Real Estate Investment Properties for Sale in Oconomowoc, WI

Looking for investment property in Oconomowoc, WI with high ROI ?

Explore a variety of short-term homes & houses in Oconomowoc, WI. Invest wisely with VRBO & Oconomowoc, WI Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Oconomowoc, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
970 Oconomowoc Pkwy Oconomowoc, WI UPDATES UPDATES! From floor to ceiling, updates are everywhere in this 2 Bedroom, 2.5 Bath...	2 beds \| 3 baths \| 2,275 sq.ft.	$444,900	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.52% Airbnb Rental Income: $1498 Traditional Rental Income: $2198 Airbnb ROI: -0.21% Traditional ROI: 2.52%
1746 Whalen Dr Oconomowoc, WI Move-in-ready, the Lauren 1805 places the generously sized primary bedroom & shared living...	3 beds \| 2 baths \| 1,805 sq.ft.	$685,900	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.72% Airbnb Rental Income: $2022 Traditional Rental Income: $2603 Airbnb ROI: 0.99% Traditional ROI: 2.72%
1750 Whalen Dr Oconomowoc, WI This home is move-in-ready. The Francesca 2428 is an ideal home that needs both communal ...	4 beds \| 3 baths \| 2,428 sq.ft.	$763,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 3% Airbnb Rental Income: $2394 Traditional Rental Income: $3069 Airbnb ROI: 1.23% Traditional ROI: 3%
1733 Hammock Ln Oconomowoc, WI This home is under construction. The Hailey 2350 offers a kitchen w/ plenty of cabinetry, ...	4 beds \| 3 baths \| 2,350 sq.ft.	$706,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 3.25% Airbnb Rental Income: $2394 Traditional Rental Income: $3027 Airbnb ROI: 1.4% Traditional ROI: 3.25%
W339s271 Foxtail Ct Oconomowoc, WI Stunning Horwath build on 5.5 acres in the Town of Delafield! Bright open concept design s...	5 beds \| 6 baths \| 6,083 sq.ft.	$1,775,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $6076 Airbnb ROI: N/A Traditional ROI: 1.89%
1267 Wild Rye Ln Oconomowoc, WI The Lauren 1805 that places the generously sized primary bedroom & shared living spaces - ...	3 beds \| 2 baths \| 1,805 sq.ft.	$668,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 2.01% Airbnb Rental Income: $2022 Traditional Rental Income: $2577 Airbnb ROI: 0.28% Traditional ROI: 2.01%
1283 Wild Rye Ln Oconomowoc, WI This Rylee is a split-bedroom ranch home currently under construction. The oversized gath...	3 beds \| 2 baths \| 1,809 sq.ft.	$673,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.99% Airbnb Rental Income: $2022 Traditional Rental Income: $2577 Airbnb ROI: 0.27% Traditional ROI: 1.99%
1268 Wild Rye Ln Oconomowoc, WI This home is under construction. The Arielle 2404 is a plan that offers all the essential ...	4 beds \| 3 baths \| 2,404 sq.ft.	$716,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.44% Airbnb Rental Income: $2394 Traditional Rental Income: $2982 Airbnb ROI: -0.32% Traditional ROI: 1.44%
1260 Wild Rye Ln Oconomowoc, WI This home is under construction. This Rylee is a split-bedroom ranch home currently under ...	3 beds \| 2 baths \| 1,809 sq.ft.	$676,900	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.03% Airbnb Rental Income: $2022 Traditional Rental Income: $2566 Airbnb ROI: -0.66% Traditional ROI: 1.03%
1252 Wild Rye Ln Oconomowoc, WI The Lauren 1851 that places the generously sized primary bedroom & shared living spaces - ...	3 beds \| 2 baths \| 1,851 sq.ft.	$685,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.04% Airbnb Rental Income: $2022 Traditional Rental Income: $2603 Airbnb ROI: -0.69% Traditional ROI: 1.04%
888 Wildwood Pl Oconomowoc, WI Unique 3-4 bedroom property on over half an acre lot, located in a fantastic neighborhood,...	3 beds \| 2 baths \| 1,650 sq.ft.	$367,400	Airbnb cash on cash: 2.19% Traditional cash on cash: 4.37% Airbnb Rental Income: $2022 Traditional Rental Income: $2245 Airbnb ROI: 2.19% Traditional ROI: 4.37%
W360n7572 Thomas Dr Oconomowoc, WI Spacious custom-built, original owner 4-bedroom, 2 full & 2 half bath home on 1.71 acres i...	4 beds \| 4 baths \| 3,100 sq.ft.	$774,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.02% Airbnb Rental Income: $2394 Traditional Rental Income: $3544 Airbnb ROI: 0.62% Traditional ROI: 3.02%
215 E Pleasant St #212 Oconomowoc, WI Welcome to the finest in lake country living! You will love the many amazing features and ...	1 beds \| 2 baths \| 1,062 sq.ft.	$549,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.87% Airbnb Rental Income: $1419 Traditional Rental Income: $1915 Airbnb ROI: -0.93% Traditional ROI: 0.87%
W356n5136 Lakeshore Dr Oconomowoc, WI This is available just in time for the July 4th celebration on Okauchee! Refined lakefront...	4 beds \| 4 baths \| 4,351 sq.ft.	$3,495,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.18% Airbnb Rental Income: $2394 Traditional Rental Income: $4357 Airbnb ROI: -0.97% Traditional ROI: -0.18%
1016 Ann Marie Way Oconomowoc, WI Welcome to refined living on Ann Marie Way in The Glen of Oconomowoc, where elevated desig...	3 beds \| 3 baths \| 2,597 sq.ft.	$715,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.97% Airbnb Rental Income: $2022 Traditional Rental Income: $3105 Airbnb ROI: -0.45% Traditional ROI: 1.97%
N67w34857 Ireland Dr Oconomowoc, WI Model Home - LAST WEEKEND!!! This home is currently under contract. Simply Luxury Homes wi...	5 beds \| 4 baths \| 4,476 sq.ft.	$2,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.88% Airbnb Rental Income: $null Traditional Rental Income: $3997 Airbnb ROI: N/A Traditional ROI: 0.88%
1320 Foxwood Pass Oconomowoc, WI Exquisite home featuring rich wood flooring throughout and a bright, open-concept design c...	4 beds \| 4 baths \| 3,376 sq.ft.	$685,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.84% Airbnb Rental Income: $2394 Traditional Rental Income: $3814 Airbnb ROI: 0.69% Traditional ROI: 3.84%
1242 Green Tree Dr Oconomowoc, WI Welcome to the Lavender; a lovely split bedroom ranch featuring 3 beds/2 baths plus a sunr...	3 beds \| 2 baths \| 1,926 sq.ft.	$644,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.14% Airbnb Rental Income: $2022 Traditional Rental Income: $2703 Airbnb ROI: 1.13% Traditional ROI: 3.14%
503 Talbot's Woods Dr #Lt36 Oconomowoc, WI CONCRETE DRIVEWAY, FRONT WALKWAY, REAR PATIO AND SOD NOW INCLUDED! Featuring more than 2,0...	3 beds \| 2 baths \| 2,004 sq.ft.	$709,990	Airbnb cash on cash: 0.25% Traditional cash on cash: 2.11% Airbnb Rental Income: $2022 Traditional Rental Income: $2729 Airbnb ROI: 0.25% Traditional ROI: 2.11%
1614 N Sugar Island Road Oconomowoc, WI A slice of the great Northwoods right here in Oconomowoc? You will feel that way the momen...	4 beds \| 2 baths \| 1,280 sq.ft.	$750,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 1.43% Airbnb Rental Income: $2394 Traditional Rental Income: $2203 Airbnb ROI: 0.86% Traditional ROI: 1.43%
972 Valentine Rd Oconomowoc, WI Welcome to easy living in this charming 3 bedroom traditional townhouse style condo, nestl...	3 beds \| 2 baths \| 1,830 sq.ft.	$309,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 5.77% Airbnb Rental Income: $2022 Traditional Rental Income: $2393 Airbnb ROI: 2.69% Traditional ROI: 5.77%
1480 Prairie Creek Blvd Oconomowoc, WI Welcome to this beautifully maintained home located in a highly sought-after, family-frien...	4 beds \| 3 baths \| 2,583 sq.ft.	$689,900	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.6% Airbnb Rental Income: $2394 Traditional Rental Income: $3076 Airbnb ROI: 0.63% Traditional ROI: 2.6%
W350s1951 Waterville Rd Oconomowoc, WI Tucked away on 8 private acres, this stunning 5 bedroom, 3.5 bathroom home offers the perf...	5 beds \| 4 baths \| 4,884 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.18% Airbnb Rental Income: $null Traditional Rental Income: $4012 Airbnb ROI: N/A Traditional ROI: 2.18%
1522 Champion Ct Oconomowoc, WI This stunning 2-bed, 2.5-bath Kingsway ranch condo at Village Crossing at Pabst Farms is m...	2 beds \| 3 baths \| 2,116 sq.ft.	$614,900	Airbnb cash on cash: -1.14% Traditional cash on cash: 2.14% Airbnb Rental Income: $1498 Traditional Rental Income: $2943 Airbnb ROI: -1.14% Traditional ROI: 2.14%
N69w34498 Oconomowoc Rd Oconomowoc, WI Discover an extraordinary private retreat tucked away on 3+ secluded acres. Surrounded by ...	4 beds \| 4 baths \| 5,294 sq.ft.	$1,300,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 1.45% Airbnb Rental Income: $2394 Traditional Rental Income: $3867 Airbnb ROI: -0.26% Traditional ROI: 1.45%
904 W Labelle Ave Oconomowoc, WI You will find this home tucked away on a dead-end street, bordering historic Merchants Pla...	3 beds \| 4 baths \| 3,380 sq.ft.	$2,300,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.17% Airbnb Rental Income: $2022 Traditional Rental Income: $4066 Airbnb ROI: -1.03% Traditional ROI: 0.17%
418 S Charles St Oconomowoc, WI Phenomenal location, walking distance to downtown, the lake, and all Oconomowoc has to off...	3 beds \| 2 baths \| 1,664 sq.ft.	$389,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 3.94% Airbnb Rental Income: $2022 Traditional Rental Income: $2238 Airbnb ROI: 1.91% Traditional ROI: 3.94%
W351n5464 Lake Dr Oconomowoc, WI 2 Homes. 1 Rare Okauchee Lake Opportunity. Spend your days on the water, your evenings aro...	2 beds \| 4 baths \| 2,012 sq.ft.	$1,500,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.83% Airbnb Rental Income: $1498 Traditional Rental Income: $3524 Airbnb ROI: -0.94% Traditional ROI: 0.83%
W349n5830 Sunflower Ct Oconomowoc, WI Nestled on a cul-de-sac in Westshore, this split-bedroom ranch offers an open-concept floo...	3 beds \| 3 baths \| 2,073 sq.ft.	$650,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.76% Airbnb Rental Income: $2022 Traditional Rental Income: $2859 Airbnb ROI: 0.52% Traditional ROI: 2.76%
W343n6980 W Circle Dr Oconomowoc, WI Enjoy the best of everything in the spacious 3BDRM 3.5BATH w/over 2300 SQ FT on a hill ove...	3 beds \| 4 baths \| 2,388 sq.ft.	$649,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.24% Airbnb Rental Income: $2022 Traditional Rental Income: $3063 Airbnb ROI: 0.66% Traditional ROI: 3.24%
69 S Chestnut St Oconomowoc, WI This meticulously maintained home has been lovingly cared for over 35 years and is availab...	3 beds \| 1 baths \| 1,440 sq.ft.	$315,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.26% Airbnb Rental Income: $2022 Traditional Rental Income: $1663 Airbnb ROI: 2.69% Traditional ROI: 3.26%
N61w37631 Parkview Dr Oconomowoc, WI From the moment you step into this home, you are greeted by two unforgettable focal points...	5 beds \| 3 baths \| 3,869 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.34% Airbnb Rental Income: $null Traditional Rental Income: $3496 Airbnb ROI: N/A Traditional ROI: 2.34%
1077 Christopher Ct Oconomowoc, WI Tucked away on a quiet cul-de-sac in a desirable Oconomowoc location, this character fille...	4 beds \| 2 baths \| 2,477 sq.ft.	$499,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.67% Airbnb Rental Income: $2394 Traditional Rental Income: $2707 Airbnb ROI: 1.74% Traditional ROI: 3.67%
725 W South St Oconomowoc, WI Charm and character is abundant in this Victorian located five blocks from the heart of do...	3 beds \| 2 baths \| 1,280 sq.ft.	$363,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.05% Airbnb Rental Income: $2022 Traditional Rental Income: $2037 Airbnb ROI: 2.46% Traditional ROI: 4.05%
34899 Pabst Rd Oconomowoc, WI You don't have to travel north to find peace, privacy, and relaxation. Set on 2 wooded acr...	4 beds \| 4 baths \| 3,819 sq.ft.	$799,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.08% Airbnb Rental Income: $2394 Traditional Rental Income: $3786 Airbnb ROI: 0.43% Traditional ROI: 3.08%
207 E Jefferson St Oconomowoc, WI Located near Downtown Oconomowoc, Roosevelt Park, and the Lake Country Rec Trail, this two...	3 beds \| 3 baths \| N/A	$420,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.64% Airbnb Rental Income: $2022 Traditional Rental Income: $2765 Airbnb ROI: 1.41% Traditional ROI: 4.64%
1370 Mamerow Ln Oconomowoc, WI Excited to present this meticulously maintained 5 bedroom, 3.5 bath home in sought-after H...	5 beds \| 4 baths \| 3,538 sq.ft.	$710,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $4302 Airbnb ROI: N/A Traditional ROI: 4.32%
W343n6293 S Bayview Rd Oconomowoc, WI Welcome to the Gold Coast of Okauchee Lake! 80 feet of prime frontage, boathouse and sunse...	4 beds \| 5 baths \| 5,034 sq.ft.	$4,199,000	Airbnb cash on cash: -1.04% Traditional cash on cash: -0.68% Airbnb Rental Income: $2394 Traditional Rental Income: $3189 Airbnb ROI: -1.04% Traditional ROI: -0.68%

Real Estate investment in Oconomowoc, WI

There are 44 properties for sale in the city of Oconomowoc . The median list price in Oconomowoc is $561,064 and the average price per square foot is $208. In July 2026, the average monthly cash on cash return in Oconomowoc is 2.00%. The average monthly rental income in Oconomowoc is $2,577.

Oconomowoc, WI Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 44 investment properties available for sale in Oconomowoc.

In 2026, the best neighborhood to buy investment property is Oconomowoc.

The ROI for Short-Term is higher than the Long-Term in Oconomowoc with average rental income of $2,022.

Your search for investment property begins and ends here

Investment Property for Sale in Oconomowoc, WI

970 Oconomowoc Pkwy

Oconomowoc, WI

2 beds | 3 baths | 2,275 sq.ft.

$444,900

Airbnb cash on cash: -0.21%

Traditional cash on cash: 2.52%

Airbnb Rental Income: $1498

Traditional Rental Income: $2198

Airbnb ROI: -0.21%

Traditional ROI: 2.52%

1746 Whalen Dr

Oconomowoc, WI

3 beds | 2 baths | 1,805 sq.ft.

$685,900

Airbnb cash on cash: 0.99%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $2022

Traditional Rental Income: $2603

Airbnb ROI: 0.99%

Traditional ROI: 2.72%

1750 Whalen Dr

Oconomowoc, WI

4 beds | 3 baths | 2,428 sq.ft.

$763,900

Airbnb cash on cash: 1.23%

Traditional cash on cash: 3%

Airbnb Rental Income: $2394

Traditional Rental Income: $3069

Airbnb ROI: 1.23%

Traditional ROI: 3%

1733 Hammock Ln

Oconomowoc, WI

4 beds | 3 baths | 2,350 sq.ft.

$706,900

Airbnb cash on cash: 1.4%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $2394

Traditional Rental Income: $3027

Airbnb ROI: 1.4%

Traditional ROI: 3.25%

W339s271 Foxtail Ct

Oconomowoc, WI

5 beds | 6 baths | 6,083 sq.ft.

$1,775,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.89%

Airbnb Rental Income: $null

Traditional Rental Income: $6076

Airbnb ROI: N/A

Traditional ROI: 1.89%

1267 Wild Rye Ln

Oconomowoc, WI

3 beds | 2 baths | 1,805 sq.ft.

$668,900

Airbnb cash on cash: 0.28%

Traditional cash on cash: 2.01%

Airbnb Rental Income: $2022

Traditional Rental Income: $2577

Airbnb ROI: 0.28%

Traditional ROI: 2.01%

1283 Wild Rye Ln

Oconomowoc, WI

3 beds | 2 baths | 1,809 sq.ft.

$673,900

Airbnb cash on cash: 0.27%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $2022

Traditional Rental Income: $2577

Airbnb ROI: 0.27%

Traditional ROI: 1.99%

1268 Wild Rye Ln

Oconomowoc, WI

4 beds | 3 baths | 2,404 sq.ft.

$716,900

Airbnb cash on cash: -0.32%

Traditional cash on cash: 1.44%

Airbnb Rental Income: $2394

Traditional Rental Income: $2982

Airbnb ROI: -0.32%