Real Estate Investment Properties for Sale in Waukesha, WI

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

Explore a variety of short-term homes & houses in Waukesha, WI. Invest wisely with VRBO & Waukesha, 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 Waukesha, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
709 N Cumberland Dr Waukesha, WI This Lannon Stone Tudor offers classic 1930s charm in a quiet central Waukesha location. ...	3 beds \| 2 baths \| 1,933 sq.ft.	$385,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 4.07% Airbnb Rental Income: $1118 Traditional Rental Income: $2492 Airbnb ROI: -0.78% Traditional ROI: 4.07%
1822 Rockridge Way Waukesha, WI Welcome home to this beautifully maintained 4BR, 2.5BA home in desirable Rolling Ridge Sou...	4 beds \| 3 baths \| 2,269 sq.ft.	$550,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.99% Airbnb Rental Income: $2478 Traditional Rental Income: $2869 Airbnb ROI: 1.06% Traditional ROI: 2.99%
1341 E Roberta Ave Waukesha, WI Meticulously maintained 4-bedroom, 2 full bath Cape Cod offering the perfect blend of comf...	4 beds \| 2 baths \| 2,439 sq.ft.	$424,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.15% Airbnb Rental Income: $2478 Traditional Rental Income: $2614 Airbnb ROI: 2.29% Traditional ROI: 4.15%
515 Wynnewood Ct Waukesha, WI Fantastic Executive Ranch with manicured landscape! Over 3800 sqft of custom design and fi...	3 beds \| 4 baths \| 3,819 sq.ft.	$659,900	Airbnb cash on cash: -1.26% Traditional cash on cash: 2.84% Airbnb Rental Income: $1118 Traditional Rental Income: $3262 Airbnb ROI: -1.26% Traditional ROI: 2.84%
313 S University Dr Waukesha, WI Come see this beautiful ranch home in the highly sought-after Merrill Crest subdivision in...	3 beds \| 2 baths \| 1,515 sq.ft.	$389,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.46% Airbnb Rental Income: $1118 Traditional Rental Income: $2196 Airbnb ROI: -0.52% Traditional ROI: 3.46%
1901 Woodburn Rd #D Waukesha, WI Welcome home to this beautifully maintained bi-level condo in Waukesha! Featuring 2 bedroo...	2 beds \| 2 baths \| 1,428 sq.ft.	$265,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 4.32% Airbnb Rental Income: $1027 Traditional Rental Income: $2029 Airbnb ROI: -1.13% Traditional ROI: 4.32%
223 NW Barstow St Waukesha, WI Charming, updated, and full of potential--this 3-bedroom, 2 full bath Waukesha home offers...	3 beds \| 2 baths \| 1,281 sq.ft.	$230,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 6.26% Airbnb Rental Income: $1118 Traditional Rental Income: $1917 Airbnb ROI: 0.86% Traditional ROI: 6.26%
3640 Madison St Waukesha, WI Welcome to 3640 Madison St., a beautifully built 2021 home a large floor plans, offering s...	4 beds \| 2 baths \| 2,403 sq.ft.	$699,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 2.04% Airbnb Rental Income: $2478 Traditional Rental Income: $3024 Airbnb ROI: 0.28% Traditional ROI: 2.04%
2424 Fox River Pkwy - #K Waukesha, WI Enjoy easy living just steps from the Fox River Trail in this bright, move-in ready 2BR, 1...	2 beds \| 2 baths \| 1,203 sq.ft.	$242,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 5.77% Airbnb Rental Income: $1027 Traditional Rental Income: $1938 Airbnb ROI: 0.21% Traditional ROI: 5.77%
W224n2507 Ridgewood Ln Waukesha, WI Completely updated 2 Story with one of the largest Lots in the Neighborhood! Open floor pl...	3 beds \| 2 baths \| 2,132 sq.ft.	$524,900	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.18% Airbnb Rental Income: $1118 Traditional Rental Income: $2475 Airbnb ROI: -0.35% Traditional ROI: 3.18%
W296n575 Bryn Dr Waukesha, WI Become only the THIRD owner of this incredible 3BR/2.5BA, 1,920+ sq. ft., Delafield Tri-Le...	3 beds \| 3 baths \| 1,920 sq.ft.	$575,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.03% Airbnb Rental Income: $1118 Traditional Rental Income: $2563 Airbnb ROI: -0.36% Traditional ROI: 3.03%
1500 Gabriel Dr #2 Waukesha, WI Lower-level 2BR, 2BA walk-out condo nestled along a wooded tree line in an extremely conve...	2 beds \| 2 baths \| 1,455 sq.ft.	$312,400	Airbnb cash on cash: -1.78% Traditional cash on cash: 3.07% Airbnb Rental Income: $1027 Traditional Rental Income: $2091 Airbnb ROI: -1.78% Traditional ROI: 3.07%
Lt28 White Oak Way Waukesha, WI This home is a representation of the starting price to build in Skyline for the home, lot,...	5 beds \| 3 baths \| 2,200 sq.ft.	$593,690	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.76% Airbnb Rental Income: $971 Traditional Rental Income: $2946 Airbnb ROI: -0.44% Traditional ROI: 3.76%
Lt14 Viewpoint Ave Waukesha, WI This home is a representation of the starting price to build in Skyline for the home, lot,...	3 beds \| 2 baths \| 1,851 sq.ft.	$591,390	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.96% Airbnb Rental Income: $1118 Traditional Rental Income: $2495 Airbnb ROI: -0.21% Traditional ROI: 2.96%
916 Arcadian Ave Waukesha, WI Charming turn-of-the-century 2-story home offering 4 bedrooms and 1 full bath in a conveni...	4 beds \| 1 baths \| 1,384 sq.ft.	$309,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 2.98% Airbnb Rental Income: $2478 Traditional Rental Income: $1674 Airbnb ROI: 3.68% Traditional ROI: 2.98%
3817 White Oak Way Waukesha, WI Now Completed! The Bristol's impressive two-story gathering room makes an immediate impact...	3 beds \| 3 baths \| 2,216 sq.ft.	$722,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.01% Airbnb Rental Income: $1118 Traditional Rental Income: $3018 Airbnb ROI: -0.37% Traditional ROI: 3.01%
805 Viewpoint Ave Waukesha, WI Completed! The Skylar, Plan 2210 makes the most of everyday living spaces. This 2-story ho...	4 beds \| 2 baths \| 2,210 sq.ft.	$748,900	Airbnb cash on cash: 1.28% Traditional cash on cash: 2.97% Airbnb Rental Income: $2478 Traditional Rental Income: $3054 Airbnb ROI: 1.28% Traditional ROI: 2.97%
801 Viewpoint Dr Waukesha, WI Now Completed! This unique living space includes everything that a family needs - a kitche...	4 beds \| 2 baths \| 2,350 sq.ft.	$735,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.07% Airbnb Rental Income: $2478 Traditional Rental Income: $3092 Airbnb ROI: 1.26% Traditional ROI: 3.07%
804 Viewpoint Ave Waukesha, WI Now Completed! This split-bedroom ranch home provides ample elbow room due to its open nat...	3 beds \| 2 baths \| 1,809 sq.ft.	$670,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.74% Airbnb Rental Income: $1118 Traditional Rental Income: $2644 Airbnb ROI: -0.3% Traditional ROI: 2.74%
3828 White Oak Way Waukesha, WI This split-bedroom ranch home provides ample elbow room due to its open nature. The oversi...	3 beds \| 2 baths \| 1,809 sq.ft.	$681,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.67% Airbnb Rental Income: $1118 Traditional Rental Income: $2611 Airbnb ROI: -0.27% Traditional ROI: 2.67%
114 Retzer View Ct Waukesha, WI This is an ideal home for the family that needs both communal and private spaces. The firs...	4 beds \| N/A baths \| 2,428 sq.ft.	$790,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.45% Airbnb Rental Income: $2478 Traditional Rental Income: $2115 Airbnb ROI: 1.13% Traditional ROI: 1.45%
110 Retzer View Ct Waukesha, WI This open-concept, split bedroom home features a centrally located kitchen with an abundan...	3 beds \| 2 baths \| 2,043 sq.ft.	$767,900	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.47% Airbnb Rental Income: $1118 Traditional Rental Income: $2042 Airbnb ROI: -0.35% Traditional ROI: 1.47%
3804 Oakmont Trl Waukesha, WI This 2-story home has plenty of everyday living space with the kitchen, morning room and g...	4 beds \| 2 baths \| 2,431 sq.ft.	$778,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 2.76% Airbnb Rental Income: $2478 Traditional Rental Income: $3010 Airbnb ROI: 1.2% Traditional ROI: 2.76%
3716 Oakmont Trl Waukesha, WI Essential living spaces get an upgrade in this home starting with the kitchen, which featu...	4 beds \| 2 baths \| 2,404 sq.ft.	$768,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 2.72% Airbnb Rental Income: $2478 Traditional Rental Income: $2964 Airbnb ROI: 1.2% Traditional ROI: 2.72%
106 Retzer View Ct Waukesha, WI The Bristol's impressive two-story gathering room makes an immediate impact as you enter t...	3 beds \| 2 baths \| 2,216 sq.ft.	$767,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.73% Airbnb Rental Income: $1118 Traditional Rental Income: $2962 Airbnb ROI: -0.38% Traditional ROI: 2.73%
W310s2748 Wild Rose Ln Waukesha, WI Welcome to this exceptional open-concept ranch nestled on a peaceful cul-de-sac in a beaut...	3 beds \| 2 baths \| 1,635 sq.ft.	$529,900	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.64% Airbnb Rental Income: $1118 Traditional Rental Income: $2282 Airbnb ROI: -0.47% Traditional ROI: 2.64%
2116 Bluestem Dr #1402 Waukesha, WI Located less than 5 minutes off I-94 this condominium is MOVE-IN-READY. This ranch style c...	2 beds \| 2 baths \| 1,600 sq.ft.	$619,900	Airbnb cash on cash: -1.52% Traditional cash on cash: 1.68% Airbnb Rental Income: $1027 Traditional Rental Income: $2520 Airbnb ROI: -1.52% Traditional ROI: 1.68%
2119 Bluestem Dr #0201 Waukesha, WI Located less than 5 minutes off I-94 this condominium is MOVE-IN-READY. This ranch style c...	2 beds \| 2 baths \| 1,600 sq.ft.	$579,900	Airbnb cash on cash: -1.56% Traditional cash on cash: 1.85% Airbnb Rental Income: $1027 Traditional Rental Income: $2511 Airbnb ROI: -1.56% Traditional ROI: 1.85%
2117 Bluestem Dr #0202 Waukesha, WI Located less than 5 minutes off I-94 this condominium is MOVE-IN-READY. This ranch style c...	2 beds \| 2 baths \| 1,600 sq.ft.	$579,900	Airbnb cash on cash: -1.56% Traditional cash on cash: 1.85% Airbnb Rental Income: $1027 Traditional Rental Income: $2511 Airbnb ROI: -1.56% Traditional ROI: 1.85%
2125 Bluestem Dr #0102 Waukesha, WI Located less than 5 minutes off I-94 this condominium is MOVE-IN-READY. This ranch style c...	2 beds \| 2 baths \| 1,600 sq.ft.	$579,900	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.1% Airbnb Rental Income: $1027 Traditional Rental Income: $2516 Airbnb ROI: -1.31% Traditional ROI: 2.1%
2127 Bluestem Dr #0101 Waukesha, WI Located less than 5 minutes off I-94 this condominium is MOVE-IN-READY. This ranch style c...	2 beds \| 2 baths \| 1,600 sq.ft.	$579,900	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.11% Airbnb Rental Income: $1027 Traditional Rental Income: $2516 Airbnb ROI: -1.31% Traditional ROI: 2.11%
2912 N University Dr #201 Waukesha, WI This bright & airy 2-bed, 2-bath condo is filled w/ natural light from large windows & fea...	2 beds \| 2 baths \| 1,334 sq.ft.	$299,900	Airbnb cash on cash: -1.7% Traditional cash on cash: 2.92% Airbnb Rental Income: $1027 Traditional Rental Income: $1971 Airbnb ROI: -1.7% Traditional ROI: 2.92%
3824 White Oak Way Waukesha, WI This fantastic home features flexible dining spaces to accommodate both quick meals and fo...	3 beds \| 2 baths \| 1,818 sq.ft.	$749,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.28% Airbnb Rental Income: $1118 Traditional Rental Income: $2613 Airbnb ROI: -0.4% Traditional ROI: 2.28%
2308 Coldwater Creek Dr Waukesha, WI Spacious Rolling Ridge South ranch on an extra-large lot with exceptional living space ins...	4 beds \| 4 baths \| 4,602 sq.ft.	$660,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 3.33% Airbnb Rental Income: $2478 Traditional Rental Income: $3745 Airbnb ROI: 0.3% Traditional ROI: 3.33%
206 Maple Ave Waukesha, WI Opportunity awaits at this 4 unit multifamily property in Waukesha, ideally suited for an ...	N/A beds \| N/A baths \| N/A	$194,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.23% Airbnb Rental Income: $null Traditional Rental Income: $1484 Airbnb ROI: N/A Traditional ROI: 5.23%
1230 Fox Point Dr Waukesha, WI Step inside this beautifully updated home featuring new windows, updated electrical outlet...	3 beds \| 2 baths \| 1,546 sq.ft.	$384,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.89% Airbnb Rental Income: $1118 Traditional Rental Income: $2337 Airbnb ROI: -0.52% Traditional ROI: 3.89%
503 Westminster Dr Waukesha, WI Perched atop a scenic hill in a desirable Waukesha neighborhood, this beautifully construc...	5 beds \| 4 baths \| 3,458 sq.ft.	$550,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 5.29% Airbnb Rental Income: $971 Traditional Rental Income: $3989 Airbnb ROI: -1.26% Traditional ROI: 5.29%
308 King William Court Ct S Waukesha, WI Welcome to this beautifully maintained Endfield Condo! The 2 bedroom, 2 bathroom condo is ...	2 beds \| 2 baths \| 1,683 sq.ft.	$350,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 4.22% Airbnb Rental Income: $1027 Traditional Rental Income: $2237 Airbnb ROI: -0.56% Traditional ROI: 4.22%
525 Catskill Rd Waukesha, WI Opportunity awaits on Catskill Road! This spacious 3 bed- 2 full bath brick ranch is ready...	3 beds \| 2 baths \| 2,472 sq.ft.	$415,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 4.42% Airbnb Rental Income: $1118 Traditional Rental Income: $2572 Airbnb ROI: -0.28% Traditional ROI: 4.42%

Real Estate investment in Waukesha, WI

There are 155 properties for sale in the city of Waukesha . The median list price in Waukesha is $539,900 and the average price per square foot is $265. In May 2026, the average monthly cash on cash return in Waukesha is 3.00%. The average monthly rental income in Waukesha is $2,540.

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

There are 155 investment properties available for sale in Waukesha.

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

The ROI for Short-Term is higher than the Long-Term in Waukesha with average rental income of $1,118.

Your search for investment property begins and ends here

Investment Property for Sale in Waukesha, WI

709 N Cumberland Dr

Waukesha, WI

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

$385,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $1118

Traditional Rental Income: $2492

Airbnb ROI: -0.78%

Traditional ROI: 4.07%

1822 Rockridge Way

Waukesha, WI

4 beds | 3 baths | 2,269 sq.ft.

$550,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $2478

Traditional Rental Income: $2869

Airbnb ROI: 1.06%

Traditional ROI: 2.99%

1341 E Roberta Ave

Waukesha, WI

4 beds | 2 baths | 2,439 sq.ft.

$424,900

Airbnb cash on cash: 2.29%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $2478

Traditional Rental Income: $2614

Airbnb ROI: 2.29%

Traditional ROI: 4.15%

515 Wynnewood Ct

Waukesha, WI

3 beds | 4 baths | 3,819 sq.ft.

$659,900

Airbnb cash on cash: -1.26%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $1118

Traditional Rental Income: $3262

Airbnb ROI: -1.26%

Traditional ROI: 2.84%

313 S University Dr

Waukesha, WI

3 beds | 2 baths | 1,515 sq.ft.

$389,900

Airbnb cash on cash: -0.52%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1118

Traditional Rental Income: $2196

Airbnb ROI: -0.52%

Traditional ROI: 3.46%

1901 Woodburn Rd #D

Waukesha, WI

2 beds | 2 baths | 1,428 sq.ft.

$265,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $1027

Traditional Rental Income: $2029

Airbnb ROI: -1.13%

Traditional ROI: 4.32%

223 NW Barstow St

Waukesha, WI

3 beds | 2 baths | 1,281 sq.ft.

$230,000

Airbnb cash on cash: 0.86%

Traditional cash on cash: 6.26%

Airbnb Rental Income: $1118

Traditional Rental Income: $1917

Airbnb ROI: 0.86%

Traditional ROI: 6.26%

3640 Madison St

Waukesha, WI

4 beds | 2 baths | 2,403 sq.ft.

$699,900

Airbnb cash on cash: 0.28%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $2478

Traditional Rental Income: $3024

Airbnb ROI: 0.28%