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
2729 Lake Shore Dr Dr E #4 Ashland, WI These remarkable waterfront condominiums located within the City of Ashland truly are one ...	2 beds \| 2 baths \| 1,647 sq.ft.	$354,900	Airbnb cash on cash: 1.83% Traditional cash on cash: 2.86% Airbnb Rental Income: $2220 Traditional Rental Income: $2005 Airbnb ROI: 1.83% Traditional ROI: 2.86%
1023 14th Ave W Ashland, WI Beautiful Cape Cod style home on dead end road close to schools and hospital. 4 bedroom, ...	3 beds \| 1 baths \| 1,764 sq.ft.	$244,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 5.06% Airbnb Rental Income: $1549 Traditional Rental Income: $1631 Airbnb ROI: 2.77% Traditional ROI: 5.06%
2812 Fellman Dr Ashland, WI This home is truly one of Ashland's finest. Situated on the picturesque 13th fairway of th...	5 beds \| 5 baths \| 3,456 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $5212 Airbnb ROI: N/A Traditional ROI: 6.33%
23920 US Highway 2 Ashland, WI Welcome to your own piece of country paradise just 15 minutes from Ashland! Situated on a ...	4 beds \| 2 baths \| 3,080 sq.ft.	$479,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 4.88% Airbnb Rental Income: $1297 Traditional Rental Income: $3007 Airbnb ROI: 0.16% Traditional ROI: 4.88%
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.	$305,500	Airbnb cash on cash: 1.68% Traditional cash on cash: 6.75% Airbnb Rental Income: $1549 Traditional Rental Income: $2558 Airbnb ROI: 1.68% Traditional ROI: 6.75%
1008 E 3rd Ave Ashland, WI Move right in! This beautifully updated home features a new kitchen, modern bathrooms, and...	2 beds \| 2 baths \| 1,125 sq.ft.	$169,900	Airbnb cash on cash: 7.8% Traditional cash on cash: 9.78% Airbnb Rental Income: $2220 Traditional Rental Income: $1982 Airbnb ROI: 7.8% Traditional ROI: 9.78%
922 MacArthur Ave Ashland, WI This home features 3 bedrooms, with one full bathroom. A main floor bedroom with a main f...	3 beds \| 1 baths \| 1,575 sq.ft.	$130,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 11.94% Airbnb Rental Income: $1549 Traditional Rental Income: $1857 Airbnb ROI: 5.9% Traditional ROI: 11.94%
2119 E 5th Ave Ashland, WI Location, location, location. This charming ranch style home, is perfect for the ones tha...	2 beds \| 2 baths \| 1,300 sq.ft.	$250,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 6.14% Airbnb Rental Income: $2220 Traditional Rental Income: $1885 Airbnb ROI: 5.19% Traditional ROI: 6.14%
1217 6th Ave Ave W Ashland, WI 1217 6th Ave Ave W, Ashland, WI 54806 \| Single Family Residential	5 beds \| 2 baths \| 2,446 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $2369 Airbnb ROI: N/A Traditional ROI: 3.64%
62543 Hegstrom Rd Ashland, WI 62543 Hegstrom Rd, Ashland, WI 54806 \| Single Family Residential	2 beds \| 1 baths \| 960 sq.ft.	$339,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.99% Airbnb Rental Income: $2220 Traditional Rental Income: $1632 Airbnb ROI: 2.08% Traditional ROI: 1.99%
119 16th Ave Ave E Ashland, WI 119 16th Ave Ave E, Ashland, WI 54806 \| Single Family Residential	4 beds \| 1 baths \| 1,240 sq.ft.	$174,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 6.38% Airbnb Rental Income: $1297 Traditional Rental Income: $1616 Airbnb ROI: 2.01% Traditional ROI: 6.38%
60445 W Summit Rd Ashland, WI 60445 W Summit Rd, Ashland, WI 54806 \| Single Family Residential	3 beds \| 2 baths \| 2,100 sq.ft.	$695,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.51% Airbnb Rental Income: $1549 Traditional Rental Income: $2260 Airbnb ROI: -1.28% Traditional ROI: 0.51%
801 4th Ave W Ashland, WI 801 4th Ave W, Ashland, WI 54806 \| Single Family Residential	N/A beds \| 1 baths \| 8,004 sq.ft.	$59,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.66% Airbnb Rental Income: $null Traditional Rental Income: $779 Airbnb ROI: N/A Traditional ROI: 8.66%
801 9th Ave W Ashland, WI 801 9th Ave W, Ashland, WI 54806 \| Single Family Residential	3 beds \| 2 baths \| 2,379 sq.ft.	$269,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 5.72% Airbnb Rental Income: $1549 Traditional Rental Income: $2262 Airbnb ROI: 1.15% Traditional ROI: 5.72%
1218 & 1222 Lake Shore Dr W Ashland, WI 1218 & 1222 Lake Shore Dr W, Ashland, WI 54806 \| Multi Family	2 beds \| 1 baths \| N/A	$260,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 1.08% Airbnb Rental Income: $2220 Traditional Rental Income: $1052 Airbnb ROI: 3.57% Traditional ROI: 1.08%
1100 Ellis Ave Ashland, WI 1100 Ellis Ave, Ashland, WI 54806 \| Single Family Residential	3 beds \| 2 baths \| 3,248 sq.ft.	$319,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.32% Airbnb Rental Income: $1549 Traditional Rental Income: $1937 Airbnb ROI: 0.53% Traditional ROI: 3.32%
208 3rd Ave W Ashland, WI 208 3rd Ave Ave W #202, Ashland, WI 54806 \| Condo/Coop	2 beds \| 2 baths \| 1,712 sq.ft.	$389,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.05% Airbnb Rental Income: $2220 Traditional Rental Income: $2262 Airbnb ROI: 0.4% Traditional ROI: 2.05%
208 3rd Ave Ave W #201 Ashland, WI 208 3rd Ave Ave W #201, Ashland, WI 54806 \| Condo/Coop	2 beds \| 2 baths \| 2,012 sq.ft.	$449,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.65% Airbnb Rental Income: $2220 Traditional Rental Income: $2368 Airbnb ROI: -0.03% Traditional ROI: 1.65%
1xxx Ellis Ave Ashland, WI 1xxx Ellis Ave, Ashland, WI 54806 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 2.64%
0000 Ashland Bayfield Rd Ashland, WI 0000 Ashland Bayfield Rd, Ashland, WI 54806 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 2.64%
000 City Heights Rd Ashland, WI 000 City Heights Rd, Ashland, WI 54806 \| Other	N/A beds \| N/A baths \| N/A	$55,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.05% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 9.05%
1707 Beaser Ave Ashland, WI 1707 Beaser Ave, Ashland, WI 54806 \| Other	N/A beds \| N/A baths \| N/A	$110,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 3.36%
28XX Junction Rd Ashland, WI 28XX Junction Rd, Ashland, WI 54806 \| Other	N/A beds \| N/A baths \| N/A	$59,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.16% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 8.16%
xx Sanborn Ave Ashland, WI xx Sanborn Ave, Ashland, WI 54806 \| Other	N/A beds \| N/A baths \| N/A	$45,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.18% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 11.18%
30995 Us Highway 2 Ashland, WI 30995 Us Highway 2, Ashland, WI 54806 \| Single Family Residential	1 beds \| 1 baths \| 2,600 sq.ft.	$500,000	Airbnb cash on cash: -0.4% Traditional cash on cash: -0.97% Airbnb Rental Income: $1705 Traditional Rental Income: $964 Airbnb ROI: -0.4% Traditional ROI: -0.97%
000 US Hwy 2 Ashland, WI 000 US Hwy 2, Ashland, WI 54847 \| Other	N/A beds \| N/A baths \| N/A	$39,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.34% Airbnb Rental Income: $null Traditional Rental Income: $625 Airbnb ROI: N/A Traditional ROI: 10.34%

Real Estate investment in Ashland, WI

There are 26 properties for sale in the city of Ashland . The median list price in Ashland is $442,000 and the average price per square foot is $196. In January 2026, the average monthly cash on cash return in Ashland is 10.00%. The average monthly rental income in Ashland is $964.

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

There are 26 investment properties available for sale in Ashland.

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

The ROI for Short-Term is higher than the Long-Term in Ashland with average rental income of $2,220.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, WI

2729 Lake Shore Dr Dr E #4

Ashland, WI

2 beds | 2 baths | 1,647 sq.ft.

$354,900

Airbnb cash on cash: 1.83%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $2220

Traditional Rental Income: $2005

Airbnb ROI: 1.83%

Traditional ROI: 2.86%

1023 14th Ave W

Ashland, WI

3 beds | 1 baths | 1,764 sq.ft.

$244,900

Airbnb cash on cash: 2.77%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $1549

Traditional Rental Income: $1631

Airbnb ROI: 2.77%

Traditional ROI: 5.06%

2812 Fellman Dr

Ashland, WI

5 beds | 5 baths | 3,456 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.33%

Airbnb Rental Income: $null

Traditional Rental Income: $5212

Airbnb ROI: N/A

Traditional ROI: 6.33%

23920 US Highway 2

Ashland, WI

4 beds | 2 baths | 3,080 sq.ft.

$479,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1297

Traditional Rental Income: $3007

Airbnb ROI: 0.16%

Traditional ROI: 4.88%

822 MacArthur Ave

Ashland, WI

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

$305,500

Airbnb cash on cash: 1.68%

Traditional cash on cash: 6.75%

Airbnb Rental Income: $1549

Traditional Rental Income: $2558

Airbnb ROI: 1.68%

Traditional ROI: 6.75%

1008 E 3rd Ave

Ashland, WI

2 beds | 2 baths | 1,125 sq.ft.

$169,900

Airbnb cash on cash: 7.8%

Traditional cash on cash: 9.78%

Airbnb Rental Income: $2220

Traditional Rental Income: $1982

Airbnb ROI: 7.8%

Traditional ROI: 9.78%

922 MacArthur Ave

Ashland, WI

3 beds | 1 baths | 1,575 sq.ft.

$130,000

Airbnb cash on cash: 5.9%

Traditional cash on cash: 11.94%

Airbnb Rental Income: $1549

Traditional Rental Income: $1857

Airbnb ROI: 5.9%

Traditional ROI: 11.94%

2119 E 5th Ave

Ashland, WI

2 beds | 2 baths | 1,300 sq.ft.

$250,000

Airbnb cash on cash: 5.19%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $2220

Traditional Rental Income: $1885

Airbnb ROI: 5.19%