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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
111 Leveridge Court JAMESTOWN, KY Spacious 5-bedroom, 3.5-bath home offering over 6540 sq ft of living space (per PVA) inclu...	5 beds \| N/A baths \| 4,540 sq.ft.	$699,995	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.57% Airbnb Rental Income: $2002 Traditional Rental Income: $3632 Airbnb ROI: 0.27% Traditional ROI: 3.57%
522 Lakeview Drive JAMESTOWN, KY This stunning 4 bedroom, 3.5 bath home combines timeless craftsmanship with modern upgrade...	4 beds \| N/A baths \| 3,369 sq.ft.	$639,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.75% Airbnb Rental Income: $1657 Traditional Rental Income: $3497 Airbnb ROI: -0.11% Traditional ROI: 3.75%
305 Glover Road JAMESTOWN, KY PRICE REDUCTION and MOVE IN READY! If you are looking for charm and convenience, this one ...	3 beds \| 2 baths \| 1,300 sq.ft.	$175,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 6.96% Airbnb Rental Income: $1114 Traditional Rental Income: $1561 Airbnb ROI: 2.03% Traditional ROI: 6.96%
168 S Main Street JAMESTOWN, KY Charming Brick Ranch in the Heart of Jamestown - Minutes from Lake Cumberland! Enjoy the b...	3 beds \| N/A baths \| 1,152 sq.ft.	$179,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 9.85% Airbnb Rental Income: $1114 Traditional Rental Income: $2097 Airbnb ROI: 1.92% Traditional ROI: 9.85%
353 W Cumberland Ave. JAMESTOWN, KY Charming 4-Bedroom Home with Detached Garage & Ideal Location Near Lake Cumberland Welcome...	4 beds \| 2 baths \| 1,500 sq.ft.	$235,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 8.17% Airbnb Rental Income: $1657 Traditional Rental Income: $2319 Airbnb ROI: 3.09% Traditional ROI: 8.17%
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: 0.35% Traditional cash on cash: 4.32% Airbnb Rental Income: $1114 Traditional Rental Income: $2208 Airbnb ROI: 0.35% Traditional ROI: 4.32%
120 Cole Lane JAMESTOWN, KY Motivated Sellers! Nestled on nearly 2 private acres, this beautifully updated 3-bedroom, ...	3 beds \| N/A baths \| 2,657 sq.ft.	$394,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 5.84% Airbnb Rental Income: $1114 Traditional Rental Income: $2959 Airbnb ROI: -0.15% Traditional ROI: 5.84%
819 Scotts Chapel Road JAMESTOWN, KY Charming Lake Cumberland Retreat - Updated & Move-In Ready! Discover your ideal weekend ge...	3 beds \| 2 baths \| 860 sq.ft.	$189,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 7.34% Airbnb Rental Income: $1114 Traditional Rental Income: $1744 Airbnb ROI: 1.75% Traditional ROI: 7.34%
145 State Park Road unit: E4 #E4 JAMESTOWN, KY Welcome to your perfect lakeside retreat!! This charming 2 bed 2 bath condo is ideally loc...	2 beds \| 2 baths \| 900 sq.ft.	$165,000	Airbnb cash on cash: -3.06% Traditional cash on cash: 5.29% Airbnb Rental Income: $570 Traditional Rental Income: $1600 Airbnb ROI: -3.06% Traditional ROI: 5.29%
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.	$430,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 1.9% Airbnb Rental Income: $1657 Traditional Rental Income: $1603 Airbnb ROI: 0.88% Traditional ROI: 1.9%
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.	$284,900	Airbnb cash on cash: 3.31% Traditional cash on cash: 8.4% Airbnb Rental Income: $2002 Traditional Rental Income: $2845 Airbnb ROI: 3.31% Traditional ROI: 8.4%
1655 KY-92 JAMESTOWN, KY Just minutes away from Lake Cumberland and the Jamestown Resort & Marina, this 3500 sq. ft...	1 beds \| N/A baths \| 3,500 sq.ft.	$659,900	Airbnb cash on cash: -1.65% Traditional cash on cash: 0.62% Airbnb Rental Income: $491 Traditional Rental Income: $1618 Airbnb ROI: -1.65% 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 \| 1 baths \| N/A	$159,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 10.88% Airbnb Rental Income: $570 Traditional Rental Income: $1921 Airbnb ROI: 0.17% Traditional ROI: 10.88%
109 Dylan Drive unit: 101 #101 JAMESTOWN, KY Spectacular Lake Cumberland townhouse conveniently located near the Jamestown Resort & Mar...	4 beds \| N/A baths \| 3,915 sq.ft.	$374,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 9.09% Airbnb Rental Income: $1657 Traditional Rental Income: $3735 Airbnb ROI: 1.84% Traditional ROI: 9.09%
1704 Harbor Springs Road JAMESTOWN, KY If you are looking for a summer retreat on Lake Cumberland then look no further than 1704 ...	3 beds \| 2 baths \| 1,375 sq.ft.	$249,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 6.97% Airbnb Rental Income: $1114 Traditional Rental Income: $2048 Airbnb ROI: 1.4% Traditional ROI: 6.97%
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.	$199,900	Airbnb cash on cash: -0.83% Traditional cash on cash: 5.42% Airbnb Rental Income: $570 Traditional Rental Income: $1473 Airbnb ROI: -0.83% Traditional ROI: 5.42%
1745 Twin Creeks Loop JAMESTOWN, KY Live the dream on the lake. Custom built home with double lot overlooking beautiful Lake C...	3 beds \| 2 baths \| 1,750 sq.ft.	$355,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 5.28% Airbnb Rental Income: $1114 Traditional Rental Income: $2472 Airbnb ROI: 0.09% Traditional ROI: 5.28%
Tract 6 Swan Pond Road 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: -1.01% Traditional cash on cash: 5.42% Airbnb Rental Income: $570 Traditional Rental Income: $1761 Airbnb ROI: -1.01% Traditional ROI: 5.42%
139 Payton Place Lane 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: 0.65% Traditional cash on cash: 5.63% Airbnb Rental Income: $1114 Traditional Rental Income: $2377 Airbnb ROI: 0.65% Traditional ROI: 5.63%
141 Cherokee Springs Court JAMESTOWN, KY BACK ON THE MARKET (buyer's financing didn't work out). You can own this immaculate, custo...	4 beds \| N/A baths \| 2,600 sq.ft.	$378,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 6.57% Airbnb Rental Income: $1657 Traditional Rental Income: $2917 Airbnb ROI: 1.7% Traditional ROI: 6.57%
198 W Cumberland Avenue JAMESTOWN, KY This beautifully updated duplex is a fantastic opportunity for real estate investors or an...	5 beds \| 3 baths \| 2,068 sq.ft.	$259,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 8.89% Airbnb Rental Income: $2002 Traditional Rental Income: $2544 Airbnb ROI: 4.53% Traditional ROI: 8.89%
444 Sparks Avenue JAMESTOWN, KY Extraordinary Country Estate Near Lake Cumberland- 5 BR Custom Home on 24+ Acres with Pool...	5 beds \| 5 baths \| 9,781 sq.ft.	$1,500,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.53% Airbnb Rental Income: $2002 Traditional Rental Income: $6778 Airbnb ROI: -0.27% Traditional ROI: 3.53%
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: 0.77% Traditional cash on cash: 3.45% Airbnb Rental Income: $2002 Traditional Rental Income: $3222 Airbnb ROI: 0.77% Traditional ROI: 3.45%
145 State Park Road #Q7 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.	$199,900	Airbnb cash on cash: -0.83% Traditional cash on cash: 5.87% Airbnb Rental Income: $570 Traditional Rental Income: $1557 Airbnb ROI: -0.83% Traditional ROI: 5.87%
2019 Clifty Creek Road JAMESTOWN, KY Tucked away in the wooded beauty of Clifty Creek Estates, this charming 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,232 sq.ft.	$259,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 6.14% Airbnb Rental Income: $1114 Traditional Rental Income: $1939 Airbnb ROI: 1.25% Traditional ROI: 6.14%
412 Murphy Lane JAMESTOWN, KY Beautiful LIKE NEW Duplex being sold as one transaction. Each side is priced at 247,500 fo...	2 beds \| 2 baths \| 1,613 sq.ft.	$247,500	Airbnb cash on cash: -0.64% Traditional cash on cash: 8.38% Airbnb Rental Income: $570 Traditional Rental Income: $2395 Airbnb ROI: -0.64% Traditional ROI: 8.38%
11 Cole Lane JAMESTOWN, KY FALL IN LOVE with this well-maintained home that sets on 2.8 acres near Lake Cumberland. F...	3 beds \| 2 baths \| 2,166 sq.ft.	$349,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.35% Airbnb Rental Income: $1114 Traditional Rental Income: $2545 Airbnb ROI: -0.14% Traditional ROI: 5.35%
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	$309,900	Airbnb cash on cash: 2.9% Traditional cash on cash: 10.32% Airbnb Rental Income: $2002 Traditional Rental Income: $3642 Airbnb ROI: 2.9% Traditional ROI: 10.32%
394 W Cumberland Avenue 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: -0.38% Traditional cash on cash: 3.9% Airbnb Rental Income: $570 Traditional Rental Income: $1474 Airbnb ROI: -0.38% Traditional ROI: 3.9%
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: -0.98% Traditional cash on cash: 5.51% Airbnb Rental Income: $570 Traditional Rental Income: $1729 Airbnb ROI: -0.98% Traditional ROI: 5.51%
335 Port of Call Drive JAMESTOWN, KY New Construction - Modern Farmhouse in Anchorage on Caney Welcome to Anchorage on Caney, a...	3 beds \| N/A baths \| 1,925 sq.ft.	$420,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 4.54% Airbnb Rental Income: $1114 Traditional Rental Income: $2609 Airbnb ROI: -0.21% Traditional ROI: 4.54%
145 State Park Road unit: B3 #B3 JAMESTOWN, KY Looking for that Airbnb, Vrbo vacation rental - Investors look at this one. Welcome to App...	2 beds \| 2 baths \| 900 sq.ft.	$144,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 8.37% Airbnb Rental Income: $570 Traditional Rental Income: $1503 Airbnb ROI: -0.45% Traditional ROI: 8.37%
145 State Park Road unit: S4 #S4 JAMESTOWN, KY Stunning 2 bedroom, 2bath Condo near Lake Cumberland in Apple Valley Resort - Jamestown Ke...	2 beds \| 2 baths \| 900 sq.ft.	$178,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 6.73% Airbnb Rental Income: $570 Traditional Rental Income: $1548 Airbnb ROI: -0.72% Traditional ROI: 6.73%
145 State Park Rd unit: I6 #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: -0.41% Traditional cash on cash: 9.49% Airbnb Rental Income: $570 Traditional Rental Income: $1606 Airbnb ROI: -0.41% Traditional ROI: 9.49%
145 State Park Road unit: S-6 #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: -0.4% Traditional cash on cash: 9.6% Airbnb Rental Income: $491 Traditional Rental Income: $1376 Airbnb ROI: -0.4% Traditional ROI: 9.6%
145 State Park Road unit: N5 #N5 JAMESTOWN, KY Your ideal Lake Cumberland retreat awaits! This beautiful condo, located in the gated Appl...	2 beds \| 2 baths \| 900 sq.ft.	$184,500	Airbnb cash on cash: -0.75% Traditional cash on cash: 6.85% Airbnb Rental Income: $570 Traditional Rental Income: $1620 Airbnb ROI: -0.75% Traditional ROI: 6.85%
78 Hoover Road JAMESTOWN, KY Charming Cape Cod style home just minutes to LAKE CUMBERLAND on 2.41 acres in Jamestown, K...	4 beds \| 3 baths \| 2,600 sq.ft.	$399,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 5.99% Airbnb Rental Income: $1657 Traditional Rental Income: $2849 Airbnb ROI: 1.57% Traditional ROI: 5.99%
120 Ivy Drive JAMESTOWN, KY Located in the highly desirable Caney Cove neighborhood; this charming home offers both th...	3 beds \| 2 baths \| 1,800 sq.ft.	$369,900	Airbnb cash on cash: 0.85% Traditional cash on cash: 5.67% Airbnb Rental Income: $1114 Traditional Rental Income: $2412 Airbnb ROI: 0.85% Traditional ROI: 5.67%
186 Lily Creek Resort Road JAMESTOWN, KY If you're looking for one of the most unique, custom homes in the Lake Cumberland area, yo...	3 beds \| 2 baths \| 1,723 sq.ft.	$349,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 6.04% Airbnb Rental Income: $1114 Traditional Rental Income: $2414 Airbnb ROI: 0.94% Traditional ROI: 6.04%
935 Clifty Creek Road JAMESTOWN, KY Custom Log Home Near Lake Cumberland - Clifty Creek Rd, Jamestown, KY This custom log home...	3 beds \| 5 baths \| 3,120 sq.ft.	$485,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.52% Airbnb Rental Income: $1114 Traditional Rental Income: $2285 Airbnb ROI: 0.11% Traditional ROI: 3.52%

Real Estate investment in Jamestown, KY

There are 40 properties for sale in the city of Jamestown . The median list price in Jamestown is $284,900 and the average price per square foot is $142. In November 2025, the average monthly cash on cash return in Jamestown is 6.00%. The average monthly rental income in Jamestown is $2,153.

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

There are 40 investment properties available for sale in Jamestown.

In 2025, 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 $1,114.

Your search for investment property begins and ends here

Investment Property for Sale in Jamestown, KY

111 Leveridge Court

JAMESTOWN, KY

5 beds | N/A baths | 4,540 sq.ft.

$699,995

Airbnb cash on cash: 0.27%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $2002

Traditional Rental Income: $3632

Airbnb ROI: 0.27%

Traditional ROI: 3.57%

522 Lakeview Drive

JAMESTOWN, KY

4 beds | N/A baths | 3,369 sq.ft.

$639,900

Airbnb cash on cash: -0.11%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1657

Traditional Rental Income: $3497

Airbnb ROI: -0.11%

Traditional ROI: 3.75%

305 Glover Road

JAMESTOWN, KY

3 beds | 2 baths | 1,300 sq.ft.

$175,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $1114

Traditional Rental Income: $1561

Airbnb ROI: 2.03%

Traditional ROI: 6.96%

168 S Main Street

JAMESTOWN, KY

3 beds | N/A baths | 1,152 sq.ft.

$179,900

Airbnb cash on cash: 1.92%

Traditional cash on cash: 9.85%

Airbnb Rental Income: $1114

Traditional Rental Income: $2097

Airbnb ROI: 1.92%

Traditional ROI: 9.85%

353 W Cumberland Ave.

JAMESTOWN, KY

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

$235,000

Airbnb cash on cash: 3.09%

Traditional cash on cash: 8.17%

Airbnb Rental Income: $1657

Traditional Rental Income: $2319

Airbnb ROI: 3.09%

Traditional ROI: 8.17%

190 Vine Dr.

JAMESTOWN, KY

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

$395,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $1114

Traditional Rental Income: $2208

Airbnb ROI: 0.35%

Traditional ROI: 4.32%

120 Cole Lane

JAMESTOWN, KY

3 beds | N/A baths | 2,657 sq.ft.

$394,900

Airbnb cash on cash: -0.15%

Traditional cash on cash: 5.84%

Airbnb Rental Income: $1114

Traditional Rental Income: $2959

Airbnb ROI: -0.15%

Traditional ROI: 5.84%

819 Scotts Chapel Road

JAMESTOWN, KY

3 beds | 2 baths | 860 sq.ft.

$189,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 7.34%

Airbnb Rental Income: $1114

Traditional Rental Income: $1744

Airbnb ROI: 1.75%