Recently Sold Homes in 53066

• 

  $665,996 Sold Dec 29, 2025

  1598 Weston Ridge Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,469 Sq Ft

  Last Sold Summary

  • 7% Above List Price
  • $270/SF

  Current Estimated Value $651,349

  Last Listing Agent Jennifer Villarreal Villa Realty

  1598 Weston Ridge Rd, Oconomowoc, WI 53066
• 

  $420,000 Sold Aug 01, 2025

  333 N Lake Rd Unit 203, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft

  Last Sold Summary

  • 5% Below List Price
  • $280/SF
  • 75 Days On Market

  Current Estimated Value $414,603

  Last Listing Agent Bonnie Lewis-Tschannen Stapleton Realty

  333 N Lake Rd Unit 203, Oconomowoc, WI 53066
• 

  $234,000 Sold Jun 13, 2025

  1061 Regent Rd Unit 614, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $231/SF
  • 137 Days On Market

  Current Estimated Value $222,844

  Last Listing Agent Lynda Stone Lynda Stone Real Estate

  1061 Regent Rd Unit 614, Oconomowoc, WI 53066
• 

  $2,275,000 Sold Nov 10, 2025

  W398N6184 Mary Ln, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 3,848 Sq Ft

  Last Sold Summary

  • $591/SF

  Current Estimated Value $2,305,105

  Last Listing Agent MetroMLS NON NON MLS

  W398N6184 Mary Ln, Oconomowoc, WI 53066
• 

  $812,500 Sold Apr 30, 2025

  1040 N Lost Woods Rd, Oconomowoc, WI 53066

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

  Last Sold Summary

  • 3% Above List Price
  • $231/SF
  • 1 Day On Market

  Current Estimated Value $826,332

  Last Listing Agent Jodi Olson Realty Executives - Integrity

  1040 N Lost Woods Rd, Oconomowoc, WI 53066
• 

  $594,900 Sold May 09, 2025

  1308 Mamerow Ln W, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,253 Sq Ft

  Last Sold Summary

  • $264/SF
  • 24 Days On Market

  Current Estimated Value $610,667

  Last Listing Agent Amy Krieghoff Coldwell Banker Realty

  1308 Mamerow Ln W, Oconomowoc, WI 53066
• 

  $1,575,000 Sold Oct 10, 2025

  W349N5389 Road b, Okauchee, WI 53069

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  Last Sold Summary

  • 2% Above List Price
  • $788/SF
  • 4 Days On Market

  Current Estimated Value $1,557,254

  Last Listing Agent Pat Bolger Patrick Bolger Realty Group

  W349N5389 Road b, Okauchee, WI 53069
• 

  $725,000 Sold Jul 15, 2025

  215 E Pleasant St Unit 208, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft

  Last Sold Summary

  • $561/SF
  • 2 Days On Market

  Current Estimated Value $705,740

  Last Listing Agent Nathanael Zastrow Abundance Real Estate

  215 E Pleasant St Unit 208, Oconomowoc, WI 53066
• 

  $625,000 Sold Apr 30, 2025

  223 Shore Cir, Oconomowoc, WI 53066

  • 5 Beds
  • 3.5 Baths
  • 3,269 Sq Ft

  Last Sold Summary

  • 9% Above List Price
  • $191/SF
  • 1 Day On Market

  Current Estimated Value $629,696

  Last Listing Agent Paul Liebe Lake Country Flat Fee

  223 Shore Cir, Oconomowoc, WI 53066
• 

  $225,000 Sold Dec 30, 2025

  Lt9 S Wayfare Trail, Summit, WI 53066

  • Land
  • 0.83 Acre
  • $271,084 per Acre

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent John Siepmann Siepmann Realty Corp.

  Lt9 S Wayfare Trail, Summit, WI 53066
• 

  $428,000 Sold Apr 08, 2025

  36635 Prairie Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,504 Sq Ft

  Last Sold Summary

  • 4% Above List Price
  • $285/SF
  • 0 Days On Market

  Current Estimated Value $434,084

  Last Listing Agent Kimberly Dove Shorewest Realtors, Inc.

  36635 Prairie Dr, Oconomowoc, WI 53066
• 

  $641,445 Sold Aug 14, 2025

  1652 Switchgrass St, Oconomowoc, WI 53066

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

  Last Sold Summary

  • 7% Above List Price
  • $320/SF
  • 75 Days On Market

  Current Estimated Value $629,873

  Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

  1652 Switchgrass St, Oconomowoc, WI 53066
• 

  $645,000 Sold Mar 18, 2026

  1690 Whalen Dr, Oconomowoc, WI 53066

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

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 158 Days On Market

  Last Listing Agent Amy Krieghoff Coldwell Banker Realty

  1690 Whalen Dr, Oconomowoc, WI 53066
• 

  $679,900 Sold Sep 19, 2025

  W351N5949 Westshore Ct, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,916 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $233/SF
  • 34 Days On Market

  Current Estimated Value $683,535

  Last Listing Agent Patrice Thiede Coldwell Banker Elite

  W351N5949 Westshore Ct, Oconomowoc, WI 53066
• 

  $699,900 Sold Dec 19, 2025

  1328 Periwinkle Pass, Oconomowoc, WI 53066

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

  Last Sold Summary

  • $280/SF
  • 50 Days On Market

  Last Listing Agent Amy Krieghoff Coldwell Banker Realty

  1328 Periwinkle Pass, Oconomowoc, WI 53066
• 

  $614,690 Sold Jan 22, 2026

  1561 Creekview Ln, Oconomowoc, WI 53066

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

  Last Sold Summary

  • 1% Above List Price
  • $307/SF
  • 66 Days On Market

  Current Estimated Value $611,822

  Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

  1561 Creekview Ln, Oconomowoc, WI 53066
• 

  $1,025,000 Sold Feb 02, 2026

  2100 N Oakwoods Ct, Oconomowoc, WI 53066

  • 5 Beds
  • 3.5 Baths
  • 6,397 Sq Ft

  Last Sold Summary

  • 15% Below List Price
  • $160/SF
  • 16 Days On Market

  Current Estimated Value $1,135,521

  Last Listing Agent Amiee Melero Realty Executives - Integrity

  2100 N Oakwoods Ct, Oconomowoc, WI 53066
• 

  $575,000 Sold Mar 12, 2026

  255 Lakeridge Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  Last Sold Summary

  • $197/SF
  • 20 Days On Market

  Current Estimated Value $582,338

  Last Listing Agent Laurie Flatt Keller Williams Realty-Lake Country

  255 Lakeridge Dr, Oconomowoc, WI 53066
• 

  $849,999 Sold Oct 29, 2025

  W389N7102 Pennsylvania St, Oconomowoc, WI 53066

  • 3 Beds
  • 3 Baths
  • 2,800 Sq Ft

  Last Sold Summary

  • $304/SF
  • 0 Days On Market

  Last Listing Agent Judy Sebastian Westar Realty

  W389N7102 Pennsylvania St, Oconomowoc, WI 53066
• 

  $750,000 Sold Mar 27, 2026

  Lot 2 Whittaker Rd, Okauchee Lake, WI 53066

  • Land
  • 0.58 Acre
  • $1,293,103 per Acre

  Last Sold Summary

  Last Listing Agent Rebecca Thomas Keller Williams - Lake Country BT

  Lot 2 Whittaker Rd, Okauchee Lake, WI 53066
• 

  $310,000 Sold May 30, 2025

  809 N Oakwood Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,566 Sq Ft

  Last Sold Summary

  • 9% Below List Price
  • $198/SF
  • 7 Days On Market

  Current Estimated Value $319,317

  Last Listing Agent Andrew Kosmicki Shorewest Realtors, Inc.

  809 N Oakwood Ave, Oconomowoc, WI 53066
• 

  

  /36

  $489,000 Sold Dec 12, 2025

  N53W35963 W Lake Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 2,144 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $228/SF
  • 28 Days On Market

  Current Estimated Value $505,218

  Last Listing Agent Jonathan Gaspero Compass Real Estate Wisconsin

  N53W35963 W Lake Dr, Oconomowoc, WI 53066
• 

  $539,900 Sold Nov 24, 2025

  843 Stirling Dr Unit Bldg 24, Unit 47, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,631 Sq Ft

  Last Sold Summary

  • $331/SF
  • 3 Days On Market

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  843 Stirling Dr Unit Bldg 24, Unit 47, Oconomowoc, WI 53066
• 

  $342,500 Sold May 15, 2025

  N51W34861 W Wisconsin Ave Unit 1122, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,514 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $226/SF
  • 6 Days On Market

  Last Listing Agent Elissa Berkoff Compass RE WI-Northshore

  N51W34861 W Wisconsin Ave Unit 1122, Oconomowoc, WI 53066
• 

  $989,000 Sold May 27, 2025

  W337N8059 Prairie Hollow Dr, Oconomowoc, WI 53066

  • 5 Beds
  • 4.5 Baths
  • 5,763 Sq Ft

  Last Sold Summary

  • $172/SF
  • 3 Days On Market

  Current Estimated Value $1,058,193

  Last Listing Agent Bruce Gallagher Keller Williams Realty-Lake Country

  W337N8059 Prairie Hollow Dr, Oconomowoc, WI 53066
• 

  $483,900 Sold May 20, 2025

  1387 Mamerow Ln W, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  Last Sold Summary

  • 9% Below List Price
  • $265/SF
  • 82 Days On Market

  Current Estimated Value $496,526

  Last Listing Agent Leslie Boyea Quorum Enterprises, Inc.

  1387 Mamerow Ln W, Oconomowoc, WI 53066
• 

  $325,000 Sold Jun 23, 2025

  267 Oconomowoc Pkwy Unit 307, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  Last Sold Summary

  • $194/SF
  • 5 Days On Market

  Current Estimated Value $314,227

  Last Listing Agent Leah Thorp Coldwell Banker Elite

  267 Oconomowoc Pkwy Unit 307, Oconomowoc, WI 53066
• 

  $561,500 Sold Aug 13, 2025

  860 S Silver Lake St, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 3,320 Sq Ft

  Last Sold Summary

  • 2% Above List Price
  • $169/SF
  • 4 Days On Market

  Current Estimated Value $557,182

  Last Listing Agent Thomas Squier Shorewest Realtors, Inc.

  860 S Silver Lake St, Oconomowoc, WI 53066
• 

  $615,000 Sold Feb 18, 2026

  1372 Macgregor Rd, Oconomowoc, WI 53066

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

  Last Sold Summary

  • $261/SF
  • 9 Days On Market

  Last Listing Agent Nicholas Tehan Lannon Stone Realty LLC

  1372 Macgregor Rd, Oconomowoc, WI 53066
• 

  $535,000 Sold Oct 07, 2025

  1790 Morgan Station Ct, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft

  Last Sold Summary

  • 2% Above List Price
  • $334/SF
  • 0 Days On Market

  Current Estimated Value $529,039

  Last Listing Agent Haley LeClaire Realty Executives - Integrity

  1790 Morgan Station Ct, Oconomowoc, WI 53066
• 

  $542,500 Sold Sep 30, 2025

  942 Spring Waters Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 3.5 Baths
  • 2,528 Sq Ft

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 24 Days On Market

  Current Estimated Value $542,094

  Last Listing Agent Sharon Tomlinson Shorewest Realtors, Inc.

  942 Spring Waters Dr, Oconomowoc, WI 53066
• 

  $571,520 Sold Apr 30, 2025

  1293 Arrowood Cir W, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,861 Sq Ft

  Last Sold Summary

  • $307/SF

  Last Listing Agent Nicole Balcitis Shorewest Realtors, Inc.

  1293 Arrowood Cir W, Oconomowoc, WI 53066
• 

  $770,000 Sold Oct 17, 2025

  N66W34306 Primrose Cir, Oconomowoc, WI 53066

  • 4 Beds
  • 3.5 Baths
  • 4,523 Sq Ft

  Last Sold Summary

  • 12% Below List Price
  • $170/SF
  • 42 Days On Market

  Current Estimated Value $782,142

  Last Listing Agent Deborah DeFere Deb DeFere Real Estate LLC

  N66W34306 Primrose Cir, Oconomowoc, WI 53066
• 

  $700,000 Sold Feb 27, 2026

  1380 Scotsland Ln, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,059 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $340/SF
  • 21 Days On Market

  Last Listing Agent Erin Russell Tim O'Brien Homes

  1380 Scotsland Ln, Oconomowoc, WI 53066
• 

  $1,120,000 Sold Dec 15, 2025

  N81W33604 Chicory Ct E, Oconomowoc, WI 53066

  • 5 Beds
  • 4.5 Baths
  • 5,025 Sq Ft

  Last Sold Summary

  • 10% Below List Price
  • $223/SF
  • 86 Days On Market

  Current Estimated Value $1,110,019

  Last Listing Agent Jeanne Jaskolski Keller Williams Realty-Lake Country

  N81W33604 Chicory Ct E, Oconomowoc, WI 53066
• 

  $490,000 Sold Jan 07, 2026

  247 Sunny Hill Ln, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 2,040 Sq Ft

  Last Sold Summary

  • 2% Above List Price
  • $240/SF
  • 0 Days On Market

  Current Estimated Value $481,947

  Last Listing Agent Haley LeClaire Realty Executives - Integrity

  247 Sunny Hill Ln, Oconomowoc, WI 53066
• 

  $335,000 Sold Jan 14, 2026

  296 Oconomowoc Pkwy Unit 296, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $279/SF
  • 57 Days On Market

  Current Estimated Value $332,570

  Last Listing Agent Kathryn Budda Shorewest Realtors, Inc.

  296 Oconomowoc Pkwy Unit 296, Oconomowoc, WI 53066
• 

  $540,000 Sold Aug 13, 2025

  1734 Arthur's Pass, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft

  Last Sold Summary

  • 5% Below List Price
  • $323/SF
  • 37 Days On Market

  Current Estimated Value $532,894

  Last Listing Agent Casey Ehler Coldwell Banker Elite

  1734 Arthur's Pass, Oconomowoc, WI 53066
• 

  $787,000 Sold Nov 18, 2025

  W344N6731 Jorgenson Way, Oconomowoc, WI 53066

  • 3 Beds
  • 3.5 Baths
  • 4,274 Sq Ft

  Last Sold Summary

  • $184/SF
  • 1 Day On Market

  Current Estimated Value $786,406

  Last Listing Agent Katie Corcoran Corcoran Realty & Co

  W344N6731 Jorgenson Way, Oconomowoc, WI 53066
• 

  $580,000 Sold Aug 29, 2025

  35085 Yahara Ct, Summit, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  Last Sold Summary

  • 1% Below List Price
  • $276/SF
  • 30 Days On Market

  Current Estimated Value $586,357

  Last Listing Agent Chuck Minette Minette Realty, LLC

  35085 Yahara Ct, Summit, WI 53066

Showing Results 241 - 280, Page 7 of 16