Real Estate Investment Properties for Sale in Jamestown, KY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
56 Lily Creek Court JAMESTOWN, KY WoW! This home shows like a Builders Model Home. All new everything. Flooring, paint, appl...	3 beds \| 2 baths \| 1,530 sq.ft.	$309,750	Airbnb cash on cash: 2.62% Traditional cash on cash: 5.99% Airbnb Rental Income: $1780 Traditional Rental Income: $2276 Airbnb ROI: 2.62% Traditional ROI: 5.99%
21 Cherokee Springs Court JAMESTOWN, KY Live at the lake, all year-round! This lovely cottage-style single family home is just a t...	4 beds \| 2 baths \| 1,495 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.3% Airbnb Rental Income: $null Traditional Rental Income: $2111 Airbnb ROI: N/A Traditional ROI: 5.3%
1360 KY-92 JAMESTOWN, KY Your Dream Home Awaits! Nestled on 12 acres just 2.4 miles from Jamestown Marina on breath...	5 beds \| 6 baths \| 9,864 sq.ft.	$2,599,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 0.57% Airbnb Rental Income: $7347 Traditional Rental Income: $5937 Airbnb ROI: 0.57% Traditional ROI: 0.57%
1700 S Hwy 127 JAMESTOWN, KY This listing features two distinct structures on scenic shores of Lake Cumberland. Nestled...	3 beds \| 3 baths \| 2,946 sq.ft.	$365,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.88% Airbnb Rental Income: $1780 Traditional Rental Income: $2742 Airbnb ROI: 1.65% Traditional ROI: 5.88%
1655 KY-92 JAMESTOWN, KY Just minutes away from Lake Cumberland and the Jamestown Resort & Marina, this 3500 sq. ft...	1 beds \| 2 baths \| 3,500 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.5% Airbnb Rental Income: $null Traditional Rental Income: $1618 Airbnb ROI: N/A Traditional ROI: 0.5%
322 Wesley Street JAMESTOWN, KY Where else would you find a fully furnished, turn-key ranch-styled home at such an afforda...	3 beds \| 2 baths \| 1,472 sq.ft.	$290,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 5.58% Airbnb Rental Income: $1780 Traditional Rental Income: $2124 Airbnb ROI: 2.54% Traditional ROI: 5.58%
231 Beech Lane JAMESTOWN, KY Discover your dream LAKEFRONT retreat! Relax and unwind in a tranquil setting, away from t...	2 beds \| 2 baths \| 1,283 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.95% Airbnb Rental Income: $null Traditional Rental Income: $1853 Airbnb ROI: N/A Traditional ROI: 3.95%
4329 Kentucky 1058 JAMESTOWN, KY Back on the market at NO fault of the home or sellers! 4329 KY 1058, Jamestown is a newly...	3 beds \| 1 baths \| 1,195 sq.ft.	$199,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 7.45% Airbnb Rental Income: $1780 Traditional Rental Income: $1857 Airbnb ROI: 4.48% Traditional ROI: 7.45%
228 Cooper Road JAMESTOWN, KY Welcome to 228 Cooper Rd in Jamestown, KYâa stunning 4-bedroom, 2-bathroom Clayton home ...	4 beds \| 2 baths \| 1,792 sq.ft.	$182,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.28% Airbnb Rental Income: $null Traditional Rental Income: $2295 Airbnb ROI: N/A Traditional ROI: 11.28%
109 Dylan Drive JAMESTOWN, KY Spectacular Lake Cumberland townhouse conveniently located near the Jamestown Resort & Mar...	4 beds \| 4 baths \| 3,915 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.81% Airbnb Rental Income: $null Traditional Rental Income: $3735 Airbnb ROI: N/A Traditional ROI: 8.81%
600 Carriage Lane JAMESTOWN, KY ONE OF A KIND listing in a gated subdivision, The Oaks. This is a very rare property with ...	4 beds \| 3 baths \| 3,120 sq.ft.	$489,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $3017 Airbnb ROI: N/A Traditional ROI: 4.91%
1962 E Highway 619 JAMESTOWN, KY Are you searching for a spacious family home or a property near the Pleasant Hill launchin...	3 beds \| 2 baths \| 1,872 sq.ft.	$181,900	Airbnb cash on cash: 5.09% Traditional cash on cash: 11.61% Airbnb Rental Income: $1780 Traditional Rental Income: $2422 Airbnb ROI: 5.09% Traditional ROI: 11.61%
196 Vine Dr. JAMESTOWN, KY Located off Boat Dock Rd. towards Jamestown Marina. Lake oriented house in a quiet neighbo...	3 beds \| 2 baths \| 1,702 sq.ft.	$320,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 5.51% Airbnb Rental Income: $1780 Traditional Rental Income: $2309 Airbnb ROI: 2.14% Traditional ROI: 5.51%
807 W Cumberland Ave. JAMESTOWN, KY Come home to Jamestown with this modest brick home a short walk from the square and shoppi...	2 beds \| 1 baths \| N/A	$169,600	Airbnb cash on cash: N/A Traditional cash on cash: 10.22% Airbnb Rental Income: $null Traditional Rental Income: $1921 Airbnb ROI: N/A Traditional ROI: 10.22%
100 Hankins Lane JAMESTOWN, KY Lakehouse located in beautiful Lily Creek Resort just minutes from Jamestown Marina! Lily ...	4 beds \| 2 baths \| 2,010 sq.ft.	$338,750	Airbnb cash on cash: N/A Traditional cash on cash: 7.35% Airbnb Rental Income: $null Traditional Rental Income: $2824 Airbnb ROI: N/A Traditional ROI: 7.35%
298 Lantern Way JAMESTOWN, KY Welcome to Lantern Way! This gorgeous property, with a seasonal lake view, is located in a...	3 beds \| 4 baths \| 2,644 sq.ft.	$450,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 7.08% Airbnb Rental Income: $1780 Traditional Rental Income: $3657 Airbnb ROI: 1.47% Traditional ROI: 7.08%
1579 Harbor Springs #Lots 55 & 56 JAMESTOWN, KY Great open plan. Wide hallway! Over 1000 square foot metal building with 12 foot overhead ...	2 beds \| 2 baths \| 900 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.53% Airbnb Rental Income: $null Traditional Rental Income: $1909 Airbnb ROI: N/A Traditional ROI: 5.53%
840 Harbor Springs #G-69 JAMESTOWN, KY Located minutes from Jamestown Marina and Safe Harbor! Seasonal Water View. Covered seatin...	3 beds \| 1 baths \| 1,260 sq.ft.	$279,900	Airbnb cash on cash: 2.86% Traditional cash on cash: 4.77% Airbnb Rental Income: $1780 Traditional Rental Income: $1797 Airbnb ROI: 2.86% Traditional ROI: 4.77%
1057 Lily Creek Resort Road JAMESTOWN, KY Get ready to fall in love with this custom-built lake view house, nestled near the Jamesto...	4 beds \| 4 baths \| 6,126 sq.ft.	$657,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $3343 Airbnb ROI: N/A Traditional ROI: 3.44%
84 Lakeview Drive JAMESTOWN, KY Located only 3.8 miles to Jamestown Marina, this is the perfect vacation or permanent home...	3 beds \| 3 baths \| 2,070 sq.ft.	$390,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.28% Airbnb Rental Income: $1780 Traditional Rental Income: $2748 Airbnb ROI: 1.3% Traditional ROI: 5.28%
104 Cardinal Lane JAMESTOWN, KY Check out this fully furnished 3 bedroom 1 bath home with a full basement, (mostly finishe...	3 beds \| 1 baths \| 1,388 sq.ft.	$189,000	Airbnb cash on cash: 5.62% Traditional cash on cash: 8.74% Airbnb Rental Income: $1780 Traditional Rental Income: $1856 Airbnb ROI: 5.62% Traditional ROI: 8.74%

Real Estate investment in Jamestown, KY

There are 21 properties for sale in the city of Jamestown . The median list price in Jamestown is $314,875 and the average price per square foot is $121. In January 2025, the average monthly cash on cash return in Jamestown is 6.00%. The average monthly rental income in Jamestown is $2,302.

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

There are 21 investment properties available for sale in Jamestown.

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

The ROI for Long-Term is higher than the Short-Term in Jamestown with average rental income of $2,302.

Your search for investment property begins and ends here

Investment Property for Sale in Jamestown, KY

56 Lily Creek Court

JAMESTOWN, KY

3 beds | 2 baths | 1,530 sq.ft.

$309,750

Airbnb cash on cash: 2.62%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $1780

Traditional Rental Income: $2276

Airbnb ROI: 2.62%

Traditional ROI: 5.99%

21 Cherokee Springs Court

JAMESTOWN, KY

4 beds | 2 baths | 1,495 sq.ft.

$299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2111

Airbnb ROI: N/A

Traditional ROI: 5.3%

1360 KY-92

JAMESTOWN, KY

5 beds | 6 baths | 9,864 sq.ft.

$2,599,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $7347

Traditional Rental Income: $5937

Airbnb ROI: 0.57%

Traditional ROI: 0.57%

1700 S Hwy 127

JAMESTOWN, KY

3 beds | 3 baths | 2,946 sq.ft.

$365,000

Airbnb cash on cash: 1.65%

Traditional cash on cash: 5.88%

Airbnb Rental Income: $1780

Traditional Rental Income: $2742

Airbnb ROI: 1.65%

Traditional ROI: 5.88%

1655 KY-92

JAMESTOWN, KY

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

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.5%

Airbnb Rental Income: $null

Traditional Rental Income: $1618

Airbnb ROI: N/A

Traditional ROI: 0.5%

322 Wesley Street

JAMESTOWN, KY

3 beds | 2 baths | 1,472 sq.ft.

$290,000

Airbnb cash on cash: 2.54%

Traditional cash on cash: 5.58%

Airbnb Rental Income: $1780

Traditional Rental Income: $2124

Airbnb ROI: 2.54%

Traditional ROI: 5.58%

231 Beech Lane

JAMESTOWN, KY

2 beds | 2 baths | 1,283 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.95%

Airbnb Rental Income: $null

Traditional Rental Income: $1853

Airbnb ROI: N/A

Traditional ROI: 3.95%

4329 Kentucky 1058

JAMESTOWN, KY

3 beds | 1 baths | 1,195 sq.ft.

$199,900

Airbnb cash on cash: 4.48%

Traditional cash on cash: 7.45%

Airbnb Rental Income: $1780

Traditional Rental Income: $1857

Airbnb ROI: 4.48%