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
N60w38457 Blackhawk Dr Oconomowoc, WI BRING YOUR BOAT! Deeded Lac LaBelle access for this spacious ranch on .5 acre double lot w...	3 beds \| 3 baths \| 2,258 sq.ft.	$849,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 1.97% Airbnb Rental Income: $4481 Traditional Rental Income: $2931 Airbnb ROI: 2.74% Traditional ROI: 1.97%
1232 REDWING Drive Oconomowoc, WI Beautiful open concept ranch with 3 bedroom, 3 bath, main floor office that could be used...	3 beds \| 3 baths \| 2,758 sq.ft.	$530,000	Airbnb cash on cash: 4.98% Traditional cash on cash: 3.57% Airbnb Rental Income: $4481 Traditional Rental Income: $2847 Airbnb ROI: 4.98% Traditional ROI: 3.57%
1232 Dorchester Dr Oconomowoc, WI Welcome to your new home in beautiful Oconomowoc! This inviting 3-bedroom, 1.5-bath ranch-...	3 beds \| 2 baths \| 1,933 sq.ft.	$394,900	Airbnb cash on cash: 7.49% Traditional cash on cash: 4.55% Airbnb Rental Income: $4481 Traditional Rental Income: $2454 Airbnb ROI: 7.49% Traditional ROI: 4.55%
708 N Oakwood Ave Oconomowoc, WI Welcome to Lake Country! This updated, charing ranch home has it all! Hardwood floors, upd...	3 beds \| 2 baths \| 1,939 sq.ft.	$419,000	Airbnb cash on cash: 6.99% Traditional cash on cash: 4.26% Airbnb Rental Income: $4481 Traditional Rental Income: $2473 Airbnb ROI: 6.99% Traditional ROI: 4.26%
4886 N Hewitts Point Rd Oconomowoc, WI Welcome home to this 5-6 bedroom European Country-style home on 4 lovely acres and 154 fee...	5 beds \| 5 baths \| 6,736 sq.ft.	$3,495,000	Airbnb cash on cash: 1.26% Traditional cash on cash: -0.34% Airbnb Rental Income: $12252 Traditional Rental Income: $4860 Airbnb ROI: 1.26% Traditional ROI: -0.34%
1691 Hammock Ln Oconomowoc, WI This home is under construction. The Lauren 1805 that places the generously sized primary ...	3 beds \| 2 baths \| 1,805 sq.ft.	$619,900	Airbnb cash on cash: 3.1% Traditional cash on cash: 1.29% Airbnb Rental Income: $4481 Traditional Rental Income: $2496 Airbnb ROI: 3.1% Traditional ROI: 1.29%
1244 Violet St Oconomowoc, WI This home is currently under construction. The Charlotte offers a gathering room featuring...	4 beds \| 3 baths \| 2,506 sq.ft.	$703,900	Airbnb cash on cash: 5.21% Traditional cash on cash: 1.57% Airbnb Rental Income: $6698 Traditional Rental Income: $3004 Airbnb ROI: 5.21% Traditional ROI: 1.57%
1635 Mamerow Ln Oconomowoc, WI Welcome home to The Lauren by Stepping Stone Homes, an award-winning home builder. Open fl...	3 beds \| 3 baths \| 1,935 sq.ft.	$594,900	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.5% Airbnb Rental Income: $4481 Traditional Rental Income: $2702 Airbnb ROI: 5.02% Traditional ROI: 3.5%
N60w34978 Lake Dr Oconomowoc, WI Okauchee Lake custom log home built by Rob Miller Homes. The spaciousgreat room with floor...	3 beds \| 4 baths \| 2,733 sq.ft.	$2,600,000	Airbnb cash on cash: -0.12% Traditional cash on cash: -0.17% Airbnb Rental Income: $4481 Traditional Rental Income: $3428 Airbnb ROI: -0.12% Traditional ROI: -0.17%
1523 Butternut Rdg Oconomowoc, WI Welcome home to The GENEVA PLAN by Stepping Stone Homes, an award-winning home builder. Op...	4 beds \| 3 baths \| 2,093 sq.ft.	$532,900	Airbnb cash on cash: 9.41% Traditional cash on cash: 4.12% Airbnb Rental Income: $6698 Traditional Rental Income: $2757 Airbnb ROI: 9.41% Traditional ROI: 4.12%
1603 Switchgrass St Oconomowoc, WI Welcome home to The CLARA PLAN by Stepping Stone Homes, an award-winning home builder. Ope...	3 beds \| 3 baths \| 2,253 sq.ft.	$604,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 1.98% Airbnb Rental Income: $4481 Traditional Rental Income: $2829 Airbnb ROI: 3.25% Traditional ROI: 1.98%
1233 Green Tree Dr Oconomowoc, WI This home is under construction. The Skylar 2431 is a 2-story home that offers plenty of l...	4 beds \| 3 baths \| 2,431 sq.ft.	$646,900	Airbnb cash on cash: 5.91% Traditional cash on cash: 1.96% Airbnb Rental Income: $6698 Traditional Rental Income: $3004 Airbnb ROI: 5.91% Traditional ROI: 1.96%
1217 Green Tree Dr Oconomowoc, WI This home is currently under construction. The Hailey 2350 offers a kitchen w/ plenty of c...	4 beds \| 3 baths \| 2,350 sq.ft.	$627,900	Airbnb cash on cash: 6.18% Traditional cash on cash: 2.02% Airbnb Rental Income: $6698 Traditional Rental Income: $2954 Airbnb ROI: 6.18% Traditional ROI: 2.02%
W340s2401 County Road C - Oconomowoc, WI Dare to Dream in This 4 bdrm, 3 bath Rustic contemporary that sits on11+privat e acres. Ch...	4 beds \| 3 baths \| 4,108 sq.ft.	$1,500,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 0.71% Airbnb Rental Income: $6698 Traditional Rental Income: $2994 Airbnb ROI: 2.43% Traditional ROI: 0.71%
36082 N Beach Rd Oconomowoc, WI Come see this timeless and beautiful home on coveted Oconomowoc Lake! Featuring 4 bedrooms...	4 beds \| 3 baths \| 3,736 sq.ft.	$2,995,000	Airbnb cash on cash: 0.55% Traditional cash on cash: -0.24% Airbnb Rental Income: $6698 Traditional Rental Income: $3214 Airbnb ROI: 0.55% Traditional ROI: -0.24%
1550 Creekview Ln Oconomowoc, WI Welcome home to The Julia by Stepping Stone Homes, an award-winning home builder. Open flo...	4 beds \| 4 baths \| 2,502 sq.ft.	$624,900	Airbnb cash on cash: 6.22% Traditional cash on cash: 2.64% Airbnb Rental Income: $6698 Traditional Rental Income: $3305 Airbnb ROI: 6.22% Traditional ROI: 2.64%
W1396 County Road O Oconomowoc, WI Glorious country property tucked away on 9.7 acres! Horses & chickens are welcome here. S...	4 beds \| 3 baths \| 2,052 sq.ft.	$619,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 2.94% Airbnb Rental Income: $6698 Traditional Rental Income: $2758 Airbnb ROI: 7.5% Traditional ROI: 2.94%
W376n7955 McMahon Rd Oconomowoc, WI Stunning Open-Concept Split-Level RanchThis beautiful open-concept split-level ranch offer...	4 beds \| 4 baths \| 3,430 sq.ft.	$819,500	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.83% Airbnb Rental Income: $6698 Traditional Rental Income: $3644 Airbnb ROI: 5.12% Traditional ROI: 2.83%
1622 Saint Andrews Dr #14 Oconomowoc, WI Experience luxury living in this custom-built condo featuring high end finishes throughout...	3 beds \| 5 baths \| 4,191 sq.ft.	$1,200,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 1.9% Airbnb Rental Income: $4481 Traditional Rental Income: $4211 Airbnb ROI: 1.31% Traditional ROI: 1.9%
N67w34320 Jorgenson Ct Oconomowoc, WI Stately 4BR/2.5BA 3,000 sq. ft. residence on half acre + parcel in Bay View Estates and Ar...	4 beds \| 3 baths \| 3,000 sq.ft.	$645,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 3.12% Airbnb Rental Income: $6698 Traditional Rental Income: $3095 Airbnb ROI: 6.94% Traditional ROI: 3.12%
245 Hillside Dr Oconomowoc, WI Priced Below Assessed Value. Spacious and Inviting is a great way to describe this beautif...	4 beds \| 4 baths \| 3,231 sq.ft.	$549,999	Airbnb cash on cash: 8.22% Traditional cash on cash: 4.8% Airbnb Rental Income: $6698 Traditional Rental Income: $3639 Airbnb ROI: 8.22% Traditional ROI: 4.8%
1275 Mamerow Ln Oconomowoc, WI Welcome home to The ELIZA PLAN by Stepping Stone Homes, an award-winning home builder. Ope...	3 beds \| 2 baths \| 2,002 sq.ft.	$576,811	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.26% Airbnb Rental Income: $4481 Traditional Rental Income: $2494 Airbnb ROI: 5.21% Traditional ROI: 3.26%
1627 Mamerow Ln Oconomowoc, WI Welcome home to The CHARLOTTE by Stepping Stone Homes, an award-winning home builder. Open...	3 beds \| 2 baths \| 2,191 sq.ft.	$612,579	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.2% Airbnb Rental Income: $4481 Traditional Rental Income: $2603 Airbnb ROI: 4.85% Traditional ROI: 3.2%
320 E Pleasant St #306 Oconomowoc, WI This top floor LAKESIDE Condo on beautiful Fowler Lake is ready for its new owner. The 2 b...	2 beds \| 2 baths \| 1,222 sq.ft.	$410,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.46% Airbnb Rental Income: $1320 Traditional Rental Income: $2160 Airbnb ROI: 0.21% Traditional ROI: 3.46%
W397n5881 Autumn Woods Dr Oconomowoc, WI This desirable first-floor condo in the vibrant Autumn Woods 55+ Community is a must-see! ...	2 beds \| 2 baths \| 1,212 sq.ft.	$300,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 4.82% Airbnb Rental Income: $1320 Traditional Rental Income: $1932 Airbnb ROI: 1.2% Traditional ROI: 4.82%
W358n6724 W Stonewood Dr Oconomowoc, WI Welcome to your dream home! This stunning walkout split-level ranch, set on nearly an acre...	3 beds \| 4 baths \| 3,682 sq.ft.	$814,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.27% Airbnb Rental Income: $4481 Traditional Rental Income: $3204 Airbnb ROI: 2.72% Traditional ROI: 2.27%
739 Lake Bluff Dr Oconomowoc, WI Welcome to this charming 3 bedroom, 2 bath ranch perfectly situated in an ideal Oconomowoc...	3 beds \| 2 baths \| 1,660 sq.ft.	$425,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 3.54% Airbnb Rental Income: $4481 Traditional Rental Income: $2340 Airbnb ROI: 6.56% Traditional ROI: 3.54%
N53w35199 Lighthouse Ln Oconomowoc, WI Explore the walking paths around the 2 PONDS that this IMMACULATE RANCH CONDO OFFERS! A pr...	3 beds \| 3 baths \| 2,700 sq.ft.	$549,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 3.49% Airbnb Rental Income: $4481 Traditional Rental Income: $2821 Airbnb ROI: 4.91% Traditional ROI: 3.49%
1281 Orchard Cir Oconomowoc, WI Discover this stunning ranch home in Oconomowoc, meticulously updated to perfection! The k...	3 beds \| 2 baths \| 2,607 sq.ft.	$550,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 2.69% Airbnb Rental Income: $4481 Traditional Rental Income: $2512 Airbnb ROI: 4.7% Traditional ROI: 2.69%
W397n5972 Autumn Woods Dr Oconomowoc, WI Nestled in a country setting minutes from Downtown Oconomowoc, this 2-bedroom, 2-bath home...	2 beds \| 2 baths \| 1,824 sq.ft.	$339,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.83% Airbnb Rental Income: $1320 Traditional Rental Income: $2506 Airbnb ROI: 0.83% Traditional ROI: 5.83%
1147 Daisy Ln Oconomowoc, WI 3BR Ranch style home available in sought after Oconomowoc neighborhood. Interior features...	3 beds \| 2 baths \| 1,484 sq.ft.	$299,900	Airbnb cash on cash: 9.97% Traditional cash on cash: 5.02% Airbnb Rental Income: $4481 Traditional Rental Income: $2148 Airbnb ROI: 9.97% Traditional ROI: 5.02%
1176 Sandpiper Dr Oconomowoc, WI Bright & sunny layout; large windows throughout. Dramatic great room with vaulted ceiling ...	3 beds \| 3 baths \| 2,698 sq.ft.	$515,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 3.85% Airbnb Rental Income: $4481 Traditional Rental Income: $2956 Airbnb ROI: 5.07% Traditional ROI: 3.85%
1252 Violet St Oconomowoc, WI New Construction - Ready in February. Introducing our Canton Model in the beautiful Prairi...	3 beds \| 2 baths \| 1,772 sq.ft.	$539,900	Airbnb cash on cash: 4.01% Traditional cash on cash: 2.09% Airbnb Rental Income: $4481 Traditional Rental Income: $2577 Airbnb ROI: 4.01% Traditional ROI: 2.09%

Real Estate investment in Oconomowoc, WI

There are 33 properties for sale in the city of Oconomowoc . The median list price in Oconomowoc is $576,811 and the average price per square foot is $225. In November 2024, the average monthly cash on cash return in Oconomowoc is 3.00%. The average monthly rental income in Oconomowoc is $2,821.

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

There are 33 investment properties available for sale in Oconomowoc.

In 2024, 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 $4,481.

Your search for investment property begins and ends here

Investment Property for Sale in Oconomowoc, WI

N60w38457 Blackhawk Dr

Oconomowoc, WI

3 beds | 3 baths | 2,258 sq.ft.

$849,900

Airbnb cash on cash: 2.74%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $4481

Traditional Rental Income: $2931

Airbnb ROI: 2.74%

Traditional ROI: 1.97%

1232 REDWING Drive

Oconomowoc, WI

3 beds | 3 baths | 2,758 sq.ft.

$530,000

Airbnb cash on cash: 4.98%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $4481

Traditional Rental Income: $2847

Airbnb ROI: 4.98%

Traditional ROI: 3.57%

1232 Dorchester Dr

Oconomowoc, WI

3 beds | 2 baths | 1,933 sq.ft.

$394,900

Airbnb cash on cash: 7.49%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $4481

Traditional Rental Income: $2454

Airbnb ROI: 7.49%

Traditional ROI: 4.55%

708 N Oakwood Ave

Oconomowoc, WI

3 beds | 2 baths | 1,939 sq.ft.

$419,000

Airbnb cash on cash: 6.99%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $4481

Traditional Rental Income: $2473

Airbnb ROI: 6.99%

Traditional ROI: 4.26%

4886 N Hewitts Point Rd

Oconomowoc, WI

5 beds | 5 baths | 6,736 sq.ft.

$3,495,000

Airbnb cash on cash: 1.26%

Traditional cash on cash: -0.34%

Airbnb Rental Income: $12252

Traditional Rental Income: $4860

Airbnb ROI: 1.26%

Traditional ROI: -0.34%

1691 Hammock Ln

Oconomowoc, WI

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

$619,900

Airbnb cash on cash: 3.1%

Traditional cash on cash: 1.29%

Airbnb Rental Income: $4481

Traditional Rental Income: $2496

Airbnb ROI: 3.1%

Traditional ROI: 1.29%

1244 Violet St

Oconomowoc, WI

4 beds | 3 baths | 2,506 sq.ft.

$703,900

Airbnb cash on cash: 5.21%

Traditional cash on cash: 1.57%

Airbnb Rental Income: $6698

Traditional Rental Income: $3004

Airbnb ROI: 5.21%

Traditional ROI: 1.57%

1635 Mamerow Ln

Oconomowoc, WI

3 beds | 3 baths | 1,935 sq.ft.

$594,900

Airbnb cash on cash: 5.02%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $4481

Traditional Rental Income: $2702

Airbnb ROI: 5.02%