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 Court JAMESTOWN, KY Spacious 5-bedroom, 3.5-bath home offering over 4,000 finished sq ft of comfortable living...	5 beds \| 4 baths \| 4,000 sq.ft.	$699,995	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.57% Airbnb Rental Income: $3924 Traditional Rental Income: $3632 Airbnb ROI: 2.72% Traditional ROI: 3.57%
522 Lakeview Drive JAMESTOWN, KY Immaculate custom home with designer finishes throughout. This beautifully upgraded 4 bed...	4 beds \| 4 baths \| 3,369 sq.ft.	$639,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.75% Airbnb Rental Income: $2292 Traditional Rental Income: $3497 Airbnb ROI: 0.78% Traditional ROI: 3.75%
305 Glover Road JAMESTOWN, KY PRICE REDUCTION! This one has it ALL! This move in ready gem is only minutes from the la...	3 beds \| 2 baths \| 1,300 sq.ft.	$184,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 6.49% Airbnb Rental Income: $991 Traditional Rental Income: $1561 Airbnb ROI: 1.24% Traditional ROI: 6.49%
629 KY-1058 JAMESTOWN, KY If country living, beautiful scenic views and being in an amazing community are what you'r...	3 beds \| 2 baths \| 1,458 sq.ft.	$443,500	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.34% Airbnb Rental Income: $991 Traditional Rental Income: $1419 Airbnb ROI: -0.54% Traditional ROI: 1.34%
120 Cole Lane JAMESTOWN, KY Motivated Sellers! Nestled on nearly 2 private acres, this beautifully updated 3-bedroom, ...	3 beds \| 4 baths \| 2,657 sq.ft.	$410,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 5.56% Airbnb Rental Income: $991 Traditional Rental Income: $2959 Airbnb ROI: -0.48% Traditional ROI: 5.56%
819 Scotts Chapel Road JAMESTOWN, KY Charming Lake Cumberland Retreat - Updated & Move-In Ready! Discover your ideal weekend g...	3 beds \| 2 baths \| 860 sq.ft.	$189,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 7.34% Airbnb Rental Income: $991 Traditional Rental Income: $1744 Airbnb ROI: 1.18% Traditional ROI: 7.34%
145 State Park Road 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: -2.8% Traditional cash on cash: 5.29% Airbnb Rental Income: $618 Traditional Rental Income: $1600 Airbnb ROI: -2.8% Traditional ROI: 5.29%
353 W Cumberland Ave. Avenue JAMESTOWN, KY Charming 4-Bedroom Home with Detached Garage & Ideal Location Near Lake Cumberland Welc...	4 beds \| 2 baths \| 1,500 sq.ft.	$235,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 8.03% Airbnb Rental Income: $2292 Traditional Rental Income: $2289 Airbnb ROI: 5.48% Traditional ROI: 8.03%
289 E Cumberland Avenue JAMESTOWN, KY Charming Fixer-Upper with Endless Potential! Located just 3 miles to Lake Cumberland an...	4 beds \| 1 baths \| 1,428 sq.ft.	$154,700	Airbnb cash on cash: 9.91% Traditional cash on cash: 11.21% Airbnb Rental Income: $2292 Traditional Rental Income: $1913 Airbnb ROI: 9.91% Traditional ROI: 11.21%
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: 2.19% Traditional cash on cash: 1.9% Airbnb Rental Income: $2292 Traditional Rental Income: $1603 Airbnb ROI: 2.19% Traditional ROI: 1.9%
8247 S. Highway 379 JAMESTOWN, KY Escape to your very own slice of heaven! Tucked away in tranquil woodland! Whether you're ...	3 beds \| 1 baths \| 1,254 sq.ft.	$205,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 6.67% Airbnb Rental Income: $991 Traditional Rental Income: $1631 Airbnb ROI: 1.56% Traditional ROI: 6.67%
216 Tall Timber Drive JAMESTOWN, KY AN UNBELIEVABLE OPPORTUNITY - NOW JUST $299,000! LAKE-ORIENTED RETREAT JUST 2.5 MILES FR...	3 beds \| 3 baths \| 1,659 sq.ft.	$299,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 4.83% Airbnb Rental Income: $991 Traditional Rental Income: $1877 Airbnb ROI: 0.42% Traditional ROI: 4.83%
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.	$288,750	Airbnb cash on cash: 9.13% Traditional cash on cash: 8.26% Airbnb Rental Income: $3924 Traditional Rental Income: $2845 Airbnb ROI: 9.13% Traditional ROI: 8.26%
459 Logan Antle Road JAMESTOWN, KY Discover the serenity of rural living with this charming new construction located in the b...	2 beds \| 1 baths \| 1,100 sq.ft.	$184,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 7.95% Airbnb Rental Income: $618 Traditional Rental Income: $1817 Airbnb ROI: -0.53% Traditional ROI: 7.95%
439 Logan Antle Road JAMESTOWN, KY Welcome to this charming new construction located in the scenic Creelsboro community of Ja...	2 beds \| 1 baths \| 1,100 sq.ft.	$184,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 7.95% Airbnb Rental Income: $618 Traditional Rental Income: $1817 Airbnb ROI: -0.53% Traditional ROI: 7.95%
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.	$659,900	Airbnb cash on cash: -1.08% Traditional cash on cash: 0.62% Airbnb Rental Income: $907 Traditional Rental Income: $1618 Airbnb ROI: -1.08% 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: 0.44% Traditional cash on cash: 10.88% Airbnb Rental Income: $618 Traditional Rental Income: $1921 Airbnb ROI: 0.44% Traditional ROI: 10.88%
109 Dylan Drive JAMESTOWN, KY Spectacular Lake Cumberland townhouse conveniently located near the Jamestown Resort & Mar...	4 beds \| 4 baths \| 3,915 sq.ft.	$374,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 9.09% Airbnb Rental Income: $2292 Traditional Rental Income: $3735 Airbnb ROI: 3.35% 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.	$259,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 6.67% Airbnb Rental Income: $991 Traditional Rental Income: $2048 Airbnb ROI: 0.89% Traditional ROI: 6.67%
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: -0.62% Traditional cash on cash: 5.42% Airbnb Rental Income: $618 Traditional Rental Income: $1473 Airbnb ROI: -0.62% 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: -0.22% Traditional cash on cash: 5.28% Airbnb Rental Income: $991 Traditional Rental Income: $2472 Airbnb ROI: -0.22% 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: -0.84% Traditional cash on cash: 5.42% Airbnb Rental Income: $618 Traditional Rental Income: $1761 Airbnb ROI: -0.84% Traditional ROI: 5.42%
258 Dutton Circle JAMESTOWN, KY Welcome to 258 Dutton Circle in Jamestown, Kentucky - a beautifully maintained ranch-style...	3 beds \| 1 baths \| 1,560 sq.ft.	$199,900	Airbnb cash on cash: 1.02% Traditional cash on cash: 7.2% Airbnb Rental Income: $991 Traditional Rental Income: $1810 Airbnb ROI: 1.02% Traditional ROI: 7.2%
105 Ivy Drive JAMESTOWN, KY Nestled in the rolling hills of south central Kentucky, this stunning custom-built home of...	3 beds \| 3 baths \| 3,600 sq.ft.	$574,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.39% Airbnb Rental Income: $991 Traditional Rental Income: $2752 Airbnb ROI: -0.55% Traditional ROI: 3.39%
131 E Jefferson Street JAMESTOWN, KY Check out this charming 1 1/2 story home with 3 bedrooms and 2 full baths. Quiet and peace...	3 beds \| 2 baths \| 1,152 sq.ft.	$168,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 9.24% Airbnb Rental Income: $991 Traditional Rental Income: $1869 Airbnb ROI: 1.55% Traditional ROI: 9.24%
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: 0.34% Traditional cash on cash: 5.63% Airbnb Rental Income: $991 Traditional Rental Income: $2377 Airbnb ROI: 0.34% Traditional ROI: 5.63%
141 Cherokee Springs Court JAMESTOWN, KY This one-owner, well-maintained custom-built home in charming Cherokee Springs is a must s...	4 beds \| 3 baths \| 2,600 sq.ft.	$399,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 6.17% Airbnb Rental Income: $2292 Traditional Rental Income: $2917 Airbnb ROI: 2.98% Traditional ROI: 6.17%
1055 KY-92 JAMESTOWN, KY Turnkey Lake Home Near Jamestown Marina - Unrestricted 1.3 Acre Retreat! Just minutes fr...	3 beds \| 2 baths \| 1,248 sq.ft.	$339,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 5.25% Airbnb Rental Income: $991 Traditional Rental Income: $2109 Airbnb ROI: 0.63% Traditional ROI: 5.25%
444 Sparks Avenue JAMESTOWN, KY Extraordinary Country Estate Near Lake Cumberland- 5 BR Custom Home on 24+ Acres with Poo...	5 beds \| 6 baths \| 9,781 sq.ft.	$1,500,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.53% Airbnb Rental Income: $3924 Traditional Rental Income: $6778 Airbnb ROI: 0.88% Traditional ROI: 3.53%
168 S Main Street Street JAMESTOWN, KY Charming Brick Ranch in the Heart of Jamestown - Minutes from Lake Cumberland! Enjoy the b...	3 beds \| 2 baths \| 1,152 sq.ft.	$190,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 9.53% Airbnb Rental Income: $991 Traditional Rental Income: $2052 Airbnb ROI: 1.69% Traditional ROI: 9.53%
273 Rosin Ridge Rd. JAMESTOWN, KY This beautiful home offers over 7 acres of land along with a beautiful 3 bedroom, two bath...	3 beds \| 2 baths \| 1,700 sq.ft.	$249,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 7.79% Airbnb Rental Income: $991 Traditional Rental Income: $2289 Airbnb ROI: 0.79% Traditional ROI: 7.79%
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: -0.62% Traditional cash on cash: 5.87% Airbnb Rental Income: $618 Traditional Rental Income: $1557 Airbnb ROI: -0.62% 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: 0.83% Traditional cash on cash: 6.14% Airbnb Rental Income: $991 Traditional Rental Income: $1939 Airbnb ROI: 0.83% Traditional ROI: 6.14%
211 Tall Timbers Road JAMESTOWN, KY PRICE DROP-$234,000 House, Huge Garage, and Up to Four Lots and Just 3 Miles from Lake ...	3 beds \| 2 baths \| 1,680 sq.ft.	$234,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 8.64% Airbnb Rental Income: $991 Traditional Rental Income: $2304 Airbnb ROI: 1.11% Traditional ROI: 8.64%
412 Murphy Lane JAMESTOWN, KY Beautiful LIKE NEW Duplex being sold as one transaction. Each side is priced at $260,000 ...	2 beds \| 2 baths \| 1,613 sq.ft.	$247,500	Airbnb cash on cash: -0.47% Traditional cash on cash: 8.38% Airbnb Rental Income: $618 Traditional Rental Income: $2395 Airbnb ROI: -0.47% Traditional ROI: 8.38%
651 S Main Street JAMESTOWN, KY Adorable farmhouse located on South Main Street, sitting on a spacious half-acre lot that ...	3 beds \| 2 baths \| 1,124 sq.ft.	$169,900	Airbnb cash on cash: 1.51% Traditional cash on cash: 9.14% Airbnb Rental Income: $991 Traditional Rental Income: $1873 Airbnb ROI: 1.51% Traditional ROI: 9.14%
11 Cole Lane JAMESTOWN, KY Price Improvement - Motivated Seller - On this well-maintained home that sets on 2.8 acres...	3 beds \| 2 baths \| 2,166 sq.ft.	$349,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 5.35% Airbnb Rental Income: $991 Traditional Rental Income: $2545 Airbnb ROI: -0.45% 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	$325,000	Airbnb cash on cash: 7.93% Traditional cash on cash: 9.76% Airbnb Rental Income: $3924 Traditional Rental Income: $3642 Airbnb ROI: 7.93% Traditional ROI: 9.76%

Real Estate investment in Jamestown, KY

There are 38 properties for sale in the city of Jamestown . The median list price in Jamestown is $249,900 and the average price per square foot is $122. In September 2025, the average monthly cash on cash return in Jamestown is 7.00%. The average monthly rental income in Jamestown is $1,994.

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

There are 38 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 $1,994.

Your search for investment property begins and ends here

Investment Property for Sale in Jamestown, KY

111 Leveridge Court

JAMESTOWN, KY

5 beds | 4 baths | 4,000 sq.ft.

$699,995

Airbnb cash on cash: 2.72%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $3924

Traditional Rental Income: $3632

Airbnb ROI: 2.72%

Traditional ROI: 3.57%

522 Lakeview Drive

JAMESTOWN, KY

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

$639,900

Airbnb cash on cash: 0.78%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2292

Traditional Rental Income: $3497

Airbnb ROI: 0.78%

Traditional ROI: 3.75%

305 Glover Road

JAMESTOWN, KY

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

$184,900

Airbnb cash on cash: 1.24%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $991

Traditional Rental Income: $1561

Airbnb ROI: 1.24%

Traditional ROI: 6.49%

629 KY-1058

JAMESTOWN, KY

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

$443,500

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $991

Traditional Rental Income: $1419

Airbnb ROI: -0.54%

Traditional ROI: 1.34%

120 Cole Lane

JAMESTOWN, KY

3 beds | 4 baths | 2,657 sq.ft.

$410,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $991

Traditional Rental Income: $2959

Airbnb ROI: -0.48%

Traditional ROI: 5.56%

819 Scotts Chapel Road

JAMESTOWN, KY

3 beds | 2 baths | 860 sq.ft.

$189,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 7.34%

Airbnb Rental Income: $991

Traditional Rental Income: $1744

Airbnb ROI: 1.18%

Traditional ROI: 7.34%

145 State Park Road

JAMESTOWN, KY

2 beds | 2 baths | 900 sq.ft.

$165,000

Airbnb cash on cash: -2.8%

Traditional cash on cash: 5.29%

Airbnb Rental Income: $618

Traditional Rental Income: $1600

Airbnb ROI: -2.8%

Traditional ROI: 5.29%

353 W Cumberland Ave. Avenue

JAMESTOWN, KY

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

$235,000

Airbnb cash on cash: 5.48%

Traditional cash on cash: 8.03%

Airbnb Rental Income: $2292

Traditional Rental Income: $2289

Airbnb ROI: 5.48%