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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
216 Rose Drive Prestonsburg, KY 3 bed 1 bath with updated kitchen and great flow!	3 beds \| 1 baths \| 960 sq.ft.	$174,900	Airbnb cash on cash: N/A Traditional cash on cash: 7% Airbnb Rental Income: $null Traditional Rental Income: $1567 Airbnb ROI: N/A Traditional ROI: 7%
10 Dickerson Street Prestonsburg, KY Very well maintained brick ranch located in town (Prestonsburg). 2 bedrooms, 1 2/3 bathroo...	2 beds \| 2 baths \| 2,016 sq.ft.	$235,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 6.65% Airbnb Rental Income: $1013 Traditional Rental Income: $1983 Airbnb ROI: 0.68% Traditional ROI: 6.65%
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 \| 3 baths \| 1,822 sq.ft.	$232,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.76% Airbnb Rental Income: $null Traditional Rental Income: $2422 Airbnb ROI: N/A Traditional ROI: 8.76%
73 Timberline Estates Prestonsburg, KY Check out this well-maintained 4 bedroom 3 full bath home in a peaceful neighborhood!! Ins...	4 beds \| 3 baths \| 2,500 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.43% Airbnb Rental Income: $null Traditional Rental Income: $2965 Airbnb ROI: N/A Traditional ROI: 7.43%
171 Clark Dr Prestonsburg, KY MOVE IN READY!!! Gorgeous brick ranch with many new updates!! Living room with hardwood ...	3 beds \| 2 baths \| 1,642 sq.ft.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.81% Airbnb Rental Income: $null Traditional Rental Income: $2107 Airbnb ROI: N/A Traditional ROI: 8.81%
1010 Mays Branch Prestonsburg, KY Schedule your appoint to view this move in ready home with kitchen updates, new flooring, ...	3 beds \| 3 baths \| 2,162 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.72% Airbnb Rental Income: $null Traditional Rental Income: $2921 Airbnb ROI: N/A Traditional ROI: 11.72%
573 Lakeview Vlg Prestonsburg, KY NEW LISTING FOR SALE! Check out this Well-Maintained Ranch style Wood siding Lake home. Fe...	3 beds \| N/A baths \| 1,850 sq.ft.	$224,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2203 Airbnb ROI: N/A Traditional ROI: 8.1%
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.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 2.57%
658 Lakeview Village Dr Prestonsburg, KY Amazing views, neat round house floor plan, indoor jacuzzi, wrap around porches and privac...	3 beds \| 2 baths \| 1,816 sq.ft.	$197,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.29% Airbnb Rental Income: $null Traditional Rental Income: $1615 Airbnb ROI: N/A Traditional ROI: 6.29%
191 Armory Rd Prestonsburg, KY Don't miss your chance on this one! This 3-bedroom, 3-bath brick home sits on 3 acres and ...	3 beds \| 3 baths \| 2,854 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.87% Airbnb Rental Income: $null Traditional Rental Income: $2130 Airbnb ROI: N/A Traditional ROI: 5.87%
179 Ky Rt 194 Prestonsburg, KY Welcome to your own majestic retreat in the bluegrass state. The main home includes 3 bedr...	3 beds \| N/A baths \| 2,244 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.53% Airbnb Rental Income: $null Traditional Rental Income: $2610 Airbnb ROI: N/A Traditional ROI: 1.53%
4589 Abbott Creek Rd Prestonsburg, KY Many options here with approximately 60 acres of country living. Options for several home ...	2 beds \| N/A baths \| 1,269 sq.ft.	$245,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 5.9% Airbnb Rental Income: $1013 Traditional Rental Income: $1888 Airbnb ROI: 0.57% Traditional ROI: 5.9%
4956 Ky Route 114 Prestonsburg, KY 4956 Ky Route 114, Prestonsburg, KY 41653 \| Single Family Residential	3 beds \| N/A baths \| 960 sq.ft.	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.95% Airbnb Rental Income: $null Traditional Rental Income: $1394 Airbnb ROI: N/A Traditional ROI: 8.95%
0 Alley Frk Prestonsburg, KY 0 Alley Frk, Prestonsburg, KY 41653 \| Other	N/A beds \| N/A baths \| N/A	$79,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.79% Airbnb Rental Income: $null Traditional Rental Income: $843 Airbnb ROI: N/A Traditional ROI: 7.79%
1265 Crestwood Drive Prestonsburg, KY Enjoy the beauty of this 5 bedroom, 4 bath home at Stone Crest Golf Course. . This home of...	5 beds \| 4 baths \| 4,060 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $3517 Airbnb ROI: N/A Traditional ROI: 4.47%
143 Taylor Loop Prestonsburg, KY Updated ranch home in a desirable Prestonsburg location offering over 1,000 square feet of...	2 beds \| 1 baths \| 1,025 sq.ft.	$222,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 6.53% Airbnb Rental Income: $1013 Traditional Rental Income: $1855 Airbnb ROI: 0.82% Traditional ROI: 6.53%
471 Rt. 1750 Prestonsburg, KY NEWLY REMODELED,, 4 BR., 2 BATH HOME! Seller has replaced flooring, lights, updated kitche...	4 beds \| 2 baths \| 1,768 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.65% Airbnb Rental Income: $null Traditional Rental Income: $2465 Airbnb ROI: N/A Traditional ROI: 8.65%
521 Abbott Mountain Rd Prestonsburg, KY Welcome to your peaceful mountain retreat! This beautiful 4 bedroom, 2 bathroom home offer...	4 beds \| 2 baths \| 2,800 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.22% Airbnb Rental Income: $null Traditional Rental Income: $2781 Airbnb ROI: N/A Traditional ROI: 7.22%
3223 Left Fork of Abbott Prestonsburg, KY This home is beautifully landscaped and well maintained. Plus, an open floor plan and feat...	4 beds \| N/A baths \| 2,280 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.29% Airbnb Rental Income: $null Traditional Rental Income: $2479 Airbnb ROI: N/A Traditional ROI: 8.29%
73 Timberline Ests Prestonsburg, KY 73 Timberline Ests, Prestonsburg, KY 41653 \| Single Family Residential	4 beds \| N/A baths \| 2,500 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $2015 Airbnb ROI: N/A Traditional ROI: 4.36%
79 Lakeview Vlg Prestonsburg, KY Escape to the beauty of Eastern KY with this A-frame home near Dewey Lake! Nestled on 2.7+...	3 beds \| 1 baths \| 1,568 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.89% Airbnb Rental Income: $null Traditional Rental Income: $2227 Airbnb ROI: N/A Traditional ROI: 11.89%
0 Lakeview Vlg Prestonsburg, KY 0 Lakeview Vlg, Prestonsburg, KY 41653 \| Other	N/A beds \| N/A baths \| N/A	$68,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.87% Airbnb Rental Income: $null Traditional Rental Income: $953 Airbnb ROI: N/A Traditional ROI: 10.87%
118 Wells Dr Prestonsburg, KY Completed Remodeled! New appliances with all new updates	3 beds \| N/A baths \| 1,308 sq.ft.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.9% Airbnb Rental Income: $null Traditional Rental Income: $2027 Airbnb ROI: N/A Traditional ROI: 8.9%
1010 Mays Branch Rd Prestonsburg, KY Schedule your appointment to view this move in ready home with kitchen updates, new floori...	3 beds \| 2 baths \| 2,162 sq.ft.	$199,500	Airbnb cash on cash: N/A Traditional cash on cash: 11.01% Airbnb Rental Income: $null Traditional Rental Income: $2528 Airbnb ROI: N/A Traditional ROI: 11.01%
357 Fred's Frk Prestonsburg, KY Spacious, stylish, and conveniently located. This stunning 4-bedroom, 5- bath home offers ...	4 beds \| 3 baths \| 4,328 sq.ft.	$579,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.14% Airbnb Rental Income: $null Traditional Rental Income: $3877 Airbnb ROI: N/A Traditional ROI: 5.14%
334 Armory Rd Prestonsburg, KY 334 Armory Rd, Prestonsburg, KY 41653 \| Single Family Residential	3 beds \| 2 baths \| 2,205 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.28% Airbnb Rental Income: $null Traditional Rental Income: $2333 Airbnb ROI: N/A Traditional ROI: 7.28%
312 Bell Lawn Drive Prestonsburg, KY Discover this charming ranch-style home nestled in the highly sought-after Bell Place Subd...	3 beds \| 2 baths \| 1,362 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $1723 Airbnb ROI: N/A Traditional ROI: 4.27%
90 Glen Dr Prestonsburg, KY Rare opportunity to own a versatile property offering 8-10 acres of flat, usable land idea...	3 beds \| 1 baths \| 1,344 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.32% Airbnb Rental Income: $null Traditional Rental Income: $1616 Airbnb ROI: N/A Traditional ROI: 2.32%
580 Conley Frk Prestonsburg, KY Welcome home to this charming 3-bedroom, 2 bath residence situated on approximately 4 acre...	3 beds \| 2 baths \| 864 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.85% Airbnb Rental Income: $null Traditional Rental Income: $1733 Airbnb ROI: N/A Traditional ROI: 5.85%
41 Trevor Ln Prestonsburg, KY Nestled on a beautiful, spacious lot, this well-maintained brick ranch offers the perfect ...	3 beds \| 2 baths \| 1,500 sq.ft.	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.13% Airbnb Rental Income: $null Traditional Rental Income: $2255 Airbnb ROI: N/A Traditional ROI: 5.13%
337 Ray Br Prestonsburg, KY 337 Ray Br, Prestonsburg, KY 41653 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.22% Airbnb Rental Income: $null Traditional Rental Income: $959 Airbnb ROI: N/A Traditional ROI: 1.22%
383 Trimble Br Prestonsburg, KY 383 Trimble Br, Prestonsburg, KY 41653 \| Single Family Residential	4 beds \| 2 baths \| 2,256 sq.ft.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.24% Airbnb Rental Income: $null Traditional Rental Income: $2445 Airbnb ROI: N/A Traditional ROI: 10.24%
359 Trimble Rd Prestonsburg, KY 359 Trimble Rd, Prestonsburg, KY 41653 \| Single Family Residential	3 beds \| 1 baths \| 1,204 sq.ft.	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.17% Airbnb Rental Income: $null Traditional Rental Income: $1766 Airbnb ROI: N/A Traditional ROI: 9.17%

Real Estate investment in Prestonsburg, KY

There are 33 properties for sale in the city of Prestonsburg . The median list price in Prestonsburg is $179,393 and the average price per square foot is $98. In August 2026, the average monthly cash on cash return in Prestonsburg is 8.00%. The average monthly rental income in Prestonsburg is $2,021.

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

There are 33 investment properties available for sale in Prestonsburg.

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

The ROI for Long-Term is higher than the Short-Term in Prestonsburg with average rental income of $2,021.

Your search for investment property begins and ends here

Investment Property for Sale in Prestonsburg, KY

216 Rose Drive

Prestonsburg, KY

3 beds | 1 baths | 960 sq.ft.

$174,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7%

Airbnb Rental Income: $null

Traditional Rental Income: $1567

Airbnb ROI: N/A

Traditional ROI: 7%

10 Dickerson Street

Prestonsburg, KY

2 beds | 2 baths | 2,016 sq.ft.

$235,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 6.65%

Airbnb Rental Income: $1013

Traditional Rental Income: $1983

Airbnb ROI: 0.68%

Traditional ROI: 6.65%

659 Clubhouse Drive

Prestonsburg, KY

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

$232,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.76%

Airbnb Rental Income: $null

Traditional Rental Income: $2422

Airbnb ROI: N/A

Traditional ROI: 8.76%

73 Timberline Estates

Prestonsburg, KY

4 beds | 3 baths | 2,500 sq.ft.

$329,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2965

Airbnb ROI: N/A

Traditional ROI: 7.43%

171 Clark Dr

Prestonsburg, KY

3 beds | 2 baths | 1,642 sq.ft.

$199,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2107

Airbnb ROI: N/A

Traditional ROI: 8.81%

1010 Mays Branch

Prestonsburg, KY

3 beds | 3 baths | 2,162 sq.ft.

$220,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.72%

Airbnb Rental Income: $null

Traditional Rental Income: $2921

Airbnb ROI: N/A

Traditional ROI: 11.72%

573 Lakeview Vlg

Prestonsburg, KY

3 beds | N/A baths | 1,850 sq.ft.

$224,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2203

Airbnb ROI: N/A

Traditional ROI: 8.1%

21 Crestwood Cir

Prestonsburg, KY

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

$615,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2632

Airbnb ROI: N/A