Oconomowoc, WI Homes

• 

  $515,000

  Sold Apr 09, 2026

  N56W36792 Cherokee Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,570 Sq Ft

  Last Sold Summary

  • 1% Below List Price
  • $328/SF
  • 1 Day On Market

  Current Estimated Value $510,123

  Last Listing Agent Jennifer Pesicek Coldwell Banker Elite

  N56W36792 Cherokee Rd, Oconomowoc, WI 53066
• 

  Est $594,526

  Not Listed For Sale

  219 Shore Cir, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,367 Sq Ft
  • Built 2003

  219 Shore Cir, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  

  

  /49

  $724,900

  Under Contract

  • 5 Beds
  • 3.5 Baths
  • 3,968 Sq Ft

  261 Ridgeway Path, Oconomowoc, WI 53066

  Schedule your showing today and discover this stunning 5-bedroom, 3.5-bath home in the highly sought-after Lakeridge neighborhood. Thoughtfully updated throughout, this move-in-ready home features a beautifully updated kitchen and lower level, plus major recent improvements including a new roof, furnace, AC, water softener, appliances, and refinished hardwood floors. The sun-drenched great room

  Mandi Miller Restaino & Associates

  261 Ridgeway Path, Oconomowoc, WI 53066
• 

  

  /2

  $524,900

  Sold Nov 26, 2025

  1279 Arrowood Cir W, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $322/SF
  • 111 Days On Market

  Veridian Homes Arrowood

  1279 Arrowood Cir W, Oconomowoc, WI 53066
• 

  Est $873,717

  Not Listed For Sale

  N52W35319 W Lake Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft
  • Built 1920

  N52W35319 W Lake Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 94 Days On Market
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

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

  The Delafield offers a spacious and versatile layout, perfect for families of all sizes. With 4 bedrooms and 2.5 baths, this 2248 square foot home provides ample living space. Choose from two elegant elevations, featuring optional stone or brick accents, to customize the exterior to your taste.

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356290, Oconomowoc, WI 53066
• 

  $289,000

  Sold Apr 23, 2026

  930 Oconomowoc Pkwy Unit 930, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,415 Sq Ft

  Last Sold Summary

  • $204/SF
  • 4 Days On Market

  Current Estimated Value $290,948

  Last Listing Agent Michael Tomich Shorewest Realtors, Inc.

  930 Oconomowoc Pkwy Unit 930, Oconomowoc, WI 53066
• 

  Est $451,539

  Not Listed For Sale

  815 N Roosevelt Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1957

  815 N Roosevelt Ave, Oconomowoc, WI 53066

  Last Sold Summary

  • 0 Days On Market
• 

  

  /15

  $210,000

  • 1,200 Sq Ft

  S13W33890 Highway 18 -, Delafield, WI 53066

  Luxury car and boat storage or your very own man cave is now available to own! Units measure 20'W x 60'L x 20'H for a total of 1,200 SQFT and will come complete with a floor drain, 100 amp service, hose bib, roughed in bath, Modine heater and the option to add a loft. The exterior will have cement fiber siding, stone accents and a 14' x 16' overhead door. Please call listing agent to discuss pre

  Christine Jasser Mahler Sotheby's International Realty-Lake Geneva

  S13W33890 Highway 18 -, Delafield, WI 53066
• 

  $790,000

  Sold Jun 18, 2026

  2335 Forest Run, Oconomowoc, WI 53066

  • 4 Beds
  • 4 Baths
  • 3,918 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $202/SF
  • 2 Days On Market

  Current Estimated Value $797,457

  Last Listing Agent Jacob Schneider Century 21 Affiliated - Delafield

  2335 Forest Run, Oconomowoc, WI 53066
• 

  Est $391,178

  Not Listed For Sale

  510 State St, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1901

  510 State St, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,254 Sq Ft

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

  The Maplewood offers a spacious and functional layout, perfect for families or those who love to entertain. With 4 bedrooms and 2.5 baths, this floor plan provides ample space for comfortable living.

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356205, Oconomowoc, WI 53066
• 

  $630,000

  Sold May 11, 2026

  2928 Winnebago Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $324/SF
  • 31 Days On Market

  Current Estimated Value $644,155

  Last Listing Agent Laurie Flatt Keller Williams Realty-Lake Country

  2928 Winnebago Dr, Oconomowoc, WI 53066
• 

  Est $364,442

  Not Listed For Sale

  613 N Oakwood Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  613 N Oakwood Ave, Oconomowoc, WI 53066

  Last Sold Summary

  • 0 Days On Market
• 

  

  /20

  $499,900

  New Construction Open House 7/12 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,996 Sq Ft

  982 Glencoe Ln, Oconomowoc, WI 53066

  Paige Sederberg Harbor Homes Inc

  982 Glencoe Ln, Oconomowoc, WI 53066
• 

  $500,000

  Sold Feb 20, 2026

  727 Browning Cir, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  Last Sold Summary

  • 10% Below List Price
  • $156/SF
  • 60 Days On Market

  Current Estimated Value $533,793

  Last Listing Agent Erin Waldron Property Dynamics/Appraisal Specialists

  727 Browning Cir, Oconomowoc, WI 53066
• 

  Est $577,249

  Not Listed For Sale

  410 Thurow Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 2,646 Sq Ft
  • Built 2008

  410 Thurow Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market
• 

  

  /34

  $315,000

  • 2 Beds
  • 2 Baths
  • 1,389 Sq Ft

  273 Oconomowoc Pkwy Unit 3082, Oconomowoc, WI 53066

  LIVE YOUR BEST LIFE in this beautifully updated 2BR/2BA condo in Silver Ridge in Oconomowoc! Although this is a 55-plus community, up to 9 of the 48 units can be owned by people under 55, and that threshold has not been met! Enjoy a prime location near downtown, the interstate, and the Lake Country Trail. This sought-after third-floor unit features cathedral ceilings, great views, & easy elevator

  Heidi Swan Shorewest Realtors, Inc.

  273 Oconomowoc Pkwy Unit 3082, Oconomowoc, WI 53066
• 

  $478,000

  Sold Dec 01, 2025

  Lt1A La Lumiere Rd, Oconomowoc, WI 53066

  • Land
  • 1.64 Acres
  • $291,463 per Acre

  Last Sold Summary

  • 9% Below List Price

  Last Listing Agent Bill Minett The Real Estate Company Lake & Country

  Lt1A La Lumiere Rd, Oconomowoc, WI 53066
• 

  Est $269,327

  Not Listed For Sale

  102 Oconomowoc Square Unit 2, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  102 Oconomowoc Square Unit 2, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  

  /31

  $569,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  273 Silver Lake Trail, Oconomowoc, WI 53066

  Stunning open-concept ranch designed for easy living and entertaining! The split 3 BD, 2 BA layout offers privacy and seamless flow. The eat-in KIT shines with an island, dinette, granite countertops, tile backsplash, and stainless appliances--perfect for gatherings. The spacious GR features a gas FP and elegant tray ceilings, connecting effortlessly to the deck and patio overlooking the

  Jennifer Adams List2Sell, LLC

  273 Silver Lake Trail, Oconomowoc, WI 53066
• 

  $850,000

  Sold Nov 07, 2025

  1640 Toscano Terrace, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,903 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $447/SF
  • 64 Days On Market

  Current Estimated Value $839,140

  Last Listing Agent The Elements Team* Elements Realty LLC

  1640 Toscano Terrace, Oconomowoc, WI 53066
• 

  Est $428,807

  Not Listed For Sale

  1211 Yorktown Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1968

  1211 Yorktown Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 2 Days On Market
• 

  

  /4

  $570,000

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  1734 Whalen Dr, Oconomowoc, WI 53066

  New Construction - Ready in July! Introducing the Lakewood model in Prairie Creek Ridge, Oconomowoc -- a beautifully designed 1,804 sq ft ranch home that blends spacious design with elevated finishes. This 3-bedroom, 2-bath layout features a striking cathedral ceiling in the living room, creating an open and inviting atmosphere centered around a cozy electric fireplace. The kitchen shines with

  Ryan Prellwitz Loos Custom Homes,LLC

  1734 Whalen Dr, Oconomowoc, WI 53066
• 

  $850,590

  Sold Jun 08, 2026

  1754 Switchgrass St, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,806 Sq Ft

  Last Sold Summary

  • 6% Above List Price
  • $303/SF
  • 60 Days On Market

  Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

  1754 Switchgrass St, Oconomowoc, WI 53066
• 

  Est $300,773

  Not Listed For Sale

  W397N5931 Autumn Woods Dr Unit 101, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,246 Sq Ft

  W397N5931 Autumn Woods Dr Unit 101, Oconomowoc, WI 53066

  Last Sold Summary

  • 7 Days On Market
• 

  

  /4

  $517,700

  New Construction

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

  The Beryl Plan at Arrowood, Oconomowoc, WI 53066

  The Beryl is great for entertaining and even better for everyday living. Its open-concept floor plan creates a welcoming space where laughter flows freely and guests naturally gather around the large kitchen island and great room. A convenient first-floor laundry adds everyday ease. Upstairs, the spacious primary suite features an en suite bath and walk-in closet, while two additional bedrooms

  Veridian Homes Builder

  1420 Arrowwood Circle St W Unit 37836425, Oconomowoc, WI 53066
• 

  $590,000

  Sold Aug 29, 2025

  1417 Clearwater Dr S, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,696 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $219/SF
  • 10 Days On Market

  Current Estimated Value $605,022

  Last Listing Agent The Hupke Team* RE/MAX Forward

  1417 Clearwater Dr S, Oconomowoc, WI 53066
• 

  Est $1,058,570

  Not Listed For Sale

  W352N5270 Lake Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,827 Sq Ft
  • Built 1920

  W352N5270 Lake Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 5 Days On Market
• 

  

  /37

  $614,900

  • 2 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1522 Champion Ct, Oconomowoc, WI 53066

  This stunning 2-bed, 2.5-bath Kingsway ranch condo at Village Crossing at Pabst Farms is move-in ready with every detail thoughtfully executed. The gourmet kitchen features a quartz island, stainless appliances, walk-in pantry, and custom backsplash, flowing into the great room with 10-ft coffered ceilings and a stone-surround gas fireplace. The owner's suite offers a spa-like walk-in shower,

  Damask Realty Group* First Weber Inc - Delafield

  1522 Champion Ct, Oconomowoc, WI 53066
• 

  $606,959

  Sold Jul 08, 2025

  1376 Prairie Creek Blvd Unit 18, Oconomowoc, WI 53066

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

  Last Sold Summary

  • 3% Above List Price
  • $345/SF
  • 0 Days On Market

  Last Listing Agent Shawn Wagner Kings Way Realty, LLC

  1376 Prairie Creek Blvd Unit 18, Oconomowoc, WI 53066
• 

  Est $382,335

  Not Listed For Sale

  689 Hickory Creek Dr Unit 2, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 2,020 Sq Ft
  • Built 2003

  689 Hickory Creek Dr Unit 2, Oconomowoc, WI 53066

  Last Sold Summary

  • 51 Days On Market
• 

  

  /31

  $315,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  69 S Chestnut St, Oconomowoc, WI 53066

  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

  Jordan Tybinko Keller Williams Realty

  69 S Chestnut St, Oconomowoc, WI 53066
• 

  $460,000

  Sold Dec 30, 2025

  215 E Pleasant St Unit 201, Oconomowoc, WI 53066

  • 1 Bed
  • 1.5 Baths
  • 1,182 Sq Ft

  Last Sold Summary

  • 19% Below List Price
  • $389/SF
  • 220 Days On Market

  Current Estimated Value $478,013

  Last Listing Agent Casey Ehler Coldwell Banker Elite

  215 E Pleasant St Unit 201, Oconomowoc, WI 53066
• 

  Est $466,043

  Not Listed For Sale

  407 State St, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1924

  407 State St, Oconomowoc, WI 53066

  Last Sold Summary

  • 8 Days On Market
• 

  

  /12

  $159,000

  $20K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $441,667 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
• 

  $566,700

  Sold Aug 08, 2025

  1326 Arrowood Cir W, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 1,763 Sq Ft

  Last Sold Summary

  • $321/SF

  Last Listing Agent Rachael Bublitz Shorewest Realtors, Inc.

  1326 Arrowood Cir W, Oconomowoc, WI 53066
• 

  Est $650,647

  Not Listed For Sale

  1166 Goldfinch Way, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 3,075 Sq Ft
  • Built 2008

  1166 Goldfinch Way, Oconomowoc, WI 53066

  Last Sold Summary

  • 38 Days On Market
• 

  

  /68

  $774,900

  $15K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft

  W360N7572 Thomas Dr, Oconomowoc, WI 53066

  Spacious custom-built, original owner 4-bedroom, 2 full & 2 half bath home on 1.71 acres in Oconomowoc offers room to live, work, and entertain. The main level features a 2-story entry and living room with gas fireplace, dining room, office or 4th bedroom, butler's pantry, and walk-in pantry. Maple woodwork throughout includes cabinetry, solid doors, and staircase. The upper level offers a

  Jay Schmidt Keller Williams Realty-Milwaukee North Shore

  W360N7572 Thomas Dr, Oconomowoc, WI 53066
• 

  $349,900

  Sold Sep 25, 2025

  138 W 2nd St Unit 140, Oconomowoc, WI 53066

  • 1,658 Sq Ft

  Last Sold Summary

  • $211/SF
  • 2 Days On Market

  Current Estimated Value $356,922

  Last Listing Agent Matt Spheeris Coldwell Banker Elite

  138 W 2nd St Unit 140, Oconomowoc, WI 53066

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