Oconomowoc, WI Homes

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  /3

  $689,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,590 Sq Ft

  The Juneberry Plan at Olde Highlander - The Estates at Olde Highlander, Oconomowoc, WI 53066

  This two-story home features an open-concept main floor designed for effortless entertaining and everyday living. The spacious kitchen includes a large island and walk-in pantry, flowing seamlessly into the dining area and great room. A rear foyer with built-in storage and a conveniently located powder room keeps daily routines organized and efficient. The flex room near the front entry offers

  Tim O'Brien Homes Builder

  1448 Olde Highlander Dr St Unit 37744968, Oconomowoc, WI 53066
• 

  $850,000

  Sold May 12, 2026

  N60W38457 Blackhawk Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  Last Sold Summary

  • 6% Above List Price
  • $369/SF
  • 1 Day On Market

  Current Estimated Value $789,895

  Last Listing Agent JJ Hausmann Compass RE WI-Lake Country

  N60W38457 Blackhawk Dr, Oconomowoc, WI 53066
• 

  Est $542,258

  Not Listed For Sale

  1281 Yosemite Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Built 2002

  1281 Yosemite Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  

  

  /47

  $1,639,900

  New Construction Under Contract

  • 4 Beds
  • 4.5 Baths
  • 5,603 Sq Ft

  N65W38082 N Woodlake Cir, Oconomowoc, WI 53066

  The Farmington II is sure to be the talk of the neighborhood, bringing together a contemporary yet rural farmhouse feel. Beautiful cedar columns compliment the rich brickwork that anchors the exterior design, while the crisp siding and dramatic gables add depth, texture, and visual interest while tying in a modern aesthetic. Expansive windows invite natural light and promise bright, airy

  Carl Tomich Westridge Realty, Inc.

  N65W38082 N Woodlake Cir, Oconomowoc, WI 53066
• 

  $575,000

  Sold Mar 20, 2026

  805 N Oakwood Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,927 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $298/SF
  • 3 Days On Market

  Current Estimated Value $571,401

  Last Listing Agent Alaina Zieman Keller Williams Realty-Lake Country

  805 N Oakwood Ave, Oconomowoc, WI 53066
• 

  Est $1,884,173

  Not Listed For Sale

  480 Lac La Belle Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 3 Baths
  • 3,005 Sq Ft
  • Built 1940

  480 Lac La Belle Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 25 Days On Market
• 

  

  /9

  $122,500

  • Land
  • 18,295 Sq Ft
  • $291,667 per Acre

  N903 Winds Way, Oconomowoc, WI 53066

  Beautiful corner lot in the sought-after Four Winds Subdivision, just a short drive north of Oconomowoc. An ideal setting to build your dream home, offering access to a private 2-acre pond and scenic common area. The community features tasteful architectural guidelines, sewer access, and private well. A rare opportunity to secure one of Lake Country's most attractive values.

  Judy Sebastian Westar Realty

  N903 Winds Way, Oconomowoc, WI 53066
• 

  $640,000

  Sold May 19, 2026

  N66W35104 Lappland Crossing, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 3,381 Sq Ft

  Last Sold Summary

  • $189/SF
  • 2 Days On Market

  Current Estimated Value $661,699

  Last Listing Agent Joseph Jewell Lake Country Flat Fee

  N66W35104 Lappland Crossing, Oconomowoc, WI 53066
• 

  Est $326,149

  Not Listed For Sale

  828 S Silver Lake St, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 1,132 Sq Ft

  828 S Silver Lake St, Oconomowoc, WI 53066

  Last Sold Summary

  • 5 Days On Market
• 

  

  /30

  $449,900

  $10K PRICE DROP

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

  957 Elderberry Rd, Oconomowoc, WI 53066

  Why wait for new construction when this practically new Veridian Twin Home is finished & move-in ready? Barely lived in & impeccably maintained, this ranch-style home offers easy, low-maintenance living with lawn care & snow removal included in the $245/month HOA fee. The open-concept floor plan features 2 BRs, 2 full BAs & spacious kitchen w/large island, pantry, & abundant cabinetry. Patio

  The Italiano Team* Lake Country Flat Fee

  957 Elderberry Rd, Oconomowoc, WI 53066
• 

  $575,000

  Sold Feb 13, 2026

  813 High St, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  Last Sold Summary

  • $273/SF
  • 16 Days On Market

  Current Estimated Value $577,138

  Last Listing Agent Sean Brown Best Life Realty

  813 High St, Oconomowoc, WI 53066
• 

  Est $484,509

  Not Listed For Sale

  36712 Clover Ln, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  36712 Clover Ln, Oconomowoc, WI 53066

  Last Sold Summary

  • 31 Days On Market
• 

  

  /25

  $289,900

  $10K PRICE DROP Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  449 W Wisconsin Ave Unit 9, Oconomowoc, WI 53066

  Great 3BR condo in an excellent location near downtown Oconomowoc! Enjoy walking to the beach, park, and downtown shops and restaurants! Spacious townhouse style unit features a private outside entrance, full basement, and a detached garage. Main level includes the kitchen with appliances included, adjoining dining room, half bath, and large living room. Private back yard patio on the back of

  Paul Liebe Lake Country Flat Fee

  449 W Wisconsin Ave Unit 9, Oconomowoc, WI 53066
• 

  $640,000

  Sold Apr 02, 2026

  W354N5315 Coastal Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 3 Baths
  • 3,600 Sq Ft

  Last Sold Summary

  • 7% Below List Price
  • $178/SF
  • 128 Days On Market

  Current Estimated Value $671,830

  Last Listing Agent Mary Steinke Shorewest Realtors, Inc.

  W354N5315 Coastal Ave, Oconomowoc, WI 53066
• 

  Est $363,523

  Not Listed For Sale

  2430 N 3rd Ln, Oconomowoc, WI 53066

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft
  • Built 1930

  2430 N 3rd Ln, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  The Richmond Plan at Prairie Creek Ridge, Oconomowoc, WI 53066

  The Richmond offers a spacious and versatile layout, perfect for families seeking comfort and functionality. With optional stone or brick elevations, this floor plan provides customizable exterior designs to suit your preferences.

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356473, Oconomowoc, WI 53066
• 

  $1,500,000

  Sold Dec 11, 2025

  N57W34599 Road G, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,561 Sq Ft

  Last Sold Summary

  • $586/SF

  Current Estimated Value $1,543,541

  Last Listing Agent JJ Hausmann Compass RE WI-Lake Country

  N57W34599 Road G, Oconomowoc, WI 53066
• 

  Est $371,989

  Not Listed For Sale

  37136 Sunset Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1860

  37136 Sunset Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 12 Days On Market
• 

  

  /23

  $554,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  1076 Elderberry Rd, Oconomowoc, WI 53066

  Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  1076 Elderberry Rd, Oconomowoc, WI 53066
• 

  $466,973

  Sold Mar 04, 2026

  944 Glencoe Ln, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,979 Sq Ft

  Last Sold Summary

  • $236/SF
  • 0 Days On Market

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  944 Glencoe Ln, Oconomowoc, WI 53066
• 

  Est $661,912

  Not Listed For Sale

  1303 Ridgeside Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft
  • Built 2005

  1303 Ridgeside Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 9 Days On Market
• 

  /2

  $589,000

  • Land
  • 1.72 Acres
  • $342,442 per Acre

  1270 Corporate Center Dr, Oconomowoc, WI 53066

  Excellent commercial/industrial/business opportunity in Oconomowoc! Good visibility with close proximity to I-94 and Hwy 67. Over 1.7 acres of vacant land in a prime location within the Oconomowoc Corporate Center near Pabst Farms.

  Dan Scardino Point Real Estate

  1270 Corporate Center Dr, Oconomowoc, WI 53066
• 

  $555,000

  Sold Apr 20, 2026

  1227 Oriole Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,901 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $191/SF
  • 7 Days On Market

  Current Estimated Value $557,151

  Last Listing Agent Heidi Swan Shorewest Realtors, Inc.

  1227 Oriole Dr, Oconomowoc, WI 53066
• 

  Est $3,375,357

  Not Listed For Sale

  W398N6150 Mary Ln, Oconomowoc, WI 53066

  • 6 Beds
  • 6 Baths
  • 5,022 Sq Ft
  • Built 2019

  W398N6150 Mary Ln, Oconomowoc, WI 53066

  Last Sold Summary

  • 148 Days On Market
• 

  

  /50

  $3,499,900

  New Construction

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

  222 E Pleasant St, Oconomowoc, WI 53066

  Sophisticated luxury meets casual elegance in this newly constructed custom lakefront home on historic Fowler Lake. With 5 BRs & 4 BAs, it offers the rare opportunity to enjoy lake living in the heart of downtown Oconomowoc. Spend summer days boating, swimming, or fishing. Enjoy weekly waterski shows & watch 4th of July fireworks from your own back yard. Restaurants, shops, and year-round

  Karen Trepton Shorewest Realtors, Inc.

  222 E Pleasant St, Oconomowoc, WI 53066
• 

  $631,985

  Sold Jan 30, 2026

  1724 Whalen Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,337 Sq Ft

  Last Sold Summary

  • 4% Above List Price
  • $270/SF
  • 284 Days On Market

  Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

  1724 Whalen Dr, Oconomowoc, WI 53066
• 

  Est $394,386

  Not Listed For Sale

  320 E Pleasant St Unit 306, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • Built 1975

  320 E Pleasant St Unit 306, Oconomowoc, WI 53066

  Last Sold Summary

  • 47 Days On Market
• 

  /2

  $624,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  1314 Lynn Cir, Oconomowoc, WI 53066

  HOUSE IS BEING FRAMED - APPROXIMATE COMPLETION MARCH 2027. 3 bedrooms/2 full baths/partial exposure/ranch. Basement has windows in exposure & drain/vent rough-in for future full bath. Walk-in shower master bath. Double sinks master & family baths/granite or equivalent vanity tops. Large WIC master suite. 9' main floor ceilings: pitched in foyer, living room, kitchen, dinette/tray ceiling in

  Joseph Behmke Kaerek Homes, Inc.

  1314 Lynn Cir, Oconomowoc, WI 53066
• 

  $722,314

  Sold Jun 02, 2026

  1374 Prairie Creek Cir Unit 19C, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  Last Sold Summary

  • 2% Above List Price
  • $374/SF
  • 0 Days On Market

  Last Listing Agent Shawn Wagner Kings Way Realty, LLC

  1374 Prairie Creek Cir Unit 19C, Oconomowoc, WI 53066
• 

  Est $862,550

  Not Listed For Sale

  1040 N Lost Woods Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 3.5 Baths
  • 3,515 Sq Ft

  1040 N Lost Woods Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market
• 

  

  /61

  $485,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,719 Sq Ft

  676 Summit Ave, Oconomowoc, WI 53066

  This classic early 1900's farmhouse will steal your heart! Gather your family & friends in the fully renovated kitchen, on the enclosed porch, under the shade trees or on the deck. This home has been tastefully renovated & is ready for you to move in. Kitchen renovations include quartz countertops and a commercial stove. You'll enjoy the oversized fenced yard, firepit and a garden area ready for

  Jean Adler Restaino & Associates

  676 Summit Ave, Oconomowoc, WI 53066
• 

  $484,900

  Sold May 12, 2026

  1442 N Lapham St, Oconomowoc, WI 53066

  • 4 Beds
  • 1.5 Baths
  • 1,701 Sq Ft

  Last Sold Summary

  • 1% Below List Price
  • $285/SF
  • 5 Days On Market

  Current Estimated Value $485,858

  Last Listing Agent Kristina Wudtke RE/MAX Service First

  1442 N Lapham St, Oconomowoc, WI 53066
• 

  Est $824,010

  Not Listed For Sale

  1355 Gridley Ct, Oconomowoc, WI 53066

  • 5 Beds
  • 3.5 Baths
  • 4,074 Sq Ft

  1355 Gridley Ct, Oconomowoc, WI 53066

  Last Sold Summary

  • 143 Days On Market
• 

  

  /27

  $674,900

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

  1616 Belmont Ln Unit 34C, Oconomowoc, WI 53066

  Popular CASTILLIAN floor plan - New Construction - Ready for Occupancy January 2027! Located in the planned community of Village Crossing II Condominiums, this beautifully appointed condo features luxury finishes throughout, including 10' ceilings, real hardwood floors, Quartz kitchen countertops, Corian bath countertops, and a complete kitchen appliance package. The full basement offers an

  Tosca Russo Kings Way Realty, LLC

  1616 Belmont Ln Unit 34C, Oconomowoc, WI 53066
• 

  $11,500,000

  Sold Aug 08, 2025

  4654 Lake Club Cir, Oconomowoc, WI 53066

  • 5 Beds
  • 5.5 Baths
  • 9,365 Sq Ft

  Last Sold Summary

  • 8% Below List Price
  • $1,228/SF

  Current Estimated Value $6,919,090

  Last Listing Agent Bruce Gallagher Keller Williams Realty-Lake Country

  4654 Lake Club Cir, Oconomowoc, WI 53066
• 

  Est $269,051

  Not Listed For Sale

  723 W Wisconsin Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft

  723 W Wisconsin Ave, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  

  /55

  $2,750,000

  $249K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  N50W35310 Wisconsin Ave, Oconomowoc, WI 53066

  Torn down and re built in 1994 w/ recent remodel inside and out by Groskopf. Incredible lake views w/ over 100 ft of frontage. Gourmet kitchen w/quartz, custom tile, luxury slow close cabinets and high end appliances. Open concept w/living rm open to dining rm w/builts ins. Main floor master suite w/luxurious bth and WIC. 2nd floor large bedrm adjacent to 1/2 bth. Back hall w/private entry to

  Kimberly Devine The Real Estate Studio

  N50W35310 Wisconsin Ave, Oconomowoc, WI 53066
• 

  $419,545

  Sold May 06, 2026

  1461 Olde Highlander Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft

  Last Sold Summary

  • $250/SF
  • 0 Days On Market

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  1461 Olde Highlander Dr, Oconomowoc, WI 53066
• 

  Est $1,309,430

  Not Listed For Sale

  N57W34476 Nickels Point Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  N57W34476 Nickels Point Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 4 Days On Market
• 

  

  /30

  $487,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,357 Sq Ft

  W646 Townline Rd, Oconomowoc, WI 53066

  Don't miss Out On This Fabulous Home! Set On just shy of 2 acres, this 4 bedroom, 2-bath home delivers the best of both worlds: room to roam outside and comfortable living inside. The open concepts kitchen is a standout with custom cabinetry and great flow for cooking plus entertaining . A large living room anchors the home with plenty of space to relax. Finished off with an attached 2.5 car

  Donald Loew RE/MAX Insight

  W646 Townline Rd, Oconomowoc, WI 53066

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