Real Estate Investment Properties for Sale in Monticello, FL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1165 Dills Road Monticello, FL Nature Loverâs Dream! Custom-Built Estate on 21+ Acres with Endless Amenities. Discover...	5 beds \| 6 baths \| 4,700 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $6829 Airbnb ROI: N/A Traditional ROI: 4.04%
129 S White Oak Drive Monticello, FL The builder is offering a $10,000 buyer's credit for closing costs or interest rate buy do...	4 beds \| 2 baths \| 1,945 sq.ft.	$539,900	Airbnb cash on cash: 4.29% Traditional cash on cash: 2.67% Airbnb Rental Income: $4157 Traditional Rental Income: $2455 Airbnb ROI: 4.29% Traditional ROI: 2.67%
87 Old Tung Grove Road Monticello, FL New Construction ready to move in. The Ridge at Tung Grove- Lot #3 of only 5 lots ranging ...	4 beds \| 3 baths \| 2,344 sq.ft.	$699,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.09% Airbnb Rental Income: $4157 Traditional Rental Income: $2686 Airbnb ROI: 3% Traditional ROI: 2.09%
193 Nautilus Drive Monticello, FL Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the ...	3 beds \| 6 baths \| 9,848 sq.ft.	$1,590,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 2.95% Airbnb Rental Income: $2992 Traditional Rental Income: $6490 Airbnb ROI: 0.12% Traditional ROI: 2.95%
17 Old Tung Grove Road Monticello, FL Ready to move into your new home. The Ridge At Tung Grove. A small subdivision of only 5 l...	3 beds \| 3 baths \| 2,344 sq.ft.	$699,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 2.07% Airbnb Rental Income: $2992 Traditional Rental Income: $2669 Airbnb ROI: 1.51% Traditional ROI: 2.07%
178 Nautilus Drive Monticello, FL Introducing an architectural gem poised for a rebirth, this expansive building spanning 12...	2 beds \| 2 baths \| 1,907 sq.ft.	$645,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 2.46% Airbnb Rental Income: $2152 Traditional Rental Income: $2274 Airbnb ROI: 1.35% Traditional ROI: 2.46%
44 Ojibwa South Road Monticello, FL Welcome to your serene retreat in beautiful Monticello! Nestled in a tranquil neighborhood...	4 beds \| 4 baths \| 2,771 sq.ft.	$625,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 4.65% Airbnb Rental Income: $4157 Traditional Rental Income: $3675 Airbnb ROI: 3.97% Traditional ROI: 4.65%
339 Silver Lake Road Monticello, FL Beautiful private country setting with large oaks and open pasture! Extra roomy home with ...	3 beds \| 3 baths \| 2,706 sq.ft.	$459,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 4.46% Airbnb Rental Income: $2992 Traditional Rental Income: $2817 Airbnb ROI: 3.26% Traditional ROI: 4.46%
478 Robert Thompson Road Monticello, FL A rare find! Acreage with a pond, an immaculately maintained home, and an ideal location s...	3 beds \| 2 baths \| 1,398 sq.ft.	$595,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 1.12% Airbnb Rental Income: $2992 Traditional Rental Income: $1764 Airbnb ROI: 2.1% Traditional ROI: 1.12%
79 Tarn Way Monticello, FL Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC. Luxurious mas...	3 beds \| 2 baths \| 1,806 sq.ft.	$440,995	Airbnb cash on cash: 3.44% Traditional cash on cash: 3.21% Airbnb Rental Income: $2992 Traditional Rental Income: $2210 Airbnb ROI: 3.44% Traditional ROI: 3.21%
136 Sutton Road Monticello, FL Nestled on 5.02 serene acres in the charming town of Monticello, this exquisite 4-bedroom,...	4 beds \| 3 baths \| 2,620 sq.ft.	$685,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 3.24% Airbnb Rental Income: $4157 Traditional Rental Income: $2805 Airbnb ROI: 3.98% Traditional ROI: 3.24%
8818 Gamble Road Monticello, FL Stunning turnkey home on 5.5 acres on the highly sought after Gamble Road in Jefferson Cou...	5 beds \| 5 baths \| 2,658 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $5198 Airbnb ROI: N/A Traditional ROI: 6.21%
6021 Old Lloyd Road Monticello, FL Very nice home located on wooded acreage, all high and dry with great access to Tallahasse...	2 beds \| 2 baths \| 1,066 sq.ft.	$269,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 4.13% Airbnb Rental Income: $2152 Traditional Rental Income: $1452 Airbnb ROI: 4.73% Traditional ROI: 4.13%
974 Hiawatha Farms Road Monticello, FL Discover your dream home perfect for multi generational families in the beautiful and sere...	5 beds \| 5 baths \| 3,770 sq.ft.	$774,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.88% Airbnb Rental Income: $null Traditional Rental Income: $5532 Airbnb ROI: N/A Traditional ROI: 5.88%
107 Tarn Way Monticello, FL Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC. Luxurious mas...	3 beds \| 2 baths \| 1,806 sq.ft.	$439,995	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.22% Airbnb Rental Income: $2992 Traditional Rental Income: $2210 Airbnb ROI: 3.45% Traditional ROI: 3.22%
1180 E Washington Street Monticello, FL SEPT 2024 APPRAISAL CAME BACK AT $ 3 1 9 , 0 0 0 ! Motivated Sellers have reduced the ...	3 beds \| 2 baths \| 1,976 sq.ft.	$309,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 5.48% Airbnb Rental Income: $2992 Traditional Rental Income: $2200 Airbnb ROI: 5.84% Traditional ROI: 5.48%
1490 HAMPTON Place Monticello, FL Great single family home situated on large lot in desirable Coopers Pond Community near I-...	3 beds \| 2 baths \| 1,210 sq.ft.	$250,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 4.49% Airbnb Rental Income: $2992 Traditional Rental Income: $1634 Airbnb ROI: 7.33% Traditional ROI: 4.49%
81 Coopers Pond Road Monticello, FL New build, under construction! Beautiful, private lot on 2.62 acres, close to downtown Mon...	3 beds \| 2 baths \| 1,601 sq.ft.	$399,900	Airbnb cash on cash: 4.01% Traditional cash on cash: 3.67% Airbnb Rental Income: $2992 Traditional Rental Income: $2177 Airbnb ROI: 4.01% Traditional ROI: 3.67%
300 Bowman Street Monticello, FL Gorgeous new construction featuring spacious open floor plan. Kitchen has raised cabinets,...	3 beds \| 3 baths \| 1,550 sq.ft.	$289,900	Airbnb cash on cash: 6.22% Traditional cash on cash: 5.63% Airbnb Rental Income: $2992 Traditional Rental Income: $2145 Airbnb ROI: 6.22% Traditional ROI: 5.63%
288 Forest Drive Monticello, FL Last house on the right! Tucked away with privacy. 2 bed 2 Bath 2020 year model mobile hom...	2 beds \| 2 baths \| 990 sq.ft.	$169,900	Airbnb cash on cash: 7.74% Traditional cash on cash: 9.6% Airbnb Rental Income: $2152 Traditional Rental Income: $1905 Airbnb ROI: 7.74% Traditional ROI: 9.6%
3827 N Jefferson Street Monticello, FL Stylish Brick Home on 5 acres with pond. Extra roomy with 3000 + sf of living area. Home ...	3 beds \| 3 baths \| 3,026 sq.ft.	$649,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.22% Airbnb Rental Income: $2992 Traditional Rental Income: $2666 Airbnb ROI: 2.62% Traditional ROI: 3.22%
44 Pine Needle Trace Monticello, FL Great location convenient to Monticello just on the west end of town and an easy commute t...	3 beds \| 2 baths \| 1,234 sq.ft.	$239,000	Airbnb cash on cash: 7.8% Traditional cash on cash: 5.28% Airbnb Rental Income: $2992 Traditional Rental Income: $1735 Airbnb ROI: 7.8% Traditional ROI: 5.28%
Xxx Taylor Road Monticello, FL Proposed Construction on 5.2 acres Taylor Rd. Wonderful Jefferson County location. Minutes...	3 beds \| 3 baths \| 1,924 sq.ft.	$599,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.9% Airbnb Rental Income: $2992 Traditional Rental Income: $2207 Airbnb ROI: 2.07% Traditional ROI: 1.9%
995 Taylor Road Monticello, FL Beautiful home on 1.37 acres! This home has over 2400 Square Feet with 3 bedrooms and 2 an...	3 beds \| 2 baths \| 2,432 sq.ft.	$264,900	Airbnb cash on cash: 7.83% Traditional cash on cash: 7.57% Airbnb Rental Income: $2992 Traditional Rental Income: $2241 Airbnb ROI: 7.83% Traditional ROI: 7.57%
136 Bob White Trail Monticello, FL Make this piece of paradise your own! As you pull into the driveway, you will feel as if y...	4 beds \| 2 baths \| 2,126 sq.ft.	$550,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 2.14% Airbnb Rental Income: $4157 Traditional Rental Income: $2196 Airbnb ROI: 4.24% Traditional ROI: 2.14%
36 Mossy Oak Lane Monticello, FL In one of Jefferson County's most sought-after neighborhoods, sits this beautiful new cons...	3 beds \| 2 baths \| 1,957 sq.ft.	$565,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 3.28% Airbnb Rental Income: $2992 Traditional Rental Income: $2423 Airbnb ROI: 3.06% Traditional ROI: 3.28%
141 SHUMARD Court Monticello, FL This stunning 3-bedroom, 3-bath home is perfectly situated on a quiet cul-de-sac, offering...	3 beds \| 3 baths \| 2,661 sq.ft.	$575,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 3% Airbnb Rental Income: $2992 Traditional Rental Income: $2891 Airbnb ROI: 1.91% Traditional ROI: 3%
4589 Ashville HWY Monticello, FL PRICED $35,000 BELOW RECENT APPRAISAL!! Welcome to your forever home on the most stunningl...	4 beds \| 3 baths \| 3,911 sq.ft.	$735,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 2.71% Airbnb Rental Income: $4157 Traditional Rental Income: $2830 Airbnb ROI: 3.36% Traditional ROI: 2.71%
39 Indian Hills Rd Road Monticello, FL Beautiful four bedroom 2 bath home; spacious kitchen with coffee bar and second sink; form...	4 beds \| 2 baths \| 1,803 sq.ft.	$399,000	Airbnb cash on cash: 6.73% Traditional cash on cash: 3.96% Airbnb Rental Income: $4157 Traditional Rental Income: $2240 Airbnb ROI: 6.73% Traditional ROI: 3.96%
1353 E Washington Street Monticello, FL Historic Monticello Florida Home . This adorable Cottage is walking distance to Downtown, ...	2 beds \| 2 baths \| 1,304 sq.ft.	$255,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 5.92% Airbnb Rental Income: $2152 Traditional Rental Income: $1840 Airbnb ROI: 4.94% Traditional ROI: 5.92%
151 Coopers Pond Road Monticello, FL Under Contract as a custom build! Pictures and updates coming soon! Follow @tiffanykasdor...	3 beds \| 2 baths \| 1,709 sq.ft.	$359,900	Airbnb cash on cash: 4.66% Traditional cash on cash: 5.6% Airbnb Rental Income: $2992 Traditional Rental Income: $2623 Airbnb ROI: 4.66% Traditional ROI: 5.6%
330 Pine Cone Drive Monticello, FL No money down with USDA loan! Discover your dream home in charming Monticello! This nearl...	3 beds \| 2 baths \| 1,601 sq.ft.	$339,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 5.48% Airbnb Rental Income: $2992 Traditional Rental Income: $2177 Airbnb ROI: 5.88% Traditional ROI: 5.48%
336 Lake Monticello, FL Nestled on the edge of serene plantation country, this charming 3-bedroom, 2-bathroom home...	3 beds \| 2 baths \| 1,456 sq.ft.	$225,000	Airbnb cash on cash: 9.06% Traditional cash on cash: 8.57% Airbnb Rental Income: $2992 Traditional Rental Income: $2200 Airbnb ROI: 9.06% Traditional ROI: 8.57%
424 S Hiawatha Farms Road Monticello, FL Stately brick home in gated community of Hiawatha Farms~high elevation with 8.2 fenced pas...	3 beds \| 3 baths \| 3,085 sq.ft.	$749,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 1.63% Airbnb Rental Income: $2992 Traditional Rental Income: $2577 Airbnb ROI: 1.24% Traditional ROI: 1.63%
390 Elliott Drive Drive Monticello, FL New construction in 2024, upscale development. Home qualifies for USDA financing. Privacy...	3 beds \| 2 baths \| 1,351 sq.ft.	$325,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 5.92% Airbnb Rental Income: $2992 Traditional Rental Income: $2478 Airbnb ROI: 5.35% Traditional ROI: 5.92%
300 Cedar Street Monticello, FL Under Contract ~ Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's c...	3 beds \| 2 baths \| 2,044 sq.ft.	$300,000	Airbnb cash on cash: 6.01% Traditional cash on cash: 6.4% Airbnb Rental Income: $2992 Traditional Rental Income: $2415 Airbnb ROI: 6.01% Traditional ROI: 6.4%
1851 Whitehouse Road Monticello, FL Nestled on a quaint country road just across the Jefferson County line, this serene 6 acre...	4 beds \| 3 baths \| 2,057 sq.ft.	$400,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 4.54% Airbnb Rental Income: $4157 Traditional Rental Income: $2409 Airbnb ROI: 6.85% Traditional ROI: 4.54%
1060 Tally Hills Drive Monticello, FL All-brick custom home on over 6 1/2 acres of meticulously landscaped property that fronts ...	5 beds \| 4 baths \| 2,970 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $3636 Airbnb ROI: N/A Traditional ROI: 4.64%

Real Estate investment in Monticello, FL

There are 38 properties for sale in the city of Monticello . The median list price in Monticello is $400,000 and the average price per square foot is $176. In December 2024, the average monthly cash on cash return in Monticello is 5.00%. The average monthly rental income in Monticello is $2,405.

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

There are 38 investment properties available for sale in Monticello.

In 2024, the best neighborhood to buy investment property is Monticello.

The ROI for Short-Term is higher than the Long-Term in Monticello with average rental income of $2,992.

Your search for investment property begins and ends here

Investment Property for Sale in Monticello, FL

1165 Dills Road

Monticello, FL

5 beds | 6 baths | 4,700 sq.ft.

$1,350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.04%

Airbnb Rental Income: $null

Traditional Rental Income: $6829

Airbnb ROI: N/A

Traditional ROI: 4.04%

129 S White Oak Drive

Monticello, FL

4 beds | 2 baths | 1,945 sq.ft.

$539,900

Airbnb cash on cash: 4.29%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $4157

Traditional Rental Income: $2455

Airbnb ROI: 4.29%

Traditional ROI: 2.67%

87 Old Tung Grove Road

Monticello, FL

4 beds | 3 baths | 2,344 sq.ft.

$699,000

Airbnb cash on cash: 3%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $4157

Traditional Rental Income: $2686

Airbnb ROI: 3%

Traditional ROI: 2.09%

193 Nautilus Drive

Monticello, FL

3 beds | 6 baths | 9,848 sq.ft.

$1,590,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $2992

Traditional Rental Income: $6490

Airbnb ROI: 0.12%

Traditional ROI: 2.95%

17 Old Tung Grove Road

Monticello, FL

3 beds | 3 baths | 2,344 sq.ft.

$699,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2992

Traditional Rental Income: $2669

Airbnb ROI: 1.51%

Traditional ROI: 2.07%

178 Nautilus Drive

Monticello, FL

2 beds | 2 baths | 1,907 sq.ft.

$645,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $2152

Traditional Rental Income: $2274

Airbnb ROI: 1.35%

Traditional ROI: 2.46%

44 Ojibwa South Road

Monticello, FL

4 beds | 4 baths | 2,771 sq.ft.

$625,000

Airbnb cash on cash: 3.97%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $4157

Traditional Rental Income: $3675

Airbnb ROI: 3.97%

Traditional ROI: 4.65%

339 Silver Lake Road

Monticello, FL

3 beds | 3 baths | 2,706 sq.ft.

$459,000

Airbnb cash on cash: 3.26%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $2992

Traditional Rental Income: $2817

Airbnb ROI: 3.26%