Oconomowoc, WI Homes

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  $499,000

  • 4 Beds
  • 2 Baths
  • 2,477 Sq Ft

  1077 Christopher Ct, Oconomowoc, WI 53066

  Tucked away on a quiet cul-de-sac in a desirable Oconomowoc location, this character filled 4 bedroom, 2 bath cape cod is just a short walk to Fowler Lake loop and downtown amenities. Beautiful hardwood floors grace the main level, while an oversized bay window floods the living room with natural light. Updated kitchen with granite counters & new white shaker cabinetry, natural fireplace, and

  

  J Tweeden & Asso Team

  First Weber Inc - Delafield

  1077 Christopher Ct, Oconomowoc, WI 53066
• Explore Oconomowoc

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  /31

  Starting at $1,420 Per Month

  • Studio - 3 Beds

  1600 Town Center Way, Oconomowoc, WI 53066

  Now pre-leasing for move-ins mid-July 2026! The Frederick brings a refined living experience to the heart of Oconomowoc, surrounded by the beauty and recreation of Wisconsin’s renowned Lake Country. This thoughtfully designed community blends modern comfort with neo-farmhouse inspiration, creating a warm and elevated place to call home. Enjoy garden-style buildings featuring

  The Frederick

  

  1600 Town Center Way, Oconomowoc, WI 53066
• 

  $680,000

  Sold Jun 18, 2026

  1460 Prairie Creek Blvd, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 3,509 Sq Ft

  Last Sold Summary

  • 9% Above List Price
  • $194/SF
  • 2 Days On Market

  Current Estimated Value $636,855

  Last Listing Agent J Tweeden & Asso Team First Weber Inc - Delafield

  1460 Prairie Creek Blvd, Oconomowoc, WI 53066
• 

  Est $878,791

  Not Listed For Sale

  W335N8953 Pleasant View Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft
  • Built 1950

  W335N8953 Pleasant View Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 161 Days On Market
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  /32

  $309,900

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,830 Sq Ft

  972 Valentine Rd, Oconomowoc, WI 53066

  Welcome to easy living in this charming 3 bedroom traditional townhouse style condo, nestled in one of Oconomowoc's most unique communities. Featuring resort style amenities including a swimming pool and tennis courts, this complex offers a lifestyle few can match. Inside, a clean and functional layout including; kitchen, dining room and living room; await your personal touch, a true blank canvas

  

  J Tweeden & Asso Team

  First Weber Inc - Delafield

  972 Valentine Rd, Oconomowoc, WI 53066
• 

  /2

  Call for Price

  • 1 - 3 Beds

  53018 US 18, Oconomowoc, WI 53066

  Timberveil Residences

  

  53018 US 18, Oconomowoc, WI 53066
• 

  $579,000

  Sold Apr 03, 2026

  712 Lake Bluff Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,560 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $226/SF
  • 7 Days On Market

  Current Estimated Value $577,061

  Last Listing Agent Dawson Mercier Coldwell Banker Elite

  712 Lake Bluff Dr, Oconomowoc, WI 53066
• 

  Est $699,206

  Not Listed For Sale

  1784 Regal Ct Unit 18, Oconomowoc, WI 53066

  • 3 Beds
  • 3 Baths
  • 3,234 Sq Ft

  1784 Regal Ct Unit 18, Oconomowoc, WI 53066

  Last Sold Summary

  • 57 Days On Market
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  /53

  $650,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,073 Sq Ft

  W349N5830 Sunflower Ct, Oconomowoc, WI 53066

  Nestled on a cul-de-sac in Westshore, this split-bedroom ranch offers an open-concept floor plan and room to grow. The spacious great room features a double tray ceiling and gas fireplace. Brazilian Cherry hardwood floors flow through the kitchen, entry, and hallways. Kitchen includes granite countertops, breakfast bar, pantry, and a bayed dining area. A versatile flex room is perfect for a home

  

  Kathryn Tessmer

  Keller Williams Realty-Lake Country

  W349N5830 Sunflower Ct, Oconomowoc, WI 53066
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  /36

  Starting at $1,375 Per Month

  • 1 Bed

  233 W Wisconsin Ave, Oconomowoc, WI 53066

  Welcome to The Worthington, perfectly positioned along beautiful Lac LaBelle, The Worthington offers stunning lake views and unbeatable walkability, just steps from the library, post office, banks, the beach, local restaurants, and more.Choose from thoughtfully designed one- and two-bedroom apartment homes featuring granite countertops, stainless steel appliances, soaring nine- and

  Worthington Apartments

  

  233 W Wisconsin Ave, Oconomowoc, WI 53066
• 

  $325,000

  Sold Oct 31, 2025

  291 Oconomowoc Pkwy Unit 3022, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  Last Sold Summary

  • $186/SF
  • 8 Days On Market

  Current Estimated Value $323,660

  Last Listing Agent Andrea McHenry Lake Country Flat Fee

  291 Oconomowoc Pkwy Unit 3022, Oconomowoc, WI 53066
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  $1,295,000

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

  180 Monastery Hill Dr, Oconomowoc, WI 53066

  Live the Lac La Belle lifestyle in one of Oconomowoc's most sought-after communities. Residents enjoy access to the neighborhood pier on Lac La Belle, plus community amenities including a pool & tennis courts. Walk around the lake, golf at nearby The Club at Lac La Belle, and enjoy the beauty of Lake Country right outside your door. Set on a private .72-acre lot, this newer construction,

  

  JJ Hausmann

  Compass RE WI-Lake Country

  180 Monastery Hill Dr, Oconomowoc, WI 53066
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  /40

  Starting at $1,290 Per Month

  • 2 Beds

  1033-1095 Lowell Dr, Oconomowoc, WI 53066

  Now under new ownership and management. Joseph Property Development is excited to be managing Whitman Park Apartments! Welcome to Whitman Park Apartments in charming Oconomowoc, WI! These spacious two-bedroom apartment homes offer an inviting atmosphere, spacious living areas and ample storage. Enjoy beautifully landscaped grounds, convenient parking, and easy access to local shops, dining, and

  Whitman Park Apartments

  

  1033-1095 Lowell Dr, Oconomowoc, WI 53066
• 

  $500,000

  Sold Jun 05, 2026

  1280 Wrenfield Way, Oconomowoc, WI 53066

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

  Last Sold Summary

  • $333/SF
  • 5 Days On Market

  Current Estimated Value $568,362

  Last Listing Agent Jennifer Pesicek Coldwell Banker Elite

  1280 Wrenfield Way, Oconomowoc, WI 53066
• 

  Est $360,507

  Not Listed For Sale

  686 Hickory Creek Dr Unit 2, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,552 Sq Ft
  • Built 2004

  686 Hickory Creek Dr Unit 2, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
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  /74

  $3,200,000

  • 4 Beds
  • 5 Baths
  • 4,133 Sq Ft

  1031 N Genesee Woods Dr, Oconomowoc, WI 53066

  Rare Lower Genesee Lake opportunity with 4.17 acres, 206' of level frontage, exceptional swimming frontage, and beautiful sunset views. This distinctive 4BR, 3 full + 2 half bath home offers 4,133 sq ft and the privacy, land, and lake access that are increasingly difficult to find. Rich in character and thoughtfully updated over time, the home features a spacious primary suite with private

  

  JJ Hausmann

  Compass RE WI-Lake Country

  1031 N Genesee Woods Dr, Oconomowoc, WI 53066
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  /40

  Starting at $1,416 Per Month

  • Studio - 3 Beds

  1350 Kari Ct, Oconomowoc, WI 53066

  There's no better place to experience the best of Lake Country living. At The Locklyn Apartments in Ocnomowoc, Wisconsin, you get easy access to all the places you love, plus the serenity of a community that makes you feel completely at home.

  The Locklyn

  

  1350 Kari Ct, Oconomowoc, WI 53066
• 

  $475,000

  Sold Sep 30, 2025

  239 S Sunflower Ct, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 1,494 Sq Ft

  Last Sold Summary

  • 30% Below List Price
  • $318/SF
  • 25 Days On Market

  Current Estimated Value $469,534

  Last Listing Agent Mark Yokosh Homestead Realty, Inc

  239 S Sunflower Ct, Oconomowoc, WI 53066
• 

  Est $605,092

  Not Listed For Sale

  W359N5278 Crestview Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  W359N5278 Crestview Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 4 Days On Market
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  /21

  $639,900

  Pending

  • 3 Beds
  • 3 Baths
  • 2,470 Sq Ft

  1538 Weston Ridge Rd, Oconomowoc, WI 53066

  Modern living at its finest in these 3bed, 3bath townhome-style ranch condos. COMPLETION est for 7/26. Several available that could include STEPLESS ENTRY. Open & thoughtful floorplans flow seamlessly, meeting the needs of every day living while maintaining that WOW factor you can feel proud to share w/guests. Beautiful kitchen designed for functionality includes full appliance package, island

  

  Jennifer Villarreal

  Villa Realty

  1538 Weston Ridge Rd, Oconomowoc, WI 53066
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  /35

  Starting at $1,527 Per Month

  • Studio - 3 Beds

  1200 Prairie Creek Blvd, Oconomowoc, WI 53066

  Experience all the luxuries you desire at The Preserve at Prairie Creek Apartments in Oconomowoc. This pristine community in exclusive Lake Country is your place to call home. Our ideal location allows you to walk to grocery, specialty stores and restaurants for a truly carefree living experience.The Preserve at Prairie Creek offers spacious one, two and three-bedroom innovative floor plans which

  The Preserve at Prairie Creek

  

  1200 Prairie Creek Blvd, Oconomowoc, WI 53066
• 

  $552,037

  Sold Apr 03, 2026

  847 Stirling Dr Unit Bldg 23, Unit 45, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,808 Sq Ft

  Last Sold Summary

  • $305/SF
  • 121 Days On Market

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  847 Stirling Dr Unit Bldg 23, Unit 45, Oconomowoc, WI 53066
• 

  Est $408,420

  Not Listed For Sale

  824 S Silver Lake St, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft

  824 S Silver Lake St, Oconomowoc, WI 53066

  Last Sold Summary

  • 43 Days On Market
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  /34

  $3,599,999

  Under Contract

  • 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
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  /35

  Starting at $1,545 Per Month

  • 1 - 3 Beds

  1550 Valley Rd, Oconomowoc, WI 53066

  Hackney House, developed on the iconic Pabst Farms and strategically located just minutes from I-94, offering easy access to Milwaukee and Madison. Hackney House offers a suburban setting with instant access to community amenities, we are just steps from the YMCA, restaurants, coffee shops, grocery stores, and more. With 1-, 2-, and 3-bedroom apartments and a select offering of townhomes, we take

  Hackney House Apartments

  

  1550 Valley Rd, Oconomowoc, WI 53066
• 

  $351,000

  Sold Jun 08, 2026

  W1852 Washington Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  Last Sold Summary

  • 10% Below List Price
  • $251/SF
  • 10 Days On Market

  Current Estimated Value $381,023

  Last Listing Agent Wendy Wendorf Homestead Realty, Inc

  W1852 Washington Rd, Oconomowoc, WI 53066
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  Est $1,155,426

  Not Listed For Sale

  1823 N Davies Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 3,084 Sq Ft

  1823 N Davies Dr, Oconomowoc, WI 53066

  Last Sold Summary
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  $524,900

  Under Contract

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  230 Thurow Dr, Oconomowoc, WI 53066

  Built in 2006, this spacious Open Concept Ranch is tucked within a private wooded subdivision setting! This split-BR design offers 3 BRs, 3 BAs, vaulted ceilings, & a bright, airy layout perfect for everyday living & entertaining. Generous KIT features pantry, snack bar, quartz countertops, & flows seamlessly into the large great room w/GFP. Primary suite includes WIC & private bath. Enjoy

  

  Kristel Sikora

  Shorewest Realtors, Inc.

  230 Thurow Dr, Oconomowoc, WI 53066
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  /14

  $1,850

  Total Monthly Price

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Townhouse for Rent

  426 W Wisconsin Ave, Oconomowoc, WI 53066

  426 W. Wisconsin Avenue – Oconomowoc, WIEnjoy living in one of Oconomowoc's most desirable neighborhoods, just a short walk from City Beach, Lac La Belle, and the charming shops, restaurants, and entertainment of historic downtown Oconomowoc.The main level features a welcoming living room, a functional kitchen with plenty of cabinet space, and a convenient half bath.Upstairs, you'll

  426 W Wisconsin Ave, Oconomowoc, WI 53066
• 

  $677,500

  Sold Jun 16, 2026

  1722 Hammock Ln, Oconomowoc, WI 53066

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

  Last Sold Summary

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

  Last Listing Agent Greggory Schmidt Gregg Schmidt Realty LLC

  1722 Hammock Ln, Oconomowoc, WI 53066
• 

  Est $501,059

  Not Listed For Sale

  1387 Mamerow Ln W, Oconomowoc, WI 53066

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

  1387 Mamerow Ln W, Oconomowoc, WI 53066

  Last Sold Summary

  • 82 Days On Market
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  /33

  $367,400

  $8K PRICE DROP Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  888 Wildwood Place, Oconomowoc, WI 53066

  Unique 3-4 bedroom property on over half an acre lot, located in a fantastic neighborhood, close to everything Oconomowoc offers! The newer addition offers so many possibilities with a family room overlooking your backyard, and a bedroom with large closet. Turn it into a master suite if you desire! The patio door off the family room also allows for separate entry to this wing. Main area of the

  

  Amy Hopfinger & Co. Team

  EXP Realty, LLC~MKE

  888 Wildwood Place, Oconomowoc, WI 53066
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  /35

  Starting at $1,725 Per Month

  • 1 - 2 Beds

  115 Silver Lake Plaza, Oconomowoc, WI 53066

  The Gateway Apartments offer the energy and convenience of downtown, coupled with the serenity and beauty of Lake Country. We are blocks to Lake Fowler and the beach. The Gateway is also only steps away from restaurants, shops, and entertainment. Enjoy the many concerts and festivals near Lac La Belle, and watch the parades, holiday lights, and Holiday Train from your balcony! Outside, The

  THE GATEWAY

  

  115 Silver Lake Plaza, Oconomowoc, WI 53066
• 

  $350,000

  Sold Nov 21, 2025

  318 S Concord Rd, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 1,183 Sq Ft

  Last Sold Summary

  • 4% Above List Price
  • $296/SF
  • 2 Days On Market

  Current Estimated Value $355,558

  Last Listing Agent Scott Surges RE/MAX Lakeside-West

  318 S Concord Rd, Oconomowoc, WI 53066
• 

  Est $743,762

  Not Listed For Sale

  1386 Waters Edge Dr, Oconomowoc, WI 53066

  • 5 Beds
  • 3.5 Baths
  • 3,948 Sq Ft
  • Built 2014

  1386 Waters Edge Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 9 Days On Market
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  /64

  $3,495,000

  $5K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,351 Sq Ft

  W356N5136 Lakeshore Dr, Oconomowoc, WI 53066

  This is available just in time for the July 4th celebration on Okauchee! Refined lakefront living with 140 ft. of flat frontage on Upper Oconomowoc Lake and full boat access to Okauchee Lake's vibrant dining and entertainment scene. This custom contemporary ranch w/ a full walkout showcases walls of floor-to-ceiling windows, soaring ceilings, fabulous finishes, and breathtaking panoramic lake

  

  Kimberly Stark

  First Weber Inc - Delafield

  W356N5136 Lakeshore Dr, Oconomowoc, WI 53066
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  /20

  $3,500 Per Month

  • 4 Beds
  • 3 Baths
  • 2,133 Sq Ft
  • House for Rent

  2310 N Lake Dr, Okauchee Lake, WI 53066

  AVAILABLE OCTOBER 15TH. This spacious home located on Upper Nemahbin Lake is perfect for enjoy lake views; lake sports and an all-around Lake Country lifestyle. Walking distance to restaurants and shopping in downtown Delafield. EVERYTHING IS INCLUDED! Fully furnished. Free utilities & Wi-Fi. Has 4 bedrooms and 3 FULL bathrooms. A 2.5 car garage. Also a great rental if you're in-between homes.

  2310 N Lake Dr, Okauchee Lake, WI 53066
• 

  $4,100,000

  Sold Dec 30, 2025

  2937 N Mill Rd, Oconomowoc, WI 53066

  • 6 Beds
  • 4 Baths
  • 4,018 Sq Ft

  Last Sold Summary

  • 9% Above List Price
  • $1,020/SF
  • 71 Days On Market

  Current Estimated Value $3,650,693

  Last Listing Agent Bruce Gallagher Keller Williams Realty-Lake Country

  2937 N Mill Rd, Oconomowoc, WI 53066
• 

  Est $604,720

  Not Listed For Sale

  1430 Woodside Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,484 Sq Ft
  • Built 2023

  1430 Woodside Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 4 Days On Market

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