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
85 Pine Cone Drive Monticello, FL This beautifully renovated 3-bedroom, 2-bathroom modular home offers modern comfort and st...	3 beds \| 2 baths \| 1,678 sq.ft.	$209,900	Airbnb cash on cash: 9.23% Traditional cash on cash: 7.47% Airbnb Rental Income: $2992 Traditional Rental Income: $1954 Airbnb ROI: 9.23% Traditional ROI: 7.47%
155 E Seminole Avenue Monticello, FL Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a ge...	4 beds \| 3 baths \| 2,223 sq.ft.	$375,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 5.55% Airbnb Rental Income: $4157 Traditional Rental Income: $2738 Airbnb ROI: 7.08% Traditional ROI: 5.55%
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.	$1,285,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 4.07% Airbnb Rental Income: $4157 Traditional Rental Income: $6490 Airbnb ROI: 1.38% Traditional ROI: 4.07%
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%
1205 E Pearl Street Monticello, FL Charming 1956 Mid-Century Home. Fully Renovated with Modern Touches. Welcome to this beaut...	3 beds \| 3 baths \| 2,373 sq.ft.	$399,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 5.2% Airbnb Rental Income: $2992 Traditional Rental Income: $2743 Airbnb ROI: 4.03% Traditional ROI: 5.2%
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%
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.	$694,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 2.1% Airbnb Rental Income: $2992 Traditional Rental Income: $2669 Airbnb ROI: 1.53% Traditional ROI: 2.1%
480 W Washington Street Monticello, FL OWNERS MOTIVATED-ALL REASONABLE OFFERS WILL BE CONSIDERED.Step Back In Time! Rare chance t...	3 beds \| 2 baths \| 1,985 sq.ft.	$389,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 5.05% Airbnb Rental Income: $2992 Traditional Rental Income: $2400 Airbnb ROI: 4.79% Traditional ROI: 5.05%
825 Rainey Run Monticello, FL Luxury Creekside Home on 10 Acres in Monticello, Florida! Discover North Florida luxury li...	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.	$499,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 2.62% Airbnb Rental Income: $2992 Traditional Rental Income: $2210 Airbnb ROI: 2.83% Traditional ROI: 2.62%
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 Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown,...	3 beds \| 2 baths \| 2,044 sq.ft.	$295,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 6.52% Airbnb Rental Income: $2992 Traditional Rental Income: $2415 Airbnb ROI: 6.13% Traditional ROI: 6.52%
490 E Palmer Mill Rd. Monticello, FL The Haile House originally built in 1893 is located in downtown Monticello FL. This wonder...	3 beds \| 2 baths \| 2,467 sq.ft.	$285,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 7.63% Airbnb Rental Income: $2992 Traditional Rental Income: $2627 Airbnb ROI: 6.43% Traditional ROI: 7.63%
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.	$635,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.05% Airbnb Rental Income: $2992 Traditional Rental Income: $2756 Airbnb ROI: 2.29% Traditional ROI: 3.05%
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%
740 Kinsey Road Monticello, FL Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Na...	3 beds \| 1 baths \| 1,146 sq.ft.	$1,125,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 0.21% Airbnb Rental Income: $2992 Traditional Rental Income: $1503 Airbnb ROI: 0.98% Traditional ROI: 0.21%
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.	$599,900	Airbnb cash on cash: 3.8% Traditional cash on cash: 5.01% Airbnb Rental Income: $4157 Traditional Rental Income: $3953 Airbnb ROI: 3.8% Traditional ROI: 5.01%
4081 Gamble Road Monticello, FL Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden ge...	4 beds \| 2 baths \| 2,162 sq.ft.	$329,500	Airbnb cash on cash: 8.39% Traditional cash on cash: 4.81% Airbnb Rental Income: $4157 Traditional Rental Income: $2166 Airbnb ROI: 8.39% Traditional ROI: 4.81%
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.	$460,995	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.72% Airbnb Rental Income: $2992 Traditional Rental Income: $2094 Airbnb ROI: 3.21% Traditional ROI: 2.72%
575 E Palmer Mill Road Monticello, FL Spacious home located within walking distance of Historic Downtown Monticello. This four b...	4 beds \| 2 baths \| 1,858 sq.ft.	$299,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 6.44% Airbnb Rental Income: $4157 Traditional Rental Income: $2437 Airbnb ROI: 9.42% Traditional ROI: 6.44%
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 Tranquil 5.1 acre retreat nestled deep in a pecan grove just outside Monticello, Florida h...	3 beds \| 3 baths \| 3,214 sq.ft.	$649,900	Airbnb cash on cash: 2.2% Traditional cash on cash: 2.66% Airbnb Rental Income: $2992 Traditional Rental Income: $2579 Airbnb ROI: 2.2% Traditional ROI: 2.66%
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 Discover your own private retreat with this charming home set on a fully fenced 10-acre lo...	3 beds \| 2 baths \| 1,841 sq.ft.	$475,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 2.84% Airbnb Rental Income: $2992 Traditional Rental Income: $1960 Airbnb ROI: 3.62% Traditional ROI: 2.84%
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.	$289,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 5.37% Airbnb Rental Income: $2992 Traditional Rental Income: $2066 Airbnb ROI: 6.24% Traditional ROI: 5.37%
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%
9497 Gamble Road Monticello, FL Nestled on 6 beautiful wooded acres, this charming 2 bedroom, 2 bath cedar house offers th...	2 beds \| 2 baths \| 1,404 sq.ft.	$285,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 6.79% Airbnb Rental Income: $2152 Traditional Rental Income: $2303 Airbnb ROI: 4.19% Traditional ROI: 6.79%
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%
282 Long Leaf Drive Monticello, FL Enjoy space, privacy, and outdoor living on this well-maintained 5-acre property in Montic...	3 beds \| 2 baths \| 2,170 sq.ft.	$519,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 3.55% Airbnb Rental Income: $2992 Traditional Rental Income: $2609 Airbnb ROI: 2.92% Traditional ROI: 3.55%
1065 S Mulberry Street Monticello, FL This cozy home located in the heart of Monticello is the perfect 2/2 for a starter family ...	2 beds \| 2 baths \| 1,356 sq.ft.	$215,900	Airbnb cash on cash: 5.23% Traditional cash on cash: 6.83% Airbnb Rental Income: $2152 Traditional Rental Income: $1931 Airbnb ROI: 5.23% Traditional ROI: 6.83%
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 \| 2,792 sq.ft.	$539,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 3.59% Airbnb Rental Income: $2992 Traditional Rental Income: $2699 Airbnb ROI: 2.81% Traditional ROI: 3.59%
860 Tally Hills Drive Monticello, FL Don't miss your chance to own one of the most striking homes in Tally Hills with lake acce...	5 beds \| 4 baths \| 4,150 sq.ft.	$900,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $5479 Airbnb ROI: N/A Traditional ROI: 4.77%
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: 1.93% Airbnb Rental Income: $2992 Traditional Rental Income: $1488 Airbnb ROI: 3.87% Traditional ROI: 1.93%

Real Estate investment in Monticello, FL

There are 38 properties for sale in the city of Monticello . The median list price in Monticello is $419,000 and the average price per square foot is $161. In September 2025, the average monthly cash on cash return in Monticello is 5.00%. The average monthly rental income in Monticello is $2,554.

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

There are 38 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 $2,554.

Your search for investment property begins and ends here

Investment Property for Sale in Monticello, FL

85 Pine Cone Drive

Monticello, FL

3 beds | 2 baths | 1,678 sq.ft.

$209,900

Airbnb cash on cash: 9.23%

Traditional cash on cash: 7.47%

Airbnb Rental Income: $2992

Traditional Rental Income: $1954

Airbnb ROI: 9.23%

Traditional ROI: 7.47%

155 E Seminole Avenue

Monticello, FL

4 beds | 3 baths | 2,223 sq.ft.

$375,000

Airbnb cash on cash: 7.08%

Traditional cash on cash: 5.55%

Airbnb Rental Income: $4157

Traditional Rental Income: $2738

Airbnb ROI: 7.08%

Traditional ROI: 5.55%

193 Nautilus Drive

Monticello, FL

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

$1,285,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $4157

Traditional Rental Income: $6490

Airbnb ROI: 1.38%

Traditional ROI: 4.07%

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%

1205 E Pearl Street

Monticello, FL

3 beds | 3 baths | 2,373 sq.ft.

$399,000

Airbnb cash on cash: 4.03%

Traditional cash on cash: 5.2%

Airbnb Rental Income: $2992

Traditional Rental Income: $2743

Airbnb ROI: 4.03%

Traditional ROI: 5.2%

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%

Traditional ROI: 5.05%

17 Old Tung Grove Road

Monticello, FL

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

$694,000

Airbnb cash on cash: 1.53%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $2992

Traditional Rental Income: $2669

Airbnb ROI: 1.53%

Traditional ROI: 2.1%

480 W Washington Street

Monticello, FL

3 beds | 2 baths | 1,985 sq.ft.

$389,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $2992

Traditional Rental Income: $2400

Airbnb ROI: 4.79%