Oconomowoc, WI Homes

• 

  $423,000

  Sold Jan 06, 2026

  2231 N Glendale Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  Last Sold Summary

  • 6% Above List Price
  • $190/SF
  • 1 Day On Market

  Current Estimated Value $448,367

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

  2231 N Glendale Rd, Oconomowoc, WI 53066
• 

  Est $471,564

  Not Listed For Sale

  N63W37795 Vista Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,945 Sq Ft

  N63W37795 Vista Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 4 Days On Market
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

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

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356302, Oconomowoc, WI 53066
• 

  $660,000

  Sold Apr 15, 2026

  1533 Fay Ln, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  Last Sold Summary

  • 4% Above List Price
  • $329/SF
  • 2 Days On Market

  Current Estimated Value $651,053

  Last Listing Agent Megan Hoy First Weber Inc - Delafield

  1533 Fay Ln, Oconomowoc, WI 53066
• 

  Est $874,363

  Not Listed For Sale

  555 River Bluff Cir, Oconomowoc, WI 53066

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

  555 River Bluff Cir, Oconomowoc, WI 53066

  Last Sold Summary

  • 30 Days On Market
• 

  

  /4

  $685,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  1252 Wild Rye Ln, Oconomowoc, WI 53066

  The Lauren 1851 that 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 WIC &

  Jennifer Durand Bielinski Homes, Inc.

  1252 Wild Rye Ln, Oconomowoc, WI 53066
• 

  $515,000

  Sold Sep 30, 2025

  622 E Grove St, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,878 Sq Ft

  Last Sold Summary

  • 7% Above List Price
  • $274/SF
  • 3 Days On Market

  Current Estimated Value $519,797

  Last Listing Agent Shay Froemming Froemming Realty LLC

  622 E Grove St, Oconomowoc, WI 53066
• 

  Est $571,163

  Not Listed For Sale

  1242 Oriole Dr, Oconomowoc, WI 53066

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

  1242 Oriole Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 11 Days On Market
• 

  

  /66

  $745,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,723 Sq Ft

  1333 N Riverline Dr, Oconomowoc, WI 53066

  Discover the ultimate blend of interior luxury and outdoor tranquility. This exceptional home offers a secluded, country-estate feel while delivering a thoughtfully designed floor plan tailored perfectly to your modern lifestyle. Step outside to enjoy a beautifully landscaped backyard featuring a serene fishpond and waterfall. Whether you are entertaining on the deck or relaxing on the patio, the

  Douglas Bartmann Shorewest Realtors, Inc.

  1333 N Riverline Dr, Oconomowoc, WI 53066
• 

  $549,900

  Sold Oct 24, 2025

  631 Summer Creek Rd, Oconomowoc, WI 53066

  • 4 Beds
  • 3 Baths
  • 2,264 Sq Ft

  Last Sold Summary

  • $243/SF
  • 9 Days On Market

  Current Estimated Value $548,393

  Last Listing Agent Jill Mullane HomeWire Realty

  631 Summer Creek Rd, Oconomowoc, WI 53066
• 

  Est $434,282

  Not Listed For Sale

  607 E Roland St, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1938

  607 E Roland St, Oconomowoc, WI 53066

  Last Sold Summary

  • 2 Days On Market
• 

  

  /4

  $769,900

  New Construction Pending

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

  1702 Switchgrass St, Oconomowoc, WI 53066

  This home is under construction. 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.

  1702 Switchgrass St, Oconomowoc, WI 53066
• 

  $660,000

  Sold Apr 24, 2026

  1331 Bluestem Trail, Oconomowoc, WI 53066

  • 4 Beds
  • 2.5 Baths
  • 2,403 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $275/SF
  • 12 Days On Market

  Current Estimated Value $668,316

  Last Listing Agent Lori Fritz First Weber Inc - Delafield

  1331 Bluestem Trail, Oconomowoc, WI 53066
• 

  Est $450,438

  Not Listed For Sale

  838 W Wisconsin Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  838 W Wisconsin Ave, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  

  /5

  $709,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,748 Sq Ft

  1763 Quail Cir, Oconomowoc, WI 53066

  HOUSE IS IN ROUGH TRADES. 4 bedrooms/2.5 baths/flex room/Partial Exposure/Elite series 2-story. Basement has windows & drain/vent rough-in for future full bath. Ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops in master bath. Double sinks family bath. 9' 1st floor ceilings/tray ceiling master bedroom. Kitchen cabinets w/hardware & cabinet crown

  Joseph Behmke Kaerek Homes, Inc.

  1763 Quail Cir, Oconomowoc, WI 53066
• 

  

  /18

  $390,000

  Sold Oct 10, 2025

  1360 S Concord Rd, Oconomowoc, WI 53066

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1957

  Last Sold Summary

  • 7% Above List Price
  • $355/SF
  • 3 Days On Market

  Current Estimated Value $394,816

  Last Listing Agent Abe Yanko First Weber Inc

  1360 S Concord Rd, Oconomowoc, WI 53066
• 

  Est $1,832,889

  Not Listed For Sale

  36645 Armour Rd, Oconomowoc, WI 53066

  • 5 Beds
  • 4.5 Baths
  • 4,780 Sq Ft
  • Built 1985

  36645 Armour Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 94 Days On Market
• 

  

  /28

  $4,100,000

  • 5 Beds
  • 3.5 Baths
  • 5,437 Sq Ft

  3005 N Silver Cedar Rd, Oconomowoc, WI 53066

  Extraordinary Custom lakefront home by Colby Construction on 102' of prime Silver Lake east shore frontage. Exceptional craftsmanship and luxury finishes throughout including hickory hardwood floors, authentic barn beams and doors, Brazilian Ipe decking, honed Quartzite countertops, and Calacatta marble in the primary bath. Chef's kitchen features double Sub-Zero refrigerator/freezers, 60'' Wolf

  Bruce Gallagher Keller Williams Realty-Lake Country

  3005 N Silver Cedar Rd, Oconomowoc, WI 53066
• 

  $539,900

  Sold May 21, 2026

  845 Stirling Dr Unit Bldg 23, Unit 46, Oconomowoc, WI 53066

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

  Last Sold Summary

  • $299/SF
  • 9 Days On Market

  Last Listing Agent Paige Sederberg Harbor Homes Inc

  845 Stirling Dr Unit Bldg 23, Unit 46, Oconomowoc, WI 53066
• 

  Est $598,065

  Not Listed For Sale

  245 Hillside Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 3.5 Baths
  • 3,231 Sq Ft

  245 Hillside Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 8 Days On Market
• 

  

  /4

  $689,900

  New Construction

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

  1367 Scotsland Ln, Oconomowoc, WI 53066

  This two-story home features an open-concept main floor designed for effortless entertaining and everyday living. The spacious kitchen includes a large island and walk-in pantry, flowing seamlessly into the dining area and great room. A rear foyer with built-in storage and a conveniently located powder room keeps daily routines organized and efficient. The flex room near the front entry offers

  Tim O'Brien Homes Builder

  1367 Scotsland Ln, Oconomowoc, WI 53066
• 

  $340,100

  Sold Aug 29, 2025

  W397N5996 Autumn Woods Dr Unit 58, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,824 Sq Ft

  Last Sold Summary

  • 3% Above List Price
  • $186/SF
  • 3 Days On Market

  Current Estimated Value $335,912

  Last Listing Agent Kathleen Schlicher Horizon Real Estate Service

  W397N5996 Autumn Woods Dr Unit 58, Oconomowoc, WI 53066
• 

  Est $300,848

  Not Listed For Sale

  265 Oconomowoc Pkwy Unit 2082, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Built 2004

  265 Oconomowoc Pkwy Unit 2082, Oconomowoc, WI 53066

  Last Sold Summary

  • 1 Day On Market
• 

  

  /43

  $325,000

  Pending

  • 2 Beds
  • 1 Bath
  • 833 Sq Ft

  834 S Silver Lake St, Oconomowoc, WI 53066

  Small but mighty, this 2BR Cottage Style Home will steal your heart and your head will enthusiastically approve! Newer appliances, roof & no maintenance siding make this not just ADORABLE, but a great value as well. Your next chapter begins on a beautifully landscaped quarter acre lot, boasting an extra-large 2 car garage with staircase to a HUGE upper room ready for your ideas & interests. Sip a

  Ann Moran Lecher Shorewest Realtors, Inc.

  834 S Silver Lake St, Oconomowoc, WI 53066
• 

  $547,744

  Sold Jul 10, 2025

  1236 Violet St, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $296/SF
  • 20 Days On Market

  Current Estimated Value $568,665

  Last Listing Agent Ryan Prellwitz Loos Custom Homes,LLC

  1236 Violet St, Oconomowoc, WI 53066
• 

  Est $355,254

  Not Listed For Sale

  723 S Silver Lake St, Oconomowoc, WI 53066

  • 3 Beds
  • 1 Bath
  • 1,195 Sq Ft

  723 S Silver Lake St, Oconomowoc, WI 53066

  Last Sold Summary

  • 2 Days On Market
• 

  

  /55

  $594,999

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,286 Sq Ft

  112 N Meadowside Ct, Oconomowoc, WI 53066

  Beautifully maintained 3-bedroom, 2.5-bath traditional colonial situated on a sizable lot backing to peaceful common shared land with scenic walking trails. This inviting home features a stunning kitchen with granite countertops, a large center island, stainless steel appliances, and ample cabinet space. The warm and welcoming living room offers a natural fireplace, while the formal dining room

  Amiee Melero Realty Executives - Integrity

  112 N Meadowside Ct, Oconomowoc, WI 53066
• 

  $385,000

  Sold Mar 13, 2026

  W277 Madison Ave, Oconomowoc, WI 53066

  • 3 Beds
  • 1.5 Baths
  • 1,288 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $299/SF
  • 90 Days On Market

  Current Estimated Value $380,280

  Last Listing Agent Anthony Alesci Alesci Realty

  W277 Madison Ave, Oconomowoc, WI 53066
• 

  Est $509,824

  Not Listed For Sale

  251 Hillside Dr, Oconomowoc, WI 53066

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft

  251 Hillside Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 2 Days On Market
• 

  

  /6

  $739,990

  New Construction Under Contract

  • 4 Beds
  • 3 Baths
  • 3,013 Sq Ft

  1779 Quail Cir, Oconomowoc, WI 53066

  House in rough carpentry -Approx. finish Jan. '27. 4 bedrooms/3 full baths/flex room or 5th bedroom/Partial exposure/elite series 2-story. Basement has windows in exposure & drain/vent rough-in for future full bath. Corner ceramic tiled walk-in shower/2 shower heads/double sinks/granite or equivalent vanity tops in master bath. Double sinks family bath. WIC's all bedrooms/2 in Master. 9' 1st

  Joseph Behmke Kaerek Homes, Inc.

  1779 Quail Cir, Oconomowoc, WI 53066
• 

  $575,000

  Sold Jul 16, 2025

  N54W35709 Hill Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2.5 Baths
  • 2,244 Sq Ft

  Last Sold Summary

  • 3% Above List Price
  • $256/SF
  • 2 Days On Market

  Current Estimated Value $588,628

  Last Listing Agent Amy Russell Stapleton Realty

  N54W35709 Hill Rd, Oconomowoc, WI 53066
• 

  Est $1,388,497

  Not Listed For Sale

  875 S Waterville Lake Rd, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,552 Sq Ft

  875 S Waterville Lake Rd, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

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

  Loos Homes Builder

  1328 Periwinkle Pass Unit 39356193, Oconomowoc, WI 53066
• 

  $1,070,000

  Sold Jan 09, 2026

  34100 Sunset Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,286 Sq Ft

  Last Sold Summary

  • 29% Below List Price
  • $468/SF

  Current Estimated Value $1,176,566

  Last Listing Agent The Elements Team* Elements Realty LLC

  34100 Sunset Dr, Oconomowoc, WI 53066
• 

  Est $1,095,224

  Not Listed For Sale

  W337N8059 Prairie Hollow Dr, Oconomowoc, WI 53066

  • 5 Beds
  • 4.5 Baths
  • 5,763 Sq Ft

  W337N8059 Prairie Hollow Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 3 Days On Market
• 

  

  /40

  $515,000

  Under Contract

  • 5 Beds
  • 2 Baths
  • 2,342 Sq Ft

  N8104 La Salle Cir, Oconomowoc, WI 53066

  Full of charm and space, this distinctive 2-story home features eye-catching dormer windows and a mansard roof that set it apart. Inside, you'll find 5 bedrooms and 2 beautifully refreshed baths, along with thoughtful updates throughout- new LVP flooring on the main level, new carpet upstairs, updated doors, and a remodeled laundry room. The newer HVAC adds comfort and peace of mind. Set on

  Sarah Keily Shorewest Realtors, Inc.

  N8104 La Salle Cir, Oconomowoc, WI 53066
• 

  $525,000

  Sold Aug 01, 2025

  901 W Wisconsin Ave, Oconomowoc, WI 53066

  • 4 Beds
  • 1.5 Baths
  • 1,804 Sq Ft

  Last Sold Summary

  • 19% Above List Price
  • $291/SF
  • 3 Days On Market

  Current Estimated Value $528,766

  Last Listing Agent Paul Liebe Lake Country Flat Fee

  901 W Wisconsin Ave, Oconomowoc, WI 53066
• 

  Est $713,939

  Not Listed For Sale

  35223 Sunset Dr, Oconomowoc, WI 53066

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  35223 Sunset Dr, Oconomowoc, WI 53066

  Last Sold Summary

  • 10 Days On Market
• 

  

  /25

  $299,900

  Under Contract

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

  W398N5953 Autumn Woods Dr Unit 62, Oconomowoc, WI 53066

  Welcome home to this beautiful 2-bedroom, 2-bathroom ground floor condo in desirable Oconomowoc. The open-concept floor plan offers a spacious and inviting living area, perfect for everyday living and entertaining. Large windows fill the home with natural light, creating a bright and airy atmosphere throughout. The primary suite features a private bath and generous closet space, while the second

  Nick Jensen Keller Williams Realty-Lake Country

  W398N5953 Autumn Woods Dr Unit 62, Oconomowoc, WI 53066
• 

  $1,030,000

  Sold Dec 19, 2025

  215 E Pleasant St Unit 508, Oconomowoc, WI 53066

  • 2 Beds
  • 2 Baths
  • 1,685 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $611/SF
  • 33 Days On Market

  Current Estimated Value $1,036,574

  Last Listing Agent Corienne Walek Keller Williams Realty-Lake Country

  215 E Pleasant St Unit 508, Oconomowoc, WI 53066

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