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
1746 Whalen Dr Oconomowoc, WI The Lauren 1805 that places the generously sized primary bedroom & shared living spaces - ...	3 beds \| 2 baths \| 1,805 sq.ft.	$664,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.09% Airbnb Rental Income: $2063 Traditional Rental Income: $2603 Airbnb ROI: 0.36% Traditional ROI: 2.09%
215 E Pleasant St #201 Oconomowoc, WI This beautifully designed, 1Bdm End Unit Condo offers stunning views of the lakes from its...	1 beds \| 2 baths \| 1,182 sq.ft.	$509,900	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.05% Airbnb Rental Income: $1009 Traditional Rental Income: $1997 Airbnb ROI: -0.77% Traditional ROI: 2.05%
1737 Hammock 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.	$672,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 2.72% Airbnb Rental Income: $2747 Traditional Rental Income: $3023 Airbnb ROI: 1.25% Traditional ROI: 2.72%
1750 Whalen Dr Oconomowoc, WI This home is under construction. The Francesca 2428 is an ideal home that needs both comm...	4 beds \| 3 baths \| 2,428 sq.ft.	$721,900	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.54% Airbnb Rental Income: $2747 Traditional Rental Income: $3069 Airbnb ROI: 1.1% Traditional ROI: 2.54%
N81w33604 Chicory Ct Oconomowoc, WI PRICE IMPROVEMENT: This gorgeous, 5 bdrm. quality build located in the desirable Prairie H...	5 beds \| 5 baths \| 5,025 sq.ft.	$1,199,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.69% Airbnb Rental Income: $3358 Traditional Rental Income: $4986 Airbnb ROI: 0.56% Traditional ROI: 2.69%
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.	$657,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 2.81% Airbnb Rental Income: $2747 Traditional Rental Income: $3027 Airbnb ROI: 1.3% Traditional ROI: 2.81%
320 E Pleasant St #202 Oconomowoc, WI Experience the perfect blend of tranquility and convenience in this beautifully updated 2-...	2 beds \| 2 baths \| 1,222 sq.ft.	$389,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.76% Airbnb Rental Income: $1362 Traditional Rental Income: $2201 Airbnb ROI: 0.32% Traditional ROI: 3.76%
208 Maple Ter Oconomowoc, WI Enjoy affordable Lake Living on Lac La Belle with this charming 1950's Lannon Stone Cape C...	3 beds \| 3 baths \| 2,872 sq.ft.	$850,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.59% Airbnb Rental Income: $2063 Traditional Rental Income: $2851 Airbnb ROI: -0.08% Traditional ROI: 1.59%
35300 Pabst Rd Oconomowoc, WI Experience luxury and privacy on 14 secluded acres in the Village of Oconomowoc Lake. This...	5 beds \| 4 baths \| 5,973 sq.ft.	$1,999,999	Airbnb cash on cash: -0.2% Traditional cash on cash: 0.48% Airbnb Rental Income: $3358 Traditional Rental Income: $3872 Airbnb ROI: -0.2% Traditional ROI: 0.48%
402 W 3rd St Oconomowoc, WI Enjoy the best of Oconomowoc living in this fully updated home, ideally situated on a corn...	3 beds \| 1 baths \| 1,400 sq.ft.	$385,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 3.84% Airbnb Rental Income: $2063 Traditional Rental Income: $2125 Airbnb ROI: 2.2% Traditional ROI: 3.84%
W339s271 Foxtail Ct Oconomowoc, WI Rare opportunity- stunning Horwath build on 5.5 acres in the Town of Delafield! Bright ope...	5 beds \| 6 baths \| 6,083 sq.ft.	$1,899,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.69% Airbnb Rental Income: $3358 Traditional Rental Income: $6076 Airbnb ROI: -0.28% Traditional ROI: 1.69%
1410 Blazing Star Dr Oconomowoc, WI Welcome to effortless living in Prairie Creek Ridge-where shopping, dining, schools & more...	4 beds \| 3 baths \| 3,453 sq.ft.	$638,500	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.08% Airbnb Rental Income: $2747 Traditional Rental Income: $3139 Airbnb ROI: 1.33% Traditional ROI: 3.08%
N49w36150 Nottingham Ln #12 Oconomowoc, WI Affordable, move-in ready 3 BR, 2 BA condo in Village with low taxes in truly private sett...	3 beds \| 2 baths \| 1,600 sq.ft.	$296,999	Airbnb cash on cash: 3.44% Traditional cash on cash: 6.16% Airbnb Rental Income: $2063 Traditional Rental Income: $2291 Airbnb ROI: 3.44% Traditional ROI: 6.16%
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.	$624,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.24% Airbnb Rental Income: $2063 Traditional Rental Income: $2577 Airbnb ROI: 0.44% Traditional ROI: 2.24%
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.	$630,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.21% Airbnb Rental Income: $2063 Traditional Rental Income: $2577 Airbnb ROI: 0.43% Traditional ROI: 2.21%
1742 Whalen Dr Oconomowoc, WI New Construction - Ready in December! The Washburn offers 3 beds and 2 baths in this split...	3 beds \| 2 baths \| 1,750 sq.ft.	$559,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.59% Airbnb Rental Income: $2063 Traditional Rental Income: $2565 Airbnb ROI: 0.61% Traditional ROI: 2.59%
1271 Thomas Trl Oconomowoc, WI Beautifully updated home just minutes from downtown Oconomowoc. Parks, lakes, golfing, sho...	3 beds \| 3 baths \| 3,080 sq.ft.	$549,500	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.43% Airbnb Rental Income: $2063 Traditional Rental Income: $2891 Airbnb ROI: 0.78% Traditional ROI: 3.43%
34352 Valley Rd Oconomowoc, WI Experience lakefront luxury on private Upper Nashotah Lake. Perched on a scenic hill with ...	4 beds \| 4 baths \| 3,100 sq.ft.	$2,500,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.03% Airbnb Rental Income: $2747 Traditional Rental Income: $4183 Airbnb ROI: -0.87% Traditional ROI: 0.03%
711 E Lisbon Rd Oconomowoc, WI This lovely ranch home is set on .29 acres with walkability to Fowler Lake and downtown Oc...	3 beds \| 2 baths \| 1,300 sq.ft.	$394,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 3.5% Airbnb Rental Income: $2063 Traditional Rental Income: $2079 Airbnb ROI: 2.02% Traditional ROI: 3.5%
W356 Allen Rd Oconomowoc, WI Set on 12+ acres with breathtaking views & an abundance of wildlife, this quality built 5 ...	5 beds \| 3 baths \| 3,298 sq.ft.	$924,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 2.12% Airbnb Rental Income: $3358 Traditional Rental Income: $3250 Airbnb ROI: 1.38% Traditional ROI: 2.12%
510 Frederick Ct Oconomowoc, WI Fantastic Opportunity in the Heart of Oconomowoc! Don't miss your chance to own this townh...	2 beds \| 3 baths \| 1,780 sq.ft.	$319,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 5.92% Airbnb Rental Income: $1362 Traditional Rental Income: $2468 Airbnb ROI: 0.84% Traditional ROI: 5.92%
1388 Periwinkle Pass Oconomowoc, WI New Construction - Ready in January! Discover the Canton model in Oconomowoc's desirable P...	3 beds \| 2 baths \| 1,772 sq.ft.	$564,900	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.63% Airbnb Rental Income: $2063 Traditional Rental Income: $2602 Airbnb ROI: 0.59% Traditional ROI: 2.63%
341 W 4th St Oconomowoc, WI Beautifully Updated Oconomowoc Ranch - Move-In Ready!Welcome to this charming and thoughtf...	3 beds \| 2 baths \| 1,372 sq.ft.	$365,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 3.98% Airbnb Rental Income: $2063 Traditional Rental Income: $2130 Airbnb ROI: 2.23% Traditional ROI: 3.98%
247 Sunny Hill Ln Oconomowoc, WI Welcome to this updated 4bdrm, 2bath bi-level designed w/functionality & flow in mind! The...	4 beds \| 2 baths \| 2,040 sq.ft.	$479,900	Airbnb cash on cash: 2.68% Traditional cash on cash: 3.98% Airbnb Rental Income: $2747 Traditional Rental Income: $2682 Airbnb ROI: 2.68% Traditional ROI: 3.98%
1710 Whalen Dr Oconomowoc, WI New Construction - Ready in February! Step into luxury living with this stunning Prentice ...	3 beds \| 2 baths \| 1,767 sq.ft.	$549,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 2.63% Airbnb Rental Income: $2063 Traditional Rental Income: $2553 Airbnb ROI: 0.64% Traditional ROI: 2.63%

Real Estate investment in Oconomowoc, WI

There are 25 properties for sale in the city of Oconomowoc . The median list price in Oconomowoc is $624,900 and the average price per square foot is $249. In December 2025, the average monthly cash on cash return in Oconomowoc is 3.00%. The average monthly rental income in Oconomowoc is $2,603.

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

There are 25 investment properties available for sale in Oconomowoc.

In 2025, the best neighborhood to buy investment property is Oconomowoc.

The ROI for Long-Term is higher than the Short-Term in Oconomowoc with average rental income of $2,603.

Your search for investment property begins and ends here

Investment Property for Sale in Oconomowoc, WI

1746 Whalen Dr

Oconomowoc, WI

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

$664,900

Airbnb cash on cash: 0.36%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $2063

Traditional Rental Income: $2603

Airbnb ROI: 0.36%

Traditional ROI: 2.09%

215 E Pleasant St #201

Oconomowoc, WI

1 beds | 2 baths | 1,182 sq.ft.

$509,900

Airbnb cash on cash: -0.77%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1009

Traditional Rental Income: $1997

Airbnb ROI: -0.77%

Traditional ROI: 2.05%

1737 Hammock Ln

Oconomowoc, WI

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

$672,900

Airbnb cash on cash: 1.25%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $2747

Traditional Rental Income: $3023

Airbnb ROI: 1.25%

Traditional ROI: 2.72%

1750 Whalen Dr

Oconomowoc, WI

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

$721,900

Airbnb cash on cash: 1.1%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $2747

Traditional Rental Income: $3069

Airbnb ROI: 1.1%

Traditional ROI: 2.54%

N81w33604 Chicory Ct

Oconomowoc, WI

5 beds | 5 baths | 5,025 sq.ft.

$1,199,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 2.69%

Airbnb Rental Income: $3358

Traditional Rental Income: $4986

Airbnb ROI: 0.56%

Traditional ROI: 2.69%

1733 Hammock Ln

Oconomowoc, WI

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

$657,900

Airbnb cash on cash: 1.3%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $2747

Traditional Rental Income: $3027

Airbnb ROI: 1.3%

Traditional ROI: 2.81%

320 E Pleasant St #202

Oconomowoc, WI

2 beds | 2 baths | 1,222 sq.ft.

$389,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1362

Traditional Rental Income: $2201

Airbnb ROI: 0.32%

Traditional ROI: 3.76%

208 Maple Ter

Oconomowoc, WI

3 beds | 3 baths | 2,872 sq.ft.

$850,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 1.59%

Airbnb Rental Income: $2063

Traditional Rental Income: $2851

Airbnb ROI: -0.08%