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
79 Lakeside Road Monticello, FL Go Back in time in this traditional farmhouse nestled on 4.44 acres totally fence and cros...	3 beds \| 3 baths \| 3,054 sq.ft.	$595,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 4.26% Airbnb Rental Income: $788 Traditional Rental Income: $3508 Airbnb ROI: -1.21% Traditional ROI: 4.26%
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.	$355,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 5.91% Airbnb Rental Income: $4157 Traditional Rental Income: $2738 Airbnb ROI: 7.52% Traditional ROI: 5.91%
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: -0.69% Traditional cash on cash: 2.43% Airbnb Rental Income: $788 Traditional Rental Income: $1449 Airbnb ROI: -0.69% 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.	$252,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.01% Airbnb Rental Income: $788 Traditional Rental Income: $1257 Airbnb ROI: -0.31% Traditional ROI: 3.01%
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.	$375,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 5.86% Airbnb Rental Income: $788 Traditional Rental Income: $2817 Airbnb ROI: -0.82% Traditional ROI: 5.86%
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: -0.82% Traditional cash on cash: 4.19% Airbnb Rental Income: $788 Traditional Rental Income: $3203 Airbnb ROI: -0.82% 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.	$995,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 4.87% Airbnb Rental Income: $4157 Traditional Rental Income: $6213 Airbnb ROI: 1.69% Traditional ROI: 4.87%
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.	$449,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 3.11% Airbnb Rental Income: $788 Traditional Rental Income: $2210 Airbnb ROI: -1.03% Traditional ROI: 3.11%
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.	$525,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 4.2% Airbnb Rental Income: $788 Traditional Rental Income: $2666 Airbnb ROI: -0.28% Traditional ROI: 4.2%
490 E Palmer Mill Road Monticello, FL This striking Victorian home built in 1892 and located near downtown Monticello. The home ...	3 beds \| 3 baths \| 2,467 sq.ft.	$189,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 11.9% Airbnb Rental Income: $788 Traditional Rental Income: $2627 Airbnb ROI: -0.12% Traditional ROI: 11.9%
181 Heritage Boulevard Monticello, FL Certified Florida Green Home on 3 acres in the highly sough after Heritage Hills s/d. Enjo...	3 beds \| 3 baths \| 2,546 sq.ft.	$599,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 3.28% Airbnb Rental Income: $788 Traditional Rental Income: $2756 Airbnb ROI: -0.8% Traditional ROI: 3.28%
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.	$365,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 5.23% Airbnb Rental Income: $788 Traditional Rental Income: $2529 Airbnb ROI: -0.79% Traditional ROI: 5.23%
47 Mire Court Monticello, FL Amazing new construction Available Now 3 bedroom 2 bathroom by Nailed It Tallahassee LLC L...	3 beds \| 2 baths \| 1,806 sq.ft.	$455,995	Airbnb cash on cash: -1.04% Traditional cash on cash: 2.77% Airbnb Rental Income: $788 Traditional Rental Income: $2094 Airbnb ROI: -1.04% Traditional ROI: 2.77%
1125 E Dogwood Street Monticello, FL Must see this brand new home built by Southern Construction in the downtown Monticello are...	3 beds \| 2 baths \| 1,290 sq.ft.	$265,900	Airbnb cash on cash: -0.39% Traditional cash on cash: 5.98% Airbnb Rental Income: $788 Traditional Rental Income: $2066 Airbnb ROI: -0.39% Traditional ROI: 5.98%
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 recently built by Southern Construction. Centrally located in do...	4 beds \| 3 baths \| 1,798 sq.ft.	$480,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 3.49% Airbnb Rental Income: $4157 Traditional Rental Income: $2508 Airbnb ROI: 5.2% Traditional ROI: 3.49%
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: -0.83% Traditional cash on cash: 5.61% Airbnb Rental Income: $788 Traditional Rental Income: $2764 Airbnb ROI: -0.83% Traditional ROI: 5.61%
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: -0.3% Traditional cash on cash: 5.24% Airbnb Rental Income: $788 Traditional Rental Income: $1916 Airbnb ROI: -0.3% Traditional ROI: 5.24%
81 Old Tung Grove Road Monticello, FL New Construction move in ready. Sacious over 2300 sq fr. with upstairs bonus room with bat...	4 beds \| 4 baths \| 2,365 sq.ft.	$725,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.72% Airbnb Rental Income: $4157 Traditional Rental Income: $3289 Airbnb ROI: 3.7% Traditional ROI: 3.72%
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.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.7% Airbnb Rental Income: $null Traditional Rental Income: $2908 Airbnb ROI: N/A Traditional ROI: 8.7%
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.	$165,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 6.85% Airbnb Rental Income: $702 Traditional Rental Income: $1511 Airbnb ROI: -0.24% Traditional ROI: 6.85%
185 Mallard Lane Monticello, FL See updated pictures - motivated Sellers. Newer 2020 mobile home on 1.95 acres. This simpl...	3 beds \| 2 baths \| 1,328 sq.ft.	$199,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 9.36% Airbnb Rental Income: $788 Traditional Rental Income: $2151 Airbnb ROI: 0.45% Traditional ROI: 9.36%
930 E Pearl Street Monticello, FL Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Montice...	4 beds \| 3 baths \| 3,188 sq.ft.	$449,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 7.33% Airbnb Rental Income: $4157 Traditional Rental Income: $3787 Airbnb ROI: 6.11% Traditional ROI: 7.33%
2664 A W Washington Highway Monticello, FL FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move...	5 beds \| 2 baths \| 2,659 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.81% Airbnb Rental Income: $null Traditional Rental Income: $2749 Airbnb ROI: N/A Traditional ROI: 6.81%
660 N Jefferson Street Monticello, FL This updated craftsman bungalow sits just minutes from historic downtown Monticello and al...	2 beds \| 2 baths \| 1,672 sq.ft.	$275,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 5.93% Airbnb Rental Income: $702 Traditional Rental Income: $2114 Airbnb ROI: -0.7% Traditional ROI: 5.93%
237 Valley View Court Monticello, FL This is an actual sunset over a 15 minute period in mid-October. Experience gorgeous sunse...	5 beds \| 4 baths \| 5,590 sq.ft.	$1,175,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $5093 Airbnb ROI: N/A Traditional ROI: 2.98%
950 E Pearl Street Monticello, FL Charming 1955 Cottage in the Heart of Monticello,Fl. Welcome home to this cozy yet surpris...	3 beds \| 2 baths \| 1,855 sq.ft.	$319,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 5.98% Airbnb Rental Income: $788 Traditional Rental Income: $2296 Airbnb ROI: -0.11% Traditional ROI: 5.98%
84 Lakeside Road Monticello, FL This beautifully maintained modular home sits on 2.77 acres, offering peaceful waterfront ...	3 beds \| 2 baths \| 2,268 sq.ft.	$375,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 4.51% Airbnb Rental Income: $788 Traditional Rental Income: $2185 Airbnb ROI: -0.37% Traditional ROI: 4.51%
1627 Lloyd Creek Road Monticello, FL Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A gated d...	3 beds \| 2 baths \| 2,400 sq.ft.	$725,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 2% Airbnb Rental Income: $788 Traditional Rental Income: $2718 Airbnb ROI: -1.33% Traditional ROI: 2%
159 W Notre Dame Street Monticello, FL A perfect redevelopment opportunity or your next home or investment property awaits! Lot c...	2 beds \| 1 baths \| 600 sq.ft.	$120,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 7.94% Airbnb Rental Income: $702 Traditional Rental Income: $1197 Airbnb ROI: 1.02% Traditional ROI: 7.94%
756 Frank Lacy Road Monticello, FL Welcome to your new farmhouse in beautiful Jefferson County! This peaceful property is loc...	3 beds \| 2 baths \| 2,432 sq.ft.	$350,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 4.88% Airbnb Rental Income: $788 Traditional Rental Income: $2222 Airbnb ROI: -0.46% Traditional ROI: 4.88%
463 Murmuring Creek Road Monticello, FL Move in ready home on over 5 acres in beautiful Monticello Florida. Newer Roof 2024, Fresh...	3 beds \| 2 baths \| 1,292 sq.ft.	$200,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 6.51% Airbnb Rental Income: $788 Traditional Rental Income: $1685 Airbnb ROI: 0.09% Traditional ROI: 6.51%
285 Mallard Lane Monticello, FL *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this ...	3 beds \| 2 baths \| 2,000 sq.ft.	$439,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 3.96% Airbnb Rental Income: $788 Traditional Rental Income: $2461 Airbnb ROI: -0.89% Traditional ROI: 3.96%
54 Woodland Drive Monticello, FL One or more photos have been virtually staged (fire in fireplace). Welcome to this beautif...	4 beds \| 3 baths \| 2,032 sq.ft.	$485,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 4.23% Airbnb Rental Income: $4157 Traditional Rental Income: $2660 Airbnb ROI: 5.59% Traditional ROI: 4.23%
1511 Spring Hollow Road Monticello, FL Charming home on large .87 acre lot in established subdivision. Sunporch overlooks wooded ...	3 beds \| 2 baths \| 1,338 sq.ft.	$269,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 4.57% Airbnb Rental Income: $788 Traditional Rental Income: $1730 Airbnb ROI: -0.41% Traditional ROI: 4.57%
655 N Cherry Street Monticello, FL New construction in the heart of Monticello's Historic District! This beautifully built 1,...	2 beds \| 2 baths \| 1,092 sq.ft.	$244,900	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.82% Airbnb Rental Income: $702 Traditional Rental Income: $1645 Airbnb ROI: -0.57% Traditional ROI: 4.82%
165 CROOKED CREEK Lane Monticello, FL Welcome to 165 Crooked Creek Lane in Monticello, Florida-a beautifully maintained home sit...	3 beds \| 2 baths \| 1,858 sq.ft.	$465,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 2.28% Airbnb Rental Income: $788 Traditional Rental Income: $1906 Airbnb ROI: -1.02% Traditional ROI: 2.28%

Real Estate investment in Monticello, FL

There are 37 properties for sale in the city of Monticello . The median list price in Monticello is $360,000 and the average price per square foot is $170. In January 2026, the average monthly cash on cash return in Monticello is 5.00%. The average monthly rental income in Monticello is $2,222.

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

There are 37 investment properties available for sale in Monticello.

In 2026, 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 $788.

Your search for investment property begins and ends here

Investment Property for Sale in Monticello, FL

79 Lakeside Road

Monticello, FL

3 beds | 3 baths | 3,054 sq.ft.

$595,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $788

Traditional Rental Income: $3508

Airbnb ROI: -1.21%

Traditional ROI: 4.26%

155 E Seminole Avenue

Monticello, FL

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

$355,000

Airbnb cash on cash: 7.52%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $4157

Traditional Rental Income: $2738

Airbnb ROI: 7.52%

Traditional ROI: 5.91%

354 Pine Cone Drive

Monticello, FL

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

$335,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 2.43%

Airbnb Rental Income: $788

Traditional Rental Income: $1449

Airbnb ROI: -0.69%

Traditional ROI: 2.43%

1160 E Washington Street

Monticello, FL

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

$252,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $788

Traditional Rental Income: $1257

Airbnb ROI: -0.31%

Traditional ROI: 3.01%

339 Silver Lake Rd.

Monticello, FL

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

$375,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $788

Traditional Rental Income: $2817

Airbnb ROI: -0.82%

Traditional ROI: 5.86%

515 E Palmer Mill Road

Monticello, FL

3 beds | 3 baths | 2,187 sq.ft.

$585,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $788

Traditional Rental Income: $3203

Airbnb ROI: -0.82%

Traditional ROI: 4.19%

825 Rainey Run

Monticello, FL

4 beds | 5 baths | 3,696 sq.ft.

$995,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $4157

Traditional Rental Income: $6213

Airbnb ROI: 1.69%

Traditional ROI: 4.87%

107 Tarn Way

Monticello, FL

3 beds | 2 baths | 1,774 sq.ft.

$449,900

Airbnb cash on cash: -1.03%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $788

Traditional Rental Income: $2210

Airbnb ROI: -1.03%