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$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.

$775,000
3 Beds ⋅ 2 Baths
Beautiful Tim O'Brien Homes new construction home located in Oconomowoc's highly desirable Olde Highlander neighborhood. This Savannah model ranch offers 3 bedrooms, 2.5 baths, a flex room with French doors and a 2.5 car garage. The open-concept kitchen and great room feature a vaulted ceiling, oversized island, solid-surface counters and an electric fireplace. Enjoy a private primary suite with tray ceiling and walk-in closet, convenient main-floor laundry and covered front porch. The 9-foot basement is plumbed for a future bath and ready for your finishing ideas. Neighborhood amenities include pools, pickleball courts and a clubhouse with its own golf simulator. Concrete driveway included; landscaping and additional concrete work are not included.

1322 Scotsland Ln, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC.

$625,000
4 Beds ⋅ 3 Baths
Built in 2020, this beautifully updated Oconomowoc home offers approx. 2,850 sq. ft. of finished living space, including 1,086 sq. ft. in the finished lower level. The open-concept main floor features a spacious kitchen with quartz countertops, large island, stainless appliances and updated backsplash. The finished lower level adds a rec room, bedroom and bathroom. Recent updates include fresh paint throughout, buried downspouts, smart switches and more. Enjoy the backyard pergola, 6-person PDC hot tub, swing set and PetSafe in-ground fence. Move-in ready with modern finishes and flexible living space!

1431 Rosewood Pass, Oconomowoc

Listing courtesy of Lannon Stone Realty LLC.

$620,000
4 Beds ⋅ 2 Baths
Welcome to easy, elevated living in Hickory Creek. This custom home on a quiet cul-de-sac, pairs thoughtful design in a convenient Oconomowoc setting. The beautifully remodeled kitchen and new wood floors flow into a welcoming family room, where the fireplace sets the scene for cozy nights at home. A versatile first-floor flex space is ready for a home office, formal dining room or whatever fits your lifestyle. The main-level primary suite and laundry add everyday efficiency, while three generous bdrms upstairs offer room for family and guests. Outside, the .38-acre yard backs to conservancy land for a private, natural backdrop. With a new roof, siding and gutters, the big updates are already done; leaving you more time to settle in, entertain and enjoy life in Hickory Creek

1052 Summer Creek Rd, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country.

$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.

$699,900
3 Beds ⋅ 3 Baths
Discover the Sierra III design by Aspen Homes in Eastlake Village. The open concept floor plan features split Bedroom wings, vaulted/tray ceilings, & skylights. Kitchen features new SS appliances & maple cabinets w/raised breakfast bar. HWFs flow throughout main level. Let's not forget LR w/GFP & formal DR. The primary suite features WIC, jetted tub, WIS, & dual vanity sinks. Patio doors off the dinette of the KIT lead to a concrete patio among the tree. The finishing touches are in the finished LL w/opportunity for in-law suite quarters complete w/kitchenette, bath & rec space. New roof! It showcases elegance & quality craftsmanship. Schedule your private showing today!

1832 La Belle Springs Ct, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country.

$459,900
3 Beds ⋅ 2 Baths
Beautifully maintained brick ranch in Oconomowoc's Hidden Ridge neighborhood! The spacious, open floor plan is highlighted by an impressive Great Room w/ vaulted ceiling, exposed beams and a full brick fireplace (gas). Updated kitchen features white cabinetry, quartz countertops, stainless appliances, breakfast bar and plenty of workspace. The primary suite offers a walk-in closet & private bath, while two additional bedrooms and a 2nd full bath complete the main level. A separate dining room provides flexible space for dining or home office. Enjoy the large deck overlooking the private fenced backyard with mature trees and wooded backdrop. Convenient main-floor laundry and attached 2-car garage. New carpet and freshly painted living spaces. New roof-22 or 23. Furnace-2013. H20 Heater-2021

928 Tanglewood Ct, Oconomowoc

Listing courtesy of Century 21 Affiliated - Delafield.

$639,900
4 Beds ⋅ 2 Baths
Energy efficient two-story home w/ walkout basement located in Prairie Creek Ridge! Kitchen features stained 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 full/walkout exposure, full bath rough-in, ERV system & space for future finishing. Home is currently under construction, estimated completion December/January.

1339 Lynn Cir, Oconomowoc

Listing courtesy of Tim O'Brien Homes LLC.

$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.

$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.

$725,000
4 Beds ⋅ 3 Baths
Magazine-worthy from the moment you arrive! Completely transformed, this 4BR/3BA home pairs lux living with modern day design, quality craftsmanship & attention to detail in Central Oconomowoc. The entertainer's dream kitchen features quartz counters, oversized island, soft close cabinetry & designer lighting. Two gas fireplaces, custom bar & spacious living areas are made for gathering. Retreat to the primary suite with walk-in closet & spa ensuite featuring heated floors, soaking tub & oversized shower. Main floor laundry adds convenience. Enjoy a large deck, above ground pool & extended 2.5 car garage. Newer roof, furnace & water heater add peace of mind. All a short bike ride to charming downtown Oconomowoc with restaurants, shops, lakes, farmers markets, festivals & year round events!

727 Browning Cir, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country.

$1,600,000
ISLAND LAKE LOT on Lac LaBelle! This vacant lake lot is the last available on LaBelle. PRICELESS features include flat terrain, beautiful seawall, exclusive neighborhood, the tranquility of Kohl's Bay, and of course the fact that you're on an island! There is also a sewer connection to the property. Please don't walk the property without an appointment.

W386N5990 Blackhawk Dr, Oconomowoc

Listing courtesy of Standard Real Estate Services, LLC.

$1,300,000
3 Beds ⋅ 3 Baths
The Kendall-Proudly selected as the 2026 St. Jude's Dream Home, with all proceeds benefiting St Jude's Research Hospital. Designed with luxury & livability in mind, this split ranch offers 3 bedrooms and 3.5 baths. The front foyer and flex room with 13' ceilings welcome you inside, and custom ceiling details add architectural detail throughout. Chef's Kitchen is equipped w/ Bosch appliances. The bright dinette opens to a screened in deck. The serene primary suite features wood wrapped beams, dual WICs, a freestanding tub & tiled shower. Finished LL offers a family room, full bathroom + bar area & wine storage room. Home features a solar system.

W358N6309 Ennis Rd, Oconomowoc

Listing courtesy of Tim O'Brien Homes LLC.

$584,900
3 Beds ⋅ 2 Baths
A beautifully maintained 2024 Veridian Home offering modern design and move-in-ready convenience in Oconomowoc. The open-concept main level features a contemporary kitchen with a spacious island, modern finishes, and seamless flow into the living and dining areas. Thoughtful details throughout include Kohler fixtures, stylish finishes, and a functional layout designed for everyday living. The upper level offers a spacious primary suite, additional bedrooms, and convenient main-floor laundry. Enjoy the benefits of newer construction with modern finishes, low-maintenance living, and a fresh, move-in-ready feel.

814 Burr Oak Ct, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country.

$449,900
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.

$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.

$1,199,000
4 Beds ⋅ 3 Baths
Exceptional craftsmanship defines this executive ranch in the heart of Oconomowoc, steps from dining, amenities & Silver Lake! Designed with 10' ceilings, arched passageways, solid wood doors & gleaming hardwood floors. Sun-filled open concept features a stone gas FP, chef's kitchen w/custom cabinetry, massive island, gas cooktop & db ovens, & bright 4-season room overlooking the private patio & mature landscaping. Luxe primary suite offers WIC, heated tile floors, dual vanities & custom steam shower. Exposed LL is a full in-law suite boasting 10' ceilings, large windows, family room, full kitchen/bar, stone FP, 2 bdrms, full bath & gym area. 3-car garage + abundant storage complete this exceptional 4BR/3BA home, blending condo living with the space, privacy & finish of a custom residence!

1612 Vico Pass, Oconomowoc

Listing courtesy of LPT Realty.

$665,900
4 Beds ⋅ 2 Baths
Welcome home to the GENEVA by Stepping Stone Homes. Homesite offers standard foundation. This open-concept floor plan offers 4 bedrooms, 2.5 bathrooms, and a 3-car garage with functional living spaces designed for today's lifestyle. Kitchen highlights include quartz countertops, island, pantry, and appliance package. Main living areas feature durable flooring selections. Quality construction includes 2x6 exterior walls, passive radon system, daylight basement windows, and 9' first-floor ceilings. Features, finishes, dimensions, and specifications subject to change without notice.

1749 Switchgrass St, Oconomowoc

Listing courtesy of Coldwell Banker Realty.

$706,900
3 Beds ⋅ 2 Baths
Welcome home to the Eliza by Stepping Stone Homes. This open-concept home features 3 bedrooms, 2 bathrooms, and a 3-car garage. Homesite offers a standard foundation. Kitchen features include quartz countertops, soft-close cabinetry, and appliance package. Quality craftsmanship throughout including 2x6 exterior walls, solid core doors, smart home features, active radon system, and 9' first-floor ceilings. Basement includes rough plumbing for future bath and egress window per plan. Features, finishes, dimensions, and specifications subject to change without notice. Concrete Driveway and walkway to front porch included.

1746 Switchgrass St, Oconomowoc

Listing courtesy of Coldwell Banker Realty.

$685,000
4 Beds ⋅ 1 Baths
A distinctive circa 1900 Oconomowoc home, this property blends historic craftsmanship with major modern upgrades! Original woodwork, hardwood floors, leaded glass, and a wraparound porch create timeless charm, while recent investments--including a 2022 roof, 2023 kitchen remodel with quartz and antique copper sink, updated electrical, and new furnace--deliver everyday comfort. Architectural details like nine foot ceilings, crown molding, and a natural fireplace elevate the main level, complemented by a basement rec room with fieldstone walls. Professionally landscaped grounds, Andersen windows, and potential third floor expansion make this a rare opportunity to grow into a beautifully preserved home. Exceptional location is just a short walk to City Beach and downtown Oconomowoc!

605 W Wisconsin Ave, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

$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.

$749,900
4 Beds ⋅ 3 Baths
Experience refined luxury in Eastlake Village at Pabst Farms with this meticulous 4BR/3.5BA estate. A striking grand foyer anchors the main level, opening to both an elegant formal dining room with a butler's pantry and a gracious great room centered by a gas fireplace. The gourmet eat-in kitchen features SS appliances, granite countertops, a breakfast bar, and direct access to a private patio. A bedroom & half bath complete the main level. Upstairs, two bedrooms reside alongside the primary with ensuite & convenient adjacent laundry. The LL is built for entertaining, boasting a custom bar, wine cooler, second gas fireplace, full bath, workshop, and direct entrance to the oversized 3.5-car garage. Set in a top-rated school district, this turnkey home offers exceptional quality throughout.

1704 River Lakes Rd N, Oconomowoc

Listing courtesy of Mahler Sotheby's International Realty-Lake Country.

$479,900
5 Beds ⋅ 2 Baths
A refreshed 5 bedroom home in The Orchards, this property delivers space, style, and a setting buyers crave! A soaring vaulted great room anchors the main level, flowing to a bright kitchen with island and adjoining dining room. Two bedrooms and a full bath offer convenience on the first floor, while three additional bedrooms and a full bath await upstairs, including a primary bedroom with walk in closet. The finished lower level rec room adds bonus living space. Patio door leads to a private backyard deck. With newer roof and siding plus fresh flooring, interior paint, patio door, and more, this home blends comfort with peace of mind in a prime Oconomowoc location!

980 Bartlett Dr, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

$165,000
Tired of competing for homes that still aren't quite right? Stop competing and start building instead! This beautiful .48-acre flat, level lot offers a rare chance to create exactly what you want in the heart of Lake Country. Bring your own builder, enjoy no HOA and no timeline to build, plus mature trees and an established setting without the feel of a typical new subdivision. Minutes from Downtown Oconomowoc, Lac La Belle, Fowler Lake, Okauchee Lake, beaches, boating, golf, parks, dining and shopping. Easy access to Hwy 16 and I-94, with Costco and Pabst Farms nearby. Buy the lot, choose your builder and create the home you've been waiting for!

N56W36834 Lisbon Rd, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

$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..

$389,500
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.

$640,000
3 Beds ⋅ 3 Baths
Tucked within the Village Crossings Condos at Pabst Farms, this beautifully maintained condo feels like a new build. A calming, neutral palette complements a variety of design styles, while the open-concept main level is designed for both everyday living and entertaining. The spacious kitchen features a large island perfect for gathering around. The finished lower level adds additional living and entertaining space, with plenty of unfinished storage area. Even the garage feels like an extension of the home with freshly painted walls and ceiling and a clean epoxy floor. Move-in ready and conveniently located!

1760 Derby Ln, Oconomowoc

Listing courtesy of Stapleton Realty.

$499,900
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.

$274,900
3 Beds ⋅ 1 Baths
Welcome home to this charming 3BR/1.5BA condo offering the space & privacy of a home w/ the ease of condo living! The inviting multi-level layout features updated laminate flooring, a spacious living room & kitchen w/ newer appliances, breakfast bar & plenty of storage. Enjoy personalized comfort w/ individually controlled heating & cooling units throughout-allowing you to easily adjust the temperature room by room. The three-season porch opens to a private patio, perfect for relaxing or entertaining. A finished lower-level rec room provides add'l living space, while the 3rd bedroom offers added privacy & flexibility. Private entry, attached 1.5-car garage, pet-friendly association & a quiet 15-unit community complete this Oconomowoc gem! Enjoy close proximity to the lakes of Lake Country!

N49W36111 Nottingham Ln Unit 3, Oconomowoc

Listing courtesy of RE/MAX Liberty.

$232,000
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.

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.