Real Estate Investment Properties for Sale in Ashland, KY

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3013 Simpson Road Ashland, KY This newly remodeled 3 bedroom, 1 1/2 bath home blends modern updates with a functional la...	3 beds \| 2 baths \| 1,172 sq.ft.	$109,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 10.81% Airbnb Rental Income: $761 Traditional Rental Income: $1366 Airbnb ROI: 2.16% Traditional ROI: 10.81%
415 Bellefonte Princess Road Rd Ashland, KY 415 Bellefonte Princess Road Rd, Ashland, KY 41101 \| Single Family Residential	5 beds \| 4 baths \| 4,932 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $2896 Airbnb ROI: N/A Traditional ROI: 4.14%
3001 29th St Ashland, KY 3001 29th St, Ashland, KY 41101 \| Single Family Residential	3 beds \| 1 baths \| 1,644 sq.ft.	$179,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 4.34% Airbnb Rental Income: $761 Traditional Rental Income: $1147 Airbnb ROI: 0.22% Traditional ROI: 4.34%
1788 Woodbury Drive Dr Ashland, KY 1788 Woodbury Drive Dr, Ashland, KY 41101 \| Manufactured Home	3 beds \| 2 baths \| 1,716 sq.ft.	$129,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 10.11% Airbnb Rental Income: $761 Traditional Rental Income: $1576 Airbnb ROI: 0.99% Traditional ROI: 10.11%
3232 Blackburn Ave Ashland, KY 3232 Blackburn Ave, Ashland, KY 41101 \| Single Family Residential	2 beds \| 2 baths \| 1,284 sq.ft.	$104,900	Airbnb cash on cash: 0.71% Traditional cash on cash: 8.53% Airbnb Rental Income: $651 Traditional Rental Income: $1149 Airbnb ROI: 0.71% Traditional ROI: 8.53%
2833 Blackburn Ave Ashland, KY 2833 Blackburn Ave, Ashland, KY 41101 \| Single Family Residential	2 beds \| 1 baths \| 980 sq.ft.	$199,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.07% Airbnb Rental Income: $651 Traditional Rental Income: $835 Airbnb ROI: -0.47% Traditional ROI: 2.07%
601 Pollard Road Rd Ashland, KY 601 Pollard Road Rd, Ashland, KY 41101 \| Single Family Residential	1 beds \| 1 baths \| 650 sq.ft.	$59,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 6.46% Airbnb Rental Income: $694 Traditional Rental Income: $585 Airbnb ROI: 3.16% Traditional ROI: 6.46%
000 Chestnut Hill Dr Ashland, KY 000 Chestnut Hill Dr, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$139,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.95% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: 0.95%
0 Kirk St Ashland, KY 0 Kirk St, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.76% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: 0.76%
0 Pollard Rd Ashland, KY 0 Pollard Rd, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: 1.25%
Ivy Creek, Lots 11 & 12 Ashland, KY Ivy Creek, Lots 11 & 12, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$59,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: 4.38%
3303 Newman St Ashland, KY 3303 Newman St, Ashland, KY 41101 \| Single Family Residential	3 beds \| 2 baths \| 1,240 sq.ft.	$229,750	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.41% Airbnb Rental Income: $761 Traditional Rental Income: $1237 Airbnb ROI: -0.23% Traditional ROI: 3.41%
27th Block OF Carter Ave Ashland, KY 27th Block OF Carter Ave, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.52% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: -0.52%
18th Street & Central Ave Ashland, KY 18th Street & Central Ave, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.24% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: -1.24%
924 29th St Ashland, KY 924 29th St, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$37,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.96% Airbnb Rental Income: $null Traditional Rental Income: $479 Airbnb ROI: N/A Traditional ROI: 7.96%
Central & Mlk Blvd Ashland, KY Central & Mlk Blvd, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.86% Airbnb Rental Income: $null Traditional Rental Income: $467 Airbnb ROI: N/A Traditional ROI: -0.86%
4851 Richardson Rd Ashland, KY 4851 Richardson Rd, Ashland, KY 41101 \| Single Family Residential	4 beds \| 2 baths \| 2,185 sq.ft.	$259,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.53% Airbnb Rental Income: $974 Traditional Rental Income: $1898 Airbnb ROI: 0.31% Traditional ROI: 5.53%
2224 Crooks St Ashland, KY 2224 Crooks St, Ashland, KY 41101 \| Single Family Residential	2 beds \| 1 baths \| 1,336 sq.ft.	$129,900	Airbnb cash on cash: 0.24% Traditional cash on cash: 5.62% Airbnb Rental Income: $651 Traditional Rental Income: $1026 Airbnb ROI: 0.24% Traditional ROI: 5.62%
Suttles Road, Lot 2 Ashland, KY Suttles Road, Lot 2, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$39,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.73% Airbnb Rental Income: $null Traditional Rental Income: $533 Airbnb ROI: N/A Traditional ROI: 8.73%
Rolling Hills, Lot 1 Ashland, KY Rolling Hills, Lot 1, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$39,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.73% Airbnb Rental Income: $null Traditional Rental Income: $533 Airbnb ROI: N/A Traditional ROI: 8.73%
714 Bellefonte Princess Rd Ashland, KY Sellers are ready to make a deal! Welcome to this beautifully refreshed two-story brick ho...	4 beds \| 3 baths \| 2,696 sq.ft.	$329,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 6.97% Airbnb Rental Income: $974 Traditional Rental Income: $2830 Airbnb ROI: -0.14% Traditional ROI: 6.97%
341 31st Street Ashland, KY Investor opportunity with this turnkey duplex with strong income potential This solid 1,63...	N/A beds \| N/A baths \| 1,632 sq.ft.	$129,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.1% Airbnb Rental Income: $null Traditional Rental Income: $1123 Airbnb ROI: N/A Traditional ROI: 7.1%
2208 Cedar Street Ashland, KY This 2-bedroom, 2-bath home offers a practical layout with a comfortable living room and a...	2 beds \| 1 baths \| 784 sq.ft.	$82,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 10.41% Airbnb Rental Income: $651 Traditional Rental Income: $1033 Airbnb ROI: 1.98% Traditional ROI: 10.41%
714 Bellefonte Princess Rd Rd Ashland, KY 714 Bellefonte Princess Rd Rd, Ashland, KY 41101 \| Single Family Residential	4 beds \| 3 baths \| 2,696 sq.ft.	$329,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.11% Airbnb Rental Income: $974 Traditional Rental Income: $2251 Airbnb ROI: -0.14% Traditional ROI: 5.11%
138 Laurel Court Ct Ashland, KY 138 Laurel Court Ct, Ashland, KY 41101 \| Single Family Residential	4 beds \| 3 baths \| 2,924 sq.ft.	$389,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.32% Airbnb Rental Income: $974 Traditional Rental Income: $2349 Airbnb ROI: -0.4% Traditional ROI: 4.32%
1021 Geiger Lane Ln Ashland, KY 1021 Geiger Lane Ln, Ashland, KY 41101 \| Single Family Residential	2 beds \| 1 baths \| 1,008 sq.ft.	$59,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 11.9% Airbnb Rental Income: $651 Traditional Rental Income: $907 Airbnb ROI: 2.56% Traditional ROI: 11.9%
2915 Dawes St Ashland, KY 2915 Dawes St, Ashland, KY 41101 \| Single Family Residential	3 beds \| 2 baths \| 2,015 sq.ft.	$239,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 5.68% Airbnb Rental Income: $761 Traditional Rental Income: $1802 Airbnb ROI: -0.3% Traditional ROI: 5.68%
395 W Central Avenue Ave Ashland, KY 395 W Central Avenue Ave, Ashland, KY 41101 \| Single Family Residential	2 beds \| 3 baths \| 2,600 sq.ft.	$225,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 6.85% Airbnb Rental Income: $651 Traditional Rental Income: $1946 Airbnb ROI: -0.63% Traditional ROI: 6.85%
101 Bellefonte Dr Ashland, KY 101 Bellefonte Dr, Ashland, KY 41101 \| Other	N/A beds \| N/A baths \| N/A	$109,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $533 Airbnb ROI: N/A Traditional ROI: 2.28%
2406 Central Parkway Pkwy Ashland, KY 2406 Central Parkway Pkwy, Ashland, KY 41101 \| Single Family Residential	4 beds \| 2 baths \| 1,992 sq.ft.	$169,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 9.23% Airbnb Rental Income: $974 Traditional Rental Income: $1879 Airbnb ROI: 1.44% Traditional ROI: 9.23%
2913 & 2915 Bath Avenue Ave Ashland, KY 2913 & 2915 Bath Ave, Ashland, KY 41101 \| Multi Family	N/A beds \| N/A baths \| N/A	$234,500	Airbnb cash on cash: 0.54% Traditional cash on cash: -0.04% Airbnb Rental Income: $974 Traditional Rental Income: $495 Airbnb ROI: 0.54% Traditional ROI: -0.04%
2409 Hilton Ave Ashland, KY 2409 Hilton Ave, Ashland, KY 41101 \| Single Family Residential	3 beds \| 2 baths \| 1,419 sq.ft.	$134,750	Airbnb cash on cash: 0.87% Traditional cash on cash: 8.37% Airbnb Rental Income: $761 Traditional Rental Income: $1416 Airbnb ROI: 0.87% Traditional ROI: 8.37%
5438 Don Rd Ashland, KY 5438 Don Rd, Ashland, KY 41101 \| Single Family Residential	4 beds \| 2 baths \| 1,898 sq.ft.	$215,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 6.3% Airbnb Rental Income: $974 Traditional Rental Income: $1754 Airbnb ROI: 0.75% Traditional ROI: 6.3%
411 Wheatley Rd Ashland, KY 411 Wheatley Rd, Ashland, KY 41101 \| Single Family Residential	3 beds \| 2 baths \| 2,220 sq.ft.	$229,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 6.18% Airbnb Rental Income: $761 Traditional Rental Income: $1841 Airbnb ROI: -0.23% Traditional ROI: 6.18%
4700 Boyd Street St Ashland, KY 4700 Boyd Street St, Ashland, KY 41101 \| Single Family Residential	3 beds \| 2 baths \| 3,100 sq.ft.	$240,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 6.29% Airbnb Rental Income: $761 Traditional Rental Income: $1940 Airbnb ROI: -0.3% Traditional ROI: 6.29%
1257 Ivy Creek Rd Ashland, KY 1257 Ivy Creek Rd, Ashland, KY 41101 \| Single Family Residential	5 beds \| 4 baths \| 5,054 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.77% Airbnb Rental Income: $null Traditional Rental Income: $2949 Airbnb ROI: N/A Traditional ROI: 2.77%
1037 Geiger Lane Ashland, KY This spacious 4-bedroom, 2-bath home sits on a large, private lot, offering room to relax,...	4 beds \| 2 baths \| 1,562 sq.ft.	$169,900	Airbnb cash on cash: 1.84% Traditional cash on cash: 11.33% Airbnb Rental Income: $974 Traditional Rental Income: $2161 Airbnb ROI: 1.84% Traditional ROI: 11.33%
406 Bellefonte Princess Rd Ashland, KY 406 Bellefonte Princess Rd, Ashland, KY 41101 \| Single Family Residential	4 beds \| 2 baths \| 2,285 sq.ft.	$389,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.11% Airbnb Rental Income: $974 Traditional Rental Income: $1905 Airbnb ROI: -0.4% Traditional ROI: 3.11%
1008 Central Avenue Ave Ashland, KY 1008 Central Avenue Ave, Ashland, KY 41101 \| Single Family Residential	3 beds \| 2 baths \| 1,638 sq.ft.	$129,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 10.11% Airbnb Rental Income: $761 Traditional Rental Income: $1587 Airbnb ROI: 0.97% Traditional ROI: 10.11%
2033 Oakview Road Rd Ashland, KY 2033 Oakview Road Rd, Ashland, KY 41101 \| Single Family Residential	2 beds \| 1 baths \| 920 sq.ft.	$60,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 11.61% Airbnb Rental Income: $651 Traditional Rental Income: $903 Airbnb ROI: 2.48% Traditional ROI: 11.61%

Real Estate investment in Ashland, KY

There are 112 properties for sale in the city of Ashland . The median list price in Ashland is $144,925 and the average price per square foot is $67. In June 2026, the average monthly cash on cash return in Ashland is 6.00%. The average monthly rental income in Ashland is $1,253.

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

There are 112 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 $761.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, KY

3013 Simpson Road

Ashland, KY

3 beds | 2 baths | 1,172 sq.ft.

$109,900

Airbnb cash on cash: 2.16%

Traditional cash on cash: 10.81%

Airbnb Rental Income: $761

Traditional Rental Income: $1366

Airbnb ROI: 2.16%

Traditional ROI: 10.81%

415 Bellefonte Princess Road Rd

Ashland, KY

5 beds | 4 baths | 4,932 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2896

Airbnb ROI: N/A

Traditional ROI: 4.14%

3001 29th St

Ashland, KY

3 beds | 1 baths | 1,644 sq.ft.

$179,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $761

Traditional Rental Income: $1147

Airbnb ROI: 0.22%

Traditional ROI: 4.34%

1788 Woodbury Drive Dr

Ashland, KY

3 beds | 2 baths | 1,716 sq.ft.

$129,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 10.11%

Airbnb Rental Income: $761

Traditional Rental Income: $1576

Airbnb ROI: 0.99%

Traditional ROI: 10.11%

3232 Blackburn Ave

Ashland, KY

2 beds | 2 baths | 1,284 sq.ft.

$104,900

Airbnb cash on cash: 0.71%

Traditional cash on cash: 8.53%

Airbnb Rental Income: $651

Traditional Rental Income: $1149

Airbnb ROI: 0.71%

Traditional ROI: 8.53%

2833 Blackburn Ave

Ashland, KY

2 beds | 1 baths | 980 sq.ft.

$199,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $651

Traditional Rental Income: $835

Airbnb ROI: -0.47%

Traditional ROI: 2.07%

601 Pollard Road Rd

Ashland, KY

1 beds | 1 baths | 650 sq.ft.

$59,000

Airbnb cash on cash: 3.16%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $694

Traditional Rental Income: $585

Airbnb ROI: 3.16%

Traditional ROI: 6.46%

000 Chestnut Hill Dr

Ashland, KY

N/A beds | N/A baths | N/A

$139,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.95%

Airbnb Rental Income: $null

Traditional Rental Income: $467

Airbnb ROI: N/A