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
415 S Concord Rd Oconomowoc, WI Updated home with old-world charm, beautiful natural light, and smart, well-designed space...	3 beds \| 2 baths \| 1,825 sq.ft.	$485,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.36% Airbnb Rental Income: $1759 Traditional Rental Income: $2413 Airbnb ROI: 0.85% Traditional ROI: 3.36%
727 E Madison St Oconomowoc, WI Enjoy the best of Lake Country living just 3 blocks from Fowler Lake Park, offering easy a...	5 beds \| 2 baths \| 3,788 sq.ft.	$627,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.95% Airbnb Rental Income: $null Traditional Rental Income: $2741 Airbnb ROI: N/A Traditional ROI: 2.95%
N59w39568 Laketon Ave Oconomowoc, WI Tucked on a picturesque .65-acre lot just 2 blocks from Lac La Belle and minutes to downto...	3 beds \| 2 baths \| 1,827 sq.ft.	$525,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 2.99% Airbnb Rental Income: $1759 Traditional Rental Income: $2427 Airbnb ROI: 0.65% Traditional ROI: 2.99%
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: 0.65% Traditional cash on cash: 2.72% Airbnb Rental Income: $1759 Traditional Rental Income: $2603 Airbnb ROI: 0.65% Traditional ROI: 2.72%
1737 Hammock Ln Oconomowoc, WI This home is under construction. The Arielle 2404 is a plan that offers all the essential ...	4 beds \| 2 baths \| 2,404 sq.ft.	$716,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 3.19% Airbnb Rental Income: $2181 Traditional Rental Income: $3023 Airbnb ROI: 1.11% Traditional ROI: 3.19%
1750 Whalen Dr Oconomowoc, WI This home is under construction. The Francesca 2428 is an ideal home that needs both comm...	4 beds \| 2 baths \| 2,428 sq.ft.	$763,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 3% Airbnb Rental Income: $2181 Traditional Rental Income: $3069 Airbnb ROI: 0.98% Traditional ROI: 3%
180 Monastery Hill Dr Oconomowoc, WI Outstanding all brick ranch home with two master suites! High end finishes and quality th...	4 beds \| 3 baths \| 4,108 sq.ft.	$1,295,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.82% Airbnb Rental Income: $2181 Traditional Rental Income: $3902 Airbnb ROI: -1.06% Traditional ROI: 0.82%
1733 Hammock Ln Oconomowoc, WI This home is under construction. The Hailey 2350 offers a kitchen w/ plenty of cabinetry, ...	4 beds \| 2 baths \| 2,350 sq.ft.	$706,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.25% Airbnb Rental Income: $2181 Traditional Rental Income: $3027 Airbnb ROI: 1.13% 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 \| 5 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: -0.07% Traditional cash on cash: 2.01% Airbnb Rental Income: $1759 Traditional Rental Income: $2577 Airbnb ROI: -0.07% 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: -0.08% Traditional cash on cash: 1.99% Airbnb Rental Income: $1759 Traditional Rental Income: $2577 Airbnb ROI: -0.08% Traditional ROI: 1.99%
1721 Arthurs Pass Oconomowoc, WI This beautiful two year new home in Morgan Station is the one you've been waiting for & mo...	4 beds \| 3 baths \| 2,031 sq.ft.	$574,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 3.3% Airbnb Rental Income: $2181 Traditional Rental Income: $2884 Airbnb ROI: 0.96% Traditional ROI: 3.3%
1268 Wild Rye Ln Oconomowoc, WI This home is under construction. The Arielle 2404 is a plan that offers all the essential ...	4 beds \| 2 baths \| 2,404 sq.ft.	$716,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.44% Airbnb Rental Income: $2181 Traditional Rental Income: $2982 Airbnb ROI: -0.58% Traditional ROI: 1.44%
1702 Switchgrass St Oconomowoc, WI This home is under construction. The Francesca 2428 is an ideal home that needs both commu...	4 beds \| 2 baths \| 2,428 sq.ft.	$769,900	Airbnb cash on cash: -0.74% Traditional cash on cash: 1.21% Airbnb Rental Income: $2181 Traditional Rental Income: $3028 Airbnb ROI: -0.74% Traditional ROI: 1.21%
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: -1.01% Traditional cash on cash: 1.03% Airbnb Rental Income: $1759 Traditional Rental Income: $2566 Airbnb ROI: -1.01% 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: -1.03% Traditional cash on cash: 1.04% Airbnb Rental Income: $1759 Traditional Rental Income: $2603 Airbnb ROI: -1.03% Traditional ROI: 1.04%
1620 CREEKVIEW Lane Oconomowoc, WI Beautiful Split bedroom ranch design with vaulted main living room, corner gas fireplace ,...	3 beds \| 2 baths \| 2,081 sq.ft.	$774,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.48% Airbnb Rental Income: $1759 Traditional Rental Income: $2544 Airbnb ROI: -0.27% Traditional ROI: 1.48%
W342N6303 Kathy Dr Oconomowoc, WI Enjoy lake-country charm just 300 yards from Okauchee Lake & Sailing Club! This home sits ...	3 beds \| 2 baths \| 2,058 sq.ft.	$599,500	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.01% Airbnb Rental Income: $1759 Traditional Rental Income: $2666 Airbnb ROI: 0.52% Traditional ROI: 3.01%
1001 Spring Waters Dr Oconomowoc, WI BEAUTIFULLY MAINTAINED ONE OWNER OPEN CONCEPT RANCH HOME. Great Rm w/ Cathedral Ceiling, ...	3 beds \| 2 baths \| 1,683 sq.ft.	$565,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.4% Airbnb Rental Income: $1759 Traditional Rental Income: $2324 Airbnb ROI: 0.41% Traditional ROI: 2.4%
426 E Pleasant St Oconomowoc, WI Step into timeless charm with classic turn of century Colonial Home, where character and c...	4 beds \| 3 baths \| 1,626 sq.ft.	$395,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 4.66% Airbnb Rental Income: $2181 Traditional Rental Income: $2504 Airbnb ROI: 2.3% Traditional ROI: 4.66%
726 W Wisconsin Ave Oconomowoc, WI Exceptional opportunity to enjoy Lac La Belle lake life with a boat slip, private neighbor...	4 beds \| 3 baths \| 2,437 sq.ft.	$679,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.32% Airbnb Rental Income: $2181 Traditional Rental Income: $3355 Airbnb ROI: 0.6% Traditional ROI: 3.32%
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: 1.56% Traditional cash on cash: 4.37% Airbnb Rental Income: $1759 Traditional Rental Income: $2245 Airbnb ROI: 1.56% 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 \| 2 baths \| 3,100 sq.ft.	$789,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.95% Airbnb Rental Income: $2181 Traditional Rental Income: $3544 Airbnb ROI: 0.34% Traditional ROI: 2.95%
W348n5818 Snapdragon Ct Oconomowoc, WI Discover this beautifully designed home in Oconomowoc's sought-after Westshore subdivision...	5 beds \| 3 baths \| 3,460 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.82% Airbnb Rental Income: $null Traditional Rental Income: $3222 Airbnb ROI: N/A Traditional ROI: 2.82%
1452 N Lapham St Oconomowoc, WI Location and lifestyle come together in this beautifully updated 4-bed, 2.5 bath bi-level ...	4 beds \| 3 baths \| 2,944 sq.ft.	$539,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 4.04% Airbnb Rental Income: $2181 Traditional Rental Income: $3108 Airbnb ROI: 1.1% Traditional ROI: 4.04%
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 \| 1 baths \| 1,062 sq.ft.	$549,900	Airbnb cash on cash: -1.67% Traditional cash on cash: 1.69% Airbnb Rental Income: $453 Traditional Rental Income: $1915 Airbnb ROI: -1.67% Traditional ROI: 1.69%
966 Valentine Rd Oconomowoc, WI Lakehouse vibes! Beautiful updated townhouse style condo with high end finishes throughout...	3 beds \| 3 baths \| 1,830 sq.ft.	$384,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 5.01% Airbnb Rental Income: $1759 Traditional Rental Income: $2526 Airbnb ROI: 1.55% Traditional ROI: 5.01%
638 Red Oak Dr Oconomowoc, WI Enjoy 3,700 square feet of open-concept living with LVP flooring throughout both levels! T...	4 beds \| 3 baths \| 3,732 sq.ft.	$972,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.33% Airbnb Rental Income: $null Traditional Rental Income: $3813 Airbnb ROI: N/A Traditional ROI: 2.33%
503 Talbot'S Woods Dr Lot 36 Oconomowoc, WI Featuring more than 2,000 square feet, this new construction 3 bedroom, 2 bath ranch boast...	3 beds \| 2 baths \| 2,004 sq.ft.	$679,990	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.25% Airbnb Rental Income: $1759 Traditional Rental Income: $2728 Airbnb ROI: -0.04% Traditional ROI: 2.25%
W354n5854 Lisbon Rd Oconomowoc, WI Welcome to Misty Meadows in the Village of Lac La Belle! This beautifully maintained 3BR, ...	3 beds \| 2 baths \| 2,753 sq.ft.	$599,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.88% Airbnb Rental Income: $1759 Traditional Rental Income: $2654 Airbnb ROI: 0.41% Traditional ROI: 2.88%
127 N Walnut St Oconomowoc, WI Rare opportunity to own in the heart of downtown Oconomowoc, just steps from Lake Fowler. ...	4 beds \| 1 baths \| 1,718 sq.ft.	$250,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 4.16% Airbnb Rental Income: $2181 Traditional Rental Income: $1702 Airbnb ROI: 3.85% Traditional ROI: 4.16%
W1852 Washington Rd Oconomowoc, WI Escape to the peace of country living at an amazing price! Huge garage and so much more. T...	3 beds \| 2 baths \| 1,400 sq.ft.	$389,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.93% Airbnb Rental Income: $1759 Traditional Rental Income: $2153 Airbnb ROI: 1.53% Traditional ROI: 3.93%
W356N5136 Lakeshore Dr Oconomowoc, WI Experience refined lakefront living on Upper Oconomowoc Lake, connected to Okauchee by boa...	4 beds \| 3 baths \| 4,351 sq.ft.	$3,500,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.18% Airbnb Rental Income: $2181 Traditional Rental Income: $4357 Airbnb ROI: -1.02% Traditional ROI: -0.18%
417 S Golden Lake Rd Oconomowoc, WI The pier is in and ready for your boat. This 2016 custom home built by Zach Builders offer...	3 beds \| 3 baths \| 2,200 sq.ft.	$1,395,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.15% Airbnb Rental Income: $1617 Traditional Rental Income: $3460 Airbnb ROI: -0.62% Traditional ROI: 1.15%
N5187 Union Hill Rd Oconomowoc, WI Your own oasis with a peaceful setting & space inside & out! This immaculately updated spr...	3 beds \| 3 baths \| 3,268 sq.ft.	$654,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 2.57% Airbnb Rental Income: $1759 Traditional Rental Income: $2678 Airbnb ROI: 0.28% Traditional ROI: 2.57%
1470 Waters Edge Dr Oconomowoc, WI Welcome to this stunning 4 BD, 2.5 BA home in the sought after Hickorywood Farms of Oconom...	4 beds \| 3 baths \| 2,444 sq.ft.	$624,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 2.8% Airbnb Rental Income: $2181 Traditional Rental Income: $2890 Airbnb ROI: 0.64% Traditional ROI: 2.8%
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.	$725,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 2.62% Airbnb Rental Income: $1759 Traditional Rental Income: $3105 Airbnb ROI: -0.08% Traditional ROI: 2.62%
1406 Mockingbird Ct Oconomowoc, WI Beautifully updated former model 3BR,3.5BA Executive Split Ranch on Cul-de-Sac in one of t...	3 beds \| 4 baths \| 3,037 sq.ft.	$665,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 3.27% Airbnb Rental Income: $1759 Traditional Rental Income: $3341 Airbnb ROI: -0.05% Traditional ROI: 3.27%

Real Estate investment in Oconomowoc, WI

There are 100 properties for sale in the city of Oconomowoc . The median list price in Oconomowoc is $673,900 and the average price per square foot is $273. In May 2026, the average monthly cash on cash return in Oconomowoc is 2.00%. The average monthly rental income in Oconomowoc is $2,535.

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

There are 100 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 $1,759.

Your search for investment property begins and ends here

Investment Property for Sale in Oconomowoc, WI

415 S Concord Rd

Oconomowoc, WI

3 beds | 2 baths | 1,825 sq.ft.

$485,000

Airbnb cash on cash: 0.85%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1759

Traditional Rental Income: $2413

Airbnb ROI: 0.85%

Traditional ROI: 3.36%

727 E Madison St

Oconomowoc, WI

5 beds | 2 baths | 3,788 sq.ft.

$627,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2741

Airbnb ROI: N/A

Traditional ROI: 2.95%

N59w39568 Laketon Ave

Oconomowoc, WI

3 beds | 2 baths | 1,827 sq.ft.

$525,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $1759

Traditional Rental Income: $2427

Airbnb ROI: 0.65%

Traditional ROI: 2.99%

1746 Whalen Dr

Oconomowoc, WI

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

$685,900

Airbnb cash on cash: 0.65%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1759

Traditional Rental Income: $2603

Airbnb ROI: 0.65%

Traditional ROI: 2.72%

1737 Hammock Ln

Oconomowoc, WI

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

$716,900

Airbnb cash on cash: 1.11%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $2181

Traditional Rental Income: $3023

Airbnb ROI: 1.11%

Traditional ROI: 3.19%

1750 Whalen Dr

Oconomowoc, WI

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

$763,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: 3%

Airbnb Rental Income: $2181

Traditional Rental Income: $3069

Airbnb ROI: 0.98%

Traditional ROI: 3%

180 Monastery Hill Dr

Oconomowoc, WI

4 beds | 3 baths | 4,108 sq.ft.

$1,295,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $2181

Traditional Rental Income: $3902

Airbnb ROI: -1.06%

Traditional ROI: 0.82%

1733 Hammock Ln

Oconomowoc, WI

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

$706,900

Airbnb cash on cash: 1.13%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $2181

Traditional Rental Income: $3027

Airbnb ROI: 1.13%