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
111 Leveridge Ct JAMESTOWN, KY Discover timeless craftsmanship & exceptional space in this 5 bedroom, 3.5 bathroom home o...	5 beds \| 3 baths \| 6,040 sq.ft.	$649,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.98% Airbnb Rental Income: $2992 Traditional Rental Income: $3632 Airbnb ROI: 1.79% Traditional ROI: 3.98%
522 Lakeview Dr JAMESTOWN, KY This stunning 4 bedroom, 3.5 bath home combines timeless craftsmanship with modern upgrade...	4 beds \| 3 baths \| 3,369 sq.ft.	$645,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $3497 Airbnb ROI: N/A Traditional ROI: 3.72%
190 Vine Dr. JAMESTOWN, KY This 3 Bedroom/2 Bath with rustic look is located in Leveridge Subdivision off of Boat Doc...	3 beds \| 2 baths \| 1,458 sq.ft.	$395,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 4.32% Airbnb Rental Income: $943 Traditional Rental Income: $2208 Airbnb ROI: -0.03% Traditional ROI: 4.32%
25 Harbor Springs Cir JAMESTOWN, KY Discover lakeside living at its finest with this beautifully refurbished home on Lake Cumb...	4 beds \| 3 baths \| 2,080 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $1603 Airbnb ROI: N/A Traditional ROI: 2.38%
145 State Park Rd #R2 JAMESTOWN, KY Discover your Lake getaway ! Tucked in a wooded setting just minutes from breathtaking Lak...	1 beds \| 2 baths \| 900 sq.ft.	$142,000	Airbnb cash on cash: -2.27% Traditional cash on cash: 5.81% Airbnb Rental Income: $731 Traditional Rental Income: $1520 Airbnb ROI: -2.27% Traditional ROI: 5.81%
120 West Cumberland Avenue JAMESTOWN, KY Duplex one Block from three New Restaurants.. Minutes from Jamestown Marina largest House ...	5 beds \| 3 baths \| 2,492 sq.ft.	$282,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 8.5% Airbnb Rental Income: $2992 Traditional Rental Income: $2845 Airbnb ROI: 6.47% Traditional ROI: 8.5%
1655 Ky-92 JAMESTOWN, KY Just minutes away from Lake Cumberland and the Jamestown Resort & Marina, this 3500 sq. ft...	1 beds \| 1 baths \| 3,500 sq.ft.	$659,900	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.62% Airbnb Rental Income: $731 Traditional Rental Income: $1618 Airbnb ROI: -1.32% Traditional ROI: 0.62%
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 \| 2 baths \| N/A	$159,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 10.88% Airbnb Rental Income: $581 Traditional Rental Income: $1921 Airbnb ROI: 0.23% Traditional ROI: 10.88%
145 State Park Road #Q6 JAMESTOWN, KY Looking to RETIRE or just want to get away? This incredible opportunity offers a TURN KEY/...	2 beds \| 2 baths \| 932 sq.ft.	$192,500	Airbnb cash on cash: -0.75% Traditional cash on cash: 5.69% Airbnb Rental Income: $581 Traditional Rental Income: $1473 Airbnb ROI: -0.75% Traditional ROI: 5.69%
Tract 6 Swan Pond Rd JAMESTOWN, KY NEW CONSTRUCTION TO BE BUILT. BUYERS: Choose Tract 6, 7, 8, or 9 for your rustic 2-bedroom...	2 beds \| 1 baths \| 864 sq.ft.	$242,500	Airbnb cash on cash: -0.97% Traditional cash on cash: 5.42% Airbnb Rental Income: $581 Traditional Rental Income: $1761 Airbnb ROI: -0.97% Traditional ROI: 5.42%
65 Wooldridge Rd JAMESTOWN, KY Discover this absolute stunning 5-bedroom, 2-bath home, offering endless possibilities as ...	5 beds \| 2 baths \| 2,340 sq.ft.	$329,000	Airbnb cash on cash: 5.74% Traditional cash on cash: 7.08% Airbnb Rental Income: $2992 Traditional Rental Income: $2717 Airbnb ROI: 5.74% Traditional ROI: 7.08%
139 Payton Place Ln JAMESTOWN, KY Claim your own piece of paradise in this beautifully maintained home with huge picture win...	3 beds \| 3 baths \| 2,200 sq.ft.	$349,999	Airbnb cash on cash: 0.22% Traditional cash on cash: 5.63% Airbnb Rental Income: $943 Traditional Rental Income: $2377 Airbnb ROI: 0.22% Traditional ROI: 5.63%
141 Cherokee Springs Ct JAMESTOWN, KY Earn instant equity with this beautiful home, priced well-below appraised value! Comparabl...	4 beds \| 2 baths \| 2,600 sq.ft.	$368,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.77% Airbnb Rental Income: $null Traditional Rental Income: $2917 Airbnb ROI: N/A Traditional ROI: 6.77%
1360 State Highway 92 JAMESTOWN, KY Luxury, privacy, and space come together in this stunning 10,076 sq ft estate in Jamestown...	5 beds \| 6 baths \| 10,076 sq.ft.	$2,299,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.38% Airbnb Rental Income: $2992 Traditional Rental Income: $6993 Airbnb ROI: -0.82% Traditional ROI: 1.38%
198 W Cumberland Ave JAMESTOWN, KY This beautifully updated duplex is a fantastic opportunity for real estate investors or an...	5 beds \| 3 baths \| 2,068 sq.ft.	$249,000	Airbnb cash on cash: 8.26% Traditional cash on cash: 9.27% Airbnb Rental Income: $2992 Traditional Rental Income: $2544 Airbnb ROI: 8.26% Traditional ROI: 9.27%
2295 Ky-92 JAMESTOWN, KY Magazine-worthy estate near Lake Cumberland! This stunning 5BR/4BA home on 9+ unrestricted...	5 beds \| 4 baths \| 2,624 sq.ft.	$699,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.45% Airbnb Rental Income: $2992 Traditional Rental Income: $3222 Airbnb ROI: 2.04% Traditional ROI: 3.45%
145 State Park Rd JAMESTOWN, KY Looking to RETIRE or just want to get away? This incredible opportunity offers a TURN KEY/...	2 beds \| 2 baths \| 932 sq.ft.	$192,500	Airbnb cash on cash: -0.75% Traditional cash on cash: 6.15% Airbnb Rental Income: $581 Traditional Rental Income: $1557 Airbnb ROI: -0.75% Traditional ROI: 6.15%
420 Campbells Ferry Ln JAMESTOWN, KY Welcome to your personal paradise, a 5-bedroom, 3-bathroom home nestled in a serene privat...	5 beds \| 3 baths \| N/A	$299,000	Airbnb cash on cash: 6% Traditional cash on cash: 10.76% Airbnb Rental Income: $2992 Traditional Rental Income: $3642 Airbnb ROI: 6% Traditional ROI: 10.76%
394 W Cumberland Ave JAMESTOWN, KY This is an exceptional investment opportunity waiting for you! This charming home features...	2 beds \| 1 baths \| 800 sq.ft.	$295,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.9% Airbnb Rental Income: $581 Traditional Rental Income: $1474 Airbnb ROI: -0.35% Traditional ROI: 3.9%
368 Jobi Falls Trl JAMESTOWN, KY "One-of-Kind" ... Doesn't Even Begin to Cover It - 25 Beautiful Unrestricted Acres with a ...	2 beds \| 4 baths \| 1,296 sq.ft.	$675,000	Airbnb cash on cash: -2.26% Traditional cash on cash: 0.81% Airbnb Rental Income: $581 Traditional Rental Income: $2227 Airbnb ROI: -2.26% Traditional ROI: 0.81%
8239 S Highway 379 JAMESTOWN, KY Discover the perfect blend of nature and comfort with this SOON TO BE BUILT 2 bedroom/ 1 f...	2 beds \| 1 baths \| 864 sq.ft.	$235,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 5.51% Airbnb Rental Income: $581 Traditional Rental Income: $1729 Airbnb ROI: -0.94% Traditional ROI: 5.51%
335 Port of Call Dr JAMESTOWN, KY New Construction - Modern Farmhouse in Anchorage on Caney Welcome to Anchorage on Caney, a...	3 beds \| 2 baths \| 1,925 sq.ft.	$420,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.54% Airbnb Rental Income: $943 Traditional Rental Income: $2609 Airbnb ROI: -0.57% Traditional ROI: 4.54%
145 State Park Rd #S4 JAMESTOWN, KY Stunning 2 bedroom, 2bath Condo near Lake Cumberland in Apple Valley Resort - Jamestown Ke...	2 beds \| 2 baths \| 900 sq.ft.	$169,900	Airbnb cash on cash: -2.15% Traditional cash on cash: 5.59% Airbnb Rental Income: $581 Traditional Rental Income: $1548 Airbnb ROI: -2.15% Traditional ROI: 5.59%
145 State Park Rd #I6 JAMESTOWN, KY Welcome to this charming condo in the highly sought-after Apple Valley Estates, located ne...	2 beds \| 2 baths \| 900 sq.ft.	$139,000	Airbnb cash on cash: -2.21% Traditional cash on cash: 7.62% Airbnb Rental Income: $581 Traditional Rental Income: $1606 Airbnb ROI: -2.21% Traditional ROI: 7.62%
145 State Park Rd #S-6 JAMESTOWN, KY This recently updated condominium in Apple Valley is perfectly suitable for a weekend geta...	1 beds \| 2 baths \| 900 sq.ft.	$119,900	Airbnb cash on cash: -1.98% Traditional cash on cash: 6.28% Airbnb Rental Income: $731 Traditional Rental Income: $1376 Airbnb ROI: -1.98% Traditional ROI: 6.28%
145 State Park Rd #B-1 JAMESTOWN, KY Apple Valley Resort. "B-1"....the best location and the best floor plan. Live year round i...	2 beds \| 2 baths \| 900 sq.ft.	$169,500	Airbnb cash on cash: -3.73% Traditional cash on cash: 3.8% Airbnb Rental Income: $581 Traditional Rental Income: $1513 Airbnb ROI: -3.73% Traditional ROI: 3.8%
145 State Park Rd #K-3 JAMESTOWN, KY Condo can be listed on Airbnb/VRBO and rented short term! Take advantage of a great invest...	2 beds \| 2 baths \| 900 sq.ft.	$119,000	Airbnb cash on cash: -3.42% Traditional cash on cash: 9.33% Airbnb Rental Income: $581 Traditional Rental Income: $1760 Airbnb ROI: -3.42% Traditional ROI: 9.33%
78 Hoover Rd JAMESTOWN, KY Charming Cape Cod style home just minutes to LAKE CUMBERLAND on 2.41 acres in Jamestown, K...	4 beds \| 2 baths \| 2,600 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.35% Airbnb Rental Income: $null Traditional Rental Income: $2849 Airbnb ROI: N/A Traditional ROI: 6.35%
120 Ivy Dr JAMESTOWN, KY Located in the highly desirable Caney Cove neighborhood; this charming home offers both th...	3 beds \| 2 baths \| 1,800 sq.ft.	$349,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 6.03% Airbnb Rental Income: $943 Traditional Rental Income: $2412 Airbnb ROI: 0.51% Traditional ROI: 6.03%
935 Clifty Creek Rd JAMESTOWN, KY Custom Log Home Near Lake Cumberland - Clifty Creek Rd, Jamestown, KY This custom log home...	3 beds \| 4 baths \| 3,120 sq.ft.	$485,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.52% Airbnb Rental Income: $943 Traditional Rental Income: $2285 Airbnb ROI: -0.21% Traditional ROI: 3.52%
324 Lawless Ln JAMESTOWN, KY This home will be adding a new heat and air unit in February! Lovely Home Near Jamestown M...	3 beds \| 2 baths \| 1,435 sq.ft.	$179,999	Airbnb cash on cash: 1.65% Traditional cash on cash: 10.84% Airbnb Rental Income: $943 Traditional Rental Income: $2171 Airbnb ROI: 1.65% Traditional ROI: 10.84%
612 Little Indian Dr JAMESTOWN, KY Looking for the perfect little getaway near Wolf Creek Dam? This cozy home is located in a...	2 beds \| 1 baths \| 1,200 sq.ft.	$259,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 5.86% Airbnb Rental Income: $581 Traditional Rental Income: $1846 Airbnb ROI: -0.48% Traditional ROI: 5.86%
893 Lily Creek Ln JAMESTOWN, KY Experience luxury lake living at its finest in this beautifully furnished, upscale lake ho...	5 beds \| 4 baths \| 3,324 sq.ft.	$635,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 4.83% Airbnb Rental Income: $2992 Traditional Rental Income: $3838 Airbnb ROI: 2.24% Traditional ROI: 4.83%
49 Linkview Rd JAMESTOWN, KY Brand-New Home Near Lake Cumberland - Ideal Vacation or Investment Property! Don't miss th...	3 beds \| 2 baths \| 1,344 sq.ft.	$185,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 9.66% Airbnb Rental Income: $943 Traditional Rental Income: $2118 Airbnb ROI: 1.01% Traditional ROI: 9.66%
130 Cumberland Ave.. JAMESTOWN, KY	N/A beds \| N/A baths \| 4,896 sq.ft.	$161,450	Airbnb cash on cash: -2.18% Traditional cash on cash: 8.85% Airbnb Rental Income: $145 Traditional Rental Income: $1632 Airbnb ROI: -2.18% Traditional ROI: 8.85%
335 Sonny Aaron Dr. #335 JAMESTOWN, KY Come Home To Sonny's Landing!!! New Construction Home situated on a nice large lot just mi...	3 beds \| 2 baths \| 1,650 sq.ft.	$339,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 5.93% Airbnb Rental Income: $943 Traditional Rental Income: $2579 Airbnb ROI: -0.28% Traditional ROI: 5.93%
167 Dylan Dr JAMESTOWN, KY 2 Bedrooms PLUS an additional flex/guest bedroom...2 full bathrooms Upscale custom, stylis...	2 beds \| 2 baths \| 1,992 sq.ft.	$319,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 6.36% Airbnb Rental Income: $581 Traditional Rental Income: $2441 Airbnb ROI: -0.79% Traditional ROI: 6.36%
303 Sonny Aaron Dr JAMESTOWN, KY Welcome to this spacious home at 303 Sonny Aaron Dr. Jamestown! This home was built in 202...	3 beds \| 2 baths \| 1,650 sq.ft.	$299,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 6.36% Airbnb Rental Income: $943 Traditional Rental Income: $2411 Airbnb ROI: -0.07% Traditional ROI: 6.36%
905 Lily Creek Resort Rd JAMESTOWN, KY Panoramic year round lake views from three levels..Lily Creek Resort's best view..fabulous...	5 beds \| 4 baths \| 3,796 sq.ft.	$695,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.25% Airbnb Rental Income: $2992 Traditional Rental Income: $4453 Airbnb ROI: 1.94% Traditional ROI: 5.25%
464 Lakeview Dr JAMESTOWN, KY Discover the epitome of lakeside sophistication at this exquisite residence located within...	3 beds \| 3 baths \| 2,862 sq.ft.	$849,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.44% Airbnb Rental Income: $943 Traditional Rental Income: $3143 Airbnb ROI: -0.78% Traditional ROI: 2.44%

Real Estate investment in Jamestown, KY

There are 76 properties for sale in the city of Jamestown . The median list price in Jamestown is $99,900 and the average price per square foot is $36. In February 2026, the average monthly cash on cash return in Jamestown is 6.00%. The average monthly rental income in Jamestown is $2,171.

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

There are 76 investment properties available for sale in Jamestown.

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

The ROI for Short-Term is higher than the Long-Term in Jamestown with average rental income of $943.

Your search for investment property begins and ends here

Investment Property for Sale in Jamestown, KY

111 Leveridge Ct

JAMESTOWN, KY

5 beds | 3 baths | 6,040 sq.ft.

$649,900

Airbnb cash on cash: 1.79%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $2992

Traditional Rental Income: $3632

Airbnb ROI: 1.79%

Traditional ROI: 3.98%

522 Lakeview Dr

JAMESTOWN, KY

4 beds | 3 baths | 3,369 sq.ft.

$645,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3497

Airbnb ROI: N/A

Traditional ROI: 3.72%

190 Vine Dr.

JAMESTOWN, KY

3 beds | 2 baths | 1,458 sq.ft.

$395,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $943

Traditional Rental Income: $2208

Airbnb ROI: -0.03%

Traditional ROI: 4.32%

25 Harbor Springs Cir

JAMESTOWN, KY

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

$380,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.38%

Airbnb Rental Income: $null

Traditional Rental Income: $1603

Airbnb ROI: N/A

Traditional ROI: 2.38%

145 State Park Rd #R2

JAMESTOWN, KY

1 beds | 2 baths | 900 sq.ft.

$142,000

Airbnb cash on cash: -2.27%

Traditional cash on cash: 5.81%

Airbnb Rental Income: $731

Traditional Rental Income: $1520

Airbnb ROI: -2.27%

Traditional ROI: 5.81%

120 West Cumberland Avenue

JAMESTOWN, KY

5 beds | 3 baths | 2,492 sq.ft.

$282,000

Airbnb cash on cash: 6.47%

Traditional cash on cash: 8.5%

Airbnb Rental Income: $2992

Traditional Rental Income: $2845

Airbnb ROI: 6.47%

Traditional ROI: 8.5%

1655 Ky-92

JAMESTOWN, KY

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

$659,900

Airbnb cash on cash: -1.32%

Traditional cash on cash: 0.62%

Airbnb Rental Income: $731

Traditional Rental Income: $1618

Airbnb ROI: -1.32%

Traditional ROI: 0.62%

807 W Cumberland Ave.

JAMESTOWN, KY

2 beds | 2 baths | N/A

$159,900

Airbnb cash on cash: 0.23%

Traditional cash on cash: 10.88%

Airbnb Rental Income: $581

Traditional Rental Income: $1921

Airbnb ROI: 0.23%