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1384 Bluestem Trl, Oconomowoc
$730,000
4 Beds ⋅ 3 Baths
Welcome to your own private backyard retreat in sought-after Prairie Creek Ridge! The showstopping outdoor living space features a low-maintenance fiberglass pool with automatic cover, an expansive patio, pergola, outdoor fireplace, and dedicated outdoor bathroom, creating a resort-style atmosphere ideal for both relaxation and entertaining. Inside, you'll find an open-concept floor plan with extensive upgrades throughout with 2500 sq ft of living space (see seller upgrade list in documents). Enjoy a prime location within walking distance to top-rated schools and fantastic neighborhood amenities, including pickleball courts. Upstairs laundry, new sodded lawn and smart controlled irrigation system + pool. Better than new construction! Don't miss this one!

1384 Bluestem Trl, Oconomowoc

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

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.

W356N6054 Anchor Ct, Oconomowoc
$917,500
4 Beds ⋅ 3 Baths
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 Ct, Oconomowoc

Listing courtesy of Lake Vida LLC. Selling Office: Shorewest Realtors, Inc..

W343N6980 W Circle Dr, Oconomowoc
$649,900
3 Beds ⋅ 3 Baths
Enjoy the best of everything in the spacious 3BDRM 3.5BATH w/over 2300 SQ FT on a hill overlooking the countryside! Property boasts immediate curb appeal w/4 car heated attached garage, landscaped gardens, & 2 tier concrete patios. Main level is perfect for entertaining! Remodeled Kitchen anchors between dining & living rooms featuring NEWER Cabinetry, Granite Counters, SS Appliances, & Ceramic Tile Flooring. LR features HWFs & GFP. Retreat to upper level w/generously sized bedrooms & updated bathrooms w/heated floors. Finished LL offers spacious rec room w/kitchenette, 2nd half bath, & access to garage! Nature surrounds you w/endless outdoor entertaining options. Minutes from Shopping, Restaurants, & Entertainment amenities! Roof-2022, Furnace-2019, AC-2010. Schedule your showing today!

W343N6980 W Circle Dr, Oconomowoc

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

N64W34206 Bayview Rd, Oconomowoc
$540,000
3 Beds ⋅ 2 Baths
Completely renovated down to the studs in 2011, this beautifully updated home blends exceptional craftsmanship with warm, functional living space. Custom woodwork enhances every room, while the stunning kitchen serves as the true heart of the home, featuring gorgeous ceiling-high maple cabinetry and quartz countertops. The wood ceiling, cozy wood-burning stove & expansive bay window create a charming atmosphere filled with warmth and natural light. Outside, the wooded yard and neighboring pond provide peaceful views and a private setting, best enjoyed from the hot tub in the 3-season room. The luxurious primary suite features a custom bath complete with dual vanities, heated floors, and a beautifully tiled walk-in shower. Arrowhead School District & close to Hwy 16!

N64W34206 Bayview Rd, Oconomowoc

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

1538 Weston Ridge Rd, Oconomowoc
$639,900
3 Beds ⋅ 3 Baths
Modern living at its finest in these 3bed, 3bath townhome-style ranch condos. COMPLETION est for 7/26. Several available that could include STEPLESS ENTRY. Open & thoughtful floorplans flow seamlessly, meeting the needs of every day living while maintaining that WOW factor you can feel proud to share w/guests. Beautiful kitchen designed for functionality includes full appliance package, island w/quartz tops, & walk in pantry. Stylish details reflect David & Goliath Builders exceptional craftsmanship & design. Master suite w/walk in closet & ensuite. Split ranch floorplan puts plenty of space between all 3 bedrooms w/full bath adjacent to EACH. Gorgeous ''out in the country'' setting, inconspicuously convenient to shops, dining & recreation. Photos are of sold units. Come Visit our Model!

1538 Weston Ridge Rd, Oconomowoc

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

457 W 5th St, Oconomowoc
$380,000
3 Beds ⋅ 1 Baths
This charming, move-in ready 3-BED, 1-BATH Cape Cod home is ready for its next chapter. Once you step inside, you will be immediately greeted by beautiful hardwood floors in the LR and two main level BEDS. With the Bonus Room, this home provides ultimate flexibility for a growing family, a dedicated home office, or guest accommodations. The home features a new roof, siding and gutters (in 2023). Insulation was added in the crawl spaces to ensure energy savings. Upstairs, the classic roofline hides an abundance of accessible storage space behind the knee walls. The sunroom, basement and garage have new windows (in 2025). You will appreciate the convenience of being nearby to Roosevelt Park, the Lake Country Trail, Parklawn Elementary and Downtown. Your private patio awaits you!

457 W 5th St, Oconomowoc

Listing courtesy of Abundance Real Estate. Selling Office: Henry Real Estate Company, LLC.

1345 Bluebird Dr, Oconomowoc
$520,000
3 Beds ⋅ 2 Baths
Beautifully maintained 3BR,2BA Oconomowoc gem is nestled in a sought-after neighborhood close to parks,schools,shopping,and everything Lake Country has to offer.You'll appreciate the inviting curb appeal, upgrades,and spacious setting.The open and functional layout creates the perfect balance of comfort and style,featuring generous living spaces designed for everyday living and entertaining alike. The kitchen flows seamlessly into the main gathering areas and large windows fill the home with natural light.Step outside to enjoy your backyard retreat ideal for relaxing, grilling, or hosting friends and family. Whether you're looking for room to grow,space to entertain,or simply a place to call home,this property checks all of the boxes.Don't miss the best of Oconomowoc living!

1345 Bluebird Dr, Oconomowoc

Listing courtesy of RE/MAX Forward. Selling Office: First Weber Inc - Delafield.

1480 Prairie Creek Blvd, Oconomowoc
$700,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully maintained home located in a highly sought-after, family-friendly subdivision! From the moment you arrive, you'll appreciate the pride of ownership and inviting curb appeal this home has to offer. Inside, you'll find spacious living areas perfect for everyday living and entertaining alike. Step outside to your own private backyard retreat featuring an incredible outdoor entertaining space complete with a TV viewing area and relaxing hot tub -- ideal for hosting gatherings or unwinding after a long day. The oversized garage provides exceptional storage and workspace options for vehicles, toys or hobbies! Conveniently located near parks, schools, and neighborhood amenities, this home offers the perfect blend of comfort, functionality, and lifestyle.

1480 Prairie Creek Blvd, Oconomowoc

Listing courtesy of First Weber Inc - Menomonee Falls. Selling Office: Keller Williams-MNS Wauwatosa.

W358N6658 Spring Hollow Cir, Oconomowoc
$815,000
3 Beds ⋅ 2 Baths
Welcome to your dream home in the highly desirable Woodside Farms subdivision! Tucked away at the end of a quiet cul-de-sac, this meticulously maintained, custom-built ranch is looking for its second owner. Step through the grand entry foyer into a sun-bathed main living space with a massive east facing window bank. The space is perfectly connected to the dining room and kitchen with a patio off the back for seamless entertaining. Retreat to the luxurious primary suite, featuring an ensuite bath with dual vanities, a separate shower, and soaking tub. The three car attached garage offer convenience and the basement has finishing potential. Enjoy premium upgrades including heated tile floors, a new roof (2022), and a new AC unit (2024). Don't miss this rare opportunity!

W358N6658 Spring Hollow Cir, Oconomowoc

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

N73W36308 S Shore Dr, Oconomowoc
$400,000
2 Beds ⋅ 1 Baths
Rare opportunity to own lake frontage property w/gorgeous sunset views & mature trees on almost 3 acres! Enjoy peaceful Ashippun Lake, approx 114 ft frontage as per GIS map. Bids available for demolish & removal of abandoned cottage & 2 car GA. Buildable portion of lot & lake frontage zoned R-2 Residential- is approx 161 ft long with 75 ft shore setback, 75 ft wetland setback with 20 ft offsets from property lines. New construction build may be limited to minimum zoning footprint of 1,110 sq ft. Largest section of parcel on east side of S Shore DR is wetland zoned HG- not buildable. Environmental corridor on south side. Any new build will require soil testing & survey w/a wetland delineation. Being sold as-is, Buyer should verify any info pertinent to Buyer's decision. See MLS# 1942430

N73W36308 S Shore Dr, Oconomowoc

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

503 N Lake Rd Unit 5, Oconomowoc
$3,917,000
3 Beds ⋅ 3 Baths
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 Rd Unit 5, Oconomowoc

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

230 Thurow Dr, Oconomowoc
$551,000
3 Beds ⋅ 3 Baths
Built in 2006, this spacious Open Concept Ranch is tucked within a private wooded subdivision setting! This split-BR design offers 3 BRs, 3 BAs, vaulted ceilings, & a bright, airy layout perfect for everyday living & entertaining. Generous KIT features pantry, snack bar, quartz countertops, & flows seamlessly into the large great room w/GFP. Primary suite includes WIC & private bath. Enjoy convenient main floor laundry plus a huge poured concrete w/ tall ceilings, full bath, & endless future rec room potential! Step outside to the deck & private backyard retreat. Major updates include roof & siding (2023), Armstrong furnace & central air (2023), + SS appliances. Within walking distance to Downtown Oconomowoc-various restaurants, Oconomowoc Lake and Lake Fowler! MUST SEE!

230 Thurow Dr, Oconomowoc

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

1534 Fay Ln, Oconomowoc
$680,000
3 Beds ⋅ 2 Baths
Outstanding 3BR/2.5BA newer ranch home in Oconomowoc's Prairie Creek Ridge! Enjoy a beautifully landscaped .55 acre lot, 4-car garage with one tandem stall, and a spacious open concept floor plan. Engineered hardwood flooring throughout the main level. Vaulted great room includes gas fireplace. Open kitchen features granite countertops, center island, pantry, SS appliances included, and adjoining dining area. French doors to den-office. Large bedrooms including the primary suite with walk-in closet and luxury bath that has a dual sink vanity and oversized tile shower. Mud area has built-in lockers, laundry room with washer-dryer included, and half bath. Lower level includes full size window and is ready for future living space. Great back yard patio space, patio furniture negotiable!

1534 Fay Ln, Oconomowoc

Listing courtesy of Lake Country Flat Fee. Selling Office: EXP Realty, LLC~MKE.

1242 Green Tree Dr, Oconomowoc
$657,000
3 Beds ⋅ 2 Baths
Welcome to the Lavender; a lovely split bedroom ranch featuring 3 beds/2 baths plus a sunroom! Located in the heart of Oconomowoc - Prairie Creek Ridge neighborhood. Kitchen features soft close cabinets, quartz countertops, walk-in pantry & SS appliances. Cathedral ceiling spans across kitchen & living room w/gas fireplace completes the space. Dinette off kitchen leads into sunroom which boasts cathedral ceiling & lets in plenty of natural light. Retreat to the Primary suite; located in the back of the home & includes 2 WICs, private bath w/double sinks & tiled shower w/bench & access to laundry room. 2 guest bedrooms & hall bath located on the opposite side of the home. Lower Level is ready for your finishing touches w/4' partial exposure, full size windows & stubbed full bath.

1242 Green Tree Dr, Oconomowoc

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

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.

1756 Switchgrass St, Oconomowoc
$621,500
3 Beds ⋅ 2 Baths
Driveway Included. Thoughtfully designed, energy efficient split ranch located in Oconomowoc's Prairie Creek Ridge! The Lavender sits on lot 382 & features upgrades throughout. Kitchen features stained soft close cabinets, exterior vented range hood & walk-in pantry. Cathedral ceiling spans across kitchen & great room. Great room is complete with an electric fireplace w/ shiplap. Primary suite is tucked away in the back of the home & has a box tray ceiling, 2 WICs, tiled shower & two sinks. Rear foyer includes a drop zone for organization & laundry room w/ pocket door. 2 secondary bedrooms + hall bathroom located on opposite side of home. Lower level includes egress window, full bath rough-in, ERV system and space for future finishing!

1756 Switchgrass St, Oconomowoc

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

122 N Maple Ter, Oconomowoc
$502,000
2 Beds ⋅ 2 Baths
A great Oconomowoc location (with lake rights!) only a short walk to the beach & downtown. This 2-bdrm ranch is ready to move in today. Main level includes a bright living room with great morning sun thru the large picture windows; adjacent kitchen/dining area with ample cabinet & counter space; two nice bedrooms; a full bath with shower stall; HWFs throughout. Lower level has a finished rec room, another full bath, exercise area, plus laundry/mechanical/storage space. 1-car detached garage includes an attached screened-in porch (covered) looking into the plush backyard. One block from the association's private park & pier located at end of road (ask about boat slip availability). New roof, furnace, water heater, water softener in past 5 years. You'll love to make this your home.

122 N Maple Ter, Oconomowoc

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

997 Elderberry Rd, Oconomowoc
$484,900
3 Beds ⋅ 2 Baths
Move-in Ready 75 ARW Olivia Cottage II Unit A, TWIN HOME! Welcome to Haven, a community of Twin Homes offering low-maintenance living in custom homes w/ private yards. Monthly association fee $245 covers lawn mowing, fertilization, & 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 & will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands & trades for your home as well. We've partnered w/ Lindsay Windows, Kohler, Floor360, & Auburn Ridge just to name a few. To top it off, Veridian Homes offers a 1-yr limited warranty, backed by our own dedicated customer service team.

997 Elderberry Rd, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc.. Selling Office: Venture Realty, LLC.

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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