Homes for Sale in 53066

• 

  Price To Be Determined New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,137 Sq Ft

  The Bridgeport Plan at Olde Highlander - The Villas at Olde Highlander, Oconomowoc, WI 53066

  Harbor Homes Builder

  994 Oconomowoc Pkwy Unit 37740850, Oconomowoc, WI 53066
• 

  Price To Be Determined New Construction

  • 4 Beds
  • 2 Baths
  • 2,355 Sq Ft

  The Atwater Plan at Olde Highlander - The Villas at Olde Highlander, Oconomowoc, WI 53066

  Harbor Homes Builder

  994 Oconomowoc Pkwy Unit 37740753, Oconomowoc, WI 53066
• 

  Price To Be Determined New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  The Bradford Plan at Olde Highlander - The Villas at Olde Highlander, Oconomowoc, WI 53066

  Harbor Homes Builder

  994 Oconomowoc Pkwy Unit 37740539, Oconomowoc, WI 53066
• 

  Price To Be Determined New Construction

  • 3 Beds
  • 2 Baths
  • 1,931 Sq Ft

  The Adrian Plan at Olde Highlander - The Villas at Olde Highlander, Oconomowoc, WI 53066

  Harbor Homes Builder

  994 Oconomowoc Pkwy Unit 37740495, Oconomowoc, WI 53066
• 

  Price To Be Determined New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,314 Sq Ft

  The Addison Plan at Olde Highlander - The Villas at Olde Highlander, Oconomowoc, WI 53066

  Harbor Homes Builder

  994 Oconomowoc Pkwy Unit 37740355, Oconomowoc, WI 53066
• 

  

  /12

  $169,000

  • Land
  • 0.36 Acre
  • $469,444 per Acre

  LT27 Lakeland Rd, Oconomowoc, WI 53066

  Build your dream home in the heart of Lake Country on this rare 0.3636-acre lot! Less than half a mile from four lakesOkauchee, Oconomowoc, Upper Oconomowoc & Florencewith public boat launches nearby within easy walking distance. Walk to downtown Okauchee and enjoy local favorites like Whisky Waters, Kiki's Cantina, Glenda's Cafe & more. Just 6 minutes to downtown Oconomowoc, 8 to Hartland, and

  The Italiano Team* Lake Country Flat Fee

  LT27 Lakeland Rd, Oconomowoc, WI 53066
• 

  

  /36

  $1,295,000

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft

  W332n6481 County Road C, Nashotah, WI 53058

  Truly exceptional w/an impressive 145 ft. of lake frontage, a residence that commands stunning water views & a spectacular lot that invites you to expand & create a haven that reflects your style. Properties w/this level of frontage, exposure & location are few & far between. Outstanding living space w/grand scale windows take advantage of endless sunrise-to-sunset lake views. GR anchors FP &

  Donna Schoessow Shorewest Realtors, Inc.

  W332n6481 County Road C, Nashotah, WI 53058
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  /8

  $644,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,247 Sq Ft

  1259 Wild Rye Ln, Oconomowoc, WI 53066

  Spacious split ranch in Prairie Creek Ridge! The Kendall features upgraded features throughout. Front foyer leads to open concept living space, with flex room on the right. Kitchen features soft close cabinets, quartz countertops, tile backsplash, walk-in pantry & exterior vented range hood. Off kitchen is the great room boasting a cathedral ceiling & complete with an electric fireplace with

  Erin Russell Tim O'Brien Homes

  1259 Wild Rye Ln, Oconomowoc, WI 53066
• 

  

  /5

  $444,900 New Construction

  • 2 Beds
  • 2 Baths
  • 1,317 Sq Ft

  1007 Elderberry Rd, Oconomowoc, WI 53066

  Move-in Ready 77 ARW Wyatt Cottage Unit B - TWIN HOME. Available 12/23/25 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. Built by Wisconsin's leading homebuilder, you can expect

  Tamra Litzau Shorewest Realtors, Inc.

  1007 Elderberry Rd, Oconomowoc, WI 53066
• 

  

  /5

  $534,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  1150 Arrowood Cir W, Oconomowoc, WI 53066

  Move-in Ready 116 ARW Harlow Farmhouse. Available 12/1/2025. All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well. We've partnered with Lindsay Windows, Kohler, Floor 360 and Auburn Ridge

  Rachael Bublitz Shorewest Realtors, Inc.

  1150 Arrowood Cir W, Oconomowoc, WI 53066
• 

  

  /5

  $624,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft

  1275 Wild Rye Ln, Oconomowoc, WI 53066

  Thoughtfully designed 2-story home in Prairie Creek Ridge! The Acacia, on lot 389, includes upgraded features throughout. Kitchen features soft close cabinets, quartz countertops, tiled backsplash, spacious walk-in pantry & exterior vented range hood. Extended dinette provides plenty of space to enjoy a meal with loved ones & the cozy great room is complete with an electric fireplace. Flex room

  Erin Russell Tim O'Brien Homes

  1275 Wild Rye Ln, Oconomowoc, WI 53066
• 

  

  /5

  $509,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft

  1238 Arrowood Cir W, Oconomowoc, WI 53066

  Move-in Ready 105 ARW Beryl Shingle. Available 12/23/25! All Veridian homes are Quality360 certified, meaning they exceed energy-efficiency industry standards and will perform, on average, better than a typical used home. As your local homebuilder, you can expect the best local brands and trades for your home as well. We've partnered with Lindsay Windows, Kohler, Floor360 and Auburn Ridge just to

  Tamra Litzau Shorewest Realtors, Inc.

  1238 Arrowood Cir W, Oconomowoc, WI 53066
• 

  

  /3

  $800,000

  • Land
  • 24.56 Acres
  • $32,573 per Acre

  Lt2 & 3 Wisconsin 67, Ashippun, WI 53066

  Prime acreage, zoned light industrial on Hwy 67 in the Town of Ashippun. Property has been divided into 2 parcels, but seller is selling both in entirety. Easy access off of Hwy 67. West side of property has a municipal sewer easement. Currently property is being crop farmed on a year to year lease. Build a dream home, a farmette or develop.

  Karen Trepton Shorewest Realtors, Inc.

  Lt2 & 3 Wisconsin 67, Ashippun, WI 53066
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  /13

  $699,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  1328 Periwinkle Pass, Oconomowoc, WI 53066

  Welcome home to THE JULIA PLAN by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 bedrooms, 3.5 baths & 3 car garage. The lot has partial exposure. Kitchen comes w/quartz countertops. doors & LG appliance package. LVP flooring in kitchen, dinette & great room. We equip our homes with Smart Technology such as a Ring Doorbell & touchless faucets. You will find

  Amy Krieghoff Coldwell Banker Realty

  1328 Periwinkle Pass, Oconomowoc, WI 53066
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  /30

  $649,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,499 Sq Ft

  1690 Whalen Dr, Oconomowoc, WI 53066

  Welcome home to The PRESCOTT by Stepping Stone Homes, an award-winning home builder. Open floor plan features 4 Beds, 2.5 Baths and a 3 Car garage. The kitchen comes w/quartz countertops, maple-stained cabinets, and LG appliance package. LVP flooring in kitchen, dinette, and great room. You will find quality craftsmanship throughout such as 2x6 construction exterior walls, 9' first floor

  Amy Krieghoff Coldwell Banker Realty

  1690 Whalen Dr, Oconomowoc, WI 53066
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  /26

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  402 W 3rd St, Oconomowoc, WI 53066

  Enjoy the best of Oconomowoc living in this fully updated home, ideally situated on a corner lot just steps from Park Lawn Elementary and a short stroll to City Beach and eclectic downtown Oconomowoc. Located in a welcoming, walkable neighborhood, this move-in-ready gem features updates including roof, windows, siding, exterior doors, gutters with guards, and a painted garage exterior. Inside,

  Catherine Gilbert Real Broker LLC

  402 W 3rd St, Oconomowoc, WI 53066
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  /18

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1320 Prairie Creek Cir Unit 2, Oconomowoc, WI 53066

  Experience easy, elegant living in this stunning new construction ranch condo ready for immediate move-in! Featuring 3 bedrooms, 2 baths, & a spacious open layout, this home impresses w/it's quality & unique architectural details. The chef's kitchen offers quartz counters, SS appliances & a large island. It flows seamlessly into the dining area & great room, complete w/a GFP that creates an

  Jessica Dunn Shorewest Realtors, Inc.

  1320 Prairie Creek Cir Unit 2, Oconomowoc, WI 53066
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  /80

  $798,999

  • 5 Beds
  • 2.5 Baths
  • 2,947 Sq Ft

  389 Juniper Ct, Delafield, WI 53018

  Welcome to this beautiful stately home located on the corner lot as you enter the Juniper cul-de-sac off of Mill Rd in Valley Rd subdivsion. A very rich interior with 9' ceilings, Maple floors, butlers pantry, full masonry fireplace are just some of the beautiful highlights. The lower level boasts a movie theatre, wet bar and office.

  Roger Ball Berkshire Hathaway HS Lake Country

  389 Juniper Ct, Delafield, WI 53018
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  /5

  $825,000

  • Land
  • 35.08 Acres
  • $23,518 per Acre

  00 W Ln, Oconomowoc, WI 53066

  Saddlebrook Farms listing of a rare 35 acre vacant-land property in the Lake Country area that is nestled among similar large single family tracts, all enclosed with wood fences. Located north of the city of Oconomowoc, the land is ready for developing into an attractive life-style living farm. Zoned agriculture-use for tax purposes with a single family dwelling allowed, a vet business, and

  John Kilmer Kilmer Real Estate Brokerage

  00 W Ln, Oconomowoc, WI 53066
• 

  

  /5

  $800,000

  • Land
  • 26.46 Acres
  • $30,234 per Acre

  Lt2 County Road O, Ashippun, WI 53066

  Build your dream home or develop your ideal neighborhood on this beautiful 26 acres of land overlooking the tranquil landscape in the Town of Ashippun. Have the best of both worlds with a rural setting just minutes north of popular Oconomowoc. Parcel is flanked by developed land, offering easy access to utilities and city sewer. Oconomowoc Schools.

  Karen Trepton Shorewest Realtors, Inc.

  Lt2 County Road O, Ashippun, WI 53066
• 

  /2

  $449,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  1117 Elderberry Rd, Oconomowoc, WI 53066

  Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  1117 Elderberry Rd, Oconomowoc, WI 53066
• 

  /2

  $464,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  1121 Elderberry Rd, Oconomowoc, WI 53066

  Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  1121 Elderberry Rd, Oconomowoc, WI 53066
• 

  

  /10

  $124,999

  • Land
  • 0.45 Acre
  • $277,776 per Acre

  N979 Winds Way, Ashippun, WI 53066

  Enchanting pond view lot awaits, perfect for a gracefully exposed lower-level home nestled within the exclusive Four Winds Subdivision. Only ten minutes from the vibrant heart of downtown Oconomowoc, where shopping, sun-kissed beaches, lively festivals, and beautiful parks await! Experience luxury living amid a tranquil countryside embrace. This subdivision boasts exquisite custom homes with

  Judy Sebastian Westar Realty

  N979 Winds Way, Ashippun, WI 53066
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  /9

  $2,991,000

  • 3 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  503 N Lake Rd Unit 2, Oconomowoc, WI 53066

  Discover timeless elegance at this exclusive Lavinia by the Lakes bespoke 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 sunroom, dual fireplaces, hydronic floor heating, butler's pantry, versatile

  Jeff Scrima Tenderland Real Estate LLC

  503 N Lake Rd Unit 2, Oconomowoc, WI 53066
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  /27

  $1,999,999

  • 5 Beds
  • 3.5 Baths
  • 5,973 Sq Ft

  35300 Pabst Rd, Oconomowoc, WI 53066

  Experience luxury and privacy on 14 secluded acres in the Village of Oconomowoc Lake. This exceptional estate offers wooded, huntable land and open spaces perfect for recreation or a future sport court. Enjoy a wraparound deck, multiple outdoor entertaining areas, and a finished outbuilding ideal as a studio, workshop, or guest retreat, with options for additional structures. Inside, the home

  Laurie Flatt Keller Williams Realty-Lake Country

  35300 Pabst Rd, Oconomowoc, WI 53066
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  /51

  $1,799,000

  • 6 Beds
  • 5.5 Baths
  • 5,666 Sq Ft

  998 N Griffith Rd, Oconomowoc, WI 53066

  Exceptional custom built home by Anthony Thomas Builders, perfectly situated on 2.5+ picturesque acres in the Village of Summit with scenic Bark River access. Impeccable craftsmanship is showcased through reclaimed wood beams, wide-plank hickory floors, and refined architectural details. This remarkable residence offers 6+ bedrooms, 5.5 spa-inspired baths, a chef's kitchen with premium

  Jennifer Pesicek Coldwell Banker Elite

  998 N Griffith Rd, Oconomowoc, WI 53066
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  /61

  $379,900

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  333 N Lake Rd Unit 507, Oconomowoc, WI 53066

  Well maintained Fowler Lake 2BR, 2Ba Condo with many updates. Enjoy Lake living within walking distance to downtown. Lake views from every room and from your wrap around balcony. Nicely updated throughout. Newer kitchen with new cabinets, granite countertops and SS appliances. Updated baths with heated floors & newer vanities with granite tops. Spacious master suite with walk-in closet. Plenty of

  Kevin Wangard Anderson Real Estate Services

  333 N Lake Rd Unit 507, Oconomowoc, WI 53066
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  /5

  $185,000

  • Land
  • 0.48 Acre
  • $385,417 per Acre

  N56W36834 E Lisbon Rd, Oconomowoc, WI 53066

  Location Location Location! Close proximity to downtown Oconomowoc and down town Okauchee as well as easy highway access. Bring your own builder to this beautiful non-HOA level lot with mature trees. No neighbors to the south or the north. There is also a 77x84 deeded area on the neighbor to the north for a future septic mound. Aerial lines are only a rough approximate of lot size, please see

  Steven Bielik Lakefront Realty, LLC

  N56W36834 E Lisbon Rd, Oconomowoc, WI 53066
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  /59

  $1,149,000

  • 4 Beds
  • 3.5 Baths
  • 4,045 Sq Ft

  3127 Monona Ct, Oconomowoc, WI 53066

  Interlaken Village is nestled in the perfect Lake Country location, close to shopping, schools, YMCA, & freeway. Spacious split ranch offers a finished lower level w/9 ft. ceilings, and open concept main living w/10 ft. ceilings. Bright, sun-filled kitchen has a massive island, large walk-in pantry, & cozy fireside seating area. The great room has another fireplace & coffered ceiling. The primary

  

  Bill Minett

  The Real Estate Company Lake & Country

  (262) 889-3171

  3127 Monona Ct, Oconomowoc, WI 53066
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  /37

  $389,000

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft

  320 E Pleasant St Unit 202, Oconomowoc, WI 53066

  Experience the perfect blend of tranquility and convenience in this beautifully updated 2-bedroom, 2-bath corner unit on scenic Fowler Lake. Remodeled in 2019, this spacious condo features an open-concept layout, abundant natural light, and a private balcony ideal for morning coffee. Located in a 55+ community, residents enjoy recently renovated common areas, an outdoor pool, and secure

  The Martha Ford Team* First Weber Inc - Delafield

  320 E Pleasant St Unit 202, Oconomowoc, WI 53066
• 

  

  /5

  $629,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,432 Sq Ft

  1749 Hammock Ln, Oconomowoc, WI 53066

  Charming 2-story home located in Prairie Creek Ridge! The Evergreen features upgrades throughout. The welcoming front foyer leads to a flex room w/ French doors, making a great office or playroom. Kitchen has a spacious island w/ overhang, soft close cabinets, oversized pantry, ext vented range hood & kitchen sink below a window overlooking the backyard. The open concept living space is a

  Erin Russell Tim O'Brien Homes

  1749 Hammock Ln, Oconomowoc, WI 53066
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  /14

  $3,700,000

  • Land
  • 0.93 Acre
  • $3,978,495 per Acre

  W343N6205 S Bayview Rd, Okauchee Lake, WI 53066

  OKAUCHEE LAKE. This is a once in a lifetime opportunity to build your dream home on one of Lake Country's most coveted properties. It sits on the Gold Coast of Okauchee Lake and was once the original and famous Breezy Point. This parcel features 250 feet of level shoreline frontage with a southern exposure for full sun all day and views of the entire lake.Mature trees provide a true ''up north''

  Pat Bolger Patrick Bolger Realty Group

  W343N6205 S Bayview Rd, Okauchee Lake, WI 53066
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  /6

  $224,900

  • Land
  • 0.35 Acre
  • $642,571 per Acre

  Pcl4 Poppy St, Oconomowoc, WI 53066

  Welcome to the last remaining lot in the coveted Flowers Street area of Oconomowoc! This spacious, flat, and open 0.35-acre parcel sits quietly at the end of a dead-end street, offering rare privacy with no through traffic. Enjoy the convenience of city utilitiessewer and water already in the streetso there's no need to deal with septic or well systems. Plus, no sidewalks mean less winter

  Christy Weber Avanti Realty LLC

  Pcl4 Poppy St, Oconomowoc, WI 53066
• 

  

  /10

  $149,900

  • Land
  • 0.31 Acre
  • $483,548 per Acre

  578 S Concord Rd, Oconomowoc, WI 53066

  Beautiful meandering scenic Oconomowoc River lot is ready for your home plans to be built upon. This rare waterfront lot has everything you may be looking for with all the amenities of a beautiful city location & kayaking right out your front door. Building envelope has been established, see survey map under ''Documents'', wetland delineation has been completed & the seller has already put in the

  Carol Euringer First Weber Inc - Delafield

  578 S Concord Rd, Oconomowoc, WI 53066
• 

  

  /13

  $718,000

  • 3 Beds
  • 3 Baths
  • 2,898 Sq Ft

  512 Pioneer Ct, Dousman, WI 53118

  This condo has a hard to find 3 car garage and a finished basement. Introducing Talbot's Woods in Lake Country, Berg Development's new luxury ranch condo project. Berg brings its signature high quality new-construction condos to Lake Country. Buyers fully customize their interiors, working with our dedicated in-house design team to create their dream home. This unit has a partial exposure bsmnt

  John Protiva Century 21 Affiliated - Delafield

  512 Pioneer Ct, Dousman, WI 53118
• 

  

  /5

  $657,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  1733 Hammock Ln, Oconomowoc, WI 53066

  This home is under construction. The Hailey 2350 offers a kitchen w/ plenty of cabinetry, quartz counters, WIP, kitchen appliances & prep island, a morning room for casual meals, a gathering room w/ gas fireplace, a formal dining room for large gatherings, a home office & a mudroom featuring a large closet & bench for everyday items. The 2nd floor rounds out this home w/ 3 secondary bedrooms, a

  Jennifer Durand Bielinski Homes, Inc.

  1733 Hammock Ln, Oconomowoc, WI 53066
• 

  /2

  $87,500

  • Land
  • 0.43 Acre
  • $203,488 per Acre

  W2426 Mariah Ln, Oconomowoc, WI 53066

  Build Your Dream Home in the Coveted Four Winds Subdivision! This affordable .43-acre lot (Lot 4) offers the perfect blend of luxury living and peaceful country charmall within the highly rated Oconomowoc School District. Situated on a large, flat homesite, one of the last abutting frontage on the subdivision's private 2-acre pond, enjoy picturesque views, a tranquil fountain, and stocked

  Carrie Kutz Real Broker Milwaukee

  W2426 Mariah Ln, Oconomowoc, WI 53066
• 

  

  /35

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,400 Sq Ft

  34436 Valley Rd, Oconomowoc, WI 53066

  Fully renovated in 2022, this luxurious 4BR, 4.5BA lakefront residence offers over 3,400 sq ft of beautiful living space on coveted Upper Nashotah Lake. Set on a private .84-acre lot with 250' of pristine frontage, the home showcases elevated design, a bright open floor plan, and sweeping lake views throughout. The chef's kitchen features Fisher & Paykel appliances, quartz counters, and a

  Maura Strickler Shorewest Realtors, Inc.

  34436 Valley Rd, Oconomowoc, WI 53066
• 

  

  /28

  $1,324,000

  • 4 Beds
  • 3.5 Baths
  • 4,108 Sq Ft

  180 Monastery Hill Dr, Oconomowoc, WI 53066

  Resort living at it's best with lake access, pool and tennis courts!! Welcome to effortless living in this stunning all-brick ranch nestled in a private setting. Thoughtfully designed, the home features two luxurious primary suites & a third bedroom/office, offering flexibility & comfort for any lifestyle. Quality, chef-inspired kitchen with granite countertops & stainless-steel appliances.

  Jonathan Spheeris Coldwell Banker Elite

  180 Monastery Hill Dr, Oconomowoc, WI 53066
• 

  

  /24

  $314,900

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  942 Oconomowoc Pkwy Unit 942, Oconomowoc, WI 53066

  Spacious 3BR condo in Oconomowoc's Village Green! Enjoy this beautifully maintained complex with mature trees. This 2nd floor unit offers an open concept main living area featuring great room with gas fireplace and patio doors to private balcony. Kitchen has newer countertops, breakfast bar, appliances included, and adjoining dining room. In-unit laundry area. 3 nice size bedrooms including the

  Paul Liebe Lake Country Flat Fee

  942 Oconomowoc Pkwy Unit 942, Oconomowoc, WI 53066

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