Real Estate Investment Properties for Sale in Ashland, WI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
822 MacArthur Ave Ashland, WI An English Cottage on Macarthur Ave with gardens to match. This corner lot has three bedro...	3 beds \| 2 baths \| 2,047 sq.ft.	$290,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 7.15% Airbnb Rental Income: $913 Traditional Rental Income: $2558 Airbnb ROI: -0.12% Traditional ROI: 7.15%
609 14th Ave E Ashland, WI	2 beds \| 1 baths \| 900 sq.ft.	$89,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 10.2% Airbnb Rental Income: $847 Traditional Rental Income: $1180 Airbnb ROI: 2.65% Traditional ROI: 10.2%
46305 Highway 112 Ashland, WI Welcome to this adorable and functional 3 bedroom, 1 bath home just outside of Ashland off...	3 beds \| 1 baths \| 1,236 sq.ft.	$270,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.4% Airbnb Rental Income: $913 Traditional Rental Income: $1762 Airbnb ROI: -0.27% Traditional ROI: 4.4%
21490 US Highway 2 Ashland, WI Cozy Cabin on 8+ Acres â Backs Up to 280 Acres of DNR Land Escape to the woods with th...	2 beds \| N/A baths \| 240 sq.ft.	$125,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 11.23% Airbnb Rental Income: $847 Traditional Rental Income: $1608 Airbnb ROI: 2.17% Traditional ROI: 11.23%
Investment Properties for Sale in Other Cities of Wisconsin
5822 N 62nd St #5824 Milwaukee , WI This 3/1 duplex is ready for its next owner! One unit was recently renovated with long ter...	6 beds \| 2 baths \| N/A	$199,000	Airbnb cash on cash: 9.32% Traditional cash on cash: 10.16% Airbnb Rental Income: $3050 Traditional Rental Income: $2512 Airbnb ROI: 9.32% Traditional ROI: 10.16%
8104 W Center St Milwaukee , WI Beautiful, well-kept open concept Cape Cod home in a desirable location very close to Wauw...	3 beds \| 2 baths \| 1,524 sq.ft.	$299,900	Airbnb cash on cash: 0.21% Traditional cash on cash: 4.97% Airbnb Rental Income: $1370 Traditional Rental Income: $2298 Airbnb ROI: 0.21% Traditional ROI: 4.97%
1924 N Hubbard St #215 Milwaukee , WI One of the Largest One Bedroom Condos. Historic Brewer's Hill condo offers the best of dow...	1 beds \| 1 baths \| 914 sq.ft.	$225,000	Airbnb cash on cash: -2.35% Traditional cash on cash: 2.78% Airbnb Rental Income: $501 Traditional Rental Income: $1323 Airbnb ROI: -2.35% Traditional ROI: 2.78%
4818 S 19th St Milwaukee , WI Move-in ready and updated 3-BR, 1.5-BA condo features a spacious kitchen w/ granite counte...	3 beds \| 2 baths \| 1,154 sq.ft.	$197,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 6.06% Airbnb Rental Income: $956 Traditional Rental Income: $1805 Airbnb ROI: -0.34% Traditional ROI: 6.06%
4076 N 93rd St Wauwatosa , WI Fully renovated 3BR, 2BA home in desirable Wauwatosa! This move-in ready property features...	3 beds \| 2 baths \| 2,004 sq.ft.	$434,900	Airbnb cash on cash: -0.91% Traditional cash on cash: 2.75% Airbnb Rental Income: $1062 Traditional Rental Income: $2186 Airbnb ROI: -0.91% Traditional ROI: 2.75%
270 E Highland Ave #446 Milwaukee , WI Located in the heart of Downtown Milwaukee, the historic Blatz Condos put the city's best ...	2 beds \| 2 baths \| 980 sq.ft.	$235,900	Airbnb cash on cash: -1.42% Traditional cash on cash: 3.77% Airbnb Rental Income: $824 Traditional Rental Income: $1655 Airbnb ROI: -1.42% Traditional ROI: 3.77%
2354 S 16th St Milwaukee , WI Completely refreshed inside and out, this 2 bedroom, 1 full bath home is located in Milwau...	2 beds \| 1 baths \| 944 sq.ft.	$199,900	Airbnb cash on cash: -0.66% Traditional cash on cash: 3.88% Airbnb Rental Income: $665 Traditional Rental Income: $1226 Airbnb ROI: -0.66% Traditional ROI: 3.88%
1409 N Prospect Ave #102 Milwaukee , WI Rare 2-Bedroom Opportunity at The Fenwick! Experience a unique blend of space and style in...	2 beds \| 1 baths \| 800 sq.ft.	$199,900	Airbnb cash on cash: -1.49% Traditional cash on cash: 3.84% Airbnb Rental Income: $629 Traditional Rental Income: $1346 Airbnb ROI: -1.49% Traditional ROI: 3.84%
1925 N Water St #100 Milwaukee , WI Riverbridge Condominiums are located right on the riverwalk for a convenient walk downtown...	2 beds \| 2 baths \| 1,490 sq.ft.	$364,900	Airbnb cash on cash: -2.11% Traditional cash on cash: 4.29% Airbnb Rental Income: $611 Traditional Rental Income: $2511 Airbnb ROI: -2.11% Traditional ROI: 4.29%
1915 N Water St #400 Milwaukee , WI Sophisticated, light-filled top-floor corner residence with an open-concept layout and pri...	2 beds \| 2 baths \| 1,314 sq.ft.	$339,900	Airbnb cash on cash: -2.21% Traditional cash on cash: 4.15% Airbnb Rental Income: $611 Traditional Rental Income: $2352 Airbnb ROI: -2.21% Traditional ROI: 4.15%
1201 N 46th St Milwaukee , WI Welcome to the Martin Drive Neighborhood, a stone's throw from historic Washington Park wi...	3 beds \| 1 baths \| 1,538 sq.ft.	$274,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.83% Airbnb Rental Income: $857 Traditional Rental Income: $1674 Airbnb ROI: -0.6% Traditional ROI: 3.83%
1313 N Franklin Pl #1002 Milwaukee , WI Embrace elevated downtown living at the prestigious Breakwater. This 10th-floor 1BR, 1.5BA...	1 beds \| 2 baths \| 1,119 sq.ft.	$429,900	Airbnb cash on cash: -2.78% Traditional cash on cash: 1.35% Airbnb Rental Income: $533 Traditional Rental Income: $1920 Airbnb ROI: -2.78% Traditional ROI: 1.35%
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: -0.37% Traditional cash on cash: 4.07% Airbnb Rental Income: $1296 Traditional Rental Income: $2492 Airbnb ROI: -0.37% Traditional ROI: 4.07%
9811 DEER TRAIL ROAD #3 Tomahawk , WI Beautiful low maintenance condominium on Lake Nokomis! This unit features 3 bedrooms, 3 fu...	3 beds \| 3 baths \| 2,490 sq.ft.	$465,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 6.19% Airbnb Rental Income: $867 Traditional Rental Income: $3470 Airbnb ROI: -0.55% Traditional ROI: 6.19%

Real Estate investment in Ashland, WI

There are 4 properties for sale in the city of Ashland . The median list price in Ashland is $549,250 and the average price per square foot is $266. In May 2026, the average monthly cash on cash return in Ashland is 9.00%. The average monthly rental income in Ashland is $1,606.

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

There are 4 investment properties available for sale in Ashland.

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

The ROI for Long-Term is higher than the Short-Term in Ashland with average rental income of $1,606.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, WI

822 MacArthur Ave

Ashland, WI

3 beds | 2 baths | 2,047 sq.ft.

$290,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 7.15%

Airbnb Rental Income: $913

Traditional Rental Income: $2558

Airbnb ROI: -0.12%

Traditional ROI: 7.15%

609 14th Ave E

Ashland, WI

2 beds | 1 baths | 900 sq.ft.

$89,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 10.2%

Airbnb Rental Income: $847

Traditional Rental Income: $1180

Airbnb ROI: 2.65%

Traditional ROI: 10.2%

46305 Highway 112

Ashland, WI

3 beds | 1 baths | 1,236 sq.ft.

$270,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $913

Traditional Rental Income: $1762

Airbnb ROI: -0.27%

Traditional ROI: 4.4%

21490 US Highway 2

Ashland, WI

2 beds | N/A baths | 240 sq.ft.

$125,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 11.23%

Airbnb Rental Income: $847

Traditional Rental Income: $1608

Airbnb ROI: 2.17%

Traditional ROI: 11.23%

Investment Properties for Sale in Other Cities of Wisconsin

Milwaukee , WI

6 beds | 2 baths | N/A

$199,000

Airbnb cash on cash: 9.32%

Traditional cash on cash: 10.16%

Airbnb Rental Income: $3050

Traditional Rental Income: $2512

Airbnb ROI: 9.32%

Traditional ROI: 10.16%

Milwaukee , WI

3 beds | 2 baths | 1,524 sq.ft.

$299,900

Airbnb cash on cash: 0.21%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $1370

Traditional Rental Income: $2298

Airbnb ROI: 0.21%

Traditional ROI: 4.97%

Milwaukee , WI

1 beds | 1 baths | 914 sq.ft.

$225,000

Airbnb cash on cash: -2.35%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $501

Traditional Rental Income: $1323

Airbnb ROI: -2.35%

Traditional ROI: 2.78%

Milwaukee , WI

3 beds | 2 baths | 1,154 sq.ft.

$197,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $956

Traditional Rental Income: $1805

Airbnb ROI: -0.34%

Traditional ROI: 6.06%

Wauwatosa , WI

3 beds | 2 baths | 2,004 sq.ft.