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
10 Dickerson Street Prestonsburg, KY Very well maintained brick ranch located in town (Prestonsburg). 2 bedrooms, 1 2/3 bathro...	2 beds \| 2 baths \| N/A	$235,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.99% Airbnb Rental Income: $830 Traditional Rental Income: $947 Airbnb ROI: -0.01% Traditional ROI: 1.99%
8107 State Road Fork Prestonsburg, KY Nestled in a quiet, rural setting, this property features a 3 bedroom, 1 bath home with a ...	3 beds \| 1 baths \| N/A	$140,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.92% Airbnb Rental Income: $null Traditional Rental Income: $1808 Airbnb ROI: N/A Traditional ROI: 10.92%
659 Clubhouse Drive Prestonsburg, KY Charming brick 3 bedroom, 2.5 bath townhouse located in a nice area close to schools and j...	3 beds \| 2 baths \| 1,822 sq.ft.	$236,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $1138 Airbnb ROI: N/A Traditional ROI: 2.83%
9 Stanley Avenue Prestonsburg, KY Beautiful 3-bed, 2-bath home with over 1,500 sq ft of comfortable living space. This home ...	3 beds \| 2 baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.54% Airbnb Rental Income: $null Traditional Rental Income: $1705 Airbnb ROI: N/A Traditional ROI: 11.54%
21 Crestwood Circle Prestonsburg, KY his 4,300 sq ft (all living) 4 Bed, 3.50 Bath, 2 story wrapped in James Hardie siding & St...	4 beds \| 4 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%
658 Lakeview Village Drive Prestonsburg, KY Amazing views, neat round house floor plan, indoor jacuzzi, wrap around porches and privac...	3 beds \| 2 baths \| 1,816 sq.ft.	$209,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.83% Airbnb Rental Income: $null Traditional Rental Income: $1615 Airbnb ROI: N/A Traditional ROI: 5.83%
2850 Abbott Creek Road Prestonsburg, KY Welcome to this beautifully maintained and thoughtfully updated brick home, built in 2003 ...	4 beds \| 4 baths \| 2,392 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.55% Airbnb Rental Income: $null Traditional Rental Income: $2273 Airbnb ROI: N/A Traditional ROI: 7.55%
1104 Brook Court #Lot 37 Prestonsburg, KY Welcome home to 1104 Brook Ct. in Franklinâs new Westbrook Subdivision! This charming ho...	3 beds \| 2 baths \| 1,308 sq.ft.	$262,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.7% Airbnb Rental Income: $null Traditional Rental Income: $1967 Airbnb ROI: N/A Traditional ROI: 5.7%
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 \| N/A	$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%
685 Mays Branch Prestonsburg, KY PRICE IMPROVEMENT â NOW $379,900 Major price improvement on this spacious home â red...	4 beds \| 5 baths \| N/A	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.74% Airbnb Rental Income: $null Traditional Rental Income: $1372 Airbnb ROI: N/A Traditional ROI: 1.74%
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 Creek Prestonsburg, KY Well maintained brick ranch on a large 60 acre tract of land. Perfect starter home or empt...	2 beds \| 2 baths \| N/A	$275,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 5.64% Airbnb Rental Income: $830 Traditional Rental Income: $2036 Airbnb ROI: -0.27% Traditional ROI: 5.64%
342 Ward Avenue Prestonsburg, KY Brick ranch on full above ground basement with garage. 3 bedrooms and 2 bathrooms with lar...	3 beds \| 2 baths \| 1,728 sq.ft.	$179,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $1138 Airbnb ROI: N/A Traditional ROI: 4.25%
1265 Crestwood Drive Prestonsburg, KY Enjoy the beauty of this 5 bedroom, 4 bath home at Stone Crest Golf Course. . This home o...	5 beds \| 4 baths \| N/A	$618,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $3517 Airbnb ROI: N/A Traditional ROI: 4.07%
143 Taylor Loop Prestonsburg, KY Updated ranch home in a desirable Prestonsburg location offering over 1,000 square feet of...	2 beds \| 2 baths \| 1,025 sq.ft.	$229,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.09% Airbnb Rental Income: $830 Traditional Rental Income: $947 Airbnb ROI: 0.04% Traditional ROI: 2.09%
471 Rt. 1750 Prestonsburg, KY NEWLY REMOLED,, 4 BR., 2 BATH HOME! Seller has replaced flooring, lights, updated kitchen...	4 beds \| 2 baths \| N/A	$269,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $1372 Airbnb ROI: N/A Traditional ROI: 3.19%
521 Abbott Mountain Road Prestonsburg, KY Welcome to your peaceful mountain retreat! This beautiful 4 bedroom, 2 bathroom home offer...	4 beds \| 2 baths \| 2,800 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $2781 Airbnb ROI: N/A Traditional ROI: 6.94%
298 E Graham St Prestonsburg, KY Charming Updated Home in Town with Endless Possibilities! Welcome to this beautifully upda...	3 beds \| 3 baths \| N/A	$209,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $1138 Airbnb ROI: N/A Traditional ROI: 3.56%

Real Estate investment in Prestonsburg, KY

There are 18 properties for sale in the city of Prestonsburg . The median list price in Prestonsburg is $209,000 and the average price per square foot is $113. In March 2026, the average monthly cash on cash return in Prestonsburg is 6.00%. The average monthly rental income in Prestonsburg is $1,888.

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

There are 18 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

10 Dickerson Street

Prestonsburg, KY

2 beds | 2 baths | N/A

$235,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $830

Traditional Rental Income: $947

Airbnb ROI: -0.01%

Traditional ROI: 1.99%

8107 State Road Fork

Prestonsburg, KY

3 beds | 1 baths | N/A

$140,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.92%

Airbnb Rental Income: $null

Traditional Rental Income: $1808

Airbnb ROI: N/A

Traditional ROI: 10.92%

659 Clubhouse Drive

Prestonsburg, KY

3 beds | 2 baths | 1,822 sq.ft.

$236,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.83%

Airbnb Rental Income: $null

Traditional Rental Income: $1138

Airbnb ROI: N/A

Traditional ROI: 2.83%

9 Stanley Avenue

Prestonsburg, KY

3 beds | 2 baths | N/A

$125,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.54%

Airbnb Rental Income: $null

Traditional Rental Income: $1705

Airbnb ROI: N/A

Traditional ROI: 11.54%

21 Crestwood Circle

Prestonsburg, KY

4 beds | 4 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%

658 Lakeview Village Drive

Prestonsburg, KY

3 beds | 2 baths | 1,816 sq.ft.

$209,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.83%

Airbnb Rental Income: $null

Traditional Rental Income: $1615

Airbnb ROI: N/A

Traditional ROI: 5.83%

2850 Abbott Creek Road

Prestonsburg, KY

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

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2273

Airbnb ROI: N/A

Traditional ROI: 7.55%

1104 Brook Court #Lot 37

Prestonsburg, KY

3 beds | 2 baths | 1,308 sq.ft.

$262,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.7%

Airbnb Rental Income: $null

Traditional Rental Income: $1967

Airbnb ROI: N/A