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
1530 Sweetbay Court Monticello, FL Like New! Barely lived in Home in the sought-after Crooked Creek Subdivision! Easy commute...	3 beds \| 2 baths \| 1,370 sq.ft.	$325,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.64% Airbnb Rental Income: $2992 Traditional Rental Income: $1904 Airbnb ROI: 4.95% Traditional ROI: 3.64%
2029 Boston Highway Monticello, FL Welcome to 2029 Boston Hwy-the perfect blend of comfort, convenience, and country charm. T...	2 beds \| 2 baths \| 1,922 sq.ft.	$259,900	Airbnb cash on cash: 4.05% Traditional cash on cash: 4.09% Airbnb Rental Income: $2152 Traditional Rental Income: $1616 Airbnb ROI: 4.05% Traditional ROI: 4.09%
354 Pine Cone Drive Monticello, FL 2024 construction, shows like brand new home on large .68 acre lot, wooded buffer adds pri...	3 beds \| 2 baths \| 1,604 sq.ft.	$335,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 2.43% Airbnb Rental Income: $2992 Traditional Rental Income: $1449 Airbnb ROI: 5.14% Traditional ROI: 2.43%
1160 E Washington Street Monticello, FL Remodeled brick home, 3 br 1 bath, open kitchen living room with fireplace. Large utility ...	3 beds \| 1 baths \| 1,334 sq.ft.	$265,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 2.77% Airbnb Rental Income: $2992 Traditional Rental Income: $1257 Airbnb ROI: 6.96% Traditional ROI: 2.77%
418 Quail Lane Monticello, FL Enjoy this quaint, well kept 2/2 mobile home on 1.5 acres of usable land. This homestead i...	2 beds \| 2 baths \| 1,050 sq.ft.	$195,000	Airbnb cash on cash: 6.28% Traditional cash on cash: 7.23% Airbnb Rental Income: $2152 Traditional Rental Income: $1781 Airbnb ROI: 6.28% Traditional ROI: 7.23%
193 Nautilus Drive Monticello, FL Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the ...	4 beds \| 6 baths \| 9,848 sq.ft.	$1,250,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 4.21% Airbnb Rental Income: $4157 Traditional Rental Income: $6490 Airbnb ROI: 1.45% Traditional ROI: 4.21%
130 Simpson Avenue Monticello, FL Beautiful home located in historic Monticello within walking distance to downtown shopping...	3 beds \| 2 baths \| 1,654 sq.ft.	$269,000	Airbnb cash on cash: 7.05% Traditional cash on cash: 7.62% Airbnb Rental Income: $2992 Traditional Rental Income: $2450 Airbnb ROI: 7.05% Traditional ROI: 7.62%
339 Silver Lake Rd. Monticello, FL Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great enterta...	3 beds \| 3 baths \| 2,706 sq.ft.	$419,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 5.05% Airbnb Rental Income: $2992 Traditional Rental Income: $2817 Airbnb ROI: 3.75% Traditional ROI: 5.05%
515 E Palmer Mill Road Monticello, FL Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downt...	3 beds \| 3 baths \| 2,187 sq.ft.	$585,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 4.19% Airbnb Rental Income: $2992 Traditional Rental Income: $3203 Airbnb ROI: 2.55% Traditional ROI: 4.19%
825 Rainey Run Monticello, FL This private 10-acre retreat is where luxury, comfort, and nature come together in perfect...	4 beds \| 5 baths \| 3,696 sq.ft.	$1,050,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.56% Airbnb Rental Income: $4157 Traditional Rental Income: $6213 Airbnb ROI: 1.55% Traditional ROI: 4.56%
2024 Old Lloyd Road Monticello, FL Square footage includes both the main house is 3200 square feet with 4 bedrooms and 3 bath...	4 beds \| 3 baths \| 4,600 sq.ft.	$989,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.26% Airbnb Rental Income: $4157 Traditional Rental Income: $3485 Airbnb ROI: 2.04% Traditional ROI: 2.26%
107 Tarn Way Monticello, FL 2024 Custom Built Home with Premium Upgrades in Hemings Pond Subdivision! Better than new ...	3 beds \| 2 baths \| 1,774 sq.ft.	$479,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.8% Airbnb Rental Income: $2992 Traditional Rental Income: $2210 Airbnb ROI: 3.01% Traditional ROI: 2.8%
3827 N Jefferson Street Monticello, FL Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peace...	3 beds \| 3 baths \| 3,026 sq.ft.	$575,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 3.75% Airbnb Rental Income: $2992 Traditional Rental Income: $2666 Airbnb ROI: 3.08% Traditional ROI: 3.75%
44 Pine Needle Trace Monticello, FL Charming Home with Open Floor Plan in Beautiful Monticello, FL! Welcome to this cozy well ...	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%
300 Cedar Street Monticello, FL Price Improvement! ~ Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello...	3 beds \| 2 baths \| 2,044 sq.ft.	$285,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 6.78% Airbnb Rental Income: $2992 Traditional Rental Income: $2415 Airbnb ROI: 6.37% Traditional ROI: 6.78%
181 Heritage Boulevard Monticello, FL Highly Desirable Heritage Hills Location! Enjoy the perfect blend of privacy and convenien...	3 beds \| 3 baths \| 2,546 sq.ft.	$624,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 3.11% Airbnb Rental Income: $2992 Traditional Rental Income: $2756 Airbnb ROI: 2.34% Traditional ROI: 3.11%
665 W Washington Street Monticello, FL Owner Financing available!! A brand new roof is being installed this week, adding immediat...	3 beds \| 3 baths \| 3,348 sq.ft.	$349,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 6.23% Airbnb Rental Income: $2992 Traditional Rental Income: $2983 Airbnb ROI: 4.16% Traditional ROI: 6.23%
3873 N Jefferson Highway Monticello, FL Back on market due to no fault of the seller or home. Stunning 4 Bedroom, 3.5 Bath Home on...	4 beds \| 4 baths \| 3,862 sq.ft.	$589,900	Airbnb cash on cash: 3.89% Traditional cash on cash: 5.12% Airbnb Rental Income: $4157 Traditional Rental Income: $3953 Airbnb ROI: 3.89% Traditional ROI: 5.12%
205 N Rhodes Street Monticello, FL Classic historical home built in the 1920's. Walking distance to charming downtown Montice...	3 beds \| 2 baths \| 2,766 sq.ft.	$379,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 4.97% Airbnb Rental Income: $2992 Traditional Rental Income: $2529 Airbnb ROI: 4.34% Traditional ROI: 4.97%
47 Mire Court Monticello, FL Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out a...	3 beds \| 2 baths \| 1,806 sq.ft.	$455,995	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.77% Airbnb Rental Income: $2992 Traditional Rental Income: $2094 Airbnb ROI: 3.27% Traditional ROI: 2.77%
2436 N Jefferson Monticello, FL Discover the perfect blend of rustic charm and opportunity with this unique country proper...	3 beds \| 2 baths \| 2,390 sq.ft.	$219,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 9.48% Airbnb Rental Income: $2992 Traditional Rental Income: $2479 Airbnb ROI: 8.64% Traditional ROI: 9.48%
150 N Ojibwa Road Monticello, FL One or more photo(s) has been virtually staged. Tranquil 5.1 acre retreat nestled deep in ...	3 beds \| 3 baths \| 3,214 sq.ft.	$629,900	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.77% Airbnb Rental Income: $2992 Traditional Rental Income: $2579 Airbnb ROI: 2.31% Traditional ROI: 2.77%
221 Kiley Drive Monticello, FL Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless el...	5 beds \| 5 baths \| 5,476 sq.ft.	$1,549,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $6394 Airbnb ROI: N/A Traditional ROI: 2.48%
952 Turney Anderson Road Monticello, FL Time travel back to 2021 Interest rates with this assumable loan for +/- $250k at 2.95% in...	3 beds \| 2 baths \| 1,841 sq.ft.	$459,900	Airbnb cash on cash: 3.77% Traditional cash on cash: 2.97% Airbnb Rental Income: $2992 Traditional Rental Income: $1960 Airbnb ROI: 3.77% Traditional ROI: 2.97%
1125 E Dogwood Street Monticello, FL Must see this brand new home being built by Southern Construction in the downtown Monticel...	3 beds \| 2 baths \| 1,290 sq.ft.	$285,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 5.47% Airbnb Rental Income: $2992 Traditional Rental Income: $2066 Airbnb ROI: 6.35% Traditional ROI: 5.47%
513 Creekside Court Monticello, FL Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivi...	4 beds \| 3 baths \| 2,660 sq.ft.	$589,900	Airbnb cash on cash: 3.87% Traditional cash on cash: 3.23% Airbnb Rental Income: $4157 Traditional Rental Income: $2925 Airbnb ROI: 3.87% Traditional ROI: 3.23%
855 S Waukeenah Street Monticello, FL Stunning New Construction home currently being built by Southern Construction. Centrally l...	4 beds \| 3 baths \| 1,798 sq.ft.	$499,900	Airbnb cash on cash: 4.92% Traditional cash on cash: 3.28% Airbnb Rental Income: $4157 Traditional Rental Income: $2508 Airbnb ROI: 4.92% Traditional ROI: 3.28%
4715 N Jefferson Street Monticello, FL This Monticello gem truly has it all! Situated on 1.8 beautifully maintained acres, this 3...	3 beds \| 3 baths \| 2,063 sq.ft.	$380,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 5.61% Airbnb Rental Income: $2992 Traditional Rental Income: $2764 Airbnb ROI: 4.32% Traditional ROI: 5.61%
625 E Washington Street Monticello, FL Amazing Investment Opportunity! Own your piece of history and enjoy some great cash flow i...	4 beds \| N/A baths \| N/A	$799,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 1.52% Airbnb Rental Income: $4157 Traditional Rental Income: $2248 Airbnb ROI: 2.9% Traditional ROI: 1.52%
160 Lineage Court Monticello, FL Beautiful 3-bedroom, 2.5-bath farmhouse offers privacy, charm, and modern conveniences. Bu...	3 beds \| 3 baths \| 1,915 sq.ft.	$509,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.86% Airbnb Rental Income: $2992 Traditional Rental Income: $2699 Airbnb ROI: 3.03% Traditional ROI: 3.86%
2497 Boston Highway Monticello, FL Charming Hillside Country Retreat with Barn and Acreage. Welcome to your dream countryside...	3 beds \| 2 baths \| 1,921 sq.ft.	$449,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 3.53% Airbnb Rental Income: $2992 Traditional Rental Income: $2161 Airbnb ROI: 3.87% Traditional ROI: 3.53%
104 Pine Cone Drive Monticello, FL This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines ...	3 beds \| 2 baths \| 1,740 sq.ft.	$277,000	Airbnb cash on cash: 6.73% Traditional cash on cash: 5.24% Airbnb Rental Income: $2992 Traditional Rental Income: $1916 Airbnb ROI: 6.73% Traditional ROI: 5.24%
81 Old Tung Grove Road Monticello, FL New Construction, to be completed in a few weeks. Sacious over 2300 sq fr. with upstairs b...	3 beds \| 4 baths \| 2,365 sq.ft.	$725,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 3.72% Airbnb Rental Income: $2992 Traditional Rental Income: $3289 Airbnb ROI: 2.27% Traditional ROI: 3.72%
532 Dills Road Monticello, FL Gorgeous Pool Home situated on 5.55 acres featuring wood floors, crown molding, quartz cou...	3 beds \| 3 baths \| 2,376 sq.ft.	$575,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 4.28% Airbnb Rental Income: $2992 Traditional Rental Income: $2932 Airbnb ROI: 3.11% Traditional ROI: 4.28%
173 Deerfield Lane Monticello, FL $30,000 PRICE DROP! NEW CONSTRUCTION COMPLETE! Walk into this stunningly crafted three-bed...	3 beds \| 2 baths \| 1,865 sq.ft.	$399,999	Airbnb cash on cash: 4.01% Traditional cash on cash: 3.53% Airbnb Rental Income: $2992 Traditional Rental Income: $2125 Airbnb ROI: 4.01% Traditional ROI: 3.53%
425 N Mulberry Street Monticello, FL Charming 1920's Two-Story Home in the Heart of Downtown Monticello, Fl. Step back in time ...	5 beds \| 2 baths \| 3,320 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2908 Airbnb ROI: N/A Traditional ROI: 8.1%
1515 Tennessee Avenue Monticello, FL Brimming with rustic charm, this 2 bedroom, 2 bathroom home sits on .29 acres just outside...	2 beds \| 2 baths \| 1,096 sq.ft.	$185,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 6.02% Airbnb Rental Income: $2152 Traditional Rental Income: $1511 Airbnb ROI: 6.55% Traditional ROI: 6.02%
12447 Gamble Road Monticello, FL This 2 bedroom, 2 bathroom home offers 1,440 sqft of living space on a full acre in Waciss...	2 beds \| 2 baths \| 1,440 sq.ft.	$169,000	Airbnb cash on cash: 7.59% Traditional cash on cash: 9.63% Airbnb Rental Income: $2152 Traditional Rental Income: $1933 Airbnb ROI: 7.59% Traditional ROI: 9.63%
185 Mallard Lane Monticello, FL Newer 2020 mobile home on 1.95 acres. This simple but beautiful property backs up to a lak...	3 beds \| 2 baths \| 1,328 sq.ft.	$219,000	Airbnb cash on cash: 9.18% Traditional cash on cash: 8.44% Airbnb Rental Income: $2992 Traditional Rental Income: $2151 Airbnb ROI: 9.18% Traditional ROI: 8.44%
240 Valley View Court Monticello, FL Spanning four full lots and over 20 acres, this private country estate offers two homes an...	5 beds \| 3 baths \| 3,656 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $3401 Airbnb ROI: N/A Traditional ROI: 1.71%

Real Estate investment in Monticello, FL

There are 44 properties for sale in the city of Monticello . The median list price in Monticello is $399,999 and the average price per square foot is $161. In October 2025, the average monthly cash on cash return in Monticello is 4.00%. The average monthly rental income in Monticello is $2,494.

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

There are 44 investment properties available for sale in Monticello.

In 2025, 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

1530 Sweetbay Court

Monticello, FL

3 beds | 2 baths | 1,370 sq.ft.

$325,000

Airbnb cash on cash: 4.95%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $2992

Traditional Rental Income: $1904

Airbnb ROI: 4.95%

Traditional ROI: 3.64%

2029 Boston Highway

Monticello, FL

2 beds | 2 baths | 1,922 sq.ft.

$259,900

Airbnb cash on cash: 4.05%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2152

Traditional Rental Income: $1616

Airbnb ROI: 4.05%

Traditional ROI: 4.09%

354 Pine Cone Drive

Monticello, FL

3 beds | 2 baths | 1,604 sq.ft.

$335,000

Airbnb cash on cash: 5.14%

Traditional cash on cash: 2.43%

Airbnb Rental Income: $2992

Traditional Rental Income: $1449

Airbnb ROI: 5.14%

Traditional ROI: 2.43%

1160 E Washington Street

Monticello, FL

3 beds | 1 baths | 1,334 sq.ft.

$265,000

Airbnb cash on cash: 6.96%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2992

Traditional Rental Income: $1257

Airbnb ROI: 6.96%

Traditional ROI: 2.77%

418 Quail Lane

Monticello, FL

2 beds | 2 baths | 1,050 sq.ft.

$195,000

Airbnb cash on cash: 6.28%

Traditional cash on cash: 7.23%

Airbnb Rental Income: $2152

Traditional Rental Income: $1781

Airbnb ROI: 6.28%

Traditional ROI: 7.23%

193 Nautilus Drive

Monticello, FL

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

$1,250,000

Airbnb cash on cash: 1.45%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $4157

Traditional Rental Income: $6490

Airbnb ROI: 1.45%

Traditional ROI: 4.21%

130 Simpson Avenue

Monticello, FL

3 beds | 2 baths | 1,654 sq.ft.

$269,000

Airbnb cash on cash: 7.05%

Traditional cash on cash: 7.62%

Airbnb Rental Income: $2992

Traditional Rental Income: $2450

Airbnb ROI: 7.05%

Traditional ROI: 7.62%

339 Silver Lake Rd.

Monticello, FL

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

$419,000

Airbnb cash on cash: 3.75%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $2992

Traditional Rental Income: $2817

Airbnb ROI: 3.75%