14,726

Oconomowoc, WI Homes

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  • 1518 Weston Ridge Rd, Oconomowoc, WI 53066
    1518 Weston Ridge Rd, Oconomowoc, WI 53066
    1518 Weston Ridge Rd, Oconomowoc, WI 53066
    /21

    $649,900

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

    1518 Weston Ridge Rd, Oconomowoc, WI 53066

    Modern living at its finest in these 3bed, 3bath townhome-style ranch condos. COMPLETION est for 4/27. Two Condos still available. 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 w/quartz tops, & walk in

    Agent Photo

    Jennifer Villarreal

    Villa Realty

    1518 Weston Ridge Rd, Oconomowoc, WI 53066
  • 1200 Prairie Creek Blvd, Oconomowoc, WI 53066
    1200 Prairie Creek Blvd, Oconomowoc, WI 53066
    1200 Prairie Creek Blvd, Oconomowoc, WI 53066
    /35

    Starting at $1,362 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
  • 318 S Concord Rd, 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 $365,033

    Last Listing Agent Scott Surges RE/MAX Lakeside-West

    318 S Concord Rd, Oconomowoc, WI 53066
    • 1430 Woodside Dr, Oconomowoc, WI 53066

      Est $623,800

      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

      Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

  • 1508 Weston Ridge Rd, Oconomowoc, WI 53066
    1508 Weston Ridge Rd, Oconomowoc, WI 53066
    1508 Weston Ridge Rd, Oconomowoc, WI 53066
    /4

    $658,900

    Pending
    • 3 Beds
    • 3 Baths
    • 2,450 Sq Ft

    1508 Weston Ridge Rd, Oconomowoc, WI 53066

    There's still a ''big sky'' location left in Lake Country! Premium corner build w/a bit of extra privacy & beautiful view of untouched wooded landscape. Home has an architecturally unique floorplan designed for daily functionality while maintaining the WOW factor you'll be proud to share w/guests. This is the kitchen you'd have designed yourself! A vast quartz island centerpiece, walk in pantry,

    Agent Photo

    Jennifer Villarreal

    Villa Realty

    1508 Weston Ridge Rd, Oconomowoc, WI 53066
  • 210 S Main St, Oconomowoc, WI 53066
    210 S Main St, Oconomowoc, WI 53066
    210 S Main St, Oconomowoc, WI 53066
    /20

    Starting at $1,458 Per Month

    • 2 Beds

    210 S Main St, Oconomowoc, WI 53066

    The Berkshire Independent Senior Apartments (AGES 55+ ) are designed to specifically meet the changing needs of. Our comfortable units are an ideal option for those who no longer want the responsibility and upkeep of a house but still desire privacy, security and independence. Our apartments are spacious and most have new flooring installed. We are located one block away from beautiful

    Berkshire Oconomowoc Senior Apartments

    210 S Main St, Oconomowoc, WI 53066
  • 1182 Arrowood Cir W, Oconomowoc, WI 53066
    1182 Arrowood Cir W, Oconomowoc, WI 53066
    /2

    $544,900

    Sold Jun 19, 2026

    1182 Arrowood Cir W, Oconomowoc, WI 53066

    • 3 Beds
    • 2 Baths
    • 1,482 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $368/SF
    • 35 Days On Market

    Veridian Homes Arrowood

    1182 Arrowood Cir W, Oconomowoc, WI 53066
    • 1500 Woodside Dr, Oconomowoc, WI 53066

      Est $684,818

      Not Listed For Sale

      1500 Woodside Dr, Oconomowoc, WI 53066

      • 4 Beds
      • 3.5 Baths
      • 3,420 Sq Ft
      1500 Woodside Dr, Oconomowoc, WI 53066

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent The Italiano Team* Lake Country Flat Fee

  • 904 W Labelle Ave, Oconomowoc, WI 53066
    904 W Labelle Ave, Oconomowoc, WI 53066
    904 W Labelle Ave, Oconomowoc, WI 53066
    /49

    $2,300,000

    • 3 Beds
    • 4 Baths
    • 3,380 Sq Ft

    904 W Labelle Ave, Oconomowoc, WI 53066

    You will find this home tucked away on a dead-end street, bordering historic Merchants Plat. With three levels of lakeside enjoyment on Lac La Belle, this home has its own sandy beach, 61.5 feet of frontage, and a boathouse renovated in 2011. The setting feels both peaceful and connected, with spaces designed for everyday living, quiet nights in, and easy gatherings. Cozy mornings and evenings

    Amy Russell Stapleton Realty

    904 W Labelle Ave, Oconomowoc, WI 53066
  • 172 Morningside Orchard Dr, Oconomowoc, WI 53066
    172 Morningside Orchard Dr, Oconomowoc, WI 53066
    172 Morningside Orchard Dr, Oconomowoc, WI 53066
    /16

    Starting at $1,275 Per Month

    • 1 - 2 Beds

    172 Morningside Orchard Dr, Oconomowoc, WI 53066

    Morningside Orchard Apartments offers both one and two bedroom units. We also have fully furnished executive apartments with flexible lease options. There is a beautiful heated pool area, and we are close to the downtown area for restaurants, city parks and beaches.

    Morningside Orchard Apartments

    172 Morningside Orchard Dr, Oconomowoc, WI 53066
  • 2937 N Mill Rd, Oconomowoc, 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 $3,478,522

    Last Listing Agent Bruce Gallagher Keller Williams Realty-Lake Country

    2937 N Mill Rd, Oconomowoc, WI 53066
  • 1299 Arrowood Cir W, Oconomowoc, WI 53066
    1299 Arrowood Cir W, Oconomowoc, WI 53066
    1299 Arrowood Cir W, Oconomowoc, WI 53066
    /34

    $619,900

    New Construction $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,033 Sq Ft

    1299 Arrowood Cir W, Oconomowoc, WI 53066

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Veridian Homes Builder
    1299 Arrowood Cir W, Oconomowoc, WI 53066
  • N68w33770-W33770 County Trunk Hwy K, Oconomowoc, WI 53066
    N68w33770-W33770 County Trunk Hwy K, Oconomowoc, WI 53066
    N68w33770-W33770 County Trunk Hwy K, Oconomowoc, WI 53066
    /12

    $1,800 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • House for Rent

    N68w33770-W33770 County Trunk Hwy K, Oconomowoc, WI 53066

    Property Id: 1589091 Available immediately. Two bedroom, two bathroom home with detached garage for one vehicle. Close to Stone Bank School. Nice, private back yard.

    N68w33770-W33770 County Trunk Hwy K, Oconomowoc, WI 53066
  • 739 Elizabeth St, Oconomowoc, WI 53066

    $394,500

    Sold Aug 22, 2025

    739 Elizabeth St, Oconomowoc, WI 53066

    • 3 Beds
    • 1.5 Baths
    • 1,496 Sq Ft

    Last Sold Summary

    • 6% Below List Price
    • $264/SF
    • 11 Days On Market

    Current Estimated Value $399,581

    Last Listing Agent Timothy Michelic Realty Executives - Integrity

    739 Elizabeth St, Oconomowoc, WI 53066
    • N53W35252 Lighthouse Ln, Oconomowoc, WI 53066

      Est $547,103

      Not Listed For Sale

      N53W35252 Lighthouse Ln, Oconomowoc, WI 53066

      • 2 Beds
      • 2 Baths
      • 1,517 Sq Ft
      • Built 2011
      N53W35252 Lighthouse Ln, Oconomowoc, WI 53066

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Scott Heyerdahl First Weber Inc - Delafield

  • 1746 Whalen Dr, Oconomowoc, WI 53066
    1746 Whalen Dr, Oconomowoc, WI 53066
    1746 Whalen Dr, Oconomowoc, WI 53066
    /28

    $685,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,805 Sq Ft

    1746 Whalen Dr, Oconomowoc, WI 53066

    Move-in-ready, the Lauren 1805 places the generously sized primary bedroom & shared living spaces - including the gathering room w/ GFP, kitchen, & dining area - at the back of the home for privacy. A large island that doubles as a snack bar, spacious walk-in-pantry, quartz counters & ample storage cabinets in the kitchen provide the perfect space for meal prep. The primary bedroom offers a large

    Jennifer Durand Bielinski Homes, Inc.

    1746 Whalen Dr, Oconomowoc, WI 53066
  • N55W34667 Road E, Oconomowoc, WI 53066
    N55W34667 Road E, Oconomowoc, WI 53066
    N55W34667 Road E, Oconomowoc, WI 53066
    /7

    $3,500

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,350 Sq Ft
    • House for Rent

    N55W34667 Road E, Oconomowoc, WI 53066

    Located on Okauchee Lake! 3+ bedrooms with walk out to lake areas. Great views! More pictures upon request

    N55W34667 Road E, Oconomowoc, WI 53066
  • 457 W 5th St, Oconomowoc, WI 53066

    $380,000

    Sold Jul 06, 2026

    457 W 5th St, Oconomowoc, WI 53066

    • 3 Beds
    • 1 Bath
    • 1,312 Sq Ft

    Last Sold Summary

    • 3% Above List Price
    • $290/SF
    • 3 Days On Market

    Current Estimated Value $371,246

    Last Listing Agent Theresa Lane Abundance Real Estate

    457 W 5th St, Oconomowoc, WI 53066
  • 1298 Juniper Ln, Oconomowoc, WI 53066
    1298 Juniper Ln, Oconomowoc, WI 53066
    1298 Juniper Ln, Oconomowoc, WI 53066
    /45

    $659,900

    Under Contract
    • 4 Beds
    • 4 Baths
    • 2,700 Sq Ft

    1298 Juniper Ln, Oconomowoc, WI 53066

    MOVE IN READY! 4-bedroom, 2 full bath, 2 half bath home in sought-after Pine Ridge Estates! Situated on a beautiful corner lot, you'll enjoy walking distance to parks, shopping, dining, and everyday conveniences, all within a highly rated school district. This well-maintained home offers 2,700 sq ft , a versatile main-floor flex room, convenient upstairs laundry, and a finished basement for

    The Elements Team* Elements Realty LLC

    1298 Juniper Ln, Oconomowoc, WI 53066
  • 906 Hancock Ct, Oconomowoc, WI 53066
    906 Hancock Ct, Oconomowoc, WI 53066
    /2

    $2,395

    Total Monthly Price

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

    906 Hancock Ct, Oconomowoc, WI 53066

    906 Hancock Ct, Oconomowoc, WI 53066
  • 1704 Whalen Dr, Oconomowoc, WI 53066

    $724,900

    Sold Sep 18, 2025

    1704 Whalen Dr, Oconomowoc, WI 53066

    • 4 Beds
    • 2.5 Baths
    • 2,903 Sq Ft

    Last Sold Summary

    • 1% Below List Price
    • $250/SF
    • 117 Days On Market

    Last Listing Agent Amy Krieghoff Coldwell Banker Realty

    1704 Whalen Dr, Oconomowoc, WI 53066
  • N76W36096 Saddlebrook Ln, Oconomowoc, WI 53066
    N76W36096 Saddlebrook Ln, Oconomowoc, WI 53066
    N76W36096 Saddlebrook Ln, Oconomowoc, WI 53066
    /49

    $2,750,000

    Under Contract
    • 5 Beds
    • 4.5 Baths
    • 4,940 Sq Ft

    N76W36096 Saddlebrook Ln, Oconomowoc, WI 53066

    Lovingly maintained executive estate in the prestigious Saddlebrook Farms. Offering abundant space for both living & hobbies. Discover elegant finishes: dining room highlighted by a striking coffered ceiling, great room with soaring 18-foot ceilings, a cozy fireplace, & direct access to the outdoor deck/patio. Maple floors lead to a large, bright kitchen featuring quartz countertops. Relax in the

    Spheeris Team* Coldwell Banker Elite

    N76W36096 Saddlebrook Ln, Oconomowoc, WI 53066
  • W379N5686 N Lake Rd, Oconomowoc, WI 53066
    W379N5686 N Lake Rd, Oconomowoc, WI 53066
    W379N5686 N Lake Rd, Oconomowoc, WI 53066
    /28

    $1,195 - $1,895

    Total Monthly Price

    • 1 - 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Condo for Rent

    W379N5686 N Lake Rd, Oconomowoc, WI 53066

    Delight in the peace and serenity of living on a country estate just one mile North from downtown Oconomowoc. This This 4,500 sq. foot converted mansion was transformed into apartments. Avavilable now is a 1200 sq. foot unit with 2 bedrooms and 2 full baths. It has gleaming hardwood maple floors , and formal living and dining rooms. An Italian marble natural fireplace will be welcome in the

    W379N5686 N Lake Rd, Oconomowoc, WI 53066
  • N50W35328 Wisconsin Ave, Oconomowoc, WI 53066

    $1,425,000

    Sold Jun 05, 2026

    N50W35328 Wisconsin Ave, Oconomowoc, WI 53066

    • 2 Beds
    • 2 Baths
    • 1,960 Sq Ft

    Last Sold Summary

    • 5% Below List Price
    • $727/SF
    • 4 Days On Market

    Current Estimated Value $1,435,998

    Last Listing Agent Cynthia Klenk Shorewest Realtors, Inc.

    N50W35328 Wisconsin Ave, Oconomowoc, WI 53066
    • N52W35293 Lighthouse Ln, Oconomowoc, WI 53066
      N52W35293 Lighthouse Ln, Oconomowoc, WI 53066
      N52W35293 Lighthouse Ln, Oconomowoc, WI 53066
      /43

      Est $503,620

      Not Listed For Sale

      N52W35293 Lighthouse Ln, Oconomowoc, WI 53066

      • 2 Beds
      • 2 Baths
      • 1,593 Sq Ft
      • Built 2005
      N52W35293 Lighthouse Ln, Oconomowoc, WI 53066

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Ashley Netzer HOMEPOINT REAL ESTATE LLC

  • 1760 Derby Ln, Oconomowoc, WI 53066
    1760 Derby Ln, Oconomowoc, WI 53066
    1760 Derby Ln, Oconomowoc, WI 53066
    /34

    $659,000

    • 3 Beds
    • 3 Baths
    • 2,619 Sq Ft

    1760 Derby Ln, Oconomowoc, WI 53066

    Tucked within the Village Crossings Condos at Pabst Farms, this beautifully maintained condo feels like a new build. A calming, neutral palette complements a variety of design styles, while the open-concept main level is designed for both everyday living and entertaining. The spacious kitchen features a large island perfect for gathering around. The finished lower level adds additional living and

    Amy Russell Stapleton Realty

    1760 Derby Ln, Oconomowoc, WI 53066
  • 900 Hancock Ct, Oconomowoc, WI 53066
    900 Hancock Ct, Oconomowoc, WI 53066
    /2

    $2,395

    Total Monthly Price

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

    900 Hancock Ct, Oconomowoc, WI 53066

    900 Hancock Ct, Oconomowoc, WI 53066
  • 211 Oconomowoc Pkwy Unit 206, Oconomowoc, WI 53066

    $310,000

    Sold Aug 27, 2025

    211 Oconomowoc Pkwy Unit 206, Oconomowoc, WI 53066

    • 3 Beds
    • 2 Baths
    • 1,580 Sq Ft

    Last Sold Summary

    • 5% Below List Price
    • $196/SF
    • 62 Days On Market

    Current Estimated Value $321,576

    Last Listing Agent Shay Froemming Froemming Realty LLC

    211 Oconomowoc Pkwy Unit 206, Oconomowoc, WI 53066
  • 1615 Belmont Ln Unit 50, Oconomowoc, WI 53066
    1615 Belmont Ln Unit 50, Oconomowoc, WI 53066
    1615 Belmont Ln Unit 50, Oconomowoc, WI 53066
    /47

    $599,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,570 Sq Ft

    1615 Belmont Ln Unit 50, Oconomowoc, WI 53066

    Experience effortless luxury in this nearly new 2024 Kingsway-built condo in desirable Oconomowoc. Offering 1,579 sq ft, this immaculate 2-bedroom, 2-bath home features soaring 10-foot ceilings & upscale finishes throughout. The inviting great room showcases a stunning crossed-beam ceiling, creating warmth & architectural charm. The spacious primary suite impresses w/ a coiffured ceiling, large

    Pat Bolger Patrick Bolger Realty Group

    1615 Belmont Ln Unit 50, Oconomowoc, WI 53066
  • 542 W 5th St, Oconomowoc, WI 53066
    542 W 5th St, Oconomowoc, WI 53066
    542 W 5th St, Oconomowoc, WI 53066
    /12

    $1,750

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • House for Rent

    542 W 5th St, Oconomowoc, WI 53066

    Could be available September 1st. This 2-bedroom, 1-bath home offers comfortable living in a quiet neighborhood. The layout includes a cozy living room, functional kitchen, and full basement with convenient laundry hookups. Enjoy a large fenced-in yard with patio, ideal for outdoor relaxation.There is central air conditioning. The property also features a 1-car garage with automatic

    542 W 5th St, Oconomowoc, WI 53066
  • 888 Wildwood Place, Oconomowoc, WI 53066

    $355,500

    Sold Jun 26, 2026

    888 Wildwood Place, Oconomowoc, WI 53066

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

    Last Sold Summary

    • 5% Below List Price
    • $215/SF
    • 27 Days On Market

    Current Estimated Value $371,116

    Last Listing Agent Amy Hopfinger & Co. Team EXP Realty, LLC~MKE

    888 Wildwood Place, Oconomowoc, WI 53066
  • 1835 N Davies Dr, Oconomowoc, WI 53066
    1835 N Davies Dr, Oconomowoc, WI 53066
    1835 N Davies Dr, Oconomowoc, WI 53066
    /36

    $1,295,000

    $455K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 3,150 Sq Ft

    1835 N Davies Dr, Oconomowoc, WI 53066

    Luxury living on Lower Nemahbin awaits, with over an acre of land and over 3,000 sq ft of beautifully updated space. Enjoy stunning lake views from the master suite, open concept living space, or fully exposed lower level. With access to Upper Nemahbin and Lower Nashotah by water, this home offers both relaxation and recreation. The possibilities are endless with two separate living spaces, 4

    Paige Foss Shorewest Realtors, Inc.

    1835 N Davies Dr, Oconomowoc, WI 53066
  • 840 S Silver Lake St, Oconomowoc, WI 53066
    840 S Silver Lake St, Oconomowoc, WI 53066
    840 S Silver Lake St, Oconomowoc, WI 53066
    /13

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • House for Rent

    840 S Silver Lake St, Oconomowoc, WI 53066

    Quaint 2-Bedroom Home for Rent Prime Downtown Oconomowoc Location Enjoy the charm and convenience of this quaint 2-bedroom, 1-bath single-family home located just minutes from downtown Oconomowoc. This well-maintained home features a central AC, updated kitchen and bathroom and includes a stove, refrigerator, dishwasher, washer, and dryer. Additional features include a full basement for extra

    Scott Johnson Johnson & Hellekson Real Estate, LLC

    840 S Silver Lake St, Oconomowoc, WI 53066
  • 1591 Creekview Ln, Oconomowoc, WI 53066

    $655,045

    Sold Mar 27, 2026

    1591 Creekview Ln, Oconomowoc, WI 53066

    • 5 Beds
    • 2.5 Baths
    • 2,874 Sq Ft

    Last Sold Summary

    • 4% Above List Price
    • $228/SF
    • 142 Days On Market

    Current Estimated Value $657,398

    Last Listing Agent Joseph Behmke Kaerek Homes, Inc.

    1591 Creekview Ln, Oconomowoc, WI 53066

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