Real Estate Investment Properties for Sale in Oakland, KY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1534 Oakland Rd Oakland, KY Welcome home to this charming 4-bedroom, 3-full-bath home situated on a spacious 1-acre lo...	4 beds \| 3 baths \| 2,186 sq.ft.	$269,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.47% Airbnb Rental Income: $null Traditional Rental Income: $2965 Airbnb ROI: N/A Traditional ROI: 9.47%
11509 Porter Pike Oakland, KY A true gem! Offering 3 bedrooms and one full bath on a beautiful acre lot PLUS a nice size...	3 beds \| 1 baths \| 765 sq.ft.	$194,900	Airbnb cash on cash: 6.46% Traditional cash on cash: 6.25% Airbnb Rental Income: $2018 Traditional Rental Income: $1455 Airbnb ROI: 6.46% Traditional ROI: 6.25%
10299 Smiths Grove- Scottsville Rd Oakland, KY Charming new construction home nestled in a peaceful country setting just minutes from Smi...	3 beds \| 2 baths \| 1,510 sq.ft.	$298,500	Airbnb cash on cash: 3.13% Traditional cash on cash: 5.82% Airbnb Rental Income: $2018 Traditional Rental Income: $2250 Airbnb ROI: 3.13% Traditional ROI: 5.82%
891 Three Forks Flatrock Rd Oakland, KY Don't miss the opportunity to view this 3 Bedroom, 2 Bath home built in 1891 situated on a...	3 beds \| 2 baths \| 1,478 sq.ft.	$161,500	Airbnb cash on cash: 7.23% Traditional cash on cash: 11.69% Airbnb Rental Income: $2018 Traditional Rental Income: $2181 Airbnb ROI: 7.23% Traditional ROI: 11.69%
12293 Louisville Rd Oakland, KY 12293 Louisville Rd, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$750,000	Airbnb cash on cash: -1.46% Traditional cash on cash: -0.7% Airbnb Rental Income: $669 Traditional Rental Income: $902 Airbnb ROI: -1.46% Traditional ROI: -0.7%
10541 Smiths Grove Scottsville Rd Oakland, KY 10541 Smiths Grove Scottsville Rd, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| N/A	$259,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.05% Airbnb Rental Income: $669 Traditional Rental Income: $805 Airbnb ROI: -0.73% Traditional ROI: 1.05%
3673 Gotts Hydro Rd Oakland, KY 3673 Gotts Hydro Rd, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| N/A	$255,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.1% Airbnb Rental Income: $669 Traditional Rental Income: $805 Airbnb ROI: -0.71% Traditional ROI: 1.1%
1930 Upper Iron Bridge Rd Oakland, KY	3 beds \| 2 baths \| 1,293 sq.ft.	$240,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 6.82% Airbnb Rental Income: $2018 Traditional Rental Income: $1978 Airbnb ROI: 4.68% Traditional ROI: 6.82%
10 AC Porter Pike Oakland, KY 10 AC Porter Pike, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| N/A	$249,500	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.66% Airbnb Rental Income: $669 Traditional Rental Income: $921 Airbnb ROI: -0.68% Traditional ROI: 1.66%
845 Louie Meeks Rd Oakland, KY 845 Louie Meeks Rd, Oakland, KY 42159 \| Other	4 beds \| N/A baths \| N/A	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.6% Airbnb Rental Income: $null Traditional Rental Income: $968 Airbnb ROI: N/A Traditional ROI: -0.6%
Lot 0 Gotts Hydro Rd Oakland, KY Lot 0 Gotts Hydro Rd, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| N/A	$229,900	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.17% Airbnb Rental Income: $669 Traditional Rental Income: $968 Airbnb ROI: -0.59% Traditional ROI: 2.17%
Tract 4-4-1 Smiths Grove Scottsville Rd Oakland, KY Tract 4-4-1 Smiths Grove Scottsville Rd, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| N/A	$79,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 9.4% Airbnb Rental Income: $669 Traditional Rental Income: $968 Airbnb ROI: 1.69% Traditional ROI: 9.4%
18 AC Ayers Rd Oakland, KY 18 AC Ayers Rd, Oakland, KY 42159 \| Other	N/A beds \| N/A baths \| N/A	$375,500	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.63% Airbnb Rental Income: $669 Traditional Rental Income: $968 Airbnb ROI: -1.07% Traditional ROI: 0.63%
330 Louie Meeks Road Oakland, KY This one-of-a-kind property is more than just a house - it's a true home place, thoughtful...	3 beds \| 3 baths \| 6,140 sq.ft.	$850,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 1.46% Airbnb Rental Income: $2018 Traditional Rental Income: $2715 Airbnb ROI: -0.09% Traditional ROI: 1.46%

Real Estate investment in Oakland, KY

There are 14 properties for sale in the city of Oakland . The median list price in Oakland is $404,000 and the average price per square foot is $239. In September 2026, the average monthly cash on cash return in Oakland is 6.00%. The average monthly rental income in Oakland is $968.

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

There are 14 investment properties available for sale in Oakland.

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

The ROI for Long-Term is higher than the Short-Term in Oakland with average rental income of $968.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, KY

1534 Oakland Rd

Oakland, KY

4 beds | 3 baths | 2,186 sq.ft.

$269,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2965

Airbnb ROI: N/A

Traditional ROI: 9.47%

11509 Porter Pike

Oakland, KY

3 beds | 1 baths | 765 sq.ft.

$194,900

Airbnb cash on cash: 6.46%

Traditional cash on cash: 6.25%

Airbnb Rental Income: $2018

Traditional Rental Income: $1455

Airbnb ROI: 6.46%

Traditional ROI: 6.25%

10299 Smiths Grove- Scottsville Rd

Oakland, KY

3 beds | 2 baths | 1,510 sq.ft.

$298,500

Airbnb cash on cash: 3.13%

Traditional cash on cash: 5.82%

Airbnb Rental Income: $2018

Traditional Rental Income: $2250

Airbnb ROI: 3.13%

Traditional ROI: 5.82%

891 Three Forks Flatrock Rd

Oakland, KY

3 beds | 2 baths | 1,478 sq.ft.

$161,500

Airbnb cash on cash: 7.23%

Traditional cash on cash: 11.69%

Airbnb Rental Income: $2018

Traditional Rental Income: $2181

Airbnb ROI: 7.23%

Traditional ROI: 11.69%

12293 Louisville Rd

Oakland, KY

N/A beds | N/A baths | 0 sq.ft.

$750,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: -0.7%

Airbnb Rental Income: $669

Traditional Rental Income: $902

Airbnb ROI: -1.46%

Traditional ROI: -0.7%

10541 Smiths Grove Scottsville Rd

Oakland, KY

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

$259,900

Airbnb cash on cash: -0.73%

Traditional cash on cash: 1.05%

Airbnb Rental Income: $669

Traditional Rental Income: $805

Airbnb ROI: -0.73%

Traditional ROI: 1.05%

3673 Gotts Hydro Rd

Oakland, KY

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

$255,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 1.1%

Airbnb Rental Income: $669

Traditional Rental Income: $805

Airbnb ROI: -0.71%

Traditional ROI: 1.1%

1930 Upper Iron Bridge Rd

Oakland, KY

3 beds | 2 baths | 1,293 sq.ft.

$240,000

Airbnb cash on cash: 4.68%

Traditional cash on cash: 6.82%

Airbnb Rental Income: $2018

Traditional Rental Income: $1978

Airbnb ROI: 4.68%