Real Estate Investment Properties for Sale in Monticello, KY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
35 Guinn Drive Monticello, KY NEW ROOF! Discover the perfect blend of comfort and convenience in this gorgeous brick hom...	4 beds \| 3 baths \| 3,416 sq.ft.	$394,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 5.07% Airbnb Rental Income: $2434 Traditional Rental Income: $2650 Airbnb ROI: 2.87% Traditional ROI: 5.07%
80 Sunset Vista Way Monticello, KY Unparalleled custom lake view home overlooking the main lake. One, of if not THE best view...	4 beds \| 2 baths \| 4,504 sq.ft.	$749,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 1.89% Airbnb Rental Income: $2434 Traditional Rental Income: $2713 Airbnb ROI: 0.64% Traditional ROI: 1.89%
314 Kendrick Avenue Monticello, KY Set on a highly desirable street, this beautifully maintained stonework home blends histor...	4 beds \| 2 baths \| 2,364 sq.ft.	$349,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 4.87% Airbnb Rental Income: $2434 Traditional Rental Income: $2298 Airbnb ROI: 3.48% Traditional ROI: 4.87%
61 Vena Court Monticello, KY Looking for an affordable home, then look at this newly remodeled home that is in the city...	3 beds \| 1 baths \| 1,144 sq.ft.	$159,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 6.93% Airbnb Rental Income: $1360 Traditional Rental Income: $1426 Airbnb ROI: 3.75% Traditional ROI: 6.93%
607 Old Lock 21 Road Monticello, KY 3 bedroom, 3 bath Home and boat slip! You won't find homes like this for sale often, Locat...	3 beds \| 3 baths \| 3,402 sq.ft.	$382,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 5.21% Airbnb Rental Income: $1360 Traditional Rental Income: $2625 Airbnb ROI: 0.52% Traditional ROI: 5.21%
106 Hwy 3284 Monticello, KY This stunning 3,700+/- square foot home perfectly blends classic charm with modern luxury....	4 beds \| 3 baths \| 3,793 sq.ft.	$389,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 3.61% Airbnb Rental Income: $2434 Traditional Rental Income: $2086 Airbnb ROI: 2.93% Traditional ROI: 3.61%
81 Eagles Bluff Road Monticello, KY LAKE LOVERS! Welcome to your perfect retreat near Lake Cumberland! This immaculate A- fram...	2 beds \| 2 baths \| 1,152 sq.ft.	$350,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.25% Airbnb Rental Income: $892 Traditional Rental Income: $1772 Airbnb ROI: -0.45% Traditional ROI: 3.25%
1415 N Main Street Monticello, KY Charming 3-bedroom, 1-bath brick home that's been totally renovated from top to bottom! Th...	3 beds \| 1 baths \| 1,176 sq.ft.	$179,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 6.09% Airbnb Rental Income: $1360 Traditional Rental Income: $1445 Airbnb ROI: 3.15% Traditional ROI: 6.09%
38 Wells Court Monticello, KY Looking for an affordable home that is close to Downtown Monticello, Wayne Co Park, Medica...	3 beds \| 1 baths \| 1,081 sq.ft.	$159,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 6.29% Airbnb Rental Income: $1360 Traditional Rental Income: $1329 Airbnb ROI: 3.75% Traditional ROI: 6.29%
1115 Highway 167 Monticello, KY This delightful listing presents a charming home. Featuring a barn and silo, along with an...	3 beds \| 2 baths \| 1,614 sq.ft.	$184,900	Airbnb cash on cash: 3.78% Traditional cash on cash: 8.94% Airbnb Rental Income: $1360 Traditional Rental Income: $1852 Airbnb ROI: 3.78% Traditional ROI: 8.94%
726 N Main Street Monticello, KY Ceiling to Floor Remodel!! This Custom built 3 Bedrooms 2.5 Bathrooms , Eat in Kitchen, La...	3 beds \| 2 baths \| 2,560 sq.ft.	$525,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.97% Airbnb Rental Income: $1360 Traditional Rental Income: $2458 Airbnb ROI: -0.12% Traditional ROI: 2.97%
500 Beaver Lodge Rd Monticello, KY Perfect Vacation Getaway - Fully Furnished & Ready to Enjoy! Welcome to your ideal lakesid...	2 beds \| 1 baths \| 1,120 sq.ft.	$219,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 5.91% Airbnb Rental Income: $892 Traditional Rental Income: $1600 Airbnb ROI: 0.86% Traditional ROI: 5.91%
99 Silverdust Circle Monticello, KY Charming home located in well established Grazeland Subdivision. Home is located 3 to 4 mi...	4 beds \| 4 baths \| 4,800 sq.ft.	$470,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 8.15% Airbnb Rental Income: $2434 Traditional Rental Income: $4345 Airbnb ROI: 2.46% Traditional ROI: 8.15%
175 Golden Pond Road Monticello, KY This remarkable duplex in Golden Pond Resort offers proven short-term rental income (renta...	8 beds \| 4 baths \| 2,688 sq.ft.	$389,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 6.42% Airbnb Rental Income: $4440 Traditional Rental Income: $3113 Airbnb ROI: 7.52% Traditional ROI: 6.42%
109 Betsey Lane Monticello, KY Welcome to this charming home nestled in a serene country setting, just 15 minutes from th...	3 beds \| 1 baths \| 1,064 sq.ft.	$199,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 5.32% Airbnb Rental Income: $1360 Traditional Rental Income: $1449 Airbnb ROI: 2.65% Traditional ROI: 5.32%
1145 Ramsey Point Road Monticello, KY This beautifully updated, move-in ready 3bed, 2 bath home comes fully furnished, so all yo...	3 beds \| 2 baths \| 1,352 sq.ft.	$220,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 6.14% Airbnb Rental Income: $1360 Traditional Rental Income: $1654 Airbnb ROI: 2.73% Traditional ROI: 6.14%
800 Red Fox Ridge Monticello, KY SELLERS RELOCATING! Discover the epitome of luxury living with this breathtaking 4-bedroom...	4 beds \| 4 baths \| 3,998 sq.ft.	$899,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.21% Airbnb Rental Income: $2434 Traditional Rental Income: $3500 Airbnb ROI: 0.23% Traditional ROI: 2.21%
137 Indian Cave Subdivision Monticello, KY This is not just a beautiful brick home on 8 acres, it's a small estate. This stately two ...	5 beds \| 4 baths \| 5,678 sq.ft.	$689,900	Airbnb cash on cash: 4.09% Traditional cash on cash: 6.1% Airbnb Rental Income: $4440 Traditional Rental Income: $4806 Airbnb ROI: 4.09% Traditional ROI: 6.1%
1636 Green Hill Estates Road Monticello, KY MOTIVATED SELLER - Says make an offer on this AIRBNB or full time living for this year rou...	5 beds \| 4 baths \| 3,848 sq.ft.	$525,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 5.7% Airbnb Rental Income: $4440 Traditional Rental Income: $3497 Airbnb ROI: 5.73% Traditional ROI: 5.7%
202 Willa Drive Monticello, KY Charming 3-Bedroom Home Minutes from Beaver Creek Resort! This beautifully maintained, new...	3 beds \| 2 baths \| 1,296 sq.ft.	$229,900	Airbnb cash on cash: 2.56% Traditional cash on cash: 5.48% Airbnb Rental Income: $1360 Traditional Rental Income: $1580 Airbnb ROI: 2.56% Traditional ROI: 5.48%
2 Lighthouse Road Monticello, KY Lake Lovers! Lot 2 Lighthouse Road, nestled in the Mill Springs Area of Monticello, is a b...	2 beds \| 2 baths \| 1,008 sq.ft.	$269,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.8% Airbnb Rental Income: $892 Traditional Rental Income: $1785 Airbnb ROI: -0.04% Traditional ROI: 4.8%
43 Farmington Ave Monticello, KY Beautifully well-maintained brick home, conveniently located between Somerset and Monticel...	3 beds \| 2 baths \| 1,990 sq.ft.	$319,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 5% Airbnb Rental Income: $1360 Traditional Rental Income: $2187 Airbnb ROI: 0.86% Traditional ROI: 5%
299 Mercer Drive Monticello, KY Welcome to this absolute dollhouse! This charming home offers 3 bedrooms and 2 bathrooms, ...	3 beds \| 2 baths \| 1,526 sq.ft.	$189,900	Airbnb cash on cash: 3.29% Traditional cash on cash: 7.83% Airbnb Rental Income: $1360 Traditional Rental Income: $1764 Airbnb ROI: 3.29% Traditional ROI: 7.83%
504 S 1808 Highway Monticello, KY This brick ranch style home boasts two bedrooms, living room, kitchen, large dining room, ...	2 beds \| 1 baths \| 1,800 sq.ft.	$139,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 7.69% Airbnb Rental Income: $892 Traditional Rental Income: $1287 Airbnb ROI: 2.23% Traditional ROI: 7.69%
25 Cart Bell Lane Monticello, KY Rustic off-grid cabin tucked away on 2.89 +/-mostly wooded acres, just minutes from multip...	1 beds \| N/A baths \| 120 sq.ft.	$79,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 10.54% Airbnb Rental Income: $896 Traditional Rental Income: $1016 Airbnb ROI: 4.65% Traditional ROI: 10.54%
8 Gehring Way Monticello, KY Welcome to your dream retreat! This beautifully custom-built 4-bedroom, 2-bathroom home si...	4 beds \| 2 baths \| 1,836 sq.ft.	$399,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 4.1% Airbnb Rental Income: $2434 Traditional Rental Income: $2147 Airbnb ROI: 3.28% Traditional ROI: 4.1%
469 Mercer Drive Monticello, KY Welcome to this beautifully remodeled 4 bedroom, 2 bath brick home offering 1,424 sq. ft. ...	4 beds \| 2 baths \| 1,424 sq.ft.	$190,000	Airbnb cash on cash: 7.82% Traditional cash on cash: 8.03% Airbnb Rental Income: $2434 Traditional Rental Income: $1878 Airbnb ROI: 7.82% Traditional ROI: 8.03%
147 Lighthouse Road Monticello, KY Unfinished barn-style home just 3 miles from Conley Bottom Marina. This property offers ap...	3 beds \| 3 baths \| N/A	$229,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 7.69% Airbnb Rental Income: $1360 Traditional Rental Income: $2161 Airbnb ROI: 2.08% Traditional ROI: 7.69%
241 Perdue Road Monticello, KY PEACEFUL RURAL LIVING with all the comforts you could imagine! This stunning home was cust...	3 beds \| 2 baths \| 2,084 sq.ft.	$459,900	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.71% Airbnb Rental Income: $1360 Traditional Rental Income: $2245 Airbnb ROI: 0.69% Traditional ROI: 3.71%
49 Mountain Laurel Way Monticello, KY Spacious 4-Bedroom Home on Double Corner Lot Near Lake Cumberland! Discover the perfect bl...	4 beds \| N/A baths \| 2,500 sq.ft.	$329,999	Airbnb cash on cash: 4.22% Traditional cash on cash: 6.15% Airbnb Rental Income: $2434 Traditional Rental Income: $2437 Airbnb ROI: 4.22% Traditional ROI: 6.15%
131 Dogwood Trail Monticello, KY You will love this immaculate 5 bedroom, 4.5 bath family home offering approximately 3,104...	5 beds \| 4 baths \| 3,104 sq.ft.	$550,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 6.48% Airbnb Rental Income: $4440 Traditional Rental Income: $4070 Airbnb ROI: 5.39% Traditional ROI: 6.48%
568 Castle Street Monticello, KY Charming Monticello Home with Room for Everyone Welcome to your new happy place in Montice...	3 beds \| 2 baths \| 4,114 sq.ft.	$425,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.95% Airbnb Rental Income: $1360 Traditional Rental Income: $2163 Airbnb ROI: 0.89% Traditional ROI: 3.95%
471 Ky-1258 Monticello, KY Looking for a secluded home on 1 acre, take a look at this 3 bedroom, 2 bath, brick ranch ...	3 beds \| 2 baths \| 1,510 sq.ft.	$182,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 8.33% Airbnb Rental Income: $1360 Traditional Rental Income: $1793 Airbnb ROI: 3.43% Traditional ROI: 8.33%
121 Shinbone Drive Monticello, KY Check on this home which is super-convenient to the lake!! If you're looking for a vacatio...	3 beds \| 2 baths \| 1,064 sq.ft.	$140,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 8.74% Airbnb Rental Income: $1360 Traditional Rental Income: $1435 Airbnb ROI: 5.09% Traditional ROI: 8.74%
64 Bess Ann Court Monticello, KY Beautiful 3-bedroom, 2-bath brick home owned by the original owner and located in a great ...	3 beds \| 2 baths \| 1,506 sq.ft.	$169,900	Airbnb cash on cash: 4.08% Traditional cash on cash: 9.67% Airbnb Rental Income: $1360 Traditional Rental Income: $1851 Airbnb ROI: 4.08% Traditional ROI: 9.67%
12 Lynne Drive Monticello, KY Looking for your perfect peaceful Lake Cumberland retreat? This cozy 3 Bedroom 3 bath home...	3 beds \| 3 baths \| 3,093 sq.ft.	$385,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 5.38% Airbnb Rental Income: $1360 Traditional Rental Income: $2484 Airbnb ROI: 1.12% Traditional ROI: 5.38%
352 American Legion Road Monticello, KY Looking for a property that is close into Monticello, but out with some privacy, then take...	3 beds \| 2 baths \| 1,248 sq.ft.	$139,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 9.52% Airbnb Rental Income: $1360 Traditional Rental Income: $1546 Airbnb ROI: 5.01% Traditional ROI: 9.52%
755 Slip Rock Canyon Road Monticello, KY Approximately 5.75 acres nestled in the country near the scenic Little South Fork Creek, t...	2 beds \| 1 baths \| 771 sq.ft.	$110,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 8.66% Airbnb Rental Income: $892 Traditional Rental Income: $1172 Airbnb ROI: 2.86% Traditional ROI: 8.66%
212 Virgil Street Monticello, KY $5,000.00 Bonus Incentive offered at closing to an Awesome Buyer from Sellers !! Charming ...	4 beds \| 2 baths \| 1,222 sq.ft.	$239,900	Airbnb cash on cash: 6.66% Traditional cash on cash: 6.06% Airbnb Rental Income: $2434 Traditional Rental Income: $1703 Airbnb ROI: 6.66% Traditional ROI: 6.06%
124 Bens Cliff Road Monticello, KY For Sale: 2019 Mobile Home on 4.13 Acres - Monticello, KY Looking for privacy, nature, and...	3 beds \| 2 baths \| 924 sq.ft.	$137,900	Airbnb cash on cash: 5.11% Traditional cash on cash: 10.16% Airbnb Rental Income: $1360 Traditional Rental Income: $1612 Airbnb ROI: 5.11% Traditional ROI: 10.16%

Real Estate investment in Monticello, KY

There are 52 properties for sale in the city of Monticello . The median list price in Monticello is $229,900 and the average price per square foot is $116. In December 2025, the average monthly cash on cash return in Monticello is 6.00%. The average monthly rental income in Monticello is $1,817.

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

There are 52 investment properties available for sale in Monticello.

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

The ROI for Long-Term is higher than the Short-Term in Monticello with average rental income of $1,817.

Your search for investment property begins and ends here

Investment Property for Sale in Monticello, KY

35 Guinn Drive

Monticello, KY

4 beds | 3 baths | 3,416 sq.ft.

$394,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $2434

Traditional Rental Income: $2650

Airbnb ROI: 2.87%

Traditional ROI: 5.07%

80 Sunset Vista Way

Monticello, KY

4 beds | 2 baths | 4,504 sq.ft.

$749,900

Airbnb cash on cash: 0.64%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $2434

Traditional Rental Income: $2713

Airbnb ROI: 0.64%

Traditional ROI: 1.89%

314 Kendrick Avenue

Monticello, KY

4 beds | 2 baths | 2,364 sq.ft.

$349,000

Airbnb cash on cash: 3.48%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $2434

Traditional Rental Income: $2298

Airbnb ROI: 3.48%

Traditional ROI: 4.87%

61 Vena Court

Monticello, KY

3 beds | 1 baths | 1,144 sq.ft.

$159,000

Airbnb cash on cash: 3.75%

Traditional cash on cash: 6.93%

Airbnb Rental Income: $1360

Traditional Rental Income: $1426

Airbnb ROI: 3.75%

Traditional ROI: 6.93%

607 Old Lock 21 Road

Monticello, KY

3 beds | 3 baths | 3,402 sq.ft.

$382,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $1360

Traditional Rental Income: $2625

Airbnb ROI: 0.52%

Traditional ROI: 5.21%

106 Hwy 3284

Monticello, KY

4 beds | 3 baths | 3,793 sq.ft.

$389,000

Airbnb cash on cash: 2.93%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $2434

Traditional Rental Income: $2086

Airbnb ROI: 2.93%

Traditional ROI: 3.61%

81 Eagles Bluff Road

Monticello, KY

2 beds | 2 baths | 1,152 sq.ft.

$350,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $892

Traditional Rental Income: $1772

Airbnb ROI: -0.45%

Traditional ROI: 3.25%

1415 N Main Street

Monticello, KY

3 beds | 1 baths | 1,176 sq.ft.

$179,000

Airbnb cash on cash: 3.15%

Traditional cash on cash: 6.09%

Airbnb Rental Income: $1360

Traditional Rental Income: $1445

Airbnb ROI: 3.15%