Real Estate Investment Properties for Sale in Hillsboro, KY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
96 Hay Drive Hillsboro, KY Welcome to this charming single-level home nestled in a quiet and peaceful neighborhood in...	3 beds \| 1 baths \| 1,697 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.69% Airbnb Rental Income: $null Traditional Rental Income: $1918 Airbnb ROI: N/A Traditional ROI: 8.69%
3454 Hillsboro Road Hillsboro, KY Spacious Amish-built home, offering a very peaceful setting on a two acre lot! This 4 or 5...	5 beds \| N/A baths \| 2,240 sq.ft.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.61% Airbnb Rental Income: $null Traditional Rental Income: $2271 Airbnb ROI: N/A Traditional ROI: 9.61%
1475 Skaggs Lane Hillsboro, KY Beautiful 3-bedroom, 2-bath ranch home on 5.77 unrestricted acres in Hillsboro, KY! This p...	3 beds \| 2 baths \| 1,144 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.16% Airbnb Rental Income: $null Traditional Rental Income: $1932 Airbnb ROI: N/A Traditional ROI: 6.16%
604 and 610 Sunset Road Hillsboro, KY Let me introduce you to this one of a kind versatile property! Take advantage of this exce...	3 beds \| N/A baths \| 2,376 sq.ft.	$729,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $2207 Airbnb ROI: N/A Traditional ROI: 2%
530 Crawford Bend Road Hillsboro, KY Peaceful country living on 9.95 acres can be yours! Escape to your own private retreat wit...	3 beds \| 2 baths \| 1,792 sq.ft.	$312,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $2299 Airbnb ROI: N/A Traditional ROI: 6.22%
4842 Orchard Road Hillsboro, KY Engineering Certification in hand! Welcome to this beautiful 3 bedroom 2 bath home on 2.5 ...	3 beds \| 2 baths \| 1,344 sq.ft.	$188,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.45% Airbnb Rental Income: $null Traditional Rental Income: $2003 Airbnb ROI: N/A Traditional ROI: 9.45%
231 Hidden Hollow Road Hillsboro, KY Built in 2019, this home sits on 4.02 flat, fully usable, unrestricted acres with plenty o...	4 beds \| 2 baths \| 1,904 sq.ft.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.26% Airbnb Rental Income: $null Traditional Rental Income: $2462 Airbnb ROI: N/A Traditional ROI: 10.26%

Real Estate investment in Hillsboro, KY

There are 7 properties for sale in the city of Hillsboro . The median list price in Hillsboro is $204,450 and the average price per square foot is $120. In December 2025, the average monthly cash on cash return in Hillsboro is 9.00%. The average monthly rental income in Hillsboro is $2,105.

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

There are 7 investment properties available for sale in Hillsboro.

In 2025, the best neighborhood to buy investment property is Hillsboro.

The ROI for Short-Term is higher than the Long-Term in Hillsboro with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Hillsboro, KY

96 Hay Drive

Hillsboro, KY

3 beds | 1 baths | 1,697 sq.ft.

$189,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.69%

Airbnb Rental Income: $null

Traditional Rental Income: $1918

Airbnb ROI: N/A

Traditional ROI: 8.69%

3454 Hillsboro Road

Hillsboro, KY

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

$199,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2271

Airbnb ROI: N/A

Traditional ROI: 9.61%

1475 Skaggs Lane

Hillsboro, KY

3 beds | 2 baths | 1,144 sq.ft.

$249,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.16%

Airbnb Rental Income: $null

Traditional Rental Income: $1932

Airbnb ROI: N/A

Traditional ROI: 6.16%

604 and 610 Sunset Road

Hillsboro, KY

3 beds | N/A baths | 2,376 sq.ft.

$729,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2%

Airbnb Rental Income: $null

Traditional Rental Income: $2207

Airbnb ROI: N/A

Traditional ROI: 2%

530 Crawford Bend Road

Hillsboro, KY

3 beds | 2 baths | 1,792 sq.ft.

$312,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6.22%

Airbnb Rental Income: $null

Traditional Rental Income: $2299

Airbnb ROI: N/A

Traditional ROI: 6.22%

4842 Orchard Road

Hillsboro, KY

3 beds | 2 baths | 1,344 sq.ft.

$188,500

Airbnb cash on cash: N/A

Traditional cash on cash: 9.45%

Airbnb Rental Income: $null

Traditional Rental Income: $2003

Airbnb ROI: N/A

Traditional ROI: 9.45%

231 Hidden Hollow Road

Hillsboro, KY

4 beds | 2 baths | 1,904 sq.ft.

$209,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2462

Airbnb ROI: N/A

Traditional ROI: 10.26%

Real Estate investment in Hillsboro, KY

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

How many investment properties are available for sale in Hillsboro?

Which neighborhoods in Hillsboro to invest in 2025?

Long-Term vs. Short-Term Rentals in Hillsboro, Kentucky: Which will earn the best returns?

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