Oconomowoc, WI Homes

• 

  

  

  /47

  $434,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  W167 Cottage Ave, Oconomowoc, WI 53066

  Move-in ready ranch on a spacious 1/2 acre lot in the highly sought-after Oconomowoc Area School District. Offering a large family room with vaulted ceilings & skylights, NFP, and 2 sets of patio doors to create a seamless transition to the outdoor patios and deck that overlooks the backyard. PLUS there is a separate living room for added living space. Enjoy the tree-lined lot, tiered gardening

  Cheryl Nettesheim The Real Estate Company Lake & Country

  W167 Cottage Ave, Oconomowoc, WI 53066
• 

  $889,900

  Sold Jul 10, 2026

  36860 Stillwater Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 3.5 Baths
  • 3,642 Sq Ft

  Last Sold Summary

  • $244/SF
  • 2 Days On Market

  Current Estimated Value $885,165

  Last Listing Agent Bonnie Jones Shorewest Realtors, Inc.

  36860 Stillwater Dr, Oconomowoc, WI 53066
• 

  Est $616,071

  Not Listed For Sale

  371 Thurow Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 4 Baths
  • 3,067 Sq Ft

  371 Thurow Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sharon Tomlinson Shorewest Realtors, Inc.
• 

  

  /2

  $79,900

  $20K PRICE DROP Under Contract

  • Land
  • 18,730 Sq Ft
  • $185,814 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 fishing

  Carrie Kutz Real Broker Milwaukee

  W2426 Mariah Ln, Oconomowoc, WI 53066
• 

  $554,100

  Sold Apr 23, 2026

  859 Stirling Dr Unit Bldg 20, Unit 39, Oconomowoc, WI 53066

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

  Last Sold Summary

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

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  859 Stirling Dr Unit Bldg 20, Unit 39, Oconomowoc, WI 53066
• 

  Est $852,612

  Not Listed For Sale

  1740 River Lakes Rd N, Oconomowoc, WI 53066

  • 5 Beds
  • 3.5 Baths
  • 5,023 Sq Ft
  • Built 2004

  1740 River Lakes Rd N, Oconomowoc, WI 53066

  Last Sold Summary

  • 98 Days On Market

  Last Listing Agent Jammie Trapp RE/MAX Preferred~Johnson Creek
• 

  

  /14

  $599,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,091 Sq Ft

  1334 Aberdeen Place, Oconomowoc, WI 53066

  New Construction - ready October 2026 - The Harrington model features 4 BR's 2.5 BA's and a 1st floor Flex Room. The Great Room includes a corner gas fireplace with 9ft stone detail to ceiling. The Primary Suite features a Box Tray Ceiling, large Walk-In Closet, a Luxury Primary Bath with Tile Floors & Tile Bench in Shower and Double Bowl Vanity. Other Highlights include a Rear Foyer with a Drop

  Paige Sederberg Harbor Homes Inc

  1334 Aberdeen Place, Oconomowoc, WI 53066
• 

  $550,000

  Sold May 15, 2026

  1039 Riverknoll Cir, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,074 Sq Ft

  Last Sold Summary

  • $265/SF

  Current Estimated Value $547,123

  Last Listing Agent Sarah Keily Shorewest Realtors, Inc.

  1039 Riverknoll Cir, Oconomowoc, WI 53066
• 

  Est $969,325

  Not Listed For Sale

  N60W38525 Blackhawk Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft
  • Built 1954

  N60W38525 Blackhawk Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Samuel Shepherd First Weber Inc - Delafield
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

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

  The Cambridge offers a spacious and functional layout with 2,128 square feet of living space. This floor plan includes 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept living area. Perfect for families or those who love to entertain, the Cambridge combines comfort and style in every detail.

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39355902, Oconomowoc, WI 53066
• 

  $480,000

  Sold Mar 02, 2026

  909 York Imperial Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $222/SF
  • 38 Days On Market

  Current Estimated Value $488,238

  Last Listing Agent Corienne Walek Keller Williams Realty-Lake Country

  909 York Imperial Dr, Oconomowoc, WI 53066
• 

  Est $385,533

  Not Listed For Sale

  1215 Lily Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 1 Bath
  • 1,436 Sq Ft

  1215 Lily Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent William Eulberg Redfin Corporation
• 

  

  /37

  $666,990

  New Construction $20K PRICE INCREASE Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  1343 Periwinkle Pass, Oconomowoc, WI 53066

  4 bedrooms/2.5 baths/elite series split ranch. 9' foundation wall/1 egress slider window/drain-vent rough in for future full bath in basement. Ceramic tiled walk-in shower/2 shower heads/double sinks/quartz vanity tops in master bathroom. Double sinks in family bath. 9' main floor ceilings/10' ceilings in foyer, living room, kitchen/dinette & tray ceiling in master bedroom. Wide millwork/paneled

  Joseph Behmke Kaerek Homes, Inc.

  1343 Periwinkle Pass, Oconomowoc, WI 53066
• 

  $540,000

  Sold Jan 22, 2026

  N67W33863 Loghouse Ct, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  Last Sold Summary

  • 5% Below List Price
  • $242/SF
  • 24 Days On Market

  Current Estimated Value $560,680

  Last Listing Agent Kim Stover Coldwell Banker Realty

  N67W33863 Loghouse Ct, Oconomowoc, WI 53066
• 

  Est $505,386

  Not Listed For Sale

  409 Pine Terrace Unit 409, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 1984

  409 Pine Terrace Unit 409, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Lynn Zwaska First Weber Inc - Delafield
• 

  

  /61

  $749,900

  Pending

  • 2 Beds
  • 2 Baths
  • 2,127 Sq Ft

  N79W34857 Petersen Rd, Oconomowoc, WI 53066

  Exceptional 7.6-Acre Country Retreat w/Expansive 5,600 Sq. Ft. Workshop! Discover the perfect blend of privacy, functionality, & country charm! This well-maintained, all-brick raised ranch features 2BR & 2BA, offering comfortable living in a peaceful rural setting. Newer roof, dishwasher, & microwave provide added value & peace of mind. Huge 40' x 140' workshop, offering 5,600 sf of main-level

  Molly Wehking Shorewest Realtors, Inc.

  N79W34857 Petersen Rd, Oconomowoc, WI 53066
• 

  $2,500,000

  Sold Oct 14, 2025

  1620 N Dousman Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 3.5 Baths
  • 3,574 Sq Ft

  Last Sold Summary

  • 16% Below List Price
  • $699/SF

  Current Estimated Value $2,611,521

  Last Listing Agent Pat McMahon Closing Time Realty, LLC

  1620 N Dousman Rd, Oconomowoc, WI 53066
• 

  Est $280,616

  Not Listed For Sale

  113 Oconomowoc Square Unit 4, Oconomowoc, WI 53066

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

  113 Oconomowoc Square Unit 4, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Shay Froemming Froemming Realty LLC
• 

  

  /36

  $685,000

  • 4 Beds
  • 1.5 Baths
  • 2,500 Sq Ft

  605 W Wisconsin Ave, Oconomowoc, WI 53066

  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

  Paul Liebe Lake Country Flat Fee

  605 W Wisconsin Ave, Oconomowoc, WI 53066
• 

  $672,990

  Sold Nov 19, 2025

  1235 Violet St, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  Last Sold Summary

  • 5% Above List Price
  • $246/SF
  • 433 Days On Market

  Current Estimated Value $711,538

  Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

  1235 Violet St, Oconomowoc, WI 53066
• 

  Est $453,785

  Not Listed For Sale

  712 Elizabeth St, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,683 Sq Ft

  712 Elizabeth St, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Lori Fritz First Weber Inc - Delafield
• 

  

  /81

  $1,674,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,571 Sq Ft

  n57w Road G, Oconomowoc, WI 53066

  A little bit of everything on Okauchee Lake! Modern contemporary design, nearly an acre wooded level lot and 113 feet of frontage! Plenty of room for the toys with two piers, located just off the main bay! Comfortable radiant in floor heat, new septic system, and a large 3 car garage plus additional parking!

  Devin Piehl First Weber Inc - Delafield

  n57w Road G, Oconomowoc, WI 53066
• 

  $342,500

  Sold Oct 14, 2025

  265 Thurow Dr Unit 109, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft

  Last Sold Summary

  • $257/SF

  Current Estimated Value $355,048

  Last Listing Agent Tammy Stelter Real Broker Milwaukee

  265 Thurow Dr Unit 109, Oconomowoc, WI 53066
• 

  Est $598,184

  Not Listed For Sale

  1223 Ridgeside Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft
  • Built 2010

  1223 Ridgeside Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Brad Parent Keller Williams Realty-Milwaukee Southwest
• 

  

  /37

  $689,900

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,045 Sq Ft

  749 Prestwick Ct, Oconomowoc, WI 53066

  Stunning contemporary on cul-de-sac with pond views! The chef's kitchen impresses with a walk-in pantry, pull-out cabinet drawers, updated appliances (2016), an octagonal island with wine rack, granite counters, tiled backsplash & hardwood floors plus a dinette leading to a patio with pergola, water feature and fire pit. The great room soars with 18' ceilings, arched windows and a gas fireplace.

  Annette Herbert Compass RE WI-Tosa

  749 Prestwick Ct, Oconomowoc, WI 53066
• 

  $365,000

  Sold Jun 09, 2026

  29 S Locust St, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  Last Sold Summary

  • 14% Above List Price
  • $238/SF
  • 3 Days On Market

  Current Estimated Value $360,312

  Last Listing Agent Sarah Keily Shorewest Realtors, Inc.

  29 S Locust St, Oconomowoc, WI 53066
• 

  Est $534,747

  Not Listed For Sale

  W357N6062 Bayshore Cir, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 2,375 Sq Ft
  • Built 1979

  W357N6062 Bayshore Cir, Oconomowoc, WI 53066

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Paul Liebe Lake Country Flat Fee
• 

  

  /25

  $479,900

  • 5 Beds
  • 2 Baths
  • 1,906 Sq Ft

  980 Bartlett Dr, Oconomowoc, WI 53066

  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

  Paul Liebe Lake Country Flat Fee

  980 Bartlett Dr, Oconomowoc, WI 53066
• 

  $895,000

  Sold Apr 22, 2026

  W336N6496 Lakeview Dr, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $1,271/SF
  • 3 Days On Market

  Current Estimated Value $869,805

  Last Listing Agent The Italiano Team* Lake Country Flat Fee

  W336N6496 Lakeview Dr, Oconomowoc, WI 53066
• 

  Est $775,934

  Not Listed For Sale

  1742 Springhaven Ct, Oconomowoc, WI 53066

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft
  • Built 2005

  1742 Springhaven Ct, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Dorene Drumel Keller Williams-MNS Wauwatosa
• 

  

  /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
• 

  $539,900

  Sold Aug 29, 2025

  522 Thurow Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,783 Sq Ft

  Last Sold Summary

  • $303/SF
  • 3 Days On Market

  Current Estimated Value $557,036

  Last Listing Agent Nancy Markos First Weber Inc - Delafield

  522 Thurow Dr, Oconomowoc, WI 53066
• 

  Est $475,145

  Not Listed For Sale

  36830 Prairie Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,720 Sq Ft
  • Built 1973

  36830 Prairie Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Mark Yokosh Homestead Realty, Inc
• 

  

  /30

  $439,900

  $20K 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
• 

  $327,000

  Sold Sep 04, 2025

  714 E Roland St, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  Last Sold Summary

  • 7% Below List Price
  • $311/SF
  • 9 Days On Market

  Current Estimated Value $333,361

  Last Listing Agent Tiffany Cusatis Redefined Realty Advisors LLC

  714 E Roland St, Oconomowoc, WI 53066
• 

  Est $627,858

  Not Listed For Sale

  1403 Bluebird Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,581 Sq Ft

  1403 Bluebird Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Justin Bruce Shorewest Realtors, Inc.
• 

  

  /102

  $798,500

  Under Contract

  • 4 Beds
  • 2 Baths
  • 3,300 Sq Ft

  1201 S Waterville Rd, Oconomowoc, WI 53066

  This Charm infused 1837 Historical Home has been lovingly restored & updated. Bringing Nature to your doorstep, it has been perfectly placed on almost 3 acres of Woods, surrounded by WildFlowers, and offers 135 of Frontage on Henrietta Lake. This majestic Icon offers 3,300 plus finished square feet of comfortable elegance. Featuring 3 fireplaces, a Great Room opening to the expansive Sun Room, a

  Sue Patti Realty Executives - Integrity

  1201 S Waterville Rd, Oconomowoc, WI 53066
• 

  $231,000

  Sold Jun 12, 2026

  39509 Golden Lake Park Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 1 Bath
  • 1,314 Sq Ft

  Last Sold Summary

  • 16% Above List Price
  • $176/SF
  • 1 Day On Market

  Current Estimated Value $326,124

  Last Listing Agent Robert Hanon Shorewest Realtors, Inc.

  39509 Golden Lake Park Rd, Oconomowoc, WI 53066
• 

  Est $551,697

  Not Listed For Sale

  1301 Blue Dahlia Rd, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft

  1301 Blue Dahlia Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lori Wittkopp Century 21 Affiliated - Delafield
• 

  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

Showing Results 161 - 200, Page 5 of 18