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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1622 Saint Andrews Dr #14 Oconomowoc, WI Experience luxury lake living in this custom-built condo featuring high end finishes throu...	3 beds \| 5 baths \| 4,191 sq.ft.	$1,195,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.93% Airbnb Rental Income: $2255 Traditional Rental Income: $4211 Airbnb ROI: -0.34% Traditional ROI: 1.93%
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.	$643,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 2.19% Airbnb Rental Income: $2255 Traditional Rental Income: $2603 Airbnb ROI: 0.67% Traditional ROI: 2.19%
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.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $1997 Airbnb ROI: N/A Traditional ROI: 1.88%
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: 1.82% Traditional cash on cash: 2.72% Airbnb Rental Income: $3179 Traditional Rental Income: $3023 Airbnb ROI: 1.82% 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: 1.63% Traditional cash on cash: 2.54% Airbnb Rental Income: $3179 Traditional Rental Income: $3069 Airbnb ROI: 1.63% Traditional ROI: 2.54%
452 River Bluff Cir Oconomowoc, WI A rare opportunity to own this stunning 3/4-acre wooded lot in the sought-after River Bluf...	4 beds \| 3 baths \| 4,363 sq.ft.	$699,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.65% Airbnb Rental Income: $3179 Traditional Rental Income: $3104 Airbnb ROI: 1.66% Traditional ROI: 2.65%
4545 N Hewitts Point Rd Oconomowoc, WI Property also listed as MLS #1926601.Presenting one of the most breathtaking & prestigious...	2 beds \| 1 baths \| 1,000 sq.ft.	$7,900,000	Airbnb cash on cash: -1.42% Traditional cash on cash: -1.39% Airbnb Rental Income: $1629 Traditional Rental Income: $1431 Airbnb ROI: -1.42% Traditional ROI: -1.39%
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: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $4986 Airbnb ROI: N/A Traditional ROI: 2.69%
180 Monastery Hill Dr Oconomowoc, WI Resort living at it's best with lake access, pool and tennis courts!! Welcome to effortles...	4 beds \| 4 baths \| 4,108 sq.ft.	$1,324,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 0.76% Airbnb Rental Income: $3179 Traditional Rental Income: $3902 Airbnb ROI: -0.42% Traditional ROI: 0.76%
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: 1.89% Traditional cash on cash: 2.81% Airbnb Rental Income: $3179 Traditional Rental Income: $3027 Airbnb ROI: 1.89% Traditional ROI: 2.81%
1047 Ann Marie Way Oconomowoc, WI Exceptionally designed open-plan Oconomowoc ranch condo w/wooded conservancy views from th...	3 beds \| 3 baths \| 2,647 sq.ft.	$719,500	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.8% Airbnb Rental Income: $2255 Traditional Rental Income: $3154 Airbnb ROI: 0.61% Traditional ROI: 2.8%
372 River Bluff Cir Oconomowoc, WI Inviting ranch home in River Bluff - located just minutes from downtown Oconomowoc, yet wr...	3 beds \| 4 baths \| 3,345 sq.ft.	$724,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.07% Airbnb Rental Income: $2255 Traditional Rental Income: $3424 Airbnb ROI: 0.51% Traditional ROI: 3.07%
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: 0.93% Traditional cash on cash: 3.76% Airbnb Rental Income: $1629 Traditional Rental Income: $2201 Airbnb ROI: 0.93% Traditional ROI: 3.76%
N66w35950 Farmstead Court Oconomowoc, WI Welcome to Woodside Farms! Nestled on a quiet cul-de-sac in one of Oconomowoc's most desi...	4 beds \| 4 baths \| 3,560 sq.ft.	$729,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.55% Airbnb Rental Income: $3179 Traditional Rental Income: $3735 Airbnb ROI: 1.68% Traditional ROI: 3.55%
208 Maple Ter Oconomowoc, WI Discover this beautifully maintained 1950s Lannon stone Cape Cod, situated in the desirabl...	3 beds \| 3 baths \| 2,310 sq.ft.	$850,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 1.59% Airbnb Rental Income: $2255 Traditional Rental Income: $2851 Airbnb ROI: 0.12% Traditional ROI: 1.59%
35300 Pabst Rd Oconomowoc, WI Discover this exceptional custom estate on 14 private acres in the prestigious Village of ...	5 beds \| 4 baths \| 5,973 sq.ft.	$2,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.29% Airbnb Rental Income: $null Traditional Rental Income: $3872 Airbnb ROI: N/A Traditional ROI: 0.29%
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: 2.64% Traditional cash on cash: 3.84% Airbnb Rental Income: $2255 Traditional Rental Income: $2125 Airbnb ROI: 2.64% Traditional ROI: 3.84%
449 Lake Bluff Dr Oconomowoc, WI Beautifully updated 4-bedroom, 2 full and 2 half bath two-story home in a desirable Oconom...	4 beds \| 4 baths \| 3,664 sq.ft.	$727,900	Airbnb cash on cash: 1.51% Traditional cash on cash: 3.52% Airbnb Rental Income: $3179 Traditional Rental Income: $3825 Airbnb ROI: 1.51% Traditional ROI: 3.52%
1479 Crestwood Dr Oconomowoc, WI Meticulously maintained & beautifully decorated, this charming home is nestled within walk...	3 beds \| 3 baths \| 2,235 sq.ft.	$495,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 3.93% Airbnb Rental Income: $2255 Traditional Rental Income: $2782 Airbnb ROI: 1.58% Traditional ROI: 3.93%
35048 Wayfare Trl Oconomowoc, WI Quaint and peaceful Oakshire development offers this one-owner, Anders-built story and a h...	4 beds \| 3 baths \| 2,758 sq.ft.	$599,900	Airbnb cash on cash: 2.24% Traditional cash on cash: 3.47% Airbnb Rental Income: $3179 Traditional Rental Income: $3154 Airbnb ROI: 2.24% Traditional ROI: 3.47%
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: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $6076 Airbnb ROI: N/A Traditional ROI: 1.69%
1506 River Highlands Dr Oconomowoc, WI Don't miss out on this one! This inviting ranch home blends modern updates with cozy charm...	3 beds \| 2 baths \| 2,393 sq.ft.	$499,900	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.41% Airbnb Rental Income: $2255 Traditional Rental Income: $2571 Airbnb ROI: 1.53% Traditional ROI: 3.41%
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.	$643,500	Airbnb cash on cash: 1.91% Traditional cash on cash: 3.05% Airbnb Rental Income: $3179 Traditional Rental Income: $3139 Airbnb ROI: 1.91% Traditional ROI: 3.05%
34994 Delafield Rd Oconomowoc, WI Terrific Opportunity in Oconomowoc! Beautiful large fenced in yard with new patio and 2 ca...	3 beds \| 2 baths \| 1,050 sq.ft.	$349,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.27% Airbnb Rental Income: $2255 Traditional Rental Income: $1890 Airbnb ROI: 2.67% Traditional ROI: 3.27%
719 S Main St Oconomowoc, WI Unbeatable location in the heart of Oconomowoc! Situated right across from Roosevelt Park ...	3 beds \| 1 baths \| 1,056 sq.ft.	$269,999	Airbnb cash on cash: 4.35% Traditional cash on cash: 4.04% Airbnb Rental Income: $2255 Traditional Rental Income: $1611 Airbnb ROI: 4.35% Traditional ROI: 4.04%
W359n5707 Surrey Dr Oconomowoc, WI Spacious ranch home nestled on a generous .734-acre lot in a peaceful, well-established ne...	3 beds \| 2 baths \| 1,640 sq.ft.	$470,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 3.13% Airbnb Rental Income: $2255 Traditional Rental Income: $2299 Airbnb ROI: 1.75% Traditional ROI: 3.13%
1755 Derby Ln Oconomowoc, WI This spotless 2100 SF ranch condo is Kingsway's largest model, the Estonian! Enter the foy...	2 beds \| 2 baths \| 2,110 sq.ft.	$674,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.29% Airbnb Rental Income: $1629 Traditional Rental Income: $2762 Airbnb ROI: -0.25% Traditional ROI: 2.29%
318 S Concord Rd Oconomowoc, WI Here's that ''perfect little ranch'' in Oconomowoc you've been looking for. Completely upd...	2 beds \| 1 baths \| 1,183 sq.ft.	$335,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.76% Airbnb Rental Income: $1629 Traditional Rental Income: $1583 Airbnb ROI: 1.45% Traditional ROI: 2.76%
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.	$299,999	Airbnb cash on cash: 3.96% Traditional cash on cash: 6.09% Airbnb Rental Income: $2255 Traditional Rental Income: $2291 Airbnb ROI: 3.96% Traditional ROI: 6.09%
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: 0.72% Traditional cash on cash: 2.24% Airbnb Rental Income: $2255 Traditional Rental Income: $2577 Airbnb ROI: 0.72% 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: 0.7% Traditional cash on cash: 2.21% Airbnb Rental Income: $2255 Traditional Rental Income: $2577 Airbnb ROI: 0.7% 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.	$569,900	Airbnb cash on cash: 0.88% Traditional cash on cash: 2.52% Airbnb Rental Income: $2255 Traditional Rental Income: $2565 Airbnb ROI: 0.88% Traditional ROI: 2.52%
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.	$559,500	Airbnb cash on cash: 1.09% Traditional cash on cash: 3.39% Airbnb Rental Income: $2255 Traditional Rental Income: $2891 Airbnb ROI: 1.09% Traditional ROI: 3.39%
704 Thackeray Trl Oconomowoc, WI Classic ranch home with an ideal, functional layout! The bright & spacious living room ope...	3 beds \| 2 baths \| 1,920 sq.ft.	$449,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 3.91% Airbnb Rental Income: $2255 Traditional Rental Income: $2531 Airbnb ROI: 1.92% Traditional ROI: 3.91%

Real Estate investment in Oconomowoc, WI

There are 34 properties for sale in the city of Oconomowoc . The median list price in Oconomowoc is $643,700 and the average price per square foot is $246. In November 2025, the average monthly cash on cash return in Oconomowoc is 3.00%. The average monthly rental income in Oconomowoc is $2,782.

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

There are 34 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 $2,782.

Your search for investment property begins and ends here

Investment Property for Sale in Oconomowoc, WI

1622 Saint Andrews Dr #14

Oconomowoc, WI

3 beds | 5 baths | 4,191 sq.ft.

$1,195,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $2255

Traditional Rental Income: $4211

Airbnb ROI: -0.34%

Traditional ROI: 1.93%

1746 Whalen Dr

Oconomowoc, WI

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

$643,900

Airbnb cash on cash: 0.67%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $2255

Traditional Rental Income: $2603

Airbnb ROI: 0.67%

Traditional ROI: 2.19%

215 E Pleasant St #201

Oconomowoc, WI

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

$539,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1997

Airbnb ROI: N/A

Traditional ROI: 1.88%

1737 Hammock Ln

Oconomowoc, WI

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

$672,900

Airbnb cash on cash: 1.82%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $3179

Traditional Rental Income: $3023

Airbnb ROI: 1.82%

Traditional ROI: 2.72%

1750 Whalen Dr

Oconomowoc, WI

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

$721,900

Airbnb cash on cash: 1.63%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $3179

Traditional Rental Income: $3069

Airbnb ROI: 1.63%

Traditional ROI: 2.54%

452 River Bluff Cir

Oconomowoc, WI

4 beds | 3 baths | 4,363 sq.ft.

$699,900

Airbnb cash on cash: 1.66%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $3179

Traditional Rental Income: $3104

Airbnb ROI: 1.66%

Traditional ROI: 2.65%

4545 N Hewitts Point Rd

Oconomowoc, WI

2 beds | 1 baths | 1,000 sq.ft.

$7,900,000

Airbnb cash on cash: -1.42%

Traditional cash on cash: -1.39%

Airbnb Rental Income: $1629

Traditional Rental Income: $1431

Airbnb ROI: -1.42%

Traditional ROI: -1.39%

N81w33604 Chicory Ct

Oconomowoc, WI

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

$1,199,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.69%

Airbnb Rental Income: $null

Traditional Rental Income: $4986

Airbnb ROI: N/A