amenities including a swimming pool and tennis courts, this complex offers a lifestyle few can match. Inside, a clean and functional layout including; kitchen, dining room and living room; await your personal touch, a true blank canvas ready for your vision. Enjoy the convenience of main-level laundry, a full unfinished basement brimming with potential and a private back patio just steps from the pool, perfect for summer entertaining. Whether you're looking to update and customize or simply move in and enjoy the surroundings, this home offers incredible value in a one-of-a-kind setting. Don't miss your chance to make it your own

972 Valentine Rd, Oconomowoc

Listing courtesy of First Weber Inc - Delafield. Selling Office: Patrick Bolger Realty Group.

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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