Oconomowoc, WI Homes

• 

  

  

  /4

  $763,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  1750 Whalen Dr, Oconomowoc, WI 53066

  This home is move-in-ready. The Francesca 2428 is an ideal home that needs both communal & private spaces. The 1st-floor is home to the gathering room, formal dining room, & dinette. The kitchen features quartz counters, a prep island w/ seating, walk-in pantry, s.s. appliances, & tile backsplash. The main floor also features a private home office. Heading upstairs, you're met w/ 3 secondary

  Jennifer Durand Bielinski Homes, Inc.

  1750 Whalen Dr, Oconomowoc, WI 53066
• 

  $750,000

  Sold Apr 21, 2026

  208 N Maple Terrace, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,872 Sq Ft

  Last Sold Summary

  • 12% Below List Price
  • $261/SF
  • 76 Days On Market

  Current Estimated Value $762,372

  Last Listing Agent Samuel Shepherd First Weber Inc - Delafield

  208 N Maple Terrace, Oconomowoc, WI 53066
• 

  Est $645,082

  Not Listed For Sale

  W350N6763 Baltic Pass, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,322 Sq Ft
  • Built 1994

  W350N6763 Baltic Pass, Oconomowoc, WI 53066

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Joe Schulteis Allied Realty Group LLC
• 

  

  

  /26

  $425,000

  • 3 Beds
  • 1 Bath
  • 1,516 Sq Ft

  N52W35379 W Lake Dr, Oconomowoc, WI 53066

  This one has it all! Perfectly located with easy access to Hwy 16 and within walking distance of beautiful Okauchee Lake, restaurants, shopping, and other local amenities. This charming home offers a versatile lower-level primary suite that can also be used as a spacious family room, giving you flexible living options to fit your lifestyle. The true showstopper is the incredible 30' x 32' heated

  Elizabeth Curro Shorewest Realtors, Inc.

  N52W35379 W Lake Dr, Oconomowoc, WI 53066
• 

  

  /2

  $589,900

  Sold Jan 14, 2026

  1213 Arrowood Cir W, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,056 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $287/SF
  • 110 Days On Market

  Veridian Homes Arrowood

  1213 Arrowood Cir W, Oconomowoc, WI 53066
• 

  Est $632,037

  Not Listed For Sale

  223 Shore Cir, Oconomowoc, WI 53066

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

  223 Shore Cir, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Paul Liebe Lake Country Flat Fee
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

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

  The Alexandria offers a spacious and functional layout, perfect for families seeking comfort and style. With four bedrooms and two-and-a-half baths, this floor plan provides ample space for relaxation and daily living.

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356182, Oconomowoc, WI 53066
• 

  $759,900

  Sold Apr 17, 2026

  1620 Creekview Ln, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,081 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $365/SF
  • 62 Days On Market

  Current Estimated Value $755,095

  Last Listing Agent Stacy Braun Score Realty Group, LLC

  1620 Creekview Ln, Oconomowoc, WI 53066
• 

  Est $546,979

  Not Listed For Sale

  209 Shore Cir, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft
  • Built 2003

  209 Shore Cir, Oconomowoc, WI 53066

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Kevin Koski 3% Real Estate
• 

  

  /5

  $470,000

  $470K PRICE INCREASE Under Contract

  • Land
  • 32,670 Sq Ft
  • $626,667 per Acre

  N73W36388 S Shore Dr, Oconomowoc, WI 53066

  Property is being sold via online auction. Auction runs July 9th thru July 30th. Rare chance to own a prime lakefront property with breath-taking views situated on a stunning 3/4-acre lot on Ashippun Lake. Here's an amazing opportunity to tear down and build your dream home! Enjoy approximately 90 feet of frontage with an expansive building envelope--ideal for constructing a substantial custom

  Randy Rosen HomeBuyers Advantage, LLC

  N73W36388 S Shore Dr, Oconomowoc, WI 53066
• 

  $410,000

  Sold Mar 31, 2026

  451 Coolidge St, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 2,010 Sq Ft

  Last Sold Summary

  • 9% Above List Price
  • $204/SF
  • 2 Days On Market

  Current Estimated Value $415,068

  Last Listing Agent Alaina Zieman Keller Williams Realty-Lake Country

  451 Coolidge St, Oconomowoc, WI 53066
• 

  Est $313,172

  Not Listed For Sale

  W397N5970 Autumn Woods Dr Unit 84, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,212 Sq Ft

  W397N5970 Autumn Woods Dr Unit 84, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Team Smith Wisco Team* Keller Williams Realty-Milwaukee Southwest
• 

  

  /36

  $549,900

  $50K PRICE INCREASE Pending

  • 2 Beds
  • 2 Baths
  • 1,506 Sq Ft

  N54W35199 Coastal Ave Unit 42-02, Oconomowoc, WI 53066

  Beautifully maintained side x side condo offering peaceful pond views & abundant wildlife right outside your door. Enjoy the perfect blend of privacy and convenience w/ private front entrance & no-step entry. Open-concept floor plan w/ spacious kitchen featuring granite countertops, SS appliances, WIP, & dining area that flows seamlessly into great room w/ GFP. Adjoining sunroom w/ access to

  Aimee Holt M3 Realty

  N54W35199 Coastal Ave Unit 42-02, Oconomowoc, WI 53066
• 

  $450,000

  Sold Oct 03, 2025

  935 Old Tower Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $268/SF
  • 9 Days On Market

  Current Estimated Value $466,146

  Last Listing Agent Ryan Lucas M3 Realty

  935 Old Tower Rd, Oconomowoc, WI 53066
• 

  

  /44

  Est $417,553

  Not Listed For Sale

  W395N5892 Laketon Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 2,064 Sq Ft
  • Built 1968

  W395N5892 Laketon Ave, Oconomowoc, WI 53066

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Stan Jones Unified Jones Auction & Realty
• 

  

  /38

  $519,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  924 N Oakwood Ave, Oconomowoc, WI 53066

  Live a short walk from Fowler Lake and in one of the city's most walkable neighborhoods, with shopping, restaurants, coffee shops, parks, and the lakefront all nearby. This completely renovated, turnkey 4-bedroom, 2.5-bath ranch offers 2,166 sq. ft. of beautifully updated single-level living. The show stopping kitchen features soaring vaulted ceilings, skylights, quartz countertops, soft-close

  Michael Lolio Epique Realty

  924 N Oakwood Ave, Oconomowoc, WI 53066
• 

  $575,000

  Sold Dec 05, 2025

  1451 Whalen Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 3,229 Sq Ft

  Last Sold Summary

  • 4% Below List Price
  • $178/SF
  • 29 Days On Market

  Current Estimated Value $621,088

  Last Listing Agent Paul Liebe Lake Country Flat Fee

  1451 Whalen Dr, Oconomowoc, WI 53066
• 

  Est $625,866

  Not Listed For Sale

  W341N6766 Lancelot Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 3 Baths
  • 2,600 Sq Ft

  W341N6766 Lancelot Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Cathy Liebert Abundance Real Estate
• 

  

  /70

  $1,250,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  1620 St Andrews Dr Unit 13, Oconomowoc, WI 53066

  DEEDED BOAT SLIP! PRIVATE BEACH! BEAUTIFUL ITALIAN STYLE VILLA! If you appreciate the look and feel of old world Italy you will absolutely adore this exquisite condo. This home has the look and feel of an authentic Italian Villa combined w/ superior quality, luxurious appointments & modern conveniences. This condo measures a tad under 4000 sq ft of living space w/ 4BR's and 3.5BA's. The large

  Pat Bolger Patrick Bolger Realty Group

  1620 St Andrews Dr Unit 13, Oconomowoc, WI 53066
• 

  $299,000

  Sold Jan 16, 2026

  510 Frederick Ct Unit 510, Oconomowoc, WI 53066

  • 2 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $168/SF
  • 34 Days On Market

  Current Estimated Value $317,542

  Last Listing Agent Jennifer Pesicek Coldwell Banker Elite

  510 Frederick Ct Unit 510, Oconomowoc, WI 53066
• 

  Est $1,477,156

  Not Listed For Sale

  W349S3090 Waterville Rd, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 5,687 Sq Ft

  W349S3090 Waterville Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Tyler Krischan Century 21 Affiliated - Delafield
• 

  

  /29

  $609,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,056 Sq Ft

  1190 Arrowood Cir W, Oconomowoc, WI 53066

  Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  1190 Arrowood Cir W, Oconomowoc, WI 53066
• 

  $379,000

  Sold Jan 05, 2026

  W179 Madison Ave, Oconomowoc, WI 53066

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

  Last Sold Summary

  • $232/SF
  • 6 Days On Market

  Current Estimated Value $383,471

  Last Listing Agent Tina Monroe Dedrick Homes

  W179 Madison Ave, Oconomowoc, WI 53066
• 

  Est $566,193

  Not Listed For Sale

  1340 Orchard Cir, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft
  • Built 2000

  1340 Orchard Cir, Oconomowoc, WI 53066

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Sue Patti Realty Executives - Integrity
• 

  

  /40

  $749,900

  • 4 Beds
  • 3.5 Baths
  • 3,334 Sq Ft

  1704 River Lakes Rd N, Oconomowoc, WI 53066

  Experience refined luxury in Eastlake Village at Pabst Farms with this meticulous 4BR/3.5BA estate. A striking grand foyer anchors the main level, opening to both an elegant formal dining room with a butler's pantry and a gracious great room centered by a gas fireplace. The gourmet eat-in kitchen features SS appliances, granite countertops, a breakfast bar, and direct access to a private patio. A

  Curtis Downes Mahler Sotheby's International Realty-Lake Country

  1704 River Lakes Rd N, Oconomowoc, WI 53066
• 

  $300,000

  Sold Apr 24, 2026

  754 Summit Ave, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 903 Sq Ft

  Last Sold Summary

  • $332/SF
  • 2 Days On Market

  Current Estimated Value $299,224

  Last Listing Agent Heidi Swan Shorewest Realtors, Inc.

  754 Summit Ave, Oconomowoc, WI 53066
• 

  Est $3,437,746

  Not Listed For Sale

  34546 Valley Rd, Oconomowoc, WI 53066

  • 6 Beds
  • 5.5 Baths
  • 4,712 Sq Ft
  • Built 2019

  34546 Valley Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 104 Days On Market

  Last Listing Agent Paul Liebe Lake Country Flat Fee
• 

  

  /62

  $829,900

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,639 Sq Ft

  W349S2296 Waterville Rd, Oconomowoc, WI 53066

  Exceptional Home - Timeless Design. Meticulously maintained 4 bedroom, 2.5 bath home with attached 2-car heated garage & 2.5-car detached garage with stairs leading up to attic above. This is your rare opportunity to live on 3 private tree lined acres complete with long front and rear covered porches & partial exposure. Main floor has large great room with stunning 2-story wood & beamed ceiling,

  Shawn Roth Shorewest Realtors, Inc.

  W349S2296 Waterville Rd, Oconomowoc, WI 53066
• 

  $497,000

  Sold Jul 31, 2026

  W646 Townline Rd, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 1,357 Sq Ft

  Last Sold Summary

  • 2% Above List Price
  • $366/SF
  • 2 Days On Market

  Current Estimated Value $485,859

  Last Listing Agent Donald Loew RE/MAX Insight

  W646 Townline Rd, Oconomowoc, WI 53066
• 

  Est $456,202

  Not Listed For Sale

  351 S Maple St, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1956

  351 S Maple St, Oconomowoc, WI 53066

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Curt Downes & Associates Team* Mahler Sotheby's International Realty
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

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

  The Lyndon offers a spacious and thoughtfully designed layout, perfect for families or those who love to entertain. With 3 bedrooms and 2.5 baths, this floor plan provides ample space for comfortable living.

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356048, Oconomowoc, WI 53066
• 

  

  /49

  $745,000

  Sold Jul 27, 2026

  261 Ridgeway Path, Oconomowoc, WI 53066

  • 5 Beds
  • 3.5 Baths
  • 3,968 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $726,795

  Last Listing Agent Mandi Miller Restaino & Associates

  261 Ridgeway Path, Oconomowoc, WI 53066
• 

  Est $812,426

  Not Listed For Sale

  547 W Labelle Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 4 Baths
  • 2,620 Sq Ft

  547 W Labelle Ave, Oconomowoc, WI 53066

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent The Italiano Team* Lake Country Flat Fee
• 

  

  /53

  $450,000

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,816 Sq Ft

  524 E Jefferson St, Oconomowoc, WI 53066

  Rarely does a property offer such exquisite craftsmanship & artistic detail while providing seemingly endless potential. Owned for decades by Master Woodworker & Fine Art Photographer Tony Casper, this amazing 2 bedroom, 1.5 bath colonial is a testament to his limitless talent & ability to create beauty, even in the most unassuming places. Whether walking up the charming front entry past his

  Ann Moran Lecher Shorewest Realtors, Inc.

  524 E Jefferson St, Oconomowoc, WI 53066
• 

  /2

  $524,900

  Sold Mar 25, 2026

  1227 Arrowood Cir W, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,647 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $319/SF
  • 75 Days On Market

  Veridian Homes Arrowood

  1227 Arrowood Cir W, Oconomowoc, WI 53066
• 

  Est $875,560

  Not Listed For Sale

  N64W33715 Lakeview Dr, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  N64W33715 Lakeview Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent JJ Hausmann Compass RE WI-Lake Country
• 

  

  /46

  $589,500

  Under Contract

  • 4 Beds
  • 3 Baths
  • 3,230 Sq Ft

  W2261 E Oak Ridge Dr, Oconomowoc, WI 53066

  Gorgeous Open Concept 4BR 3 Full BA 3,230 Sq FT Exposed Ranch Located on a Cul-De-Sac Large Private Lot Abutting Farmland. Step onto the Covered Front Porch and Walk into a Large Open Concept LR w HWF's, Cathedral Ceilings, a GFP, and 2 Large Patio Doors w a 2nd Covered Porch w Patio to the Backyard. Beautiful Kitchen Overlooks the LR w Cherry Cabs and Granite Counters and Breakfast Bar w all

  Hoffmann Team* RE/MAX Lakeside-Central

  W2261 E Oak Ridge Dr, Oconomowoc, WI 53066
• 

  $579,960

  Sold Jul 14, 2026

  1354 Macgregor Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  Last Sold Summary

  • $320/SF
  • 0 Days On Market

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  1354 Macgregor Rd, Oconomowoc, WI 53066
• 

  Est $750,239

  Not Listed For Sale

  N67W34320 Jorgenson Ct, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft
  • Built 2004

  N67W34320 Jorgenson Ct, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Breanna Bertschinger EXP Realty, LLC~MKE
• 

  

  /19

  $249,900

  $20K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 819 Sq Ft

  423 W South St, Oconomowoc, WI 53066

  Prime location and affordability! Don't miss your chance to own this charming bungalow in the heart of Oconomowoc--perfect for a starter home or an investment property. This 2-bedroom home has an enclosed front porch for year-round enjoyment. The bathroom has been updated with heated floors and the kitchen features SS appliances. The backyard is a gardener's oasis, with garden beds already set up

  Andrea Kane Century 21 Affiliated - Delafield

  423 W South St, Oconomowoc, WI 53066

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