Real Estate Investment Properties for Sale in Prestonsburg, KY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
216 Rose Dr Prestonsburg, KY This cozy home is cute beyond words, featuring 3 bedrooms, 1 bath, a covered front porch a...	3 beds \| N/A baths \| 960 sq.ft.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.51% Airbnb Rental Income: $null Traditional Rental Income: $1567 Airbnb ROI: N/A Traditional ROI: 7.51%
632 Clubhouse Drive Prestonsburg, KY Well maintained 4 bedroom, 3 bath townhouse offering scenic golf course views from 2 priva...	4 beds \| 3 baths \| 2,080 sq.ft.	$248,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.97% Airbnb Rental Income: $null Traditional Rental Income: $2614 Airbnb ROI: N/A Traditional ROI: 8.97%
21 Crestwood Cir Prestonsburg, KY his 4,300 sq ft (all living) 4 Bed, 3.50 Bath, 2 story wrapped in James Hardie siding & St...	4 beds \| 3 baths \| 4,398 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 2.43%
2850 Abbott Creek Rd Prestonsburg, KY GREAT NEIGHBORHOOD! 4 bed 3 bath with mother in law suite on a corner lot!	4 beds \| 3 baths \| 2,392 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.93% Airbnb Rental Income: $null Traditional Rental Income: $2273 Airbnb ROI: N/A Traditional ROI: 6.93%
366 Highland Prestonsburg, KY Multiple possibilities await the Buyer of this property. You could be an investor looking ...	N/A beds \| N/A baths \| 2,600 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.43% Airbnb Rental Income: $null Traditional Rental Income: $1783 Airbnb ROI: N/A Traditional ROI: 6.43%
19 Magnolia Lane Prestonsburg, KY Privacy, peace and room to roam are just a few amenities this property has to offer! 4 bed...	4 beds \| 2 baths \| 3,000 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.2% Airbnb Rental Income: $null Traditional Rental Income: $2767 Airbnb ROI: N/A Traditional ROI: 10.2%
60 Ridge Run Prestonsburg, KY Price Reduced to $209,900! Experience the perfect mix of privacy and convenience in this c...	3 beds \| 2 baths \| 1,952 sq.ft.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.12% Airbnb Rental Income: $null Traditional Rental Income: $2276 Airbnb ROI: N/A Traditional ROI: 9.12%
6403 Spurlock Crk Prestonsburg, KY Large well maintained 4 bedroom 2.5 bathroom home with over 3000 square feet of living spa...	4 beds \| N/A baths \| 3,280 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 5.9%
5528 Ky Rt 114 Prestonsburg, KY Investment opportunity! This property includes 8-1 bedroom 1 bath apartments and 24-2 bedr...	2 beds \| 1 baths \| 27,186 sq.ft.	$1,885,650	Airbnb cash on cash: -1.62% Traditional cash on cash: -0.95% Airbnb Rental Income: $830 Traditional Rental Income: $1677 Airbnb ROI: -1.62% Traditional ROI: -0.95%
611 Blue River Branch Prestonsburg, KY Beautiful 4 bedroom, 2.5 bath home situated on 50 acres. Privacy and country living close ...	4 beds \| 3 baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.74% Airbnb Rental Income: $null Traditional Rental Income: $3247 Airbnb ROI: N/A Traditional ROI: 7.74%
611 Blue River Branch Road Prestonsburg, KY Contemporary 4 bedroom home situated on 50 acres. Privacy while being only minutes to town...	4 beds \| 2 baths \| 2,336 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $2367 Airbnb ROI: N/A Traditional ROI: 5.06%
4589 Abbott Crk Prestonsburg, KY Well maintained brick ranch on a large 60 acre tract of land. Perfect starter home or empt...	2 beds \| N/A baths \| 1,270 sq.ft.	$299,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 5.03% Airbnb Rental Income: $830 Traditional Rental Income: $2036 Airbnb ROI: -0.4% Traditional ROI: 5.03%
163 South Cardinal Dr Prestonsburg, KY 4 bedroom, 3 bath home located in a highly convenient neighborhood close to shopping, dini...	4 beds \| 3 baths \| 2,932 sq.ft.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.3% Airbnb Rental Income: $null Traditional Rental Income: $3321 Airbnb ROI: N/A Traditional ROI: 11.3%
1320 RIVERSIDE Prestonsburg, KY Super excited to announce this gem! A completely remodeled 3 bed, 2 bath home, move-in rea...	3 beds \| 2 baths \| N/A	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.87% Airbnb Rental Income: $null Traditional Rental Income: $2380 Airbnb ROI: N/A Traditional ROI: 11.87%

Real Estate investment in Prestonsburg, KY

There are 25 properties for sale in the city of Prestonsburg . The median list price in Prestonsburg is $209,900 and the average price per square foot is $62. In February 2026, the average monthly cash on cash return in Prestonsburg is 9.00%. The average monthly rental income in Prestonsburg is $2,276.

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

There are 25 investment properties available for sale in Prestonsburg.

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

The ROI for Short-Term is higher than the Long-Term in Prestonsburg with average rental income of $830.

Your search for investment property begins and ends here

Investment Property for Sale in Prestonsburg, KY

216 Rose Dr

Prestonsburg, KY

3 beds | N/A baths | 960 sq.ft.

$165,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.51%

Airbnb Rental Income: $null

Traditional Rental Income: $1567

Airbnb ROI: N/A

Traditional ROI: 7.51%

632 Clubhouse Drive

Prestonsburg, KY

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

$248,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.97%

Airbnb Rental Income: $null

Traditional Rental Income: $2614

Airbnb ROI: N/A

Traditional ROI: 8.97%

21 Crestwood Cir

Prestonsburg, KY

4 beds | 3 baths | 4,398 sq.ft.

$635,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2632

Airbnb ROI: N/A

Traditional ROI: 2.43%

2850 Abbott Creek Rd

Prestonsburg, KY

4 beds | 3 baths | 2,392 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2273

Airbnb ROI: N/A

Traditional ROI: 6.93%

366 Highland

Prestonsburg, KY

N/A beds | N/A baths | 2,600 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.43%

Airbnb Rental Income: $null

Traditional Rental Income: $1783

Airbnb ROI: N/A

Traditional ROI: 6.43%

19 Magnolia Lane

Prestonsburg, KY

4 beds | 2 baths | 3,000 sq.ft.

$249,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.2%

Airbnb Rental Income: $null

Traditional Rental Income: $2767

Airbnb ROI: N/A

Traditional ROI: 10.2%

60 Ridge Run

Prestonsburg, KY

3 beds | 2 baths | 1,952 sq.ft.

$209,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2276

Airbnb ROI: N/A

Traditional ROI: 9.12%

6403 Spurlock Crk

Prestonsburg, KY

4 beds | N/A baths | 3,280 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2966

Airbnb ROI: N/A